Compound, organic electroluminescent element and electronic device

Abstract

An organic electroluminescent element (1) has an anode (3), a cathode (4) and a light-emitting layer (5). The light-emitting layer (5) contains a compound M2 which is represented by general formula (1) and exhibits delayed fluorescence. The compound M2 has one or more deuterium atoms in the molecule. In general formula (1), CN is a cyano group, D11 and D12 are each independently a group represented by general formula (11), (12) or (13), with at least one D11 being a group represented by general formula (12) or (13), and R is a hydrogen atom, an aryl group, or the like.

Description

Compound, organic electroluminescence element and electronic device

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), 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 elements that utilize light emission from singlet excitons are increasingly being applied to full-color displays such as those for mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, efforts are being made to improve the performance of organic EL elements.

[0003] For example, it is expected that organic EL elements will emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. Against this background, highly efficient fluorescent organic EL elements utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and studied. The TADF (thermally activated delayed fluorescence) 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. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Adachi Chinaya, Kodansha, published April 1, 2012, pp. 261-268. Known compounds that exhibit thermally activated delayed fluorescence (TADF) properties (hereinafter also referred to as TADF compounds) include, for example, compounds in which a donor moiety and an acceptor moiety are bound within the molecule.

[0004] Documents relating to organic EL devices and compounds used in organic EL devices include Patent Documents 1, 2, 3 and 4.

[0005] International Publication No. 2014 / 208698 International Publication No. 2019 / 195104 International Publication No. 2019 / 190235 International Publication No. 2021 / 066059

[0006] In order to improve the performance of electronic devices such as displays, there is a demand for further improvements in the performance of organic EL elements, such as luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0007] An object of the present invention is to provide a compound capable of realizing high performance, particularly at least one of high efficiency and long life, of an organic electroluminescent device. Another object of the present invention is to provide an organic electroluminescent device capable of realizing high performance, particularly at least one of high efficiency and long life, and to provide an electronic device equipped with the organic electroluminescent device.

[0008] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an emitting layer between the anode and the cathode, wherein the emitting layer contains a delayed fluorescent compound M2 represented by the following general formula (1), and the compound M2 has one or more deuterium atoms in a molecule:

[0009]

[0010] (In the general formula (1), CN is a cyano group, and D １１ and D １２ are each independently a group represented by the following general formula (11), general formula (12) or general formula (13), provided that at least one D １１ is a group represented by the following general formula (12) or (13), and each R is 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 ) (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 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, wherein at least one R is a substituent, and at least one R as the substituent is bonded to the benzene ring in general formula (1) via a carbon-carbon bond, k is 1 or 2, m is 0, 1 or 2, n is 1, 2 or 3, k+m+n is 4, and when k is 2, a plurality of D １１ are the same or different from each other, and when m is 2, a plurality of D １２ are the same or different from each other, and when n is 2 or 3, multiple R's are the same or different from each other.

[0011]

[0012]

[0013]

[0014] (R in the general formula (11) １ ~R ８ at least one pair of adjacent two or more of R in the general formula (12) is 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 is not bonded to each other,１１ ~R １８ at least one pair of adjacent two or more of R in the general formula (13) 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, １１１ ~R １１８ 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 general formula (11) and do not form a substituted or unsubstituted fused ring. １ ~R ８ R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１ ~R １８ and R in the general formula (13) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１１ ~R １１８ 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 ９３２a 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 general formula (12) and the general formula (13), 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 general formula (14) and general formula (15), 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 as or different from each other, when px is 2, 3 or 4, multiple rings B are the same as or different from each other, when py is 2, 3 or 4, multiple rings C are the same as or different from each other, with the proviso that at least one D １１ is a group represented by the general formula (12) or (13), and this D １１ In the general formula (12), p is 4, and the four rings A include two ring structures represented by the following general formula (14) and two ring structures represented by the following general formula (15), １１ In the general formula (13), px and py are 2, two rings B include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and two rings C include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and * in the general formulas (11) to (13) indicates the bonding position with the benzene ring in the general formula (1).

[0015]

[0016] (In the general formula (14), r is 0, 2 or 4, and a plurality of R １９are 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 general formula (15), X １ is a sulfur atom or an oxygen atom, and R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １９ 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 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, １９ are the same or different from each other, and a plurality of X １ are the same or different from each other, provided that D is a group represented by the general formula (13) １１satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3): Condition (Pv1): When k is 2, X in the ring structure represented by the general formula (15) as ring B satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3). １ and X in the ring structure represented by the general formula (15) as ring C. １ At least one of the following is an oxygen atom. Condition (Pv2): When k is 2, two D １１ Condition (Pv3): When n is 3, X in the ring structure represented by the general formula (15) as ring B is different from each other. １ and X in the ring structure represented by the general formula (15) as ring C. １ are each independently a sulfur atom or an oxygen atom. 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 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 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, 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.)

[0017] 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.

[0018] According to one aspect of the present invention, there is provided a compound having at least one deuterium atom in the molecule and represented by the following general formula (150):

[0019]

[0020] (In the general formula (150), R １０２ and R １０４are 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 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 R １０２ and R １０４ At least one of R is a substituent, and R as a substituent １０２ and R １０４ is bonded to the benzene ring in the general formula (150) via a carbon-carbon bond, and R １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８are 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, provided that R １ ~R ８ At least one of R is a substituent other than a hydrogen atom, and １ ~R ８ At least one of R is a deuterium atom. 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 R９３７ 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, 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, R９３６ 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.)

[0021] According to one embodiment of the present invention, a compound capable of realizing high performance, particularly at least one of high efficiency and long life of an organic electroluminescence device can be provided. Furthermore, according to another embodiment of the present invention, it is also possible to provide an organic electroluminescence device capable of realizing high performance, particularly at least one of high efficiency and long life, and an electronic device equipped with the organic electroluminescence device.

[0022] 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 compounds M1 and M2 in the emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention; FIG. 5 is a diagram showing the energy levels and energy transfer relationship of compounds M1, M2, and M3 in the emitting layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention; and FIG. 6 is a diagram showing the energy levels and energy transfer relationship of compounds M2 and M3 in the emitting layer of an example of an organic electroluminescence element according to a fifth embodiment of the present invention.

[0023] [Definitions] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] "Substituents Described in This Specification" The substituents described in this specification are explained below.

[0031] 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.

[0032] "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.

[0033] 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, A 9,9'-spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0034]

[0035]

[0036] 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 group, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0037] "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.

[0038] 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).

[0039] 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).

[0040] 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.

[0041] 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.

[0042] 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).

[0043] 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):

[0044]

[0045]

[0046] 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:

[0047] 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.

[0048] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0049] Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3): a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0050] 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):

[0051] 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).

[0052] "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.

[0053] 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.

[0054] 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.

[0055] "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.

[0056] 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.

[0057] 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.

[0058] - "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.

[0059] Unsubstituted alkynyl groups (specific example group G5A): ethynyl group.

[0060] "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.

[0061] 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.

[0062] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0063] -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.

[0064] ・「-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.

[0065] ・"-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.

[0066] ・「-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.

[0067] "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.

[0068] "Substituted or unsubstituted fluoroalkyl group" As used herein, a "substituted or unsubstituted fluoroalkyl 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 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. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. Note that the "substituted fluoroalkyl group" described 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.

[0069] "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.

[0070] - "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.

[0071] - "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.

[0072] - "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.

[0073] - "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.

[0074] - "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.

[0075] "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.

[0076] 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.

[0077] 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.

[0078] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0079]

[0080] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically any of the following groups:

[0081]

[0082] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0083] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0084]

[0085] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0086] 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.

[0087] "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.

[0088] "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.

[0089] "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.

[0090] 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).

[0091]

[0092]

[0093] 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.

[0094]

[0095] 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.

[0096]

[0097] 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.

[0098] 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).

[0099]

[0100]

[0101]

[0102] In the general formulae (TEMP-69) to (TEMP-82), Q １ ~Q ９ are each independently a hydrogen atom or a substituent.

[0103]

[0104]

[0105]

[0106]

[0107] In the general formulae (TEMP-83) to (TEMP-102), Q １ ~Q ８ are each independently a hydrogen atom or a substituent.

[0108] The above is the explanation of "substituents described in this specification."

[0109] "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.

[0110]

[0111] 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.

[0112] 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).

[0113]

[0114] 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.

[0115]

[0116] 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.

[0117] 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

[0118] 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.

[0119] 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").

[0120] Substituents in the case of "substituted or unsubstituted" In one embodiment of the present specification, the substituents in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituents" in the present specification) include, 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.

[0121] 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.

[0122] 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.

[0123] 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."

[0124] 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.

[0125] 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.

[0126] In this specification, the expression "A≧B" means that the value of A is equal to the value of B, or the value of A is greater than the value of B. In this specification, the expression "A≦B" means that the value of A is equal to the value of B, or the value of A is smaller than the value of B.

[0127] [First embodiment] <Compound> A compound according to this embodiment is a compound M2 represented by the following general formula (1): Compound M2 has one or more deuterium atoms in the molecule.

[0128]

[0129] (In the general formula (1), CN is a cyano group, and D １１ and D １２ are each independently a group represented by the following general formula (11), general formula (12) or general formula (13), provided that at least one D １１is a group represented by the following general formula (12) or (13), and each R is 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 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, wherein at least one R is a substituent, and at least one R as the substituent is bonded to the benzene ring in general formula (1) via a carbon-carbon bond, k is 1 or 2, m is 0, 1 or 2, n is 1, 2 or 3, k+m+n is 4, and when k is 2, a plurality of D １１ are the same or different from each other, and when m is 2, a plurality of D １２ are the same or different from each other, and when n is 2 or 3, multiple R's are the same or different from each other.

[0130]

[0131]

[0132]

[0133] (R in the general formula (11) １ ~R ８ at least one pair of adjacent two or more of R in the general formula (12) is 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 is not bonded to each other, １１ ~R １８ at least one pair of adjacent two or more of R in the general formula (13) 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, １１１ ~R １１８ 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 general formula (11) and do not form a substituted or unsubstituted fused ring. １ ~R ８ R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１ ~R １８ and R in the general formula (13) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １１１ ~R １１８ 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 ９０４a 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, in the general formula (12) and the general formula (13), 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 general formula (14) and general formula (15), 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 as or different from each other, when px is 2, 3 or 4, multiple rings B are the same as or different from each other, when py is 2, 3 or 4, multiple rings C are the same as or different from each other, with the proviso that at least one D １１ is a group represented by the general formula (12) or (13), and this D １１ In the general formula (12), p is 4, and the four rings A include two ring structures represented by the following general formula (14) and two ring structures represented by the following general formula (15), １１In the general formula (13), px and py are 2, two rings B include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and two rings C include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and * in the general formulas (11) to (13) indicates the bonding position with the benzene ring in the general formula (1).

[0134]

[0135] (In the general formula (14), r is 0, 2 or 4, and a plurality of R １９ 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 general formula (15), X １ is a sulfur atom or an oxygen atom, and R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. １９ 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 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 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, １９ are the same or different from each other, and a plurality of X １ are the same or different from each other, provided that D is a group represented by the general formula (13) １１ satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3): Condition (Pv1): When k is 2, X in the ring structure represented by the general formula (15) as ring B satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3). １ and X in the ring structure represented by the general formula (15) as ring C. １ At least one of the following is an oxygen atom. Condition (Pv2): When k is 2, two D １１ Condition (Pv3): When n is 3, X in the ring structure represented by the general formula (15) as ring B is different from each other. １ and X in the ring structure represented by the general formula (15) as ring C. １ are each independently a sulfur atom or an oxygen atom.

[0136] (In the general formula of compound M2, 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 ９０１If 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, 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.)

[0137] According to this embodiment, it is possible to provide a compound that can realize high performance of an organic electroluminescence device, particularly at least one of high efficiency and long life.

[0138] In the compound M2 according to this embodiment, D １１ and D １２ are different groups, or when a plurality of D １１ In the case where D are different groups, when the compound M2 according to this embodiment is used in an organic layer of an organic EL device, the hole injection characteristics are improved, and at least one of the luminous efficiency and the lifetime is improved. １１ and D １２ This is because holes are injected into the organic layer in a stepwise manner since the D １１ and D １２ But, X １ When the chemical structures of the groups are the same except for the above, at least one X １ If at least one X is an oxygen atom, the life of the organic EL element is extended. １ The group in which X is an oxygen atom is １ is a sulfur atom, the bond angle with respect to the benzene ring shown in general formula (1) is smaller than that of a group in which M is a sulfur atom, and therefore, by using compound M2 according to this embodiment in an organic layer, it is thought that the life span of the organic electroluminescence device using compound M2 is extended. Furthermore, compound M2 according to this embodiment has one or more deuterium atoms in the molecule.

[0139] The compound M2 according to this embodiment preferably has two or more deuterium atoms in the molecule.

[0140] The presence of deuterium atoms in a compound can be determined by mass spectrometry or １ The bond position of the deuterium atom in the compound is confirmed by H-NMR analysis. １ The compound is identified by H-NMR analysis. Specifically, the method is as follows. Mass analysis is performed on the target compound, and compared with a corresponding compound in which all hydrogen atoms are protons, the presence of deuterium atoms can be confirmed by, for example, an increase in molecular weight by 1. In addition, deuterium atoms are１ Since no signal was detected in the H-NMR analysis, the target compound １ The number of deuterium atoms contained in the molecule can be confirmed by the integral value obtained by H-NMR analysis. １ By performing H-NMR analysis and assigning signals, the bonding position of the deuterium atom can be identified.

[0141] In the compound M2 according to this embodiment, the benzene ring of the general formula (1) to which the groups represented by the general formulas (11) to (13) are bonded is the benzene ring explicitly shown in the general formula (1), and R, D １１ and D １２ In the compounds represented by the general formulae (110), (120), (130), (126), (127), (126A), (126C), (126D), (127A), (127B), (127C), (127D), (111), (112), and (113) described below, the groups represented by the general formulae (11) to (13) are bonded to the benzene ring itself explicitly shown in these general formulae, as in the case of the general formula (1).

[0142] At least one D in the compound M2 of this embodiment １１ is preferably a group represented by the following general formula (121), general formula (122) or general formula (131).

[0143]

[0144]

[0145]

[0146] (In the general formula (121) and the general formula (122), R １１ ~R １８ is R in the general formula (12). １１ ~R １８ and ring A is the same as １、 Ring A ２ , ring A ３ and Ring A ４Among these, two are ring structures represented by the general formula (14) and the remaining two are ring structures represented by the general formula (15), and in the general formula (131), R １１１ ~R １１８ is R in the general formula (13). １１１ ~R １１８ and ring B １ and Ring B ２ one of the ring structures represented by the general formula (14) is a ring structure represented by the general formula (14), and ring B １ and Ring B ２ the other is a ring structure represented by the general formula (15), and Ring C １ and Ring C ２ is a ring structure represented by the general formula (14), and ring C １ and Ring C ２ the other is a ring structure represented by the general formula (15), and * in the general formulas (121), (122) and (131) indicates the bonding position with the benzene ring in the general formula (1).

[0147] Ring A in Compound M2 of this embodiment １ and Ring A ３ is a ring structure represented by the general formula (14), and ring A ２ and Ring A ４ is preferably a ring structure represented by the general formula (15). １ is a ring structure represented by the general formula (14), and ring B ２ is preferably a ring structure represented by the general formula (15). １ is a ring structure represented by the general formula (14), and ring C ２ is preferably a ring structure represented by the general formula (15).

[0148] At least one D in the compound M2 of this embodiment １１ is preferably a group represented by the general formula (131).

[0149] At least one D in the compound M2 of this embodiment １１is preferably a group represented by the following general formula (123), general formula (124), general formula (125) or general formula (132).

[0150]

[0151]

[0152]

[0153]

[0154] (In the general formula (123), general formula (124) and general formula (125), R １１ ~R １８ is R in the general formula (12). １１ ~R １８ is synonymous with R １９１ ~R １９４ are each independently R in the general formula (14). １９ In the general formula (132), R １１１ ~R １１８ is R in the general formula (13). １１１ ~R １１８ is synonymous with R １９５ ~R １９８ are each independently R in the general formula (14). １９ In the general formulae (123), (124), (125) and (132), X １１ and X １２ are each independently X in the general formula (15). １ and * indicates the bonding position to the benzene ring in the general formula (1).

