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

Abstract

To provide a compound with high PLQY.SOLUTION: The present invention provides a compound represented by general formula (1) below. 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); where, at least one D11 is a group represented by general formula (12) or (13); and R is, for instance, a hydrogen atom or an aryl group.SELECTED DRAWING: Figure 3

Description

[Technical Field]

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

[0002] When a voltage is applied to an organic electroluminescence device (hereinafter sometimes referred to as an "organic EL device"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25% and triplet excitons are generated at a rate of 75%. Fluorescent organic EL devices that use light emitted from singlet excitons are 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 devices.

[0003] For example, it is expected that organic EL devices will emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being 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, April 1, 2012, pp. 261-268. Known compounds that exhibit thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF compounds) include, for example, compounds in which a donor moiety and an acceptor moiety are bonded within the molecule.

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

[0005] [Patent Document 1] International Publication No. 2014 / 208698 [Patent Document 2] International Publication No. 2019 / 195104 [Patent Document 3] International Publication No. 2019 / 190235 [Patent Document 4] International Publication No. 2021 / 066059 Summary of the Invention [Problem to be solved by the invention]

[0006] In order to improve the performance of electronic devices such as displays, further improvements in the performance of organic EL elements are desired. Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime. Factors for improving the luminous efficiency of organic EL elements include, for example, the use of compounds with high photoluminescence quantum yield (PLQY). Longer lifetimes are also desired for organic EL elements.

[0007] An object of the present invention is to provide a compound with a high PLQY. Another object of the present invention is to provide a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device incorporating the organic electroluminescence device, each containing a compound with a high PLQY. Another object of the present invention is to provide a compound that can achieve high performance, particularly at least one of high efficiency and long life, of an organic electroluminescence device. Another object of the present invention is to provide an organic electroluminescence device that can achieve high performance, particularly at least one of high efficiency and long life, and to provide an electronic device incorporating the organic electroluminescence device. [Means for solving the problem]

[0008] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1):

[0009] [ka]

[0010] (In the general formula (1), CN is a cyano group, 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 general formula (13), R is independently hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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, However, at least one R is a substituent, and at least one R as a substituent is It is bonded to the benzene ring in the 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, When k is 2, multiple D 11 are identical to or different from each other, When m is 2, multiple D 12 are identical to or different from each other, When n is 2 or 3, the multiple R's are the same or different.

[0011] [ka]

[0012] [ka]

[0013] [ka]

[0014] (R in the general formula (12) 11 ~R 18 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (13) 111 ~R 118 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 to R8 in the general formula (11), R in the general formula (12) that 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, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 each independently represent a 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 the adjacent ring at any position; p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, the rings A are the same or different from each other, When px is 2, 3 or 4, the rings B are the same or different from each other, When py is 2, 3 or 4, the rings C are the same or different from each other; However, 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), and this D 11 wherein px and py in the general formula (13) are 2, 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 general formulae (11) to (13), * indicates the bonding position to the benzene ring in the general formula (1).

[0015] [ka]

[0016] (In the general formula (14), r is 0, 2 or 4; Multiple R 19 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (15), X1 is a sulfur atom or an oxygen atom, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring 19 teeth, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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, Multiple R 19 are the same or different from each other, Multiple X1's are the same or different, However, the group D 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, at least one of X1 in the ring structure represented by the general formula (15) as ring B and X1 in the ring structure represented by the general formula (15) as ring C is an oxygen atom. Condition (Pv2): When k is 2, two D 11 are different from each other. Condition (Pv3): When n is 3, X1 in the ring structure represented by the general formula (15) as ring B and X1 in the ring structure represented by the general formula (15) as ring C are each independently 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 atoms, 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, 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 either identical or different.)

[0017] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, which contains a compound according to one aspect of the present invention.

[0018] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an organic layer, wherein the organic layer contains a compound according to one aspect of the present invention as compound M2.

[0019] 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.

[0020] According to one aspect of the present invention, a compound with a high PLQY can be provided. Furthermore, according to another aspect of the present invention, a material for an organic electroluminescence device or an organic electroluminescence device containing a compound with a high PLQY can be provided. Furthermore, according to another aspect of the present invention, an electronic device incorporating the organic electroluminescence device can be provided. Furthermore, according to another aspect of the present invention, a compound capable of realizing high performance of an organic electroluminescence device, particularly at least one of high efficiency and long life, can be provided. Furthermore, according to another aspect 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 to provide an electronic device incorporating the organic electroluminescence device. [Brief explanation of the drawings]

[0021] [Figure 1] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Figure 2] FIG. 10 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 3] FIG. 10 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 4] FIG. 10 is a diagram showing the energy levels of compounds M1 and M2 in an emitting layer of an example of an organic electroluminescence device according to a third embodiment of the present invention, and the relationship between energy transfer. [Figure 5] FIG. 10 is a diagram showing the energy levels of compounds M1, M2, and M3 in an example of an emitting layer of an organic electroluminescence device according to a fourth embodiment of the present invention, and the relationship between energy transfer. [Figure 6] FIG. 10 is a diagram showing the energy levels of compounds M2 and M3 in an example of an emitting layer of an organic electroluminescence device according to a fifth embodiment of the present invention, and the relationship between energy transfer. DETAILED DESCRIPTION OF THE INVENTION

[0022] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0023] In this specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly marked with a symbol such as "R" or "D" representing a deuterium atom.

[0024] 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. Furthermore, 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 the benzene ring substituted with an alkyl group is 6. Furthermore, when a 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.

[0025] 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 are 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.

[0026] 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" refers to 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.

[0027] In this specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY atoms" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of 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, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group". In this specification, "unsubstituted" in the context 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. In this specification, "substituted" in the context 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 context 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.

[0029] "Substituents described herein" The substituents described in this specification will be explained below.

[0030] The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification. Unless otherwise specified in this specification, the "unsubstituted alkenyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. Unless otherwise specified, the "unsubstituted alkynyl group" described in this specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms. The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30 ring carbon atoms, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification. The "unsubstituted divalent heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30 ring atoms, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification. The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

[0031] "Substituted or unsubstituted aryl group" Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and the term "substituted aryl group" refers to the case where the "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 a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent, and examples of the substituted aryl group in the specific example group G1A below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

[0032] Unsubstituted aryl groups (specific example group G1A): phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, a triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl group, benzofluorenyl groups, dibenzofluorenyl groups, fluoranthenyl group, benzofluoranthenyl group, perylenyl groups, and A monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0033] [ka]

[0034] [ka]

[0035] 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 groups, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl groups, and A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by any one of the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0036] "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 groups" described herein are either monocyclic or fused ring groups. The "heterocyclic group" described herein may be an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which a hydrogen atom of the "unsubstituted heterocyclic group" in the specific example group G2A below is replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are also included. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in the "substituted heterocyclic group" in the specific example group G2B is further replaced with a substituent.