[0155] In the compound M2 of this embodiment, R １９１ ~R １９４ In the compound M2 of this embodiment, it is preferable that any pair of adjacent two or more of R １９５ ~R １９８ It is preferable that any pair of two or more adjacent groups of the above do not bond to each other.

[0156] X in compound M2 of this embodiment１１ is preferably a sulfur atom.

[0157] In the compound M2 of this embodiment, X in the groups represented by the general formula (123), the general formula (124), and the general formula (125) １１ is preferably a sulfur atom.

[0158] At least one D in the compound M2 of this embodiment １１ is preferably a group represented by the general formula (132).

[0159] In the compound M2 of this embodiment, X in the group represented by general formula (132) １１ In the compound M2 of this embodiment, X in the group represented by general formula (132) is preferably a sulfur atom. １１ is a sulfur atom, and X １２ is more preferably a sulfur atom or an oxygen atom.

[0160] D in compound M2 of this embodiment １２ is preferably a group represented by the general formula (11) or the general formula (12).

[0161] D in compound M2 of this embodiment １２ is preferably a group represented by the general formula (11).

[0162] D in compound M2 of this embodiment １２ is preferably a group represented by the general formula (12).

[0163] In the compound M2 of the present embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E), and (12F):

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170] (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), R １１ ~R １８ are each independently R in the general formula (12). １１ ~R １８ is synonymous with R １９ and R ２０ are each independently R in the general formula (14). １９ and X １ represents X in the general formula (15). １ In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), * indicates the bonding position to the benzene ring in the general formula (1).

[0171] In this embodiment, the compound M2 represented by the general formula (1) is preferably represented by the following general formula (110), general formula (120), or general formula (130).

[0172]

[0173] (In the general formula (110), the general formula (120) and the general formula (130), D １１ , D １２ , R, k, m and n are each the D in the general formula (1). １１ , D １２ , R, k, m, and n are synonymous with each other.)

[0174] In the compound M2 of this embodiment, n in the general formula (1) is preferably 2 or 3.

[0175] In the compound M2 of this embodiment, it is also preferable that n in the general formula (1) is 2.

[0176] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (126) or (127).

[0177]

[0178] (In the general formula (126) and the general formula (127), D １１ represents D in the general formula (1). １１ is synonymous with D １２ represents D in the general formula (1). １２ is synonymous with R １０１ ~R １０４ are each independently defined as R in the general formula (1), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0179] In the compound M2 of this embodiment, k is 2, and two D １１ Of these, one D １１ is a group represented by the general formula (12), and the other D １１ is also preferably a group represented by the general formula (13).

[0180] In the compound M2 of this embodiment, k is 2, and two D １１ is a group represented by the general formula (13), and D １１ It is also preferable that the two groups represented by the general formula (13) as are different from each other.

[0181] In the compound M2 of this embodiment, k and m are 1, and D １１ and D １２ It is also preferred that one of the above is a group represented by the general formula (12) and the other is a group represented by the general formula (13).

[0182] In the compound M2 of this embodiment, k and m are 1, and D １１ and D １２ It is also preferred that one of the above is a group represented by the general formula (11) and the other is a group represented by the general formula (13).

[0183] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (126A), general formula (127A), or general formula (127B).

[0184]

[0185] (In the general formula (126A), the general formula (127A) and the general formula (127B), D １１ represents D in the general formula (1). １１ is synonymous with D １２ represents D in the general formula (1). １２ is synonymous with R １０１ ~R １０４ are each independently defined as R in the general formula (1).

[0186] In the general formula (126A), the general formula (127A) and the general formula (127B), D １１ and D １２ are preferably different groups.

[0187] In the compound M2 of this embodiment, R １０１ and R １０３ In the compound M2 of this embodiment, R １０２ and R １０４ are the same or different from each other.

[0188] In the compound M2 of this embodiment, it is also preferable that n in the general formula (1) is 3.

[0189] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (111), general formula (112), or general formula (113).

[0190]

[0191] (In the general formula (111), general formula (112) and general formula (113), D １１ represents D in the general formula (1). １１ is synonymous with R １０１ ~R １０４ are each independently defined as R in the general formula (1).

[0192] In the compound M2 of this embodiment, any pair of two or more adjacent Rs is not bonded to each other. １０１ ~R １０４Any pair of two or more adjacent pairs of

[0193] In the compound M2 of this embodiment, it is preferable that R in the general formula (1) are each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

[0194] In the compound M2 of this embodiment, it is preferable that each R in the general formula (1) is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted heterocyclic group having 6 ring atoms.

[0195] In the compound M2 of this embodiment, R １０１ ~R １０４ are preferably each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms. １０１ ~R １０４ are preferably each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted heterocyclic group having 6 ring atoms.

[0196] In this embodiment, the compound M2 represented by the general formula (1) is also preferably a compound represented by the following general formula (150): The compound represented by the following general formula (150) also has at least one deuterium atom in the molecule.

[0197]

[0198] (In the general formula (150), R １０２ and R １０４ 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 ９０３a 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 R １０２ and R １０４ At least one of R is a substituent, and R as a substituent １０２ and R １０４ is bonded to the benzene ring in the general formula (150) via a carbon-carbon bond, and R １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８ 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 ９０７a 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, provided that R １ ~R ８ At least one of R is a substituent other than a hydrogen atom, and １ ~R ８ At least one of is a deuterium atom.

[0199] In the compound M2 of this embodiment, "R １ ~R ８ At least one of R is a substituent other than a hydrogen atom, and １ ~R ８ At least one of R is a deuterium atom. ２ is a substituent that is not a hydrogen atom, and R １ , R ３ ~R ８ At least one of the atoms is a deuterium atom.

[0200] In the compound M2 of this embodiment, R １ ~R ８ at least one of R is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and １ ~R ８ It is also preferable that at least one of the groups is a deuterium atom.

[0201] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (126C) or (127C).

[0202]

[0203] (In the general formula (126C) and the general formula (127C), D １１ represents D in the general formula (1). １１ is synonymous with D １２ represents D in the general formula (1). １２ is synonymous with R １３１ ~R １４０ and R １４１ ~R １５０ are each independently defined as R in the general formula (1), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0204] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (126D) or (127D).

[0205]

[0206] (In the general formulae (126D) and (127D), D １１ is D in the general formula (1). １１ is synonymous with D １２ is D in the general formula (1). １２ is synonymous with R １３１ ~R １４０ and R １４１ ~R １５０ are each independently defined as R in the general formula (1).

[0207] In the compound M2 of this embodiment, D １１ is a group represented by the general formula (132), and D １２ is also preferably a group represented by any one of the general formulae (12A) to (12F).

[0208] In the compound M2 of this embodiment, D １１ is a group represented by the general formula (132), and D １２ is also preferably a group represented by the general formula (11).

[0209] In the compound M2 of this embodiment, R １３１ ~R１４０ and R １４１ ~R １５０ are 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 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.

[0210] In the compound M2 of this embodiment, R １ ~R ８ In the compound M2 of this embodiment, it is preferable that any pair of adjacent two or more of R １１ ~R １８ In the compound M2 of this embodiment, it is preferable that any pair of adjacent two or more of R １１ ~R ２０ In the compound M2 of this embodiment, it is preferable that any pair of adjacent two or more of R １１１ ~R １１８ It is preferable that any pair of two or more adjacent groups of the above do not bond to each other.

[0211] In this embodiment, R in compound M2 １ ~R ８ , R １１ ~R １８ , R １１１ ~R １１８ and R １９ are preferably 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, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0212] In this embodiment, R in compound M2 １ ~R ８ , R １１ ~R １８ , R １１１ ~R１１８ and R １９ are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0213] In the compound M2 of this embodiment, R １ ~R ８ It is preferable that at least one of the groups is 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, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0214] In the compound M2 of this embodiment, R ２ , R ３ , R ６ and R ７ It is preferable that at least one of the groups is 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, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0215] In the compound M2 of this embodiment, R １０２ and R １０４ are preferably each independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

[0216] In the compound M2 of this embodiment, R １０２ and R １０４ At least one of the groups preferably has a deuterium atom.

[0217] In this embodiment, the compound M2 represented by the general formula (1) is also preferably represented by the following general formula (151).

[0218]

[0219] (In the general formula (151), R １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R１９８ are R in the general formula (150), respectively. １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８ is synonymous with R １３１ ~R １４０ 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.

[0220] In the compound M2 of this embodiment, R １３１ ~R １４０ At least one of the groups is preferably a deuterium atom.

[0221] In the compound M2 of this embodiment, R １１１ ~R １１８ , and R１９５ ~R １９８ At least one of the groups preferably has a deuterium atom.

[0222] In the compound M2 of this embodiment, R １１１ ~R １１８ , and R １９５ ~R １９８ At least one of the groups is preferably a deuterium atom.

[0223] In the compound M2 of this embodiment, R １ ~R ８ It is also preferable that at least one of the above is a group represented by the following general formula (152).

[0224] In the compound M2 of this embodiment, R １１１ ~R １１８ , and R １９５ ~R １９８ It is also preferable that at least one of the above is a group represented by the following general formula (152).

[0225]

[0226] (In the general formula (152), R １８１ ~R １８５ 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)(R９３１ ) (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, where * indicates the bonding position.

[0227] In the compound M2 of this embodiment, R １１１ , R １１８ , R １９６ and R １９７ It is also preferable that at least one of the above is a group represented by the general formula (152).

[0228] In the compound M2 of this embodiment, R １１１ and R １１８ is also preferably a group represented by the general formula (152).

[0229] In the compound M2 of this embodiment, R ２ , R ３ , R ６ and R ７ It is also preferable that at least one of the above is a group represented by the general formula (152).

[0230] In the compound M2 of this embodiment, R ２ and R ３ is also preferably a group represented by the general formula (152).

[0231] In the compound M2 of this embodiment, R ３ and R ６ is also preferably a group represented by the general formula (152).

[0232] When the compound M2 of this embodiment has a group represented by the general formula (152), R １８１ ~R １８５ In the compound M2 of this embodiment, when the group represented by the general formula (152) contains a deuterium atom, at least one of R １８１ ~R １８５Preferably, two or more of R are deuterium atoms, １８１ ~R １８５ More preferably, is a deuterium atom.

[0233] In the compound M2 of this embodiment, R １９１ ~R １９８ are 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, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0234] In the compound according to this 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 ９３８a 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.

[0235] In the compound according to this embodiment, the substituent in the term "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.

[0236] In the compound according to this embodiment, the substituent in the term "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.

[0237] In the compounds according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0238] In this specification, —O—(R ９０４ ) is a group represented by R ９０４ is a hydrogen atom, it is a hydroxy group. ９０５ ) is a group represented by R ９０５ is a hydrogen atom, it is a thiol group. ９３１ ) (R ９３２ ) is a group represented by R ９３１ and R ９３２ When —Ge(R ９３３ ) (R ９３４ ) (R ９３５ ) is a group represented by R ９３３ , R ９３４and R ９３５ is a substituent, it is a substituted germanium group. ９３６ ) (R ９３７ ) is a group represented by R ９３６ and R ９３７ is a substituent, it is a substituted boryl group.

[0239] (Delayed Fluorescence) The compound M2 of this embodiment is preferably a delayed fluorescent compound. Delayed fluorescence is explained on pages 261 to 268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chinaya, 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, the reverse energy transfer from the excited triplet state to the excited singlet state, which usually has a low transition probability, occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is exhibited. Furthermore, Figure 10.38 in this document explains the mechanism by which delayed fluorescence occurs. The compound according to this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0240] In general, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0241] 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 materials 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.

[0242] 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.

[0243] 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.

[0244] 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.

[0245] 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.

[0246] 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.

[0247]

[0248] 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.

[0249] FIG. 2 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0250]

[0251] 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.

[0252] 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.

[0253] 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.

[0254] Furthermore, to measure the delayed fluorescence of the compound according to this embodiment, a sample prepared by the following method is used. For example, the 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 capped 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.

[0255] 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 compound according to this embodiment in this specification are measured in the same manner as the amount and ratio of prompt luminescence and delay luminescence of the compound according to this embodiment.

[0256] (ΔST) In this embodiment, the lowest excited singlet energy S １ and the energy gap T at 77[K] ７７Ｋ The difference between １ -T ７７Ｋ ) is defined as ΔST.

[0257] The lowest excited singlet energy S of the compound M2 according to this embodiment １ (M2) and the energy gap T at 77 [K] of the compound M2 according to this embodiment ７７Ｋ The difference ΔST(M2) between ΔST(M2) and ΔST(M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies the relationship of the following formula (10), (11), (12), or (13): ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.3eV...(Math. 10) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.2eV...(Math. 11) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.1eV...(Math. 12) ΔST(M2)=S １ (M2)-T ７７Ｋ (M2)<0.01eV...(Math. 13)

[0258] (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 ７７Ｋ The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this 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 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

[0259] 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.

[0260] (Lowest excited singlet energy S １ ) The lowest excited singlet energy S １ The 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 trailing edge on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of this tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S １ [eV]=1239.85 / λedge. The absorption spectrum measuring device may be, for example, a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0261] 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.

[0262] (Method for Producing Compound According to First Embodiment) The compound according to the first 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.

[0263] (Specific Examples of Compounds According to the First Embodiment) Specific examples of compounds according to the first embodiment include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is represented as D in a chemical formula, and a protium atom is represented as H or is not represented at all.

[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]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374] [Second Embodiment] <Material for Organic Electroluminescence Device> The material for organic electroluminescence devices according to this 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 this embodiment, the compound according to the first embodiment is preferably a host material. In this case, the material for organic electroluminescence devices may contain the compound according to the first embodiment as a host material and another compound such as a dopant material. Furthermore, in the material for organic electroluminescence devices according to this embodiment, the compound according to the first embodiment is preferably a delayed fluorescent material.

[0375] Third Embodiment Organic Electroluminescence Element An organic EL element according to this embodiment will be described. The organic EL element according to this embodiment includes an organic layer between an anode and a cathode. This organic layer includes at least one layer made of an organic compound. Alternatively, this organic layer is formed by stacking multiple layers made of organic compounds. The organic layer may further include an inorganic compound.

[0376] In the organic EL element according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL element according to this embodiment has an anode, a cathode, and an organic layer, and the organic layer contains the compound according to the first embodiment as compound M2.

[0377] In the organic EL device of this embodiment, the organic layer preferably has at least one light-emitting layer, and the light-emitting layer preferably contains the compound according to the first embodiment as compound M2.

[0378] The organic layer may be composed of, for example, a single light-emitting layer, or may include a layer that can be used in an organic EL device. The layer that can be used in an organic EL device is not particularly limited, and examples thereof include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0379] In one embodiment, the light-emitting layer may contain a metal complex. Also, in one embodiment, it is preferable that the light-emitting layer does not contain a metal complex. Also, in one embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent material (dopant material). Also, in one embodiment, it is preferable that the light-emitting layer does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of heavy metal complexes include an iridium complex, an osmium complex, and a platinum complex.

[0380] Fig. 3 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 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.

[0381] (Light-emitting layer) In the organic EL device of this embodiment, the light-emitting layer preferably contains compound M1 and compound M2. Compound M2 in the light-emitting layer is preferably the compound according to the first embodiment. In this embodiment, compound M2 is preferably a host material (sometimes referred to as a matrix material), and compound M1 is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material). In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0382] (Compound M2) Compound M2 is a compound according to the first embodiment. Compound M2 of this embodiment is preferably a thermally activated delayed fluorescent compound.

[0383] (Compound M1) Compound M1 is preferably a fluorescent compound. Compound M1 is preferably a compound that does not exhibit delayed fluorescence. Compound M1 of this embodiment is not a phosphorescent metal complex. Compound M1 is preferably not a heavy metal complex. Furthermore, compound M1 is preferably not a metal complex.

[0384] The compound M1 of this embodiment may be a fluorescent material. Specific examples of the fluorescent material 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.

[0385] The compound M1 is preferably a compound that exhibits luminescence with a maximum peak wavelength of 400 nm or more and 700 nm or less. －６ 10 moles / liter or more －５ The peak wavelength of the fluorescence spectrum at which the emission intensity is maximum is measured for a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / L or less. The measurement device used is a spectrofluorometer (F-7000, manufactured by Hitachi High-Tech Science Corporation).

[0386] Compound M1 preferably exhibits red or green emission. In this specification, red emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 600 nm to 660 nm. When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm to 660 nm, more preferably 600 nm to 640 nm, and even more preferably 610 nm to 630 nm. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 500 nm to 560 nm. When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum in the range of 430 nm to 480 nm. When compound M1 is a blue fluorescent compound, the maximum peak wavelength of compound M1 is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0387] The maximum peak wavelength of light emitted from the organic EL element is measured as follows: ２ A 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).

[0388] (Compound Represented by General Formula (D1)) In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D1).

[0389]

[0390] (In the general formula (D1), ring A, ring B, ring D, ring E, and ring F each independently represent a ring structure selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocycle having 5 to 30 ring atoms; one of ring B and ring D is present, or both ring B and ring D are present; when both ring B and ring D are present, ring B and ring D share a bond connecting Zc and Zh; one of ring E and ring F is present, or both ring E and ring F are present; when both ring E and ring F are present, ring E and ring F share a bond connecting Zf and Zi; Za is a nitrogen atom or a carbon atom; Zb, when ring B is present, is a nitrogen atom or a carbon atom; when ring B is not present, is an oxygen atom, a sulfur atom, NRb, C(Rb １ ) (Rb ２ ) or Si(Rb ３ ) (Rb ４ ), Zc is a nitrogen atom or a carbon atom, Zd is, when ring D is present, a nitrogen atom or a carbon atom, when ring D is not present, an oxygen atom, a sulfur atom or NRd, Ze is, when ring E is present, a nitrogen atom or a carbon atom, when ring E is not present, an oxygen atom, a sulfur atom or NRe, Zf is a nitrogen atom or a carbon atom, Zg is, when ring F is present, a nitrogen atom or a carbon atom, when ring F is not present, an oxygen atom, a sulfur atom, NRg, C(Rg １ ) (Rg ２ ) or Si(Rg ３ ) (Rg ４ ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh are each independently a hydrogen atom or a substituent, and Rb, Rb as a substituent１ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh each independently represent 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, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R ９１１ ) (R ９１２ ) (R ９１３ a group represented by —O—(R ９１４ a group represented by —S—(R ９１５ ), or a group represented by —N(R ９１６ ) (R ９１７ ) wherein the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0391] (In the compound M1, R ９１１ ~R ９１７ 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 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, R９１６ 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.)

[0392] The bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds, and these single bonds are covalent bonds and not coordinate bonds.

[0393] In this specification, examples of heterocycles include ring structures (heterocycles) obtained by removing a bond from the "heterocyclic group" exemplified in the above-mentioned "substituents described in this specification." These heterocycles may have a substituent or may be unsubstituted. In this specification, examples of aryl rings include ring structures (aryl rings) obtained by removing a bond from the "aryl group" exemplified in the above-mentioned "substituents described in this specification." These aryl rings may have a substituent or may be unsubstituted.

[0394] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D11): The compound represented by the general formula (D1) is also preferably a compound represented by the following general formula (D11):

[0395]

[0396] (In the general formula (D11), ring A, ring D, and ring E each independently represent a ring structure selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms; Za represents a nitrogen atom or a carbon atom; Zb represents an oxygen atom, a sulfur atom, NRb, C(Rb １ ) (Rb ２ ) or Si(Rb ３ ) (Rb ４ ), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg １ ) (Rg２ ) or Si(Rg ３ ) (Rg ４ ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh each independently represent Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ and Rh.)

[0397] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D16).

[0398]

[0399] (In the general formula (D16), R １６１ ~R １７７ one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring １６１ ~R １７７ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R ９６１ ) (R ９６２ ) (R９６３ a group represented by —O—(R ９６４ a group represented by —S—(R ９６５ a group represented by —N(R ９６６ ) (R ９６７ a group represented by —C(═O)R ９６８ a group represented by -COOR ９６９ 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, ９６１ ~R ９６９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R ９６１ If there are multiple R ９６１ are the same or different from each other, R ９６２ If there are multiple R ９６２ are the same or different from each other, R ９６３ If there are multiple R ９６３ are the same or different from each other, R ９６４ If there are multiple R ９６４ are the same or different from each other, R ９６５ If there are multiple R ９６５ are the same or different from each other, R ９６６ If there are multiple R ９６６ are the same or different from each other, R ９６７ If there are multiple R ９６７ are the same or different from each other, R ９６８ If there are multiple R ９６８ are the same or different from each other, R ９６９ If there are multiple R ９６９ are the same or different from each other.)

[0400] (Compound Represented by General Formula (D10)) In the organic EL element according to this embodiment, the compound M1 is preferably a compound represented by the following general formula (D10): The compound represented by the general formula (D1) is preferably a compound represented by the following general formula (D10):

[0401]

[0402] (In the general formula (D10), X １ is CR １ or a nitrogen atom, X ２ is CR ２ or a nitrogen atom, X ３ is CR ３ or a nitrogen atom, X ４ is CR ４ or a nitrogen atom, X ５ is CR ５ or a nitrogen atom, X ６ is CR ６ or a nitrogen atom, X ７ is CR ７ or a nitrogen atom, or X ８ is a carbon atom bonded to X by a single bond; ８ is CR ８ or a nitrogen atom, or X ７ is a carbon atom bonded to X by a single bond; ９ is CR ９ or a nitrogen atom, X １０ is CR １０ or a nitrogen atom, X １１ is CR １１ or a nitrogen atom, X １２ is CR １２ or a nitrogen atom, Q is CR Ｑ or a nitrogen atom, and Y is NR Ｙ１ , oxygen atom, sulfur atom, C(R Ｙ２ ) (R Ｙ３ ) or Si(R Ｙ４ ) (R Ｙ５ ) and R １ ~R ６ and R ９ ~R１１ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４ and R Ｙ１ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３、 R ４ and R Ｙ１ At least one hydrogen atom in a single ring or a condensed ring formed by bonding together one or more pairs of adjacent groups selected from the group consisting of -O-(R ９２０ ), and a group represented by —N(R ９２１ ) (R ９２２ at least one hydrogen atom in the substituent is substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted; R does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring; １ ~R １１ , and R １２ ~R １３ , and R Ｑ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ９１１ ) (R ９１２ ) (R ９１３ a group represented by —O—(R ９１４ a group represented by —S—(R ９１５a group represented by —N(R ９１６ ) (R ９１７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９１８ a group represented by -COOR ９１９ 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, wherein R does not form the substituted or unsubstituted monocycle and does not form the substituted or unsubstituted fused ring. Ｙ１ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a 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 R Ｙ２ and R Ｙ３ 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 do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. Ｙ２ and R Ｙ３ , and R Ｙ４ and R Ｙ５ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 50 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 ９１１ ~R ９２２ 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, R９１１ 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, R ９１９ If there are multiple R ９１９ are the same or different from each other, R ９２０ If there are multiple R ９２０ are the same or different from each other, R ９２１ If there are multiple R ９２１ are the same or different from each other, R ９２２ If there are multiple R ９２２ are the same or different from each other.)

[0403] In the compound represented by the general formula (D10), X ７ is X ８ is a carbon atom bonded to X by a single bond, ８ is X ７ and is a carbon atom bonded to by a single bond, for example, general formula (D10) is represented by the following general formula (D10A).

[0404]

[0405] (In the general formula (D10A), X １ ~X６ , X ９ ~X １２ , Y, Q, and R １３ are each independently as defined in general formula (D10).

[0406] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12).

[0407]

[0408] (In the general formula (D12), R １ ~R １３ , R Ｙ１ , R Ｑ are each independently as defined in general formula (D10).

[0409] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12A).

[0410]

[0411] (In the general formula (D12A), R １ ~R ６ , R ９ ~R １３ , R Ｙ１ , R Ｑ are each independently as defined in general formula (D10).

[0412] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13).

[0413]

[0414] (In the general formula (D13), R １ ~R ３ , R ５ ~R １３ and R Ｑ are each independently as defined in formula (D10), ｘ１ ~R ｘ４one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring Ｘ１ ~R ｘ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -Si(R ９３１ ) (R ９３２ ) (R ９３３ a group represented by —O—(R ９３４ a group represented by —S—(R ９３５ a group represented by —N(R ９３６ ) (R ９３７ a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, —C(═O)R ９３８ a group represented by -COOR ９３９ 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, ９３１ ~R ９３９ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, 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, R９３４ 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.)

[0415] In the general formula (D13), for example, R ５ and R ６ 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.

[0416] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13A).

[0417]

[0418] (In the general formula (D13A), R １ ~R ３ , R ５ ~R ６ , R ９ ~R １３ and R Ｑ are each independently as defined in general formula (D10), and R ｘ１ ~R ｘ４ are each independently as defined in general formula (D13).

[0419] In the compound represented by the general formula (D10), R １ ~R １３ and R Ｑare also preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0420] In the compound represented by the general formula (D10), R １ ~R １３ and R Ｑ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0421] In the compound represented by the general formula (D10), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are also preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0422] In the compound represented by the general formula (D10), R １ ~R ３ , R ５ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0423] In the compound represented by the general formula (D10), R １ ~R １３ , R Ｑ and R ｘ１~R ｘ４ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0424] In the compound represented by the general formula (D10), R １ ~R １３ , R Ｑ and R ｘ１ ~R ｘ４ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0425] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D14).

[0426]

[0427] (In the general formula (D14), R ２ , R ６、 R １３、 R Ｑ and R ｘ２ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0428] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D15).

[0429]

[0430] (In the general formula (D15), R ２ , R ６、 R １３、 R Ｑ and R ｘ２are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0431] In the compound represented by the general formula (D10), R １３ and R Ｑ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0432] In the compound represented by the general formula (D10), R ６ and R ｘ２ are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0433] (Compound Represented by General Formula (20)) In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (20).

[0434]

[0435] (In the general formula (20), X is a nitrogen atom or a carbon atom bonded to Y, Y is a hydrogen atom or a substituent, and R ２１ ~R ２６ are each independently a hydrogen atom or a substituent, or R ２１ and R ２２ Group R ２２ and R ２３ Group R ２４ and R ２５ and R ２５ and R ２６ any one or more pairs of Y and R are bonded to each other to form a ring; ２１ ~R ２６are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, a carboxy group, a substituted or unsubstituted ester group, is selected from the group consisting of a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group; ２１ and Z ２２ are each independently a substituent, or Z ２１ and Z ２２ are bonded to each other to form a ring, and Z as a substituent ２１ and Z ２２ are each independently selected from the group consisting of a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

[0436] (Method for Producing Compound M1) Compound M1 according to this embodiment can be produced according to a known synthesis method or by imitating the synthesis method and using known alternative reactions and raw materials suited to the target product.

[0437] (Specific Examples of Compound M1) Specific examples of compound M1 of this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds. The coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be represented in various ways, such as by a solid line, a dashed line, an arrow, or by omission. In this specification, it is represented by a solid line, a dashed line, or is omitted.

[0438]

[0439]

[0440]

[0441] <Relationship between Compound M1 and Compound M2 in the Emitting Layer> In the organic EL device of this embodiment, the lowest excited singlet energy S １ (M2) and the lowest excited singlet energy S of compound M1 １ (M1) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1): １ (M2) > S １ (M1) ... (Equation 1)

[0442] In one aspect of this embodiment, the organic EL device has an anode, a cathode, and an emitting layer between the anode and the cathode, the emitting layer containing a delayed fluorescent compound M2 represented by the general formula (1) and a fluorescent compound M1, the compound M2 having one or more deuterium atoms in the molecule, and the lowest excited singlet energy S of the compound M1 １ (M1) and the lowest excited singlet energy S of compound M2 １ (M2) satisfy the relationship of the following mathematical formula (Math. 1).

[0443] The energy gap T of compound M2 at 77 K ７７Ｋ (M2) is the energy gap T of compound M1 at 77 [K] ７７Ｋ It is preferable that the relationship between the thickness of the slab and the surface of the substrate is larger than (M1). That is, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 5) is satisfied. ７７Ｋ (M2) > T ７７Ｋ (M1) ... (Equation 5)

[0444] When the organic EL device of this embodiment is caused to emit light, it is preferable that the compound M1 mainly emits light in the light-emitting layer.

[0445] <TADF mechanism> Figure 4 is a diagram showing an example of the relationship between the energy levels of compound M2 and compound M1 in the light-emitting layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1. T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2. T1(M2) represents the lowest excited triplet state of compound M2. The dashed arrow from S1(M2) to S1(M1) in Figure 4 represents Förster energy transfer from the lowest excited singlet state of compound M2 to compound M1. As shown in Figure 4, when a compound with a small ΔST(M2) is used as compound M2, 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 energy transfer occurs from the lowest excited singlet state S1 (M2) of compound M2 to compound M1, generating the lowest excited singlet state S1 (M1). As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of compound M1 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.

[0446] The organic EL element of this embodiment preferably emits red or green light. When the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. When the organic EL element of this embodiment emits red light, the main peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less. When the organic EL element of this embodiment emits blue light, the main peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0447] The main 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 main peak wavelength (unit: nm).

[0448] (Thickness of the Light-Emitting Layer) The thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. 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.

[0449] (Compound Content in Light-Emitting Layer) The contents of compound M2 and compound M1 contained in the light-emitting layer are preferably within the following ranges, for example. The content of compound M2 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 99% by mass or more and 99.9% by mass or less. The content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than compound M2 and compound M1. The light-emitting layer may contain only one type of compound M2, or may contain two or more types. The light-emitting layer may contain only one type of compound M1, or may contain two or more types.

[0450] (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 plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. An inorganic vapor deposition film can also be used.

[0451] (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, and graphene. 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). These materials are usually deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass to 10% by 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% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide relative to indium oxide. Other methods for preparation include vacuum deposition, coating, inkjet printing, and spin coating. 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 (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, including elements belonging to Group 1 or Group 2 of the periodic table) can be used. It is also possible to use materials with small work functions, such as 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.When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form the anode, a vacuum deposition method or a sputtering method can be used. Furthermore, when a silver paste or the like is used, a coating method or an inkjet method can be used.

[0452] (Cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials 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), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys containing these. When forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering can be used. When using silver paste or the like, coating or inkjet printing can be used. By providing an electron injection layer, a cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide. These conductive materials can be formed into films by sputtering, ink jetting, spin coating, or the like.

[0453] (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.

[0454] (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.

[0455] (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.

[0456] (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.

[0457] (Layer Formation Method) The method for forming each layer of the organic EL element of this embodiment 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.

[0458] (Film Thickness) The film thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. However, in general, if the film thickness is too thin, defects such as pinholes are likely to occur, whereas if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a range of several nm to 1 μm is usually preferred.

[0459] The organic EL element according to the third embodiment contains, in the light-emitting layer, the compound according to the first embodiment as compound M2 and compound M1 having a minimum excited singlet energy smaller than that of compound M2. According to the third embodiment, a high-performance organic EL element that can achieve at least one of high efficiency and long life can be provided.

[0460] [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.

[0461] The organic EL element according to the fourth embodiment differs from the organic EL element according to the third embodiment in that the emitting layer further contains a compound M3. The other features are the same as those of the third embodiment. That is, in the fourth embodiment, the emitting layer contains a compound M3, a compound M2, and a compound M1. In this embodiment, the compound M2 is preferably a host material, and the compound M1 is preferably a dopant material.

[0462] (Compound M3) The compound M3 of the present embodiment may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0463] The compound M3 is not particularly limited, but is preferably a compound other than an amine compound. For example, the compound M3 may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0464] In this embodiment, the compound M3 is preferably a compound represented by the following general formula (3X) or (3Y).

[0465] (Compound Represented by General Formula (3X)) Compound M3 is also preferably a compound represented by the following general formula (3X).