[0037] 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).

[0038] 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 a substituent (specific example group G2B4).

[0039] Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1): pyrrolyl group, imidazolyl group, pyrazolyl group, a triazolyl group, tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, a triazinyl group, Indolyl groups, isoindolyl groups, an indolizinyl group, a quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, a quinazolinyl group, quinoxalinyl group, benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, acridinyl group, phenazinyl group, a carbazolyl group, a benzocarbazolyl group, morpholino group, phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and Diazacarbazolyl group.

[0040] Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2): furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl groups, benzoisoxazolyl group, phenoxazinyl group, morpholino group, a dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0041] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): thienyl group, a thiazolyl group, isothiazolyl group, a thiadiazolyl group, Benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (naphthobenzothienyl group), benzothiazolyl group, benzoisothiazolyl group, a phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), Azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0042] 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):

[0043] [ka]

[0044] [ka]

[0045] 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 CH2. A and Y A At least one of is an oxygen atom, a sulfur atom, or NH. In the general formulae (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from NH or CH2.

[0046] 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, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0047] Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2): phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0048] Substituted heterocyclic groups containing sulfur atoms (specific example group G2B3): phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0049] 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):

[0050] 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 or more hydrogen atoms selected from the hydrogen atoms of a methylene group when one of the groups is CH2.

[0051] "Substituted or unsubstituted alkyl groups" 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 unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when simply referring to an "alkyl group," both an "unsubstituted alkyl group" and a "substituted alkyl group" are included. The term "substituted alkyl group" refers to an "unsubstituted alkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkyl group" include the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms have been replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group." Note that the examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in specific example group G3B is further replaced with a substituent.

[0052] Unsubstituted alkyl groups (specific example group G3A): methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0053] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0054] "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, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group." A "substituted alkenyl group" refers to an "unsubstituted alkenyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl groups" (specific example group G4A) having a substituent, and the 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 the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of the alkenyl group itself has been further replaced with a substituent, and groups in the "substituted alkenyl groups" of specific example group G4B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0055] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0056] Substituted alkenyl groups (specific example group G4B): 1,3-butadienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0057] "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 groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to a case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when simply referring to an "alkynyl group," it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group." A "substituted alkynyl group" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with substituents. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with substituents, etc.

[0058] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0059] "Substituted or unsubstituted cycloalkyl groups" 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 unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, when the term "cycloalkyl group" is simply used, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group." A "substituted cycloalkyl group" refers to an "unsubstituted cycloalkyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms have been replaced with a substituent, 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 group" described in this specification also includes a group in the "substituted cycloalkyl group" of specific example group G6B in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself have been replaced with a substituent, and a group in the "substituted cycloalkyl group" of specific example group G6B in which a hydrogen atom of a substituent has been further replaced with a substituent.

[0060] Unsubstituted cycloalkyl groups (specific example group G6A): a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0061] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0062] -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 -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 the specific example group G6. The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other. The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other. The multiple G1s in —Si(G1)(G1)(G2) are the same as or different from each other. The multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other. The multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other. The multiple G6s in -Si(G6)(G6)(G6) may be the same as or different from each other.

[0063] -O-(R 904 ) a group represented by As described herein, —O—(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) Examples include: where: 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 the specific example group G6.

[0064] -S-(R 905 ) a group represented by -S-(R 905 Specific examples (specific example group G9) of the group represented by -S(G1), -S(G2), -S(G3), and -S(G6) Examples include: where: 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 the specific example group G6.

[0065] -N(R 906 )(R 907 ) a group represented by -N(R 906 )(R 907 Specific examples (specific example group G10) of the group represented by -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) Examples include: where: 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 the specific example group G6. -The multiple G1s in N(G1)(G1) are the same as or different from each other. The multiple G2's in -N(G2)(G2) are the same as or different from each other. -The multiple G3s in N(G3)(G3) are the same as or different from each other. The multiple G6s in -N(G6)(G6) are the same as or different from each other.

[0066] "Halogen atoms" 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.

[0067] "Substituted or unsubstituted fluoroalkyl groups" The term "substituted or unsubstituted fluoroalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). Unless otherwise specified herein, the number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The term "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. The term "substituted fluoroalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the 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 are replaced with a fluorine atom.

[0068] "Substituted or unsubstituted haloalkyl groups" The term "substituted or unsubstituted haloalkyl group" as used herein refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a 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. The term "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include the examples of the above-mentioned "alkyl groups" (specific example group G3) in which one or more hydrogen atoms are replaced with halogen atoms. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

[0069] "Substituted or unsubstituted alkoxy group" A specific example of the "substituted or unsubstituted alkoxy group" described herein 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 herein, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0070] "Substituted or unsubstituted alkylthio group" A specific example of the "substituted or unsubstituted alkylthio group" described herein 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 herein, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms.

[0071] "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. 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, unless otherwise specified in this specification.

[0072] "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. 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, unless otherwise specified in this specification.

[0073] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) may be the same or different. Unless otherwise specified herein, 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.

[0074] "Substituted or unsubstituted aralkyl group" A specific example of the "substituted or unsubstituted aralkyl group" described herein is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Thus, 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 herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl groups.

[0075] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present 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.

[0076] Unless otherwise specified in the present specification, the substituted or unsubstituted heterocyclic group described herein 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 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.

[0077] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0078] [ka]

[0079] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0080] [ka]

[0081] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0082] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0083] [ka]

[0084] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0085] 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.

[0086] "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 of the "substituted or unsubstituted arylene group" (specific example group G12) 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.

[0087] "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.

[0088] "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 of the "substituted or unsubstituted alkylene group" (specific example group G14) 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.

[0089] 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).

[0090] [ka]

[0091] [ka]

[0092] In the general formulae (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-42) to (TEMP-52), * represents a bonding position.

[0093] [ka]

[0094] In the general formulae (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent. Equations Q9 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 a bonding position.

[0095] [ka]

[0096] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-63) to (TEMP-68), * represents a bonding position.

[0097] 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).

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent.

[0107] The above is the explanation of "substituents described in this specification."

[0108] - "When bonded to form a ring" In this specification, the phrase "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle, bond with each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocycle", the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring", or the case where "one or more pairs of adjacent groups do not bond with each other". In this specification, the cases where "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and "one or more groups of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "a case where they bond to form a ring") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the main skeleton is an anthracene ring, will be explained as an example.