[0466]

[0467] (In the general formula (3X), A ３ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, L ３ is a single 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 divalent group formed by bonding together two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a divalent group formed by bonding together three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, R ３１ ~R ３８ one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３１ ~R ３８ 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 ９０８a 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, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the following general formula (3A):

[0468]

[0469] (In the general formula (3A), R Ｂ represents 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 ９３７a 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, Ｂ When there are multiple R Ｂ are the same or different from each other, and L ３１ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the arylene group, a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the heterocyclic group, or a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms and substituted or unsubstituted divalent heterocyclic groups having 5 to 50 ring atoms, or a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from the divalent group, ３２ 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, ３ is 1, 2, 3, 4 or 5, and L ３１ When is a single bond, n ３ is 1, and L ３２ is bonded to a carbon atom of the six-membered ring in the general formula (3X), ３２ When there are multiple L ３２ are the same or different, and * is the bonding site to the carbon atom of the six-membered ring in the general formula (3X).

[0470] (In compound M3, 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 ９３６and 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, 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, R９３６ 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.)

[0471] The compound M3 is also preferably a compound represented by any one of the following general formulas (31) to (36).

[0472]

[0473]

[0474]

[0475] (In the general formulae (31) to (36), A ３ and L ３ are A in the general formula (3X), respectively. ３ and L ３ is synonymous with R ３４１ ~R ３５０ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３１ represents a sulfur atom, an oxygen atom, and NR ３５２ or CR ３５３ R ３５４ and R ３５３ and R ３５４ 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 do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３４１ ~R ３５０ And, R ３５２ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５３ and R ３５４ and R each independently represent a group that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３１~R ３８ is synonymous with

[0476] In compound M3, R ３５２ is preferably a substituted or unsubstituted alkyl group having 1 to 50 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.

[0477] In compound M3, R ３５３ and R ３５４ 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 to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ３５３ and R ３５４ are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 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.

[0478] In compound M3, X ３１ is preferably a sulfur atom or an oxygen atom.

[0479] In compound M3, A ３ is preferably a group represented by any one of the following general formulae (A31) to (A37).

[0480]

[0481]

[0482] (In the general formulae (A31) to (A37), a plurality of R ３００ one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３００ , and R ３３３each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ * in the general formulae (A31) to (A37) respectively represents L of the compound M3. ３ indicates the bonding position with

[0483] In compound M3, A ３ is also preferably a group represented by the general formula (A34), (A35) or (A37).

[0484] The compound M3 is also preferably a compound represented by any one of the following general formulas (311) to (316).

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491] (In the general formulae (311) to (316), L ３ represents L in the general formula (3X). ３ and plural R ３００ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３４１ ~R ３５０ one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３００and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３４１ ~R ３５０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0492] The compound M3 is also preferably a compound represented by the following general formula (321).

[0493]

[0494] (In the general formula (321), L ３ represents L in the general formula (3X). ３ is synonymous with R ３１ ~R ３８ , and R ３０１ ~R ３０８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0495] In compound M3, L ３ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0496] In compound M3, L ３ is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0497] In compound M3, L ３ is preferably a group represented by the following general formula (317).

[0498]

[0499] (In the general formula (317), R ３１０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R３８ and * each independently indicates a bonding position.)

[0500] In compound M3, L ３ It is also preferable that L contains a divalent group represented by the following general formula (318) or general formula (319). ３ is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0501] The compound M3 is also preferably a compound represented by the following general formula (322) or (323).

[0502]

[0503]

[0504] (In the general formula (322) and the general formula (323), L ３１ represents a divalent group formed by bonding two groups selected from the group consisting of 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, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, with the proviso that L ３１ R contains a divalent group represented by the following general formula (318) or general formula (319): ３１ ~R ３８ , R ３００ , and R ３２１ ~R ３２８ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0505]

[0506] (In the general formula (319), a plurality of R ３０４ a pair of adjacent two of these is bonded to each other to form a ring represented by the general formula (320), and in the general formula (320), 1* and 2* each independently represent R３０４ represents the bonding position with the ring to which R is bonded, ３０２ , R in the general formula (319) ３０３ R which does not form a ring represented by the general formula (320) ３０４ and R in the general formula (320) ３０５ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ In the general formulae (318) to (320), * indicates the bonding position.

[0507] In compound M3, L ３ or L ３１ The group represented by the general formula (319) as is, for example, a group represented by the following general formula (319A).

[0508]

[0509] (In the general formula (319A), R ３０３ , R ３０４ and R ３０５ each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ and * in the general formula (319A) indicates a bonding position.)

[0510] Compound M3 is a compound represented by the general formula (322), and L ３１ is also preferably a group represented by the general formula (318).

[0511] The compound M3 is also preferably a compound represented by the following general formula (324).

[0512]

[0513] (In the general formula (324), R ３１ ~R ３８ , R ３００ , and R ３０２each independently represents R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring; ３１ ~R ３８ is synonymous with

[0514] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the general formula (3A), and R in the general formula (3A) is Ｂ is preferably a substituted or unsubstituted alkyl group having 1 to 50 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.

[0515] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the general formula (3A), and R in the general formula (3A) Ｂ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0516] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring ３１ ~R ３８ are each independently a hydrogen atom, a substituted or unsubstituted phenyl group, or a group represented by the general formula (3A), and R in the general formula (3A) Ｂ is preferably a substituted or unsubstituted phenyl group.

[0517] It is also preferable that the compound M3 is a compound that does not have a pyridine ring, a pyrimidine ring, or a triazine ring.

[0518] (Compound Represented by General Formula (3Y)) Compound M3 is also preferably a compound represented by the following general formula (3Y).

[0519]

[0520] (In the general formula (3Y), Y ３１ ~Y ３６ are each independently CR ３ or a nitrogen atom, provided that Y ３１ ~Y ３６ two or more of R are nitrogen atoms; ３ If there are multiple R ３ one or more pairs of adjacent two or more 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, do not form the substituted or unsubstituted monocycle, and do not form the substituted or unsubstituted fused ring ３ 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 ) (R９３５ ), a group represented by —B(R ９３６ ) (R ９３７ ) 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, or a group represented by the following general formula (3B):

[0521]

[0522] (In the general formula (3B), R Ｂ , L ３１ , L ３２ and n ３ are each independently R in the general formula (3A). Ｂ , L ３１ , L ３２ and n ３ is synonymous with R Ｂ When there are multiple R Ｂ are the same or different from each other, and L ３１ When is a single bond, n ３ is 1, and L ３２ is bonded to a carbon atom of the six-membered ring in the general formula (3Y), and L ３２ When there are multiple L ３２ are the same or different, and * is the bonding site to the carbon atom of the six-membered ring in general formula (3Y).

[0523] In the compound represented by the general formula (3Y), R ９０１ ~R ９０９ and R ９３１ ~R ９３７ are R in the general formula (3X), respectively. ９０１ ~R ９０９ and R ９３１ ~R ９３７ is synonymous with.

[0524] Compound M3 preferably does not contain a pyridine ring in the molecule.

[0525] The compound M3 is also preferably a compound represented by the following general formula (31a) or general formula (32a).

[0526]

[0527] (In the general formula (32a), R ３５ ~R ３７ at least one pair of adjacent two or more of R in the general formula (31a) is 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 is not bonded to each other, ３１ ~R ３３ and R in the general formula (32a) ３４ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５ ~R ３７ are each independently R in the general formula (3Y). ３ is synonymous with

[0528] The compound M3 is also preferably a compound represented by the general formula (31a).

[0529] R in the general formula (3Y) ３ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by general formula (3B).

[0530] R in the general formula (3Y) ３ are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by general formula (3B).

[0531] The compound M3 represented by the general formula (3Y) preferably has, in the molecule, at least one group selected from the group consisting of groups represented by the following general formulae (B31) to (B44).

[0532]

[0533]

[0534] (In the general formulae (B31) to (B38), a plurality of R ３００ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, ３３１ and R ３３２ 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 do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３００ , R ３３１ and R ３３２ , and R ３３３ 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, 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 general formulas (B31) to (B38) respectively indicates the bonding position to other atoms in the molecule of compound M3.

[0535]

[0536]

[0537]

[0538] (In the general formulae (B39) to (B44), R ３４１ ~R ３５０ 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 bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other, with the proviso that R ３４１ ~R ３５１ At least one of X indicates a bonding position to another atom in the molecule of the compound M3, ３１ represents a sulfur atom, an oxygen atom, and NR ３５２ or CR ３５３ R ３５４ and R ３５３ and R ３５４ 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 are not at a bonding position with another atom in the molecule of the compound M3, and do not form the substituted or unsubstituted monocycle and do not form the substituted or unsubstituted fused ring. ３４１ ~R ３５１ And, R ３５２ and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. ３５３ and R ３５４ and 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 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 ９０７a 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, 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.

[0539] The compound M3 represented by the general formula (3Y) preferably has, in the molecule, at least one group selected from the group consisting of the groups represented by the general formulae (B38) to (B44).

[0540] In the general formula (3Y), Y ３１ ~Y ３６ At least one of the following is CR ３ and at least one R ３ is a group represented by the general formula (3B), and R Ｂ is preferably any one of the groups represented by the above general formulae (B31) to (B44).

[0541] In the general formula (3Y), Y ３１ ~Y ３６ At least one of the following is CR ３ and at least one R ３ is a group represented by the general formula (3B), and R Ｂ is preferably any one of the groups represented by the general formulae (B38) to (B44).

[0542] In the general formulas (3A) and (3B), L ３１ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, or a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms, or a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group, ３２are each preferably independently a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0543] In the general formulas (3A) and (3B), L ３１ represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and n ３ is 1, and L ３２ is preferably a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0544] In the general formulas (3A) and (3B), L ３１ represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, or a trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; ３ is 1, and L ３２ is preferably a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0545] In the compounds represented by the general formulas (3X) and (3Y), R ３５２ is preferably a substituted or unsubstituted alkyl group having 1 to 50 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.

[0546] In the compounds represented by the general formulas (3X) and (3Y), R ３５３ and R ３５４ 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 to form a substituted or unsubstituted monocycle and a substituted or unsubstituted fused ring ３５３ and R ３５４are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 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.

[0547] In the compounds represented by the general formulae (3X) and (3Y), the substituent in the case of "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.

[0548] In the compounds represented by the general formulae (3X) and (3Y), 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.

[0549] In the compounds represented by the general formulae (3X) and (3Y), 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.

[0550] In the compounds represented by the general formulae (3X) and (3Y), it is also preferable that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[0551] (Method for Producing Compound M3) Compound M3 according to this embodiment can be produced by a known method.

[0552] (Specific Examples of Compound M3) Specific examples of compound M3 of this embodiment include the following compounds: However, the present invention is not limited to these specific examples of compounds.

[0553]

[0554]

[0555]

[0556]

[0557]

[0558]

[0559]

[0560]

[0561]

[0562]

[0563]

[0564]

[0565]

[0566]

[0567]

[0568]

[0569] <Relationship between Compound M3, Compound M2, and Compound M1 in the Emitting Layer> In the organic EL device of this embodiment, the lowest excited singlet energy S １ (M2) and the lowest excited singlet energy S of compound M1 １ (M1) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1): １ (M2) > S １ (M1) ... (Equation 1)

[0570] In the organic EL device of this embodiment, the lowest excited singlet energy S １ (M2) and the lowest excited singlet energy S of compound M3 １ (M3) preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2): １ (M3) > S １ (M2) ...(Math. 2)

[0571] The lowest excited singlet energy S of compound M3 １ (M3) is the lowest excited singlet energy S of compound M1 １ It is preferable that it is larger than (M1). １ (M3) > S １ (M1) ...(Math 2A)

[0572] The lowest excited singlet energy S of compound M3 １ (M3) and the lowest excited singlet energy S of compound M2 １ (M2) and the lowest excited singlet energy S of compound M1 １ It is preferable that (M1) satisfies the relationship of the following mathematical formula (Mathematical Formula 2B): S １ (M3) > S１ (M2) > S １ (M1) ... (Mathematical formula 2B)

[0573] In the organic EL device of this embodiment, the energy gap T ７７Ｋ (M3) is the energy gap T of compound M2 at 77 [K] ７７Ｋ It is preferable that it is larger than (M2).

[0574] In the organic EL device of this embodiment, the energy gap T ７７Ｋ (M2) is the energy gap T of compound M1 at 77 [K] ７７Ｋ It is preferable that it is larger than (M1).

[0575] In the organic EL element of this embodiment, it is preferable that the compounds M3, M2, and M1 satisfy the relationship of the following mathematical formula (Mathematical Formula 5A): T ７７Ｋ (M3) > T ７７Ｋ (M2) > T ７７Ｋ (M1) ...(Number 5A)

[0576] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound M1 mainly emits light in the light-emitting layer. The organic EL device of this embodiment preferably emits red or green light.

[0577] (Compound Content in Light-Emitting Layer) The contents of compound M3, compound M2, and compound M1 contained in the light-emitting layer are preferably within the following ranges, for example. The content of compound M3 is preferably 10% by mass or more and 80% by mass or less. The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The upper limit of the total content of compound M3, compound M2, and compound M1 in the light-emitting layer is 100% by mass. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than compound M3, compound M2, and compound M1. The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3. The light-emitting layer may contain only one type of compound M2 or two or more types thereof. The light-emitting layer may contain only one type of compound M1 or two or more types thereof.

[0578] 5 is a diagram showing an example of the relationship between the energy levels of compounds M3, M2, and M1 in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1, and T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1. As shown in Figure 5, when a compound with a small ΔST (M2) is used as compound M2, 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 compound M2 to compound M1, generating the lowest excited singlet state S1 (M1). As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of compound M1 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.

[0579] The organic EL element according to the fourth embodiment contains, in the light-emitting layer, the compound of the first embodiment as compound M2, compound M1 having a minimum excited singlet energy smaller than that of compound M2, and compound M3 having a minimum excited singlet energy larger than that of compound M2. According to the fourth embodiment, it is possible to provide a high-performance organic EL element that can achieve at least one of high efficiency and long life.

[0580] [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 or fourth embodiment 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 or fourth embodiment can be used.

[0581] The organic EL element according to the fifth embodiment differs from the organic EL element according to the third or fourth embodiment in that the emitting layer contains compound M2 and compound M3, but does not contain compound M1. The remaining features are the same as those of the third or fourth embodiment. That is, in the fifth embodiment, the emitting layer contains compound M2 and compound M3. In this embodiment, compound M3 is preferably a host material, and compound M2 is preferably a dopant material. In this embodiment, when the emitting layer contains the compound according to the first embodiment, the emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain any metal complex other than the phosphorescent metal complex.

[0582] (Compound M2) The compound M2 is a compound according to the first embodiment. The compound M2 is preferably a delayed fluorescent compound.

[0583] (Compound M3) Compound M3 is the same as compound M3 described in the fourth embodiment.

[0584] <Relationship between Compound M2 and Compound M3 in Emitting Layer> In the organic EL device of this embodiment, the lowest excited singlet energy S １ (M2) and the lowest excited singlet energy S of compound M3 １ It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 2): S １ (M3) > S １ (M2) ...(Math. 2)

[0585] The energy gap T of compound M3 at 77 K ７７Ｋ (M3) is the energy gap T of compound M2 at 77 [K] ７７ＫIt is preferable that it is larger than (M2).

[0586] FIG. 6 is a diagram illustrating the principle of luminescence according to an embodiment of the present invention. In FIG. 6, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. As shown in FIG. 6, when a compound with a small ΔST(M2) is used as compound M2, the lowest excited triplet state T1(M2) of compound M2 can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. By utilizing the reverse intersystem crossing that occurs in this compound M2, for example, luminescence as shown in (i) or (ii) below can be observed. (i) When the emitting layer does not contain a fluorescent dopant whose lowest excited singlet state S1 is smaller than the lowest excited singlet state S1 (M2) of compound M2, light emission from the lowest excited singlet state S1 (M2) of compound M2 can be observed. (ii) When the emitting layer contains a fluorescent dopant whose lowest excited singlet state S1 is smaller than the lowest excited singlet state S1 (M2) of compound M2 (fluorescent compound M1 in the third or fourth embodiment), light emission from the fluorescent dopant can be observed. Note that in the organic EL element of this embodiment, the light emission shown in (i) above can be observed. In the organic EL element of the third or fourth embodiment described above, the light emission shown in (ii) above can be observed.