[0109] [ka]

[0110] For example, R921 ~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," one 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 Pairs with and R 929 and R 921 It is paired with.

[0111] The above "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 At the same time, 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).

[0112] [ka]

[0113] When a "set of two or more adjacent units" forms a ring, it does not only mean that a set of two adjacent units is bonded, as in the previous example, but also that a set of three or more adjacent units is bonded. For example, R 921 and R 922 and are bonded to each other to form ring Q A and R 922 and R923 and are bonded to each other to form ring Q C and form three adjacent (R 921 , R 922 and R 923 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.

[0114] [ka]

[0115] The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. 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", respectively. A , and ring Q C is a "fused ring". A and Tamaki Q C That is, Tamaki Q A and Tamaki Q C The ring Q in the general formula (TMEP-104) is fused to form a fused ring. A If is a benzene ring, then ring Q A The ring Q in the general formula (TMEP-104) is a monocyclic ring. A If is a naphthalene ring, then ring Q A is a fused ring.

[0116] The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring. Specific examples of the aromatic hydrocarbon ring 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 the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom. Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom. The term "forming a ring" means that a ring is formed 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 are bonded to form a ring Q A is R 921 The carbon atom of the anthracene skeleton to which R is bonded 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 The carbon atom of the anthracene skeleton to which R is bonded 922 When a monocyclic unsaturated ring is formed with the carbon atom of the anthracene skeleton to which R is bonded and four carbon atoms, 921 and R 922 The ring formed by

[0117] Here, unless otherwise specified in this specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than carbon is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the monocyclic or fused ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less. Unless otherwise specified in this specification, of the "monocyclic ring" and the "fused ring", the "monocyclic ring" is preferred. Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred. Unless otherwise specified herein, a "monocyclic ring" 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 groups" "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 groups 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.

[0118] When the above-mentioned "monocyclic ring" or "fused ring" has a substituent, the substituent is, for example, the "optional substituent" described later. 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 in this specification." 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 in this specification." The above is an explanation of the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond to each other to form a substituted or unsubstituted fused ring" ("when bonded to form a ring").

[0119] Substituents in "substituted or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) includes, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atoms, cyano groups, nitro groups, a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms, where R 901 ~R 907 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. R 901 If there are two or more, there are two or more R 901 are identical to or different from each other, R 902 If there are two or more, there are two or more R 902 are identical to or different from each other, R 903 If there are two or more, there are two or more R 903are identical to or different from each other, R 904 If there are two or more, there are two or more R 904 are identical to or different from each other, R 905 If there are two or more, there are two or more R 905 are identical to or different from each other, R 906 If there are two or more, there are two or more R 906 are identical to or different from each other, R 907 If there are two or more, there are two or more R 907 are the same or different from each other.

[0120] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 50 ring carbon atoms and heterocyclic groups having 5 to 50 ring atoms.

[0121] In one embodiment, the substituents in the "substituted or unsubstituted" are: an alkyl group having 1 to 18 carbon atoms; The group is selected from the group consisting of aryl groups having 6 to 18 ring carbon atoms and heterocyclic groups having 5 to 18 ring atoms.

[0122] 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."

[0123] Unless otherwise specified in this specification, any adjacent substituents may be bonded to each other to 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 substituent that the optional substituent further has is the same as the optional substituent described above.

[0124] 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.

[0125] First Embodiment <Compound> The compound according to this embodiment is a compound represented by the following general formula (1).

[0126] [ka]

[0127] (In the general formula (1), CN is a cyano group, 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 general formula (13), R is independently hydrogen atoms, 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-(R905 ) a group represented by -N(R 906 )(R 907 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, provided that at least one R is a substituent, and the at least one R as the substituent is bonded to the benzene ring in the 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, When k is 2, multiple D 11 are identical to or different from each other, When m is 2, multiple D 12 are identical to or different from each other, When n is 2 or 3, the multiple R's are the same or different.

[0128] [ka]

[0129] [ka]

[0130] [ka]

[0131] (R in the general formula (12) 11 ~R 18 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (13) 111 ~R 118 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R1 to R8 in the general formula (11), R in the general formula (12) that 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, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 each independently represent a 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 the adjacent ring at any position; p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, the rings A are the same or different from each other, When px is 2, 3 or 4, the rings B are the same or different from each other, When py is 2, 3 or 4, the rings C are the same or different from each other; However, at least one D 11 is a group represented by the general formula (12) or (13), and this D11 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), and this D 11 wherein px and py in the general formula (13) are 2, 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 general formulae (11) to (13), * indicates the bonding position to the benzene ring in the general formula (1).

[0132] [ka]

[0133] (In the general formula (14), r is 0, 2 or 4; Multiple R 19 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (15), X1 is a sulfur atom or an oxygen atom, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring 19 teeth, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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, Multiple R 19 are the same or different from each other, Multiple X1's are the same or different, However, the group represented by the general formula (13) D 11 satisfies at least one of the following conditions (Pv1), (Pv2), and (Pv3). Condition (Pv1): When k is 2, at least one of X1 in the ring structure represented by the general formula (15) as ring B and X1 in the ring structure represented by the general formula (15) as ring C is an oxygen atom. Condition (Pv2): When k is 2, two D 11 are different from each other. Condition (Pv3): When n is 3, X1 in the ring structure represented by the general formula (15) as ring B and X1 in the ring structure represented by the general formula (15) as ring C are each independently 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 atoms, 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 907If 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 either identical or different.)

[0134] According to this embodiment, a compound with a high PLQY can be provided.

[0135] In the compound according to this embodiment, D 11 and D 12 are different groups, or when there are multiple D 11 When the groups D are different from each other, when the compound 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 12have different oxidation potentials, holes are injected into the organic layer in a stepwise manner. In addition, in the compound according to this embodiment, all of D 11 and D 12 However, when the groups have the same chemical structure except for X1, if at least one X1 is an oxygen atom, the lifetime of the organic EL device will be extended. A group in which at least one X1 is an oxygen atom has a smaller bond angle to the benzene ring shown in general formula (1) than a group in which all X1 are sulfur atoms, and therefore, it is believed that the use of the compound according to this embodiment in the organic layer will extend the lifetime.

[0136] In the compound according to this embodiment, the benzene ring of the general formula (1) to which the groups represented by the general formulae (11) to (13) are bonded is the benzene ring explicitly shown in the general formula (1), and R, D 11 and D 12 It is not a benzene ring contained in In the compounds represented by the general formulae (110), (120), (130), (126), (127), (126A), (127A), (127B), (111), (112), and (113) described below, the groups represented by the general formulae (11) to (13) are bonded to the benzene rings themselves explicitly shown in these general formulae, in the same manner as in the case of the general formula (1).

[0137] In the compound according to this embodiment, at least one D 11 is preferably a group represented by the following general formula (121), general formula (122), or general formula (131).

[0138] [ka]

[0139] [ka]

[0140] [ka]

[0141] (In the general formula (121) and the general formula (122), R 11 ~R 18 is R in the general formula (12). 11 ~R 18 is synonymous with Ring A 1、 two of ring A2, ring A3, and ring A4 are ring structures represented by the general formula (14) and the remaining two are ring structures represented by the general formula (15); In the general formula (131), R 111 ~R 118 is R in the general formula (13). 111 ~R 118 is synonymous with one of ring B1 and ring B2 is a ring structure represented by general formula (14) above, and the other of ring B1 and ring B2 is a ring structure represented by general formula (15) above, one of ring C1 and ring C2 is a ring structure represented by general formula (14) above, and the other of ring C1 and ring C2 is a ring structure represented by general formula (15) above, * in the general formula (121), general formula (122) and general formula (131) indicates the bonding position to the benzene ring in the general formula (1).

[0142] In the compound according to this embodiment, it is preferable that ring A1 and ring A3 are ring structures represented by the general formula (14) above, and ring A2 and ring A4 are ring structures represented by the general formula (15) above. In the compound according to this embodiment, it is preferable that ring B1 is a ring structure represented by general formula (14), ring B2 is a ring structure represented by general formula (15), ring C1 is a ring structure represented by general formula (14), and ring C2 is a ring structure represented by general formula (15).

[0143] In the compound according to this embodiment, at least one D 11 is preferably a group represented by the general formula (131).

[0144] In the compound according to this embodiment, at least one D 11 is preferably a group represented by the following general formula (123), general formula (124), general formula (125) or general formula (132).

[0145] [ka]

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] (In the general formula (123), the general formula (124), and the 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 is synonymous with 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 is synonymous with In the general formula (123), the general formula (124), the general formula (125) and the general formula (132), X 11 and X 12are each independently defined as X1 in the general formula (15), and * indicates the bonding position to the benzene ring in the general formula (1).

[0150] In the compound according to this embodiment, R 191 ~R 194 It is preferable that no adjacent pairs of two or more of the above are bonded to each other. In the compound according to this embodiment, R 195 ~R 198 It is preferable that no adjacent pairs of two or more of the above are bonded to each other.

[0151] In the compound according to this embodiment, X 11 is preferably a sulfur atom.

[0152] In the compounds according to this embodiment, X in the groups represented by general formula (123), general formula (124), and general formula (125) 11 is preferably a sulfur atom.

[0153] In the compound according to this embodiment, at least one D 11 is preferably a group represented by the general formula (132). In the compound according to this embodiment, X in the group represented by general formula (132) 11 In the compound according to 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.

[0154] In the compound according to this embodiment, D 12 is preferably a group represented by the general formula (11) or the general formula (12).

[0155] In the compound according to this embodiment, D 12 is preferably a group represented by the general formula (12).

[0156] In the compound according to this 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):

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] [ka]

[0163] (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 is synonymous with X1 has the same meaning as X1 in general formula (15). * in the general formulae (12A), (12B), (12C), (12D), (12E) and (12F) indicates the bonding position to the benzene ring in the general formula (1).

[0164] In the compound according to this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (110), general formula (120), or general formula (130).

[0165] [ka]

[0166] (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.)

[0167] In the compound according to this embodiment, n in the general formula (1) is preferably 2 or 3.

[0168] In the compound according to this embodiment, it is also preferable that n in the general formula (1) is 2.

[0169] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126) or (127).

[0170] [ka]

[0171] (In the general formula (126) and the general formula (127), 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 R101 ~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.

[0172] In the compound according to this embodiment, k is 2, and two D 11 One of the 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).

[0173] In the compound according to 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 formula (13) as are different from each other.

[0174] In the compound according to this embodiment, k and m are 1, and D 11 and D 12 It is also preferred that one of them is a group represented by the general formula (12) and the other is a group represented by the general formula (13).

[0175] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126A), general formula (127A), or general formula (127B).

[0176] [ka]

[0177] (In the general formula (126A), the general formula (127A) and the general formula (127B), 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 101 ~R 104 each independently has the same meaning as R in the general formula (1).

[0178] In the general formula (126A), the general formula (127A), and the general formula (127B), D 11 and D 12 are preferably different groups.

[0179] In the compound according to this embodiment, it is also preferable that n in the general formula (1) is 3.

[0180] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (111), general formula (112), or general formula (113).

[0181] [ka]

[0182] (In the general formula (111), general formula (112) and general formula (113), D 11 is D in the general formula (1). 11 is synonymous with R 101 ~R 104 each independently has the same meaning as R in the general formula (1).

[0183] In the compound according to this embodiment, any pair of two or more adjacent Rs among the plurality of Rs are not bonded to each other. In the compound according to this embodiment, R 101 ~R 104 Any pair of two or more adjacent ones of these is not bonded to each other.

[0184] In the compound according to this embodiment, it is preferable that R in the general formula (1) is 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.

[0185] In the compound according to 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.

[0186] In the compound according to 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. In the compound according to this embodiment, R 101 ~R 104 are preferably each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted heterocyclic group having 6 ring atoms.

[0187] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126C) or (127C).

[0188] [ka]

[0189] (In the general formula (126C) and the general formula (127C), 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), k is 1 or 2, m is 0 or 1, and k+m is 2.

[0190] In the compound according to this embodiment, the compound represented by the general formula (1) is also preferably represented by the following general formula (126D) or (127D).

[0191] [ka]

[0192] (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 each independently has the same meaning as R in the general formula (1).

[0193] In the compound according to this embodiment, D 11 is a group represented by the general formula (132), and D 12 is preferably a group represented by any one of the general formulae (12A) to (12F).

[0194] In the compound according to this embodiment, R 131 ~R 140 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.

[0195] In the compound according to this embodiment, any pair of two or more adjacent groups among R1 to R8 are not bonded to each other. In the compound according to this embodiment, R 11 ~R 18 It is preferable that no adjacent pairs of two or more of the above are bonded to each other. In the compound according to this embodiment, R 11~R 20 It is preferable that no adjacent pairs of two or more of the above are bonded to each other. In the compound according to this embodiment, R 111 ~R 118 It is preferable that no adjacent pairs of two or more of the above are bonded to each other.