[0587] (Compound Content in Light-Emitting Layer) The contents of compound M2 and compound M3 contained in the light-emitting layer are preferably within the following ranges, for example. The content of compound M2 is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, even more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of compound M3 is preferably 10% by mass or more and 90% by mass or less. The upper limit of the total content of compound M2 and compound M3 in the light-emitting layer is 100% by mass. The light-emitting layer may contain only one type of compound M2, or may contain two or more types. The light-emitting layer may contain only one type of compound M3, or may contain two or more types.

[0588] The organic EL element according to the fifth embodiment contains, in the light-emitting layer, the compound of the first embodiment as compound M2 and compound M3 having a minimum excited singlet energy greater than that of compound M2. According to the fifth embodiment, a high-performance organic EL element that can achieve at least one of high efficiency and long life can be provided.

[0589] Sixth Embodiment Electronic Device An electronic device according to this 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), a television, a mobile phone, a tablet, and a personal computer. Examples of the light-emitting device include lighting and vehicle lighting fixtures.

[0590] [Modifications of the Embodiment] The present invention is not limited to the above-described embodiment, and any modifications, improvements, etc. that can achieve the object of the present invention are included in the present invention.

[0591] 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 of the light-emitting layers 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.

[0592] 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.

[0593] 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.

[0594] 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.

[0595] <Compounds> The structures of the compounds represented by general formula (1) used in the production of the organic EL devices according to Examples 1-1 to 1-10 and Examples 2-1 to 2-10 are shown below.

[0596]

[0597]

[0598]

[0599] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1-1, 1-2, 2-1 and 2-2 are shown below.

[0600]

[0601] The structures of other compounds used in the production of the organic EL devices according to Examples 1-1 to 1-10, Examples 2-1 to 2-10, and Comparative Examples 1-1, 1-2, 2-1, and 2-2 are shown below.

[0602]

[0603] <Preparation of Organic EL Device (1)> Organic EL devices were prepared as follows and evaluated.

[0604] Example 1-1 A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness 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 HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, forming a hole injection layer with a film thickness of 10 nm. The concentration of compound HT-1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, compound HT-1 was vapor-deposited on this hole injection layer to form a first hole transport layer with a film thickness of 90 nm. Next, compound HT-2 was vapor-deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 30 nm. Next, on this second hole transport layer, compound M3-1 as compound M3, compound A-32 as compound M2, and compound GD1 as compound M1 were co-deposited to form an emitting layer with a film thickness of 25 nm. In the emitting layer, the concentration of compound M3-1 was 74.4% by mass, the concentration of compound A-32 was 25% by mass, and the concentration of compound GD1 was 0.6% by mass. Next, compound ET-1 was deposited on this emitting layer to form a hole blocking layer with a film thickness of 5 nm. Next, compound ET-2 and compound Liq were co-deposited on this hole blocking layer to form an electron transport layer with a film thickness of 50 nm. In the electron transport layer, the concentration of compound ET-2 was 50% by mass, and the concentration of compound Liq was 50% by mass. Note that Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was vapor-deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode with a thickness of 80 nm. The device configuration of the organic EL device according to Example 1-1 is schematically shown as follows.ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / M3-1:A-32:GD1(25,74.4%:25%:0.6%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80) Note that the numbers in parentheses indicate film thickness (unit: nm). Also in parentheses, the percentage numbers (97%:3%) indicate the proportions (mass%) of Compound HT-1 and Compound HA in the hole injection layer, the percentage numbers (74.4%:25%:0.6%) indicate the proportions (mass%) of Compound M3-1, Compound A-32, and Compound GD1 in the light-emitting layer, and the percentage numbers (50%:50%) indicate the proportions (mass%) of Compound ET-2 and Compound Liq in the electron transport layer. The same notation will be used below.

[0605] (Examples 1-2 to 1-8) The organic EL devices of Examples 1-2 to 1-8 were fabricated in the same manner as in Example 1-1, except that the compound A-32 used as the compound M2 in the emitting layer of Example 1-1 was changed to the compound M2 shown in Table 1.

[0606] Comparative Example 1-1 The organic EL element of Comparative Example 1-1 was produced in the same manner as in Example 1-1, except that compound A-32 used as compound M2 in the emitting layer of Example 1-1 was changed to a compound shown in Table 1.

[0607] <Evaluation of Organic EL Devices (1)> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Table 1. Note that although the comparative compound Ref-1 used in Comparative Example 1-1 does not correspond to compound M2, it is listed in the same column as compound M2 for convenience. Table 1 also shows the evaluation results of the compounds used in the emitting layer of each example.

[0608] (External Quantum Efficiency EQE) The fabricated organic EL device was exposed to a current density of 10.00 mA / cm ２The spectral radiance spectrum when a voltage was applied so that the value was 0.01 was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. Table 1 shows the "EQE (relative value)" (unit: %). The "EQE (relative value)" shown in Table 1 was calculated based on the measured EQE values ​​of each example (Example 1-1 to Example 1-8 and Comparative Example 1-1) and the following mathematical formula (Math 1X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 1-1) × 100 (Math 1X).

[0609] (Maximum peak wavelength λ ｐ and emission half-width FWHM) when the current density of the organic EL element is 10.00 mA / cm ２ The spectral radiance spectrum when a voltage was applied to the element was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the maximum peak wavelength λ ｐ The full width at half maximum (FWHM) (unit: nm) and the full width at half maximum (FWHM) were measured.

[0610] (CIE 1931 chromaticity) The current density of the organic EL element is 10.00 mA / cm ２ The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the element so as to satisfy the following equation were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0611]

[0612] The luminous efficiency of the organic EL elements of Examples 1-1 to 1-8 was improved compared to that of the organic EL element of Comparative Example 1-1.

[0613] <Preparation of Organic EL Device (2)> An organic EL device was prepared as follows and evaluated.

[0614] (Examples 1-9 and 1-10) The organic EL devices of Examples 1-9 and 1-10 were prepared in the same manner as in Example 1-1, except that the compound A-32 used as the compound M2 in the emitting layer of Example 1-1 was changed to the compound M2 shown in Table 2.

[0615] Comparative Example 1-2 The organic EL element of Comparative Example 1-2 was produced in the same manner as in Example 1-1, except that the compound A-32 used as the compound M2 in the light-emitting layer of Example 1-1 was changed to a compound shown in Table 2.

[0616] <Evaluation of Organic EL Devices (2)> The organic EL devices fabricated in Examples 1-1 to 1-3, 1-9, and 1-10, and Comparative Example 1-2 were evaluated for the items shown in Table 2 by the methods described in <Evaluation of Organic EL Devices (1)> and the following methods. The evaluation results are shown in Table 2. Note that although comparative compound Ref-2 used in Comparative Example 1-2 does not correspond to compound M2, it is listed in the same column as compound M2 for convenience. Table 2 also shows the evaluation results of the compounds used in the emitting layer of each Example.

[0617] (External Quantum Efficiency EQE) The "EQE (relative value)" shown in Table 2 was calculated based on the measured EQE values ​​of each example (Examples 1-1 to 1-3, 1-9, and 1-10, and Comparative Example 1-2) and the following formula (2X): EQE (relative value) = (EQE of each example / EQE of Comparative Example 1-2) × 100 (2X).

[0618] (Lifespan LT95) The fabricated organic EL element was subjected to a current density of 50 mA / cm ２ A voltage was applied so that the voltage was such that the voltage was 0.01 V, and the time (LT95 (unit: hour)) until the luminance reached 95% of the initial luminance was measured as the lifespan. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 2 shows the "LT95 (relative value)" (unit: %). The "LT95 (relative value)" shown in Table 2 was calculated based on the measured LT95 values ​​of each example (Examples 1-1 to 1-3, 1-9 and 1-10, and Comparative Example 1-2) and the following mathematical formula (Math 1Y). LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1-2) × 100 (Math 1Y)

[0619]

[0620] The organic EL elements of Examples 1-1 to 1-3, 1-9, and 1-10 achieved at least one of improved luminous efficiency and longer life compared to the organic EL element of Comparative Example 1-2.

[0621] <Preparation of Organic EL Device (3)> Organic EL devices were prepared as follows and evaluated.

[0622] (Example 2-1) The organic EL element of Example 2-1 was fabricated in the same manner as in Example 1-1, except that instead of the emitting layer of Example 1-1, a compound M3-1 as compound M3 and a compound A-32 as compound M2 were co-deposited to form an emitting layer having a thickness of 25 nm, and the concentration of compound M3-1 in the emitting layer was set to 75% by mass, and the concentration of compound A-32 was set to 25% by mass. The element configuration of the organic EL element of Example 2-1 is schematically shown as follows: ITO(130) / HT-1:HA(10,97%:3%) / HT-1(90) / HT-2(30) / M3-1:A-32(25,75%:25%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80)

[0623] (Examples 2-2 to 2-8) The organic EL devices of Examples 2-2 to 2-8 were fabricated in the same manner as in Example 2-1, except that the compound A-32 used as the compound M2 in the emitting layer of Example 2-1 was changed to the compound M2 shown in Table 3.

[0624] Comparative Example 2-1 The organic EL element of Comparative Example 2-1 was produced in the same manner as in Example 2-1, except that compound A-32 as compound M2 used in the emitting layer of Example 2-1 was changed to a compound shown in Table 3.

[0625] <Evaluation of Organic EL Elements (3)> The organic EL elements prepared in Examples 2-1 to 2-8 and Comparative Example 2-1 were evaluated for the items shown in Table 3 by the methods described in <Evaluation of Organic EL Elements (1)>. The evaluation results are shown in Table 3.

[0626] (External Quantum Efficiency EQE) The "EQE (relative value)" shown in Table 3 was calculated based on the measured EQE values ​​of each example (Examples 2-1 to 2-8 and Comparative Example 2-1) and the following formula (3X): EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) × 100 (3X).

[0627]

[0628] The luminous efficiency of the organic EL elements of Examples 2-1 to 2-8 was improved compared to that of the organic EL element of Comparative Example 2-1.

[0629] <Preparation of Organic EL Device (4)> An organic EL device was prepared as follows and evaluated.

[0630] (Examples 2-9 and 2-10) The organic EL devices of Examples 2-9 and 2-10 were prepared in the same manner as in Example 2-1, except that the compound A-32 used as the compound M2 in the emitting layer of Example 2-1 was changed to the compound M2 shown in Table 4.

[0631] Comparative Example 2-2 The organic EL element of Comparative Example 2-2 was produced in the same manner as in Example 2-1, except that the compound A-32 used as the compound M2 in the light-emitting layer of Example 2-1 was changed to a compound shown in Table 4.

[0632] <Evaluation of Organic EL Elements (4)> The organic EL elements fabricated in Examples 2-1 to 2-3, 2-9, and 2-10, and Comparative Example 2-2 were evaluated for the items shown in Table 4 using the methods described in <Evaluation of Organic EL Elements (1)> and <Evaluation of Organic EL Elements (2)>. The evaluation results are shown in Table 4. Note that although the comparative compound Ref-2 used in Comparative Example 2-2 does not correspond to compound M2, it is listed in the same column as compound M2 for convenience. Table 4 also shows the evaluation results of the compounds used in the emitting layer of each Example.

[0633] (External Quantum Efficiency EQE) The "EQE (relative value)" shown in Table 4 was calculated based on the measured EQE values ​​of each example (Examples 2-1 to 2-3, 2-9, and 2-10, and Comparative Example 2-2) and the following formula (4X): EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-2) × 100 (4X).

[0634] (LT95 Lifetime) "LT95 (relative value)" shown in Table 4 was calculated based on the measured LT95 values ​​of each example (Examples 2-1 to 2-3, 2-9, and 2-10, and Comparative Example 2-2) and the following formula (Math 2Y): LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 2-2) × 100 (Math 2Y)

[0635]

[0636] The organic EL elements of Examples 2-1 to 2-3, 2-9, and 2-10 achieved at least one of improved luminous efficiency and longer life compared to the organic EL element of Comparative Example 2-2.

[0637] <Evaluation of Compounds> The compounds used in the production of the Examples were evaluated.

[0638] (Measurement of Fluorescence Quantum Yield (PLQY)) A compound to be measured was dissolved in toluene to a concentration of 5 μmol / L to prepare a toluene solution. The prepared solution was then bubbled with nitrogen for 5 minutes and sealed to prevent contamination with outside air. The PLQY of the prepared toluene solution of the compound to be measured was measured using an absolute PL (photoluminescence) quantum yield measurement device, Quantaurus-QY (manufactured by Hamamatsu Photonics K.K.).

[0639] (Maximum Peak Wavelength of Compound) The maximum peak wavelength λ of a compound was measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0640] (Delayed Fluorescence of Compound) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 1. Compound A-32 was 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 was frozen and degassed, then sealed in a capped cell under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound A-32, there are two types of luminescence: prompt luminescence (immediate luminescence) that is observed immediately from the excited state, and delay luminescence (delayed luminescence) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence luminescence means that the amount of delay luminescence (delayed luminescence) is 5% or more of the amount of prompt luminescence (immediate luminescence). Specifically, the amount of prompt luminescence (immediate luminescence) is X Ｐ The amount of delayed light emission is set to X Ｄ When this is done, X Ｄ / X Ｐmeans that the value of is 0.05 or more. 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). The apparatus used to calculate the amounts of prompt luminescence and delay luminescence is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 1. Compounds A-33 to A-39, A-50, and A-51, and comparative compounds Ref-1 and Ref-2 were also measured in the same manner as compound A-32. It was confirmed that the amount of delay luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (immediate luminescence) for compounds A-32 to A-39, A-50, and A-51, and comparative compounds Ref-1 and Ref-2. Specifically, for compounds A-32 to A-39, A-50 and A-51, and comparative compounds Ref-1 and Ref-2, Ｄ / X Ｐ The value was 0.05 or more.

[0641] (Lowest excited singlet energy S １ ) The lowest excited singlet energy S of the compound to be measured １ was measured by the solution method described above.

[0642] (energy gap T ７７Ｋ and ΔST) Energy gap T of the compound to be measured ７７Ｋ is the energy gap T described in the above "Relationship between triplet energy and energy gap at 77 [K]" ７７Ｋ The energy gap T ７７Ｋ and the above-mentioned lowest excited singlet energy S １ The value of "<0.01" in the table indicates that ΔST is less than 0.01 eV.

[0643]

[0644] <Synthesis Examples> Synthesis examples of the compounds used in the Examples and Comparative Examples are described below.

[0645] (Synthesis of Compound A-32) The synthesis method of Compound A-32 is described below.

[0646]

[0647] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (165 g, 607 mmol), cyanocopper (120 g, 1335 mmol), and NMP (800 ml) were placed in a 2 L three-neck flask and stirred at 150°C for 5 hours. 1 L of methylene chloride was added to the reaction mixture, which was then filtered through Celite. The filtrate was concentrated using an evaporator. The solid obtained after concentration was purified by silica gel chromatography to yield 58 g of a white solid. The resulting white solid was identified as intermediate Ma by GC-MS (Gas Chromatograph Mass Spectrometry) analysis (yield: 58%). NMP is an abbreviation for N-methyl-2-pyrrolidone.

[0648]

[0649] Under a nitrogen atmosphere, intermediate Ma (34 g, 207 mmol), diacetoxypalladium (1.40 g, 6.22 mmol), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (5.93 g, 12.4 mmol), potassium carbonate (86 g, 622 mmol), and Xylene (414 ml) were added to a 1000 mL three-neck flask and stirred for 30 minutes at room temperature. 2-Ethylhexanoic acid (6.64 ml, 41.4 mmol) and bromobenzene-d5 (101 g, 622 mmol) were added to the stirred reaction solution and stirred at 100°C for 5 hours. After stirring, the reaction solution was returned to room temperature, and the precipitated solid was filtered. The resulting solid was recrystallized from xylene to obtain 48 g of a white solid. The resulting white solid was identified as intermediate Mx by GC-MS analysis (yield 71%).