[0196] In the compound according to this embodiment, R1 to R8 in the general formula (11) and R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 and R in the general formula (14) 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.

[0197] In the compound according to this embodiment, R1 to R8 in the general formula (11) and R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 and R in the general formula (14) 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.

[0198] In the compound according to 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.

[0199] The compound according to this embodiment is preferably a delayed fluorescent compound.

[0200] Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, 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, which normally has a low transition probability, to the excited singlet state occurs with high efficiency, resulting in the appearance of thermally activated delayed fluorescence (TADF). 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.

[0201] Generally, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0202] 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 the decay behavior (transient characteristics) of the PL emission is measured after the irradiation is stopped. PL emission from 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 extremely short, on the order of nanoseconds. Therefore, the emission from these singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long lifetime. Thus, there is a large time difference between the emission from the singlet excitons generated by the initial PL excitation and the emission from the singlet excitons generated via triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be measured.

[0203] 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 using Figure 1.

[0204] 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. 1.

[0205] The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate, in which the matrix material is doped with a doping material at a concentration of 12 mass %.

[0206] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample placed 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 the spectrometer 103, forming a two-dimensional image in the 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. By cutting out this two-dimensional image along a predetermined time axis, an emission spectrum can be obtained in which the vertical axis represents emission intensity and the horizontal axis represents wavelength. Furthermore, by cutting out the two-dimensional image along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis represents the logarithm of emission intensity and the horizontal axis represents time.

[0207] For example, a thin film sample A was prepared as described above using the following reference compound H1 as the matrix material and the following reference compound D1 as the doping material, and transient PL measurement was carried out.

[0208] [ka]

[0209] Here, the decay 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 reference compound H2 as a matrix material and the above-mentioned reference compound D1 as a doping material.

[0210] FIG. 2 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0211] [ka]

[0212] As described above, transient PL measurements can be used to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. 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 back 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 larger.

[0213] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed 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) with a wavelength that the delayed fluorescent material absorbs. Delayed luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0214] 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.

[0215] 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 lidded 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 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra according to equation (1) in Morris et al., J. Phys. Chem. 80 (1976) 969.

[0216] In this embodiment, the amount of prompt luminescence (instant luminescence) of the compound to be measured is X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. The amounts and ratios of prompt luminescence and delayed luminescence of compounds other than the compounds according to this embodiment in this specification are measured in the same manner as the amounts and ratios of prompt luminescence and delayed luminescence of the compounds according to this embodiment.

[0217] ΔST In this embodiment, the lowest excited singlet energy S1 and the energy gap T at 77 [K] 77K The difference between (S1-T 77K) is defined as ΔST.

[0218] The lowest excited singlet energy S1 (M1) of the compound according to this embodiment and the energy gap T at 77 [K] of the compound according to this embodiment 77K The difference ΔST(M1) from (M1) 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(M1) preferably satisfies the relationship of the following mathematical formula (10), (11), (12), or (13). ΔST(M1)=S1(M1)-T 77K (M1)<0.3eV …(Number 10) ΔST(M1)=S1(M1)-T 77K (M1)<0.2 eV …(Equation 11) ΔST(M1)=S1(M1)-T 77K (M1)<0.1 eV …(Equation 12) ΔST(M1)=S1(M1)-T 77K (M1)<0.01 eV…(Equation 13)

[0219] Relationship between triplet energy and energy gap at 77[K] Here, the relationship between the 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 that is usually defined. Triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77 K). A tangent line is drawn to the rising edge of 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 fluorescent 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 and excited triplet states, and although it is difficult to clearly distinguish which state the light emission originates from, it is generally considered that the triplet energy value is 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 the 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 [nm], the amount of energy calculated using the following conversion formula (F1) is the energy gap T at 77 [K]. 77K Let's say. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0220] The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side is drawn as follows: When moving along the spectral curve from the short wavelength side of the phosphorescence spectrum to the shortest maximum of 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 the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity that is 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is defined as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using an F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a cryogenic container, an excitation light source, and a light-receiving device.

[0221] Lowest excited singlet energy S1 The following method can be used to measure the lowest excited singlet energy S1 using a solution (sometimes referred to as a 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 (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long wavelength side of this absorption spectrum, and the wavelength value 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): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0222] The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the longest maximum value on the longest wavelength side of the absorption spectrum toward 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 on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum values ​​on the longest wavelength side.

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

[0224] (Specific examples of compounds according to this embodiment) Specific examples of the compound according to this 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 proton atom is represented as H or is not represented at all.

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[0314] Second Embodiment <Materials for organic electroluminescence devices> The material for an organic electroluminescence device according to this embodiment contains the compound according to the first embodiment. One aspect of the material for an organic electroluminescence device includes only the compound according to the first embodiment, and another aspect of the material for an organic electroluminescence device includes the compound according to the first embodiment and another compound different from the compound according to the first embodiment. In the material for an organic electroluminescence device of this embodiment, the compound according to the first embodiment is preferably a host material. In this case, the material for an organic electroluminescence device may contain the compound according to the first embodiment as a host material and other compounds such as a dopant material. In the material for an organic electroluminescence device of this embodiment, the compound according to the first embodiment is preferably a delayed fluorescent material.

[0315] Third Embodiment <Organic electroluminescence element> The organic EL element according to this embodiment will be described. The organic EL device according to this embodiment includes an organic layer between an anode and a cathode. The organic layer includes at least one layer made of an organic compound. Alternatively, the organic layer includes a plurality of layers made of organic compounds stacked together. The organic layer may further include an inorganic compound.

[0316] In the organic EL device according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL device 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.

[0317] 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.

[0318] 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.

[0319] In one embodiment, the light-emitting layer may include a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material). In one embodiment, the light-emitting layer preferably does not contain heavy metal complexes or phosphorescent rare earth metal complexes, such as iridium complexes, osmium complexes, and platinum complexes.

[0320] FIG. 3 shows a schematic configuration of an example of the 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.

[0321] (light-emitting layer) In the organic EL device of this embodiment, the emitting layer contains compound M1 and compound M2. Compound M2 in the 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 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.

[0322] (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.

[0323] (Compound M1) Compound M1 is preferably a fluorescent compound, and compound M1 is preferably a compound that does not exhibit delayed fluorescence. The compound M1 of this embodiment is not a phosphorescent metal complex. The compound M1 is preferably not a heavy metal complex. Furthermore, the compound M1 is preferably not a metal complex.

[0324] 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.

[0325] The compound M1 is preferably a compound that emits light with a maximum peak wavelength of 400 nm or more and 700 nm or less. In this specification, the maximum peak wavelength is the wavelength at which the compound to be measured is 10 -6 moles / liter over 10 -5 This is the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of 1 / 4 mole / liter or less. The measurement device used is a spectrofluorometer (F-7000, manufactured by Hitachi High-Tech Science Corporation).

[0326] Compound M1 preferably exhibits red or green emission. In this specification, red light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 600 nm or more and 660 nm or less. When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and even more preferably 610 nm or more and 630 nm or less. In this specification, green light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 500 nm or more and 560 nm or less. When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 540 nm or less. In this specification, blue light emission refers to light emission whose maximum peak wavelength in the fluorescence spectrum is in the range of 430 nm or more and 480 nm or less. 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.

[0327] The maximum peak wavelength of light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum 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).

[0328] (Compound represented by general formula (D1)) In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D1).

[0329] [ka]

[0330] (In the general formula (D1), Ring A, ring B, ring D, ring E and ring F each independently represent a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of substituted or unsubstituted heterocycles 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 is Ring B, when present, is a nitrogen atom or a carbon atom; When ring B does not exist, it is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2), or Si(Rb3)(Rb4), Zc is a nitrogen atom or a carbon atom, Zd is Ring D, when present, is a nitrogen atom or a carbon atom; When ring D is absent, it is an oxygen atom, a sulfur atom, or NRd. Ze is, Ring E, if present, is a nitrogen atom or a carbon atom; When ring E is absent, it is an oxygen atom, a sulfur atom, or NRe; Zf is a nitrogen atom or a carbon atom; Zg is Ring F, when present, is a nitrogen atom or a carbon atom; When ring F does not exist, it is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2), or Si(Rg3)(Rg4), 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, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4 and Rh each independently represent a hydrogen atom or a substituent; Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4 and Rh as substituents 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 ) a group represented by -N(R 916 )(R 917 ) is a group represented by However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0331] (In the compound M1, R 911 ~R 917 are each independently, hydrogen atoms, 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, 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 either identical or different.)

[0332] 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.

[0333] In this specification, examples of the heterocycle include a ring structure (heterocycle) 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 the aryl ring include ring structures (aryl rings) obtained by removing a bond from the "aryl group" exemplified above in "Substituents described in this specification." These aryl rings may have a substituent or may be unsubstituted.

[0334] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D11).

[0335] [ka]

[0336] (In the general formula (D11), Ring A, ring D and ring E each independently represent a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of substituted or unsubstituted heterocycles having 5 to 30 ring atoms, Za is a nitrogen atom or a carbon atom, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2), or Si(Rb3)(Rb4), 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(Rg1)(Rg2), or Si(Rg3)(Rg4), 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, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4, and Rh each independently have the same meaning as Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4, and Rh in general formula (D1).

[0337] In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (D16).

[0338] [ka]

[0339] (In the general formula (D16), R 161 ~R 177 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 161 ~R 177 are each independently, hydrogen atoms, 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 )(R 963 ) 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 group represented by halogen atoms, cyano group, 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, R 961 ~R 969 are each independently, hydrogen atoms, 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 either identical or different.)

[0340] (Compound represented by general formula (D10)) In the organic EL device 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):

[0341] [ka]

[0342] (In the general formula (D10), X1 is CR1 or a nitrogen atom; X2 is CR2 or a nitrogen atom; X3 is CR3 or a nitrogen atom; X4 is CR4 or a nitrogen atom; X5 is CR5 or a nitrogen atom; X6 is CR6 or a nitrogen atom; X7 is CR7, a nitrogen atom, or a carbon atom bonded to X8 by a single bond; X8 is CR8, a nitrogen atom, or a carbon atom bonded to X7 by a single bond; X9 is CR9 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, Y is NR Y1 , oxygen atom, sulfur atom, C(R Y2 )(R Y3 ) or Si(R Y4 )(R Y5 ) and R1 to R6 and R9 to R 11 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、 R4 and R Y1 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 3、 R4 and R Y1 At least one hydrogen atom in a single ring or a fused ring formed by bonding together one or more pairs of adjacent two or more of an alkyl group having 1 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms; a heterocyclic group having 5 to 50 ring atoms, -O-(R 920 ), and -N(R 921 )(R 922 or is unsubstituted with at least one substituent selected from the group consisting of groups represented by at least one hydrogen atom in the substituent is either unsubstituted or substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 carbon atoms; R to R do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted fused ring. 11 , and R 12 ~R 13 , and R Q are each independently, hydrogen atoms, 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 915 ) a group represented by -N(R 916 )(R 917 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 918 a group represented by -COOR 919 a group represented by halogen atoms, cyano group, 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, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring Y1 teeth, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R Y2 and R Y3 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring Y2 and R Y3 , and R Y4 and R Y5 are each independently, hydrogen atoms, halogen atoms, 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, hydrogen atoms, 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, 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 either identical or different.)

[0343] In the compound represented by the general formula (D10), when X7 is a carbon atom bonded to X8 via a single bond and X8 is a carbon atom bonded to X7 via a single bond, for example, the general formula (D10) is represented by the following general formula (D10A).

[0344] [ka]

[0345] (In the general formula (D10A), X1 to X6, X9 to X 12 , Y, Q, and R 13 are each independently as defined in general formula (D10).

[0346] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12).

[0347] [ka]

[0348] (In the general formula (D12), R1 to R 13 , R Y1 , R Q are each independently as defined in general formula (D10).

[0349] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D12A).

[0350] [ka]

[0351] (In the general formula (D12A), R1 to R6, R9 to R 13 , R Y1 , R Q are each independently as defined in general formula (D10).

[0352] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13).

[0353] [ka]

[0354] (In the general formula (D13), R1 to R3, R5 to R 13 and R Q are each independently as defined in general formula (D10), R x1 ~R x4 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring X1 ~R x4 are each independently, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 938 a group represented by -COOR 939 a group represented by halogen atoms, cyano group, 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, R 931 ~R 939 are each independently, hydrogen atoms, 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, R 934 If there are multiple R 934 are the same or different from each other, R 935 If there are multiple R 935 are the same or different from each other, R 936 If there are multiple R 936 are the same or different from each other, R 937 If there are multiple R 937 are the same or different from each other, R 938 If there are multiple R 938 are the same or different from each other, R 939If there are multiple R 939 are either identical or different.)

[0355] In the general formula (D13), for example, a pair of R5 and R6 may be bonded to each other to form a substituted or unsubstituted monocycle, or may be bonded to each other to form a substituted or unsubstituted fused ring, or may not be bonded to each other.

[0356] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D13A).