[0650]

[0651] Under a nitrogen atmosphere, 3-bromodibenzothiophene (26.3 g, 100 mmol), chlorotrimethylsilane (33 g, 300 mmol), and THF (150 mL) were placed in a 500 mL three-neck flask. The contents of the three-neck flask were cooled to -78°C in a dry ice / acetone bath, and 125 mL of lithium diisopropylamide (2 M THF solution) was added dropwise. The mixture was stirred at -78°C for 2 hours, then returned to room temperature and stirred for an additional 2 hours. After stirring, water (100 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, and then iodine monochloride (49 g, 300 mmol) was added dropwise at 0°C, followed by stirring at 40°C for 6 hours. The mixture was returned to room temperature, saturated aqueous sodium hydrogen sulfite solution (100 mL) was added, the organic layer was extracted with dichloromethane, the extracted organic layer was washed with water and brine, the washed organic layer was dried over magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mc (28 g, 72 mmol, yield 72%).

[0652] Under a nitrogen atmosphere, intermediate Mc (24.5 g, 63.0 mmol), dibenzo[b,d]thiophen-4-amine (12.55 g, 63.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.865 g, 0.945 mmol), Xantphos (1.385 g, 1.889 mmol), sodium tert-butoxide (9.08 g, 94 mmol), and 210 mL of toluene were added to a 500 mL three-neck flask, heated and stirred at 60 ° C. for 8 hours, and then cooled to room temperature (25 ° C.). The precipitated solid was collected by filtration and washed with 200 mL of toluene to obtain 25 g of a white solid. The resulting white solid was identified as intermediate M-d by GC-MS analysis (yield 86%).

[0653] Under a nitrogen atmosphere, intermediate M-d (9.5 g, 20.7 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.36 g, 0.82 mmol), palladium(II) acetate (0.093 g, 0.41 mmol), potassium carbonate (5.8 g, 42 mmol), and 60 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 10 hours, and then cooled to room temperature (25°C). The precipitated solid was collected by filtration and washed with acetone to obtain 6.9 g of a white solid. The resulting white solid was identified as intermediate M-e by ASAP-MS analysis (yield 86%). ASAP-MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0654]

[0655] Under a nitrogen atmosphere, intermediate M-x (19.6 g, 60.0 mmol), cesium fluoride (16.6 g, 109 mmol), intermediate Me (20.7 g, 54.5 mmol), and DMF (182 ml) were placed in a 300 ml three-neck flask and stirred at room temperature for 20 hours. After stirring, 200 ml of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 2.4 g of a yellow solid. The obtained yellow solid was identified as intermediate T-14 by ASAP-MS analysis (yield 91%).

[0656]

[0657] Under a nitrogen atmosphere, carbazole-1,2,3,4,5,6,7,8-d8 (1.2 g, 6.6 mmol), sodium hydride (40% by mass oil content) (0.27 g, 6.6 mmol), and DMF (45 ml) were placed in a 100 mL three-neck flask and stirred at 0°C for 30 minutes. Next, intermediate T-14 (3.0 g, 4.4 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.2 g of a yellow solid. The resulting yellow solid was identified as compound A-32 by ASAP-MS analysis (yield 87%).

[0658] (Synthesis of Compound A-33) The synthesis method of Compound A-33 is described below.

[0659]

[0660] Under a nitrogen atmosphere, 2-bromo-9H-carbazole (16 g, 65 mmol), phenyl-d5-boronic acid (9.90 g, 78 mmol), potassium carbonate (27.0 g, 195 mmol), tetrakistriphenylphosphine palladium(0) (1.50 g, 1.30 mmol), toluene (108 ml), THF (54 ml), and ion-exchanged water (54 ml) were placed in a 300 mL three-neck flask and stirred at 80°C for 4 hours. The organic layer of the reaction solution was extracted with toluene, and the extracted organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was then removed under reduced pressure using a rotary evaporator. The compound obtained after removing the solvent under reduced pressure was purified by silica gel column chromatography to obtain intermediate T-13 (2.50 g, 5.89 mmol, yield 13%).

[0661]

[0662] Under a nitrogen atmosphere, intermediate T-14 (2.5 g, 3.65 mmol), intermediate T-13 (1.36 g, 5.47 mmol), cesium fluoride (1.66 g, 10.9 mmol), and DMF (37 ml) were placed in a 100 ml recovery flask and stirred at 80°C for 4 hours. After stirring and cooling, 70 ml of methanol was added to the reaction solution, and the precipitated solid was filtered. The resulting solid was purified by column chromatography to obtain 1.71 g of a yellow solid. The resulting yellow solid was identified as compound A-33 by ASAP-MS analysis (yield 51%).

[0663] (Synthesis of Compound A-34) The synthesis method of Compound A-34 is described below.

[0664]

[0665] Under a nitrogen atmosphere, copper(II) chloride (12.1 g, 90 mmol), acetonitrile (70 ml), and tert-butyl nitrite (13.18 ml, 113 mmol) were placed in a 300 mL three-neck flask and heated to 65°C. Dibenzo[b,d]thiophene-3-amine (15 g, 75 mmol) was dissolved in acetonitrile (90 ml) to prepare a solution, and this solution was added dropwise to the reaction solution over 15 minutes. After the dropwise addition, the reaction solution was stirred for 1 hour, allowed to cool, and 6N hydrochloric acid (150 ml) was added and stirred. The reaction solution after stirring was extracted with toluene, washed with brine, and then concentrated. The compound obtained after concentration was purified by silica gel column chromatography to obtain 12 g of a white solid. The resulting white solid was identified as intermediate T-6 by ASAP-MS analysis (yield 73%).

[0666] Under a nitrogen atmosphere, intermediate T-6 (12.0 g, 54.9 mmol), chlorotrimethylsilane (17.5 g, 110 mmol), and THF (180 mL) were placed in a 500 mL three-neck flask. The materials in the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and 30 mL of lithium diisopropylamide (LDA) (2 M THF solution) was added dropwise. The mixture was stirred at -78 °C for 30 minutes, then returned to room temperature and stirred for an additional 3 hours. After stirring, water (100 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, and then bromine (13.2 g, 83 mmol) was added dropwise at 0 °C, followed by stirring at room temperature for 4 hours. A saturated aqueous solution of sodium hydrogen sulfite (100 mL) was added to the stirred reaction solution, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, and the washed organic layer was dried over magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate T-7 (14 g, 47 mmol, yield 86%).

[0667] Under a nitrogen atmosphere, intermediate T-7 (12.0 g, 54.9 mmol), chlorotrimethylsilane (15.0 g, 94 mmol), and THF (160 mL) were placed in a 500 mL three-neck flask. The materials in the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and 26 mL of lithium diisopropylamide (2 M THF solution) was added dropwise. The mixture was stirred at -78 °C for 20 minutes, then returned to room temperature and stirred for an additional 3 hours. After stirring, water (100 mL) was added to the three-neck flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, and then iodine monochloride (11.6 g, 71.4 mmol) was added dropwise at 0 °C, followed by stirring at room temperature for 4 hours. A saturated aqueous solution of sodium hydrogen sulfite (100 mL) was added to the stirred reaction solution, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, and the washed organic layer was dried over magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate T-8 (19.5 g, 46 mmol, yield 97%).

[0668] Under a nitrogen atmosphere, intermediate T-8 (19.5 g, 46 mmol), phenylboronic acid (5.61 g, 46 mmol), potassium carbonate (19.1 g, 138 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.13 g, 1.38 mmol), THF (123 ml), and ion-exchanged water (31 ml) were placed in a 200 mL three-neck flask and stirred at 40°C for 7 hours. After concentrating the reaction solution, 100 ml of ion-exchanged water was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine and dried over magnesium sulfate, after which the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after removing the solvent under reduced pressure was purified by silica gel column chromatography to obtain intermediate T-9 (2.50 g, 5.89 mmol, 13% yield).

[0669] Under a nitrogen atmosphere, intermediate T-9 (2.5 g, 5.89 mmol), dibenzo[b,d]thiophen-4-amine (1.33 g, 6.69 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.092 g, 0.10 mmol), Xantphos (0.116 g, 0.401 mmol), sodium tert-butoxide (0.964 g, 10.0 mmol), and 35 mL of Xylene were added to a 500 mL three-neck flask, heated with stirring at 60 ° C. for 17 hours, and then cooled to room temperature (25 ° C.). The reaction solution was concentrated and purified by silica gel column chromatography to obtain 2.5 g of a white solid. The resulting white solid was identified as intermediate T-10 by ASAP-MS analysis (yield 68%).

[0670] Under a nitrogen atmosphere, intermediate T-10 (2.5 g, 4.57 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.086 g, 0.203 mmol), palladium(II) acetate (0.023 g, 0.102 mmol), potassium carbonate (1.76 g, 12.7 mmol), and 17 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask. The mixture was stirred at 180°C for 9 hours and then cooled to room temperature (25°C). 30 mL of ion-exchanged water was added to the reaction solution, and the organic layer was extracted with ethyl acetate and concentrated. The resulting solid was purified by silica gel column chromatography to obtain 1.7 g of a white solid. The resulting white solid was identified as intermediate T-11 by ASAP-MS analysis (yield 73%).

[0671]

[0672] Under a nitrogen atmosphere, intermediate M-x (1.11 g, 34.0 mmol), cesium fluoride (1.15 g, 10.2 mmol), intermediate T-11 (1.55 g, 3.40 mmol), and DMF (11.3 ml) were placed in a 100 mL recovery flask and stirred at room temperature for 20 hours. After stirring, 20 ml of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 2.4 g of a yellow solid. The obtained yellow solid was identified as intermediate T-15 by ASAP-MS analysis (yield 91%).

[0673] Under a nitrogen atmosphere, intermediate T-15 (2.4 g, 3.19 mmol), intermediate T-13 (1.17 g, 4.72 mmol), cesium fluoride (1.44 g, 9.45 mmol), and DMF (11 ml) were placed in a 100 mL recovery flask and stirred at 80°C for 2 hours. The precipitated solid was filtered and purified by column chromatography to obtain 1.46 g of a yellow solid. The obtained yellow solid was identified as compound A-34 by ASAP-MS analysis (yield 47%).

[0674] (Synthesis of Compound A-35) The synthesis method of Compound A-35 is described below.

[0675]

[0676] Under a nitrogen atmosphere, B-(6-phenyl-4-dibenzothienyl)boronic acid (40 g, 132 mmol), sulfamic acid (29.7 g, 263 mmol), acetonitrile (658 ml), and sodium hydroxide (1 M) (881 ml, 881 mmol) were placed in a 1000 mL three-neck flask and stirred at room temperature for 24 hours. After stirring, the mixture was extracted with toluene and the organic layer was recovered. The next day, the recovered organic layer was evaporated to remove the solvent. The resulting solid was purified by silica gel column chromatography to obtain 17 g of a white solid. The resulting white solid was identified as intermediate M-1 by GC-MS analysis (yield 48%).

[0677] Under a nitrogen atmosphere, intermediate M-1 (10.6 g, 38.6 mmol), intermediate Mc (15 g, 38.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.353 g, 0.386 mmol), Xantphos (1.13 g, 1.54 mmol), sodium tert-butoxide (5.56 g, 57.8 mmol), and toluene (129 ml) were added to a 500 ml three-neck flask, heated with stirring at 100°C for 8 hours, and then cooled to room temperature (25°C). After cooling, the resulting solution was purified by silica gel chromatography to obtain 25 g of a white solid. The resulting white solid was identified as intermediate M-2 by ASAP-MS analysis (yield 77%).

[0678] Under a nitrogen atmosphere, intermediate M-2 (8.5 g, 15.84 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.202 g, 0.475 mmol), palladium(II) acetate (0.053 g, 0.238 mmol), potassium carbonate (4.60 g, 33.3 mmol), and N,N-dimethylacetamide (DMAc) (52.8 ml) were placed in a 200 ml three-neck flask and stirred at 160°C for 10 hours, followed by cooling to room temperature (25°C). The precipitated solid was collected by filtration and washed with methanol to obtain 7.2 g of a white solid. The resulting white solid was identified as intermediate M-3 by ASAP-MS analysis (yield 73%).

[0679]

[0680] Under a nitrogen atmosphere, intermediate M-3 (3.5 g, 7.7 mmol), cesium fluoride (2.3 g, 15.4 mmol), intermediate M-x (2.3 g, 8.07 mmol), and DMF (30 ml) were placed in a 100 ml recovery flask and stirred at room temperature for 12 hours. After stirring, 50 ml of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 5.1 g of a yellow solid. The obtained yellow solid was identified as intermediate M-14 by ASAP-MS analysis (yield 87%).

[0681]

[0682] Under a nitrogen atmosphere, carbazole-1,2,3,4,5,6,7,8-d8 (0.24 g, 1.34 mmol), sodium hydride (40% by mass oil content) (0.058 g, 1.34 mmol), and DMF (10 ml) were placed in a 50 mL three-neck flask and stirred at 0°C for 1 hour. Intermediate M-14 (0.6 g, 0.79 mmol) was added to the stirred reaction solution at 0°C, and the mixture was slowly warmed to room temperature and further stirred at room temperature for 1 hour. 10 ml of ion-exchanged water was added to the reaction mixture, and the precipitated solid was filtered. The resulting solid was purified by silica gel column chromatography to obtain 0.47 g of a yellow solid. The resulting yellow solid was identified as Compound A-35 by ASAP-MS analysis (yield: 65%).

[0683] (Synthesis of Compound A-36) The synthesis method of Compound A-36 is described below.

[0684]

[0685] Under a nitrogen atmosphere, B-(6-phenyl-4-dibenzothienyl)boronic acid (50 g, 164 mmol), N-bromosuccinimide (NBS) (32.2 g, 181 mmol), potassium acetate (KOAc) (3.23 g, 32.9 mmol), and acetonitrile (470 ml) were placed in a 1000 mL three-neck flask and stirred for 6 hours at 50 °C. After stirring, 400 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 44 g of a white solid. The resulting white solid was identified as intermediate M-5 by ASAP-MS analysis (yield 79%).

[0686] Under a nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (26.1 ml, 153 mmol) and THF (236 ml) were placed in a 1000 mL three-neck flask and cooled to 0°C using an ice bath. After cooling, n-butyllithium (1.6 M hexane solution) (96 ml, 153 mmol) was added dropwise to the ice-cooled reaction solution. After the dropwise addition, the mixture was stirred at 0°C for 30 minutes. The mixture was then cooled to -78°C using a dry ice / methanol bath. After cooling, triisopropyl borate (33.3 g, 177 mmol) and intermediate M-5 (40 g, 118 mmol) were added in this order, and the mixture was stirred while slowly warming from -78°C to room temperature. After completion of the reaction, 100 ml of 10% hydrochloric acid was added dropwise. After the dropwise addition, the organic layer was recovered, and the resulting solid was washed with toluene to obtain 40 g of a white solid. The resulting white solid was identified as intermediate M-6 by ASAP-MS analysis (yield 89%).

[0687] Under a nitrogen atmosphere, intermediate M-6 (40 g, 104 mmol), N-chlorosuccinimide (NCS) (13.94 g, 104 mmol), copper(I) chloride (10.34 g, 104 mmol), and acetonitrile (348 mL) were placed in a 1000 mL three-neck flask and stirred at 60°C for 6 hours. 300 mL of methylene chloride was added to the reaction mixture, which was then passed through Celite, and the resulting solution was concentrated. The resulting solid was purified by silica gel column chromatography to obtain 28 g of a white solid. The resulting white solid was identified as intermediate M-7 by ASAP-MS analysis (yield 72%).

[0688]

[0689] Under a nitrogen atmosphere, intermediate M-1 (3.5 g, 12.6 mmol), intermediate M-7 (4.7 g, 12.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.353 g, 0.386 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.17 g, 0.19 mmol), sodium tert-butoxide (1.8 g, 19.0 mmol), and toluene (42 ml) were added to a 100 ml three-neck flask, heated with stirring at 60°C for 8 hours, and then cooled to room temperature (25°C). The resulting solution was purified by silica gel chromatography to obtain 5 g of a white solid. The resulting white solid was identified as intermediate M-8 by ASAP-MS analysis (yield 70%).