[0357] [ka]

[0358] (In the general formula (D13A), R1 to R3, R5 to R6, R9 to 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).

[0359] In the compound represented by the general formula (D10), R1 to R 13 and R Q are each independently, hydrogen atoms, 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 is also preferred.

[0360] In the compound represented by the general formula (D10), R1 to R 13 and R Q are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms is also preferred.

[0361] In the compound represented by the general formula (D10), R1 to R3, R5 to R 13 , R Q and R x1 ~R x4 are each independently, hydrogen atoms, 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 is also preferred.

[0362] In the compound represented by the general formula (D10), R1 to R3, R5 to R 13 , R Q and R x1 ~R x4 are each independently, hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms is also preferred.

[0363] In the compound represented by the general formula (D10), R1 to R 13 , R Q and R x1 ~R x4 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[0364] In the compound represented by the general formula (D10), R1 to R 13 , R Q and R x1 ~R x4 are each independently, hydrogen atoms, 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 It is preferably a substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[0365] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D14).

[0366] [ka]

[0367] (In the general formula (D14), R2, R 6、 R 13、 R Q and R x2 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0368] The compound represented by the general formula (D10) is also preferably represented by the following general formula (D15).

[0369] [ka]

[0370] (In the general formula (D15), R2, R 6、 R 13、 R Q and R x2 are each independently, hydrogen atoms, 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 It is a substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[0371] In the compound represented by the general formula (D10), R 13 and R Q are each independently, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or A substituted or unsubstituted dibenzofuranyl group is preferred.

[0372] In the compound represented by the general formula (D10), R6 and R x2 are preferably each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0373] (Compound represented by general formula (20)) In this embodiment, the compound M1 is also preferably a compound represented by the following general formula (20).

[0374] [ka]

[0375] 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; 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 R25 and R 25 and R 26 any one or more pairs of the groups are bonded to each other to form a ring, Y and R as substituents 21 ~R 26 are 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; halogen atoms, carboxyl group, a substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, nitro group, cyano group, a substituted or unsubstituted silyl group, and is selected from the group consisting of substituted or unsubstituted siloxanyl groups; Z 21 and Z 22 are each independently a substituent, or Z 21 and Z 22 are bonded to each other to form a ring, Z as a substituent 21and Z 22 are each independently, halogen atoms, 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 The aryloxy group is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

[0376] (Production method of compound M1) The 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 compound.

[0377] (Specific example 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.

[0378] [ka]

[0379] [ka]

[0380] [ka]

[0381] [ka]

[0382] [ka]

[0383] [ka]

[0384] [ka]

[0385] [ka]

[0386] [ka]

[0387] [ka]

[0388] <Relationship between Compound M1 and Compound M2 in the Light-Emitting Layer> In the organic EL device of this embodiment, it is preferable that the lowest excited singlet energy S1(M2) of the compound M2 and the lowest excited singlet energy S1(M1) of the compound M1 satisfy the relationship of the following mathematical formula (Mathematical Formula 1). S1(M2)>S1(M1)…(Math 1)

[0389] 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 value is larger than (M1). That is, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 5) is satisfied. T 77K(M2)>T 77K (M1) ... (Number 5)

[0390] 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.

[0391] TADF mechanism Fig. 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 Fig. 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 FIG. 4 represents a Förster type 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-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 via this TADF mechanism.

[0392] 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.

[0393] The main peak wavelength of light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage is applied to the organic EL element so that the spectral radiance is as follows: In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured and this is defined as the main peak wavelength (unit: nm).

[0394] Thickness of the light-emitting layer The thickness of the light-emitting layer in the organic EL device 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, the formation of the light-emitting layer and the adjustment of chromaticity tend to be easy, and when the thickness of the light-emitting layer is 50 nm or less, an increase in driving voltage is easily suppressed.

[0395] Compound content in the light-emitting layer The content of the compound M2 and the compound M1 in the light-emitting layer is preferably, for example, in the following range. 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. In this embodiment, the light-emitting layer may contain materials other than the compound M2 and the compound M1. 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.

[0396] (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 include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. An inorganic vapor deposition film can also be used.

[0397] (anode) The anode formed on the substrate is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or higher). Specific examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium 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), and nitrides of metal materials (e.g., titanium nitride). These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% by mass or more and 10% by mass or less 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 or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide relative to indium oxide. Alternatively, the films may be formed by vacuum deposition, coating, inkjet printing, spin coating, or the like. 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 easily injects holes regardless of the work function of the anode, so materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used. Materials with low work functions, such as elements belonging to Group 1 or 2 of the periodic table, can also be used. These include 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 metals (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these metals. Vacuum deposition and sputtering methods can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating methods and inkjet methods can be used.

[0398] (cathode) The cathode is preferably made of a metal, alloy, electrically conductive compound, or mixture thereof, each 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), 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 a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used. By providing an electron injection layer, the cathode can be formed using various conductive materials, regardless of the magnitude of the work function, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, etc. These conductive materials can be deposited by sputtering, inkjet printing, spin coating, or the like.

[0399] (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. In addition, materials 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, Other examples include aromatic amine compounds such as 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, polymeric compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples 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). Acid-added polymeric compounds such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[0400] (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), Aromatic amine 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), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. The substances mentioned here are mainly 10 -6 cm 2 It is a material with a hole mobility of 1 / Vs or more. The hole transport layer may be made of carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used. However, other substances may be used as long as they have a higher hole-transporting property than an electron-transporting property. The layer containing the substance 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 substances are stacked.

[0401] (electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties. Examples of materials that can be used for the electron transport layer include: 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. Specifically, examples of low-molecular-weight organic compounds that can be used include metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ. 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: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances mentioned here are mainly from the 10 -6 cm 2The electron-transporting layer is a substance having an electron mobility of 1 / Vs or higher. Note that any substance other than those mentioned above may be used as the electron-transporting layer as long as it has 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. The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0402] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF), and lithium oxide (LiOx), or compounds thereof can be used. Alternatively, a substance having electron transport properties containing an alkali metal, alkaline earth metal, or a compound thereof, such as Alq containing magnesium (Mg), can be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, the electron injection layer may be formed using a composite material obtained by mixing an organic compound and an electron donor (donor). 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, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance 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. Alkali metal oxides and alkaline earth metal oxides are also 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 (TTF) can also be used.

[0403] (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 known methods can be used, such as dry film formation methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet film formation methods such as spin coating, dipping, flow coating, and inkjet deposition.

[0404] (film thickness) The 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 thickness is too thin, defects such as pinholes are likely to occur, whereas if the thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a thickness in the range of several nm to 1 μm is usually preferred.