[0690] Under a nitrogen atmosphere, intermediate M-8 (25 g, 44 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.202 g, 0.475 mmol), palladium(II) acetate (0.15 g, 0.66 mmol), potassium carbonate (13 g, 92 mmol), and N,N-dimethylacetamide (DMAc) (220 ml) were placed in a 500 ml three-neck flask and stirred at 160°C for 10 hours, followed by cooling to room temperature (25°C). The precipitated solid was collected by filtration and washed with methanol to obtain 18 g of a white solid. The resulting white solid was identified as intermediate M-9 by ASAP-MS analysis (yield 77%).

[0691]

[0692] Under a nitrogen atmosphere, intermediate M-9 (3.0 g, 5.60 mmol), cesium fluoride (2.6 g, 16.9 mmol), intermediate M-x (1.9 g, 5.92 mmol), and DMF (20 ml) were placed in a 100 ml recovery flask and stirred at room temperature for 12 hours. After stirring, 20 ml of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 4.4 g of a yellow solid. The obtained yellow solid was identified as intermediate M-15 by ASAP-MS analysis (yield 93%).

[0693]

[0694] Under a nitrogen atmosphere, intermediate T-13 (0.76 g, 3.04 mmol), sodium hydride (containing 40% by mass of oil) (0.12 g, 3.04 mmol), and DMF (20 ml) were placed in a 100 mL three-neck flask and stirred at 0°C for 1 hour. Intermediate M-15 (1.7 g, 2.03 mmol) was added to the stirred reaction solution at 0°C, and the mixture was slowly heated to room temperature and further stirred at room temperature for 1 hour. 20 ml of ion-exchanged water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 1.84 g of a yellow solid. The obtained yellow solid was identified as compound A-36 by ASAP-MS analysis (yield 85%).

[0695] (Synthesis of Compound A-37) The synthesis method of Compound A-37 is described below.

[0696]

[0697] Under a nitrogen atmosphere, 3,6-dibromo-9H-carbazole (10 g, 30.8 mmol), phenyl-d5-boronic acid (8.59 g, 67.7 mmol), potassium carbonate (12.8.0 g, 92 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.754 g, 0.923 mmol), DME (82 ml), and ion-exchanged water (20.5 ml) were placed in a 200 mL three-neck flask and stirred for 4 hours at 80° C. After concentrating the reaction solution, the organic layer was extracted with dichloromethane, washed with water and brine, and dried over magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. After removing the solvent under reduced pressure, the resulting compound was purified by silica gel column chromatography and toluene recrystallization to obtain intermediate T-16 (7.64 g, 23.0 mmol, yield 75%).

[0698]

[0699] Under a nitrogen atmosphere, intermediate T-14 (2.5 g, 3.65 mmol), intermediate T-16 (1.80 g, 5.47 mmol), cesium fluoride (1.66 g, 10.9 mmol), and DMF (36.5 ml) were placed in a 100 mL recovery flask and stirred at 80°C for 3 hours. After stirring and cooling, 70 ml of methanol was added to the reaction solution, and the precipitated solid was filtered. The resulting solid was purified by column chromatography to obtain 1.50 g of a yellow solid. The resulting yellow solid was identified as compound A-37 by ASAP-MS analysis (yield 41%).

[0700] (Synthesis of Compound A-38) The synthesis method of Compound A-38 is described below.

[0701]

[0702] Under a nitrogen atmosphere, intermediate Ma (20 g, 122 mmol), diacetoxypalladium (0.41 g, 1.83 mmol), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (1.74 g, 3.66 mmol), potassium carbonate (25.3 g, 183 mmol), and toluene (300 ml) were added to a 1000 ml three-neck flask and stirred at room temperature for 30 minutes. Then, 2-ethylhexanoic acid (1.95 ml, 12.19 mmol) and bromobenzene (10.84 ml, 104 mmol) were added to the reaction solution, and the mixture was stirred overnight at 40°C. After stirring, the reaction solution was returned to room temperature, water was added, and the precipitated solid was filtered. The resulting solid was passed through a silica pad and recrystallized with toluene to obtain 13.2 g of a white solid, which was identified as intermediate X-4 by GC-MS analysis (yield 44%).

[0703] Under a nitrogen atmosphere, intermediate X-4 (2 g, 8.33 mmol), 5'-bromo-1,1':3',1''-terphenyl (3 g, 9.70 mmol), diacetoxypalladium (0.20 g, 0.82 mmol), XPhos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (0.80 g, 1.678 mmol), potassium carbonate (3 g, 21.71 mmol), and Xylene (40 ml) were added to a 200 ml three-neck flask and stirred at room temperature for 10 minutes. Thereafter, 2-ethylhexanoic acid (0.06 ml, 0.374 mmol) was added to the reaction solution, and the mixture was stirred at 130°C for 5 hours. After stirring, the reaction solution was returned to room temperature, water was added, and the organic layer was extracted twice with ethyl acetate. The extracted organic layer was washed with water and then with sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 2.20 g of a white solid. The resulting white solid was identified as Intermediate X-5 by ASAP-MS analysis (yield 56%).

[0704]

[0705] Under a nitrogen atmosphere, intermediate X-5 (2.70 g, 5.76 mmol), cesium fluoride (2.50 g, 16.46 mmol), intermediate Me (2.20 g, 5.80 mmol), and DMF (50 ml) were added to a 300 ml recovery flask and stirred at room temperature for 20 hours. 50 ml of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration and washed with methanol. The washed solid was purified by silica gel column chromatography to obtain 3.14 g of a yellow solid. The obtained yellow solid was identified as intermediate X-6 by ASAP-MS analysis (yield 65%).

[0706]

[0707] Under a nitrogen atmosphere, sodium hydride (60% by mass, 0.087 g, 2.17 mmol) was added to a DMF (10 mL) solution of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.41 g, 2.36 mmol) in a 100 mL recovery flask under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After stirring, a DMF (10 mL) solution of intermediate X-6 (1.63 g, 1.969 mmol) was added dropwise to the reaction solution, and the mixture was warmed to room temperature and stirred for 18 hours. Water was added to the reaction mixture, and the precipitated solid was washed with methanol. The washed solid was purified by column chromatography to obtain 1.14 g of a yellow solid. The resulting yellow solid was identified as compound A-38 by ASAP-MS analysis (yield: 59%).

[0708] (Synthesis of Compound A-39) The synthesis method of Compound A-39 is described below.

[0709]

[0710] Under a nitrogen atmosphere, 1-bromo-4,5-dichloro-2-nitrobenzene (10 g, 36.9 mmol), (phenyl-d5)boronic acid (42.1 g, 332 mmol), tripotassium phosphate (15.67 g, 73.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.69 g, 1.846 mmol), SPhos (3.03 g, 7.38 mmol), and toluene (PhMe) (369 ml) were added to a 1000 mL three-neck flask and stirred at 110°C for 9 hours. After stirring, the reaction solution was allowed to cool to room temperature, and after cooling, ion-exchanged water was added, and the organic layer was extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after removing the solvent under reduced pressure was purified by silica gel column chromatography (hexane / dichloromethane=67%:33%) to obtain intermediate X-7 (3.01 g, 8.21 mmol, yield 22%).

[0711] Under a nitrogen atmosphere, intermediate X-7 (3 g, 8.19 mmol), triphenylphosphine (7 g, 26.69 mmol), and o-dichlorobenzene (30 ml) were placed in a 200 mL recovery flask and stirred at 180°C for 12 hours. After stirring, the reaction solution was allowed to cool to room temperature, and after cooling, the reaction solution was concentrated by distillation under reduced pressure. The resulting compound was purified by silica gel column chromatography (hexane / ethyl acetate = 95%:5%-50%:50%) to obtain intermediate X-8 (1.47 g, 4.41 mmol, yield 58%).

[0712]

[0713] Under a nitrogen atmosphere, sodium hydride (60% by mass, 0.09 g, 2.29 mmol) was added to a DMF (7.0 mL) solution of intermediate X-8 (0.77 g, 2.31 mmol) in a 50 mL three-neck flask under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. After stirring, a DMF (7.0 mL) solution of intermediate T-14 (1.50 g, 2.19 mmol) was added dropwise to the reaction solution, and the mixture was warmed to room temperature and stirred for 15 hours. Water was added to the reaction mixture, and the precipitated solid was washed with methanol. The washed solid was purified by column chromatography to obtain 1.03 g of a yellow solid. The obtained yellow solid was identified as compound A-39 by ASAP-MS analysis (yield 47%).

[0714] (Synthesis of Compound A-50) The synthesis method of Compound A-50 is described below.

[0715]

[0716] Synthesis of Intermediate T-1: Under an argon atmosphere, 5-bromo-2-chloroaniline (10 g), (phenyl-d5)boronic acid (6.50 g), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (PdCl ２ (amphos) ２) (1 g), sodium carbonate (8 g), 1,4-dioxane (300 mL), and ion-exchanged water (30 mL) were added to a flask and stirred under reflux for 8 hours. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate. Insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:dichloromethane=90%:10%-75%:25%-50%:50%) to obtain 6.60 g of a white solid. The obtained white solid was identified as intermediate T-1 by ASAP-MS analysis (yield 65%).

[0717]

[0718] Synthesis of Intermediate T-2 Under a nitrogen atmosphere, intermediate T-1 (6.60 g, 31.6 mmol), bromobenzene-d5 (3.50 mL, 32.2 mmol), palladium(II) acetate (0.35 g, 1.56 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (3 g, 6.29 mmol), cesium carbonate (15 g, 46.0 mmol), and 1,4-dioxane (300 mL) were placed in a 500 mL three-neck flask and heated with stirring at 100°C for 5 hours. Bromobenzene-d6 (1.00 mL, 9.20 mmol) was added, and the mixture was stirred for an additional hour and then cooled to room temperature (25°C). Water was added to the reaction solution, which was then extracted twice with ethyl acetate. The organic layer was washed twice with water and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:dichloromethane=95%:5%-85%:15%-70%:30%-50%:50%) to obtain 6.83 g of a white solid, which was identified as intermediate T-2 by ASAP-MS analysis (yield 75%).

[0719]

[0720] Synthesis of Intermediate T-3 (Dibenzothiophene Intermediate) Under a nitrogen atmosphere, intermediate T-2 (6.80 g, 23.46 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.80 g, 1.88 mmol), palladium(II) acetate (0.21 g, 0.935 mmol), potassium carbonate (6.50 g, 47.0 mmol), and N,N-dimethylacetamide (DMAc) (200 mL) were added to a 200 mL three-neck flask and stirred at a bath temperature of 150°C for 5 hours. After cooling to room temperature (25°C), 30 mL of ion-exchanged water was added to the reaction solution, and the resulting solid was filtered to obtain 3.88 g of a white solid. The resulting white solid was identified as intermediate T-3 by ASAP-MS analysis (yield 65%).

[0721]

[0722] Synthesis of Compound A-50 (Dicyanobenzene Derivative) Under an argon atmosphere, 3'-(14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazol-14-yl)-5'-fluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (Intermediate T-14) (1.10 g), Intermediate T-3 (0.44 g), and N,N-dimethylformamide (16 mL) were added to a flask, and cesium fluoride (0.75 g) was added under an argon atmosphere. The mixture was stirred at room temperature for 10 hours. A small amount of ethyl acetate and water were added to the reaction solution, and the resulting solid was collected by filtration and washed with methanol. The resulting solid was purified by column chromatography to obtain 1.03 g of a yellow solid. The resulting yellow solid was identified as Compound A-50 by ASAP-MS analysis (yield 70%).

[0723] (Synthesis of Compound A-51) A method for synthesizing Compound A-51 is described below.

[0724]

[0725] Under a nitrogen atmosphere, intermediate Ma (20 g, 122 mmol), potassium carbonate (33.7 g, 244 mmol), diacetoxypalladium (1.368 g, 6.09 mmol), tricyclohexylphosphine (5.13 g, 18.28 mmol), bromobenzene (31.9 ml, 305 mmol), 2-ethylhexanoic acid (7.81 ml, 48.7 mmol), and xylene (250 ml) were placed in a 500 mL three-neck flask and stirred at 100°C for 5 hours. 200 ml of methylene chloride was added to the reaction solution, which was then passed through Celite. The methylene chloride was removed from the resulting solution, and the precipitated solid was filtered. The resulting solid was purified by silica gel column chromatography, yielding 12 g of a white solid. The resulting white solid was identified as intermediate Mb by GC-MS analysis (yield: 31%).

[0726]

[0727] Under a nitrogen atmosphere, intermediate M-b (3.0 g, 9.48 mmol), intermediate Me (3.6 g, 9.5 mmol), potassium carbonate (2.6 g, 19 mmol), and DMF (50 mL) were placed in a 200 mL three-neck flask and stirred at 100°C for 4 hours. 100 mL of ion-exchanged water was added to the reaction solution, and the precipitated solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 4.1 g of a yellow solid. The obtained yellow solid was identified as intermediate M-f by ASAP-MS analysis (yield 64%). DMF is an abbreviation for N,N-dimethylformamide.

[0728]

[0729] Under a nitrogen atmosphere, 2-phenyl-9h-carbazole (1.1 g, 4.44 mmol), sodium hydride (40% by mass oil content) (0.18 g, 4.44 mmol), and DMF (37 ml) were placed in a 100 ml three-neck flask and stirred at 0°C for 1 hour. Next, intermediate M-f (2.5 g, 3.70 mmol) was added at 0°C, and the mixture was slowly heated to room temperature and further stirred at room temperature for 1 hour. 30 ml of ion-exchanged water was added to the reaction mixture, and the precipitated solid was filtered. The resulting solid was purified by silica gel column chromatography to obtain a yellow solid. The resulting yellow solid was identified as compound A-16 by ASAP-MS analysis (yield 63%).

[0730]

[0731] Synthesis of Compound A-51 (dicyanobenzene derivative) Under a nitrogen atmosphere, 3'-(14H-benzo[4,5]thieno[2,3-a]benzo[4,5]thieno[3,2-i]carbazol-14-yl)-5'-(2-phenyl-9H-carbazol-9-yl)-[1,1':4',1''-terphenyl]-2',6'-dicarbonitrile (Compound A-16) (0.60 g) synthesized by a known method and o-dichlorobenzene (10 mL) were placed in a 300 mL three-neck flask, and the mixture was heated to a bath temperature of 80°C for dissolution, followed by the addition of benzene-d6 (5.91 mL) under ice cooling. After the temperature of the liquid in the three-necked flask was lowered to 10°C, trifluoromethanesulfonic anhydride (0.30 mL) was added, and the mixture was stirred at the same temperature for 0.5 hours, then for 2 hours while warming to room temperature, for 2 hours at a bath temperature of 40°C, and for 2 hours at a bath temperature of 80°C. After cooling to room temperature, heavy water was added, and the organic layer was separated. The organic layer was washed once with a saturated aqueous solution of potassium phosphate tripotassium and twice with purified water, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The solid was washed with methanol and then purified by column chromatography to obtain 0.40 g of a yellow solid. The resulting yellow solid was identified as A-51 by ASAP-MS analysis (yield 64%).

[0732] (Synthesis of Comparative Compound Ref-1) Comparative compound Ref-1 was synthesized according to the description in WO2021 / 066059 A1.

[0733] (Synthesis of Comparative Compound Ref-2) The above-mentioned compound A-16 was synthesized as comparative compound Ref-2.

[0734] 1... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer

Claims

1. Anode and, Cathode and, It has a light-emitting layer included between the anode and the cathode, The light-emitting layer contains a delayed-fluorescence compound M2 represented by the following general formula (1), The aforementioned compound M2 has one or more deuterium atoms in its molecule. Organic electroluminescent element. 【Chemistry 1】 (In the above general formula (1), CN is a cyano group, D １１ and D １２ Each of these is independently a group represented by the following general formula (11), general formula (12), or general formula (13), provided that at least one D １１ This is a group represented by the following general formula (12) or general formula (13), Each R is independent of the others. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R ９０６ )(R ９０７ ) group represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, at least one R is a substituent, and at least one R as a substituent is bonded to the benzene ring in the general formula (1) by a carbon-carbon bond. k is either 1 or 2. m is 0, 1, or 2. n is 1, 2, or 3. k + m + n is 4, When k is 2, multiple D １１ They are either identical or different from each other. When m is 2, multiple D １２ They are either identical or different from each other. When n is 2 or 3, multiple Rs are either identical or different from one another. 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 (R in the general formula (11) above) １ ~R ８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (12), R １１ ~R １８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (13), R １１１ ~R １１８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R does not form a substituted or unsubstituted monoring in the general formula (11) and does not form a substituted or unsubstituted fused ring. １ ~R ８ R that does not form a substituted or unsubstituted monoring in the general formula (12) and does not form a substituted or unsubstituted condensed ring. １１ ~R １８ Furthermore, R that does not form a substituted or unsubstituted monoring in the general formula (13) and does not form a substituted or unsubstituted condensed ring. １１１ ~R １１８ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, In the above general formula (12) and the above general formula (13), Rings A, B, and C are each independently selected from the group consisting of ring structures represented by the following general formulas (14) and (15). Rings A, B, and C condense with adjacent rings at any position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, the multiple rings A are either identical or different from each other. If px is 2, 3, or 4, the multiple rings B are either identical or different from each other. If py is 2, 3, or 4, the multiple rings C are either identical or different from one another. However, at least one D １１ This is a group represented by the general formula (12) or general formula (13), and this D １１ In the aforementioned general formula (12), p is 4, and the four rings A include two ring structures represented by the following general formula (14) and two ring structures represented by the following general formula (15), and this D １１ In the aforementioned general formula (13), px and py are 2, and the two rings B include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and the two rings C include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), In the above general formulas (11) to (13), the asterisk (*) indicates the bond position with the benzene ring in the above general formula (1). 【Transformation 5】 (In the above general formula (14), r is 0, 2, or 4. Multiple R １９ A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (15), X １ is a sulfur atom or an oxygen atom, R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. １９ teeth, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Multiple R １９ They are either identical or different from one another. Multiple X １ They are either identical or different from one another. However, D is a group represented by the general formula (13) above. １１ It satisfies at least one of the following conditions (Pv1), (Pv2), and (Pv3). Condition (Pv1): When k is 2, X in the ring structure represented by the general formula (15) as ring B. １ and X in the ring structure represented by the general formula (15) as ring C １ At least one of them is an oxygen atom. Condition (Pv2): When k is 2, two D １１ They are different from each other. Condition (Pv3): When n is 3, X in the ring structure represented by the general formula (15) as ring B. １ and X in the ring structure represented by the general formula (15) as ring C １ These are, independently, either a sulfur atom or an oxygen atom. (In the general formula, 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, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R ９０１ When there are a plurality of R's ９０１ they may be the same as or different from each other R ９０２ If multiple R ９０２ They are either identical or different from one another. R ９０３ If multiple R ９０３ They are either identical or different from one another. R ９０４ If multiple R ９０４ They are either identical or different from one another. R ９０５ If multiple R ９０５ They are either identical or different from one another. R ９０６ If multiple R ９０６ They are either identical or different from one another. R ９０７ If multiple R ９０７ They are either identical or different from one another. R ９０８ If multiple R ９０８ They are either identical or different from one another. R ９０９ If multiple R ９０９ They are either identical or different from one another. R ９３１ If multiple R ９３１ They are either identical or different from one another. R ９３２ If multiple R ９３２ They are either identical or different from one another. R ９３３ If multiple R ９３３ They are either identical or different from one another. R ９３４ If multiple R ９３４ They are either identical or different from one another. R ９３５ If multiple R ９３５ They are either identical or different from one another. R ９３６ If multiple R ９３６ They are either identical or different from one another. R ９３７ If multiple R ９３７ (They are either identical or different to each other.)

2. At least one D in compound M2 １１ This is a group represented by the following general formulas (121), (122), or (131): The organic electroluminescent element according to claim 1. 【Transformation 6】 【Transformation 7】 【Transformation 8】 (In the above general formulas (121) and (122), R １１ ~R １８ R in the general formula (12) is １１ ~R １８ It is synonymous with, Ring A １、 Ring A ２ , ring A ３ and ring A ４ Of these, two are ring structures represented by the general formula (14), and the remaining two are ring structures represented by the general formula (15). In the above general formula (131), R １１１ ~R １１８ R in the general formula (13) is １１１ ~R １１８ It is synonymous with, Ring B １ and ring B ２ One of them is a ring structure represented by the general formula (14), and ring B １ and ring B ２ The other is a ring structure represented by the general formula (15), Ring C １ and ring C ２ One of them is a ring structure represented by the general formula (14), and ring C １ and ring C ２ The other is a ring structure represented by the general formula (15), The asterisks (*) in general formulas (121), (122), and (131) indicate the bonding position with the benzene ring in general formula (1).

3. Ring A in compound M2 １ and ring A ３ However, it is a ring structure represented by the general formula (14), and ring A ２ and ring A ４ This is a ring structure represented by the general formula (15), Ring B in compound M2 １ However, it is a ring structure represented by the general formula (14), and ring B ２ However, it is a ring structure represented by the general formula (15) above, Ring C in compound M2 １ However, it is a ring structure represented by the general formula (14), and ring C ２ However, the ring structure is represented by the general formula (15) above. The organic electroluminescent element according to claim 2.

4. At least one D in compound M2 １１ However, the group is represented by the general formula (131) above, The organic electroluminescent element according to claim 2.

5. At least one D in compound M2 １１ However, the group is represented by the following general formulas (123), (124), (125), or (132): The organic electroluminescent element according to claim 2. 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 (In the above general formulas (123), (124), and (125), R １１ ~R １８ R in the general formula (12) is １１ ~R １８ It is synonymous with R １９１ ~R １９４ Each of these independently corresponds to R in the general formula (14) １９ It is synonymous with, In the above general formula (132), R １１１ ~R １１８ R in the general formula (13) is １１１ ~R １１８ It is synonymous with R １９５ ~R １９８ Each of these independently corresponds to R in the general formula (14) １９ It is synonymous with, In the above general formulas (123), (124), (125), and (132), X １１ and X １２ Each of these independently corresponds to X in the general formula (15). １ This is synonymous with the above general formula (1), where * indicates the bond position with the benzene ring.

6. X in the aforementioned compound M2 １１ The organic electroluminescent element according to claim 5, wherein is a sulfur atom.

7. At least one D in compound M2 １１ However, the group is represented by the general formula (132) above, The organic electroluminescent element according to claim 5.

8. D in compound M2 １２ is a group represented by the general formula (11) or the general formula (12), The organic electroluminescent element according to claim 1.

9. D in compound M2 １２ This is a group represented by the general formula (12) above, The organic electroluminescent element according to claim 1.

10. The group represented by the general formula (12) is one of the groups selected from the group consisting of the following general formulas (12A), (12B), (12C), (12D), (12E), and (12F). The organic electroluminescent element according to claim 1. 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] (In the above general formulas (12A), (12B), (12C), (12D), (12E), and (12F), R １１ ~R １８ Each of these independently corresponds to R in the general formula (12) １１ ~R １８ It is synonymous with, R １９ and R ２０ Each of these independently corresponds to R in the general formula (14) １９ It is synonymous with, X １ X in the general formula (15) is １ It is synonymous with, In the general formulas (12A), (12B), (12C), (12D), (12E), and (12F), the asterisk (*) indicates the bond position with the benzene ring in the general formula (1).

11. The compound represented by the above general formula (1) is represented by the following general formulas (110), (120), or (130): The organic electroluminescent element according to claim 1. 【Chemistry 19】 (In the above general formulas (110), (120), and (130), D １１ , D １２ R, k, m, and n are, respectively, D in the general formula (1) above. １１ , D １２ (This is synonymous with R, k, m, and n.)

12. In the above general formula (1), n ​​is 2. The organic electroluminescent element according to claim 1.

13. The compound represented by the above general formula (1) is represented by the following general formulas (111), (112), or (113): The organic electroluminescent element according to claim 1. 【Chemistry 20】 (In the above general formulas (111), (112), and (113), D １１ D in the general formula (1) is １１ It is synonymous with R １０１ ~R １０４ Each of these terms independently has the same meaning as R in the general formula (1) above.

14. In the general formula (1) above, R is independent of each other. A substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or These are heterocyclic groups with 5 to 14 substituted or unsubstituted ring-forming atoms. The organic electroluminescent element according to claim 1.

15. In the general formula (1) above, R is independent of each other. A substituted or unsubstituted phenyl group, It is a heterocyclic group with 6 substituted or unsubstituted ring-forming atoms. The organic electroluminescent element according to claim 1.

16. R in compound M2 １ ~R ８ , R １１ ~R １８ , R １１１ ~R １１８ And R １９ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The organic electroluminescent element according to claim 1.

17. R in compound M2 １ ~R ８ , R １１ ~R １８ , R １１１ ~R １１８ And R １９ Each of them operates independently. hydrogen atom, Unsubstituted alkyl groups having 1 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, or Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, The organic electroluminescent element according to claim 1.

18. The light-emitting layer further comprises a fluorescent compound M1, The lowest singlet excitation energy S of compound M1 １ (M1) and the lowest excitation singlet energy S of compound M2. １ (M2) and satisfy the following relationship (Equation 1): The organic electroluminescent element according to claim 1. S １ (M2) > S １ (M1)…(Number 1)

19. The aforementioned compound M1 is a compound represented by the following general formula (D1): The organic electroluminescent element according to claim 18. 【Chemistry 21】 (In the above general formula (D1), Rings A, B, D, E, and F are each independent of each other. Substituted or unsubstituted aryl rings having 6 to 30 carbon atoms, and A ring structure selected from the group consisting of heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms. Either ring B or ring D exists, or both ring B and ring D exist. If both ring B and ring D exist, ring B and ring D share a bond connecting Zc and Zh. Either ring E or ring F exists, or both ring E and ring F exist. If both ring E and ring F exist, ring E and ring F share a bond connecting Zf and Zi. Za is a nitrogen atom or a carbon atom, Zb is, If ring B is present, it is a nitrogen atom or a carbon atom. If ring B is not present, oxygen atom, sulfur atom, NRb, C(Rb) １ ) (Rb ２ ) or Si (Rb ３ ) (Rb ４ ) and Zc is a nitrogen atom or a carbon atom, Zd is, If ring D is present, it is a nitrogen atom or a carbon atom. If ring D is not present, it is an oxygen atom, a sulfur atom, or NRd. Ze is, If ring E is present, it is a nitrogen atom or a carbon atom. If ring E is not present, it is an oxygen atom, a sulfur atom, or NRe. Zf is a nitrogen atom or a carbon atom, Zg is, If ring F is present, it is a nitrogen atom or a carbon atom. If ring F is not present, oxygen atom, sulfur atom, NRg, C(Rg) １ ) (Rg ２ ) or Si (Rg ３ ) (Rg ４ ) and Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O, or P=S. Rb, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ And Rh are, independently, a hydrogen atom or a substituent. Rb as a substituent, Rb １ , Rb ２ , Rb ３ , Rb ４ , Rd, Re, Rg, Rg １ , Rg ２ , Rg ３ , Rg ４ And Rh are independent of each other. Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R ９１１ ) (Caution ９１２ ) (Caution ９１３ ) a base represented by -O-(R ９１４ ) a base represented by -S-(R ９１５ A base represented by ) or -N(R) ９１６ ) (Caution ９１７ It is a base represented by ), However, the bonds between Y and Za, Y and Zd, and Y and Ze are all single bonds. (In the above compound M1, R ９１１ ~R ９１７ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R ９１１ If multiple R ９１１ They are either identical or different from one another. R ９１２ If multiple R ９１２ They are either identical or different from one another. R ９１３ If multiple R ９１３ They are either identical or different from one another. R ９１４ If multiple R ９１４ They are either identical or different from one another. R ９１５ If multiple R ９１５ They are either identical or different from one another. R ９１６ If multiple R ９１６ They are either identical or different from one another. R ９１７ If multiple R ９１７ (They are either identical or different to each other.)

20. The aforementioned compound M1 is a compound represented by the following general formula (20): The organic electroluminescent element according to claim 18. 【Chemistry 22】 (In the above general formula (20), X is a nitrogen atom, or a carbon atom bonded to Y. Y is a hydrogen atom or substituent, R ２１ ~R ２６ Each of these is independently either a hydrogen atom or a substituent, or R ２１ and R ２２ Group R ２２ and R ２３ Group R ２４ and R ２５ The group, and R ２５ and R ２６ One or more of these pairs join together to form a ring, Y and R as substituents ２１ ~R ２６ Each of them operates independently. Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted C1-C30 alkyl halogens, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, Substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted halogenated alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms, Substituted or unsubstituted ring-forming arylthio groups having 6 to 30 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms, halogen atom, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Substituted or unsubstituted amino groups, Nitro group, Cyano group, Substituted or unsubstituted silyl groups, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, Z ２１ and Z ２２ Each of these is independently either a substituent or Z ２１ and Z ２２ They bond to each other to form a ring, Z as a substituent ２１ and Z ２２ Each of them operates independently. halogen atom, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted C1-C30 alkyl halogens, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, Substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted halogenated alkoxy groups having 1 to 30 carbon atoms, and (Selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms in a ring-forming structure.)

21. The light-emitting layer further comprises compound M3, The lowest excitation singlet energy S of compound M2 １ (M2) and the lowest excitation singlet energy S of compound M3. １ (M3) and satisfy the following relationship (Equation 2): The organic electroluminescent element according to claim 1. S １ (M3) > S １ (M2) … (Number 2)

22. An electronic device equipped with an organic electroluminescent element according to any one of claims 1 to 21.

23. A compound having at least one deuterium atom in its molecule and represented by the following general formula (150). 【Chemistry 23】 (In the above general formula (150), R １０２ and R １０４ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, R １０２ and R １０４ At least one of them is a substituent, and R as a substituent １０２ and R １０４ It is bonded by a carbon-carbon bond with the benzene ring in the general formula (150), R １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, R １ ~R ８ At least one of them is a substituent that is not a hydrogen atom, and R １ ~R ８ At least one of them is a deuterium atom. (In the general formula, 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 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R ９０１ If multiple R ９０１ They are either identical or different from one another. R ９０２ If multiple R ９０２ They are either identical or different from one another. R ９０３ If multiple R ９０３ They are either identical or different from one another. R ９０４ If multiple R ９０４ They are either identical or different from one another. R ９０５ If multiple R ９０５ They are either identical or different from one another. R ９０６ If multiple R ９０６ They are either identical or different from one another. R ９０７ If multiple R ９０７ They are either identical or different from one another. R ９０８ If multiple R ９０８ They are either identical or different from one another. R ９０９ If multiple R ９０９ They are either identical or different from one another. R ９３１ If multiple R ９３１ They are either identical or different from one another. R ９３２ If multiple R ９３２ They are either identical or different from one another. R ９３３ If multiple R ９３３ They are either identical or different from one another. R ９３４ If multiple R ９３４ They are either identical or different from one another. R ９３５ If multiple R ９３５ They are either identical or different from one another. R ９３６ If multiple R ９３６ They are either identical or different from one another. R ９３７ If multiple R ９３７ (They are either identical or different to each other.)

24. R １ ~R ８ At least one of them Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to claim 23.

25. R ２ , R ３ , R ６ and R ７ At least one of them Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to claim 23.

26. R １０２ and R １０４ These are, independently, substituted or unsubstituted aryl groups with 6 to 14 ring-forming carbon atoms, or substituted or unsubstituted heterocyclic groups with 5 to 14 ring-forming atoms. The compound according to claim 23.

27. R １０２ and R １０４ At least one of them has a deuterium atom, The compound according to claim 23.

28. The following general formula (151) is used: The compound according to claim 23. 【Chemistry 24】 (In the above general formula (151), R １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８ These are, respectively, R in the general formula (150) １ ~R ８ , R １１１ ~R １１８ , and R １９５ ~R １９８ It is synonymous with, R １３１ ~R １４０ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution ９０７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R ９０８ A base represented by - COOR ９０９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R ９３１ ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, (It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.)

29. R １３１ ~R １４０ At least one of them is a deuterium atom. The compound according to claim 28.

30. R １１１ ~R １１８ , and R １９５ ~R １９８ At least one of them has a deuterium atom, The compound according to claim 23.

31. R １１１ ~R １１８ , and R １９５ ~R １９８ At least one of them is a deuterium atom. The compound according to any one of claims 23 to 30.

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