[0405] The organic EL device 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 lowest excited singlet energy smaller than that of compound M2. Since the organic EL device according to the third embodiment contains the compound according to the first embodiment (compound M2) having a high PLQY, the third embodiment can provide a high-performance organic EL device that can achieve at least one of high efficiency and long life.

[0406] Fourth Embodiment The configuration of an organic EL element according to the 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.

[0407] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the emitting layer further contains a compound M3, but is otherwise similar to the organic EL device according to the third embodiment. That is, in the fourth embodiment, the emitting layer contains compound M3, compound M2, and compound M1. In this embodiment, compound M2 is preferably a host material, and compound M1 is preferably a dopant material.

[0408] (Compound M3) The compound M3 of this 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.

[0409] 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.

[0410] In this embodiment, the compound M3 is preferably a compound represented by the following general formula (3X) or (3Y).

[0411] (Compound represented by general formula (3X)) The compound M3 is also preferably a compound represented by the following general formula (3X).

[0412] [ka]

[0413] (In the general formula (3X), A3 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, L3 is 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 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 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 pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, 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, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 It is a group represented by the following general formula (3A):

[0414] [ka]

[0415] (In the general formula (3A), R B teeth, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 B When there are multiple R B are the same or different from each other, L 31 teeth, 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 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 trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the divalent group; L 32 teeth, 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, n3 is 1, 2, 3, 4 or 5; L 31 is a single bond, n3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in the general formula (3X), L 32 When there are multiple L 32 are the same or different from each other, * represents the bonding site to the carbon atom of the six-membered ring in the general formula (3X).

[0416] (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 936 and R 937 are each independently, hydrogen atoms, 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 R933 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 either identical or different.)

[0417] The compound M3 is also preferably a compound represented by any one of the following general formulas (31) to (36).

[0418] [ka]

[0419] [ka]

[0420] [ka]

[0421] (In the general formulas (31) to (36), A3 and L3 are defined as A3 and L3 in the general formula (3X), respectively. R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, X 31 is a sulfur atom, an oxygen atom, and NR352 or CR 353 R 354 and R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does 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 equivalent to

[0422] In compound M3, R 352 teeth, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0423] In compound M3, R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring 353 and R 354 are 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0424] In compound M3, X 31 is preferably a sulfur atom or an oxygen atom.

[0425] In the compound M3, A3 is preferably a group represented by any one of the following general formulae (A31) to (A37).

[0426] [ka]

[0427] [ka]

[0428] (In the general formulae (A31) to (A37), Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 300 , and R 333 R each independently 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 In the general formulae (A31) to (A37), * indicates the bonding position of the compound M3 to L3.

[0429] In the compound M3, A3 is also preferably a group represented by the general formula (A34), (A35) or (A37).

[0430] The compound M3 is also preferably a compound represented by any one of the following general formulas (311) to (316).

[0431] [ka]

[0432] [ka]

[0433] [ka]

[0434] [ka]

[0435] [ka]

[0436] [ka]

[0437] (In the general formulae (311) to (316), L3 has the same meaning as L3 in general formula (3X). Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 300 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 341 ~R 350 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0438] The compound M3 is also preferably a compound represented by the following general formula (321).

[0439] [ka]

[0440] (In the general formula (321), L3 has the same meaning as L3 in general formula (3X). R 31 ~R 38 , and R 301 ~R 308 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0441] In the compound M3, L3 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0442] In the compound M3, L3 is preferably a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[0443] In the compound M3, L3 is preferably a group represented by the following general formula (317).

[0444] [ka]

[0445] (In the general formula (317), R 310 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 and * each independently indicates a bonding position.)

[0446] In the compound M3, it is also preferable that L3 contains a divalent group represented by the following general formula (318) or general formula (319). In the compound M3, L3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0447] The compound M3 is also preferably a compound represented by the following general formula (322) or general formula (323).

[0448] [ka]

[0449] [ka]

[0450] (In the general formula (322) and the general formula (323), L 31 teeth, 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 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 and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, However, L 31 includes a divalent group represented by the following general formula (318) or general formula (319): R 31 ~R 38 , R 300 , and R 321 ~R 328 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0451] [ka]

[0452] (In the general formula (319), Multiple R 304 a pair of adjacent two of these is bonded to each other to form a ring represented by the general formula (320), In the general formula (320), 1* and 2* each independently represent R 304 indicates the bonding position with the ring to which it is attached, R in the general formula (318) 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 R each independently 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 In the general formulae (318) to (320), * indicates the bonding position.

[0453] In compound M3, L3 or L 31The group represented by the general formula (319) as above is, for example, a group represented by the following general formula (319A).

[0454] [ka]

[0455] (In the general formula (319A), R 303 , R 304 and R 305 R each independently 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 the bonding position.)

[0456] 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).

[0457] The compound M3 is also preferably a compound represented by the following general formula (324).

[0458] [ka]

[0459] (In the general formula (324), R 31 ~R 38 , R 300 , and R 302 R each independently does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 38 is equivalent to

[0460] 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, hydrogen atoms, 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), R in the general formula (3A) B teeth, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0461] 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, hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or A group represented by the general formula (3A), R in the general formula (3A) B is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0462] 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, hydrogen atoms, a substituted or unsubstituted phenyl group, or A group represented by the general formula (3A), R in the general formula (3A) B is preferably a substituted or unsubstituted phenyl group.

[0463] 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.

[0464] (Compound represented by general formula (3Y)) The compound M3 is also preferably a compound represented by the following general formula (3Y).

[0465] [ka]

[0466] (In the general formula (3Y), Y 31 ~Y 36 are each independently CR or a nitrogen atom, However, Y 31 ~Y 36 two or more of which are nitrogen atoms, When a plurality of R3's are present, one or more pairs of adjacent two or more of the plurality of R3's are joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R3 that does not form a substituted or unsubstituted monocycle and does not form a substituted or unsubstituted fused ring each independently represents hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R 931 )(R 932 ) a group represented by -Ge(R 933 )(R 934 )(R 935 ) a group represented by -B(R 936 )(R 937 ) a group represented by 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 It is a group represented by the following general formula (3B):

[0467] [ka]

[0468] (In the general formula (3B), R B , L 31 , L 32 and n3 each independently represent R in the general formula (3A). B , L 31 , L 32 and n3, R B When there are multiple R B are the same or different from each other, L 31 is a single bond, n3 is 1, and L 32 is bonded to a carbon atom of the six-membered ring in general formula (3Y), L 32 When there are multiple L 32 are the same or different from each other, * represents the bonding site to the carbon atom of the six-membered ring in general formula (3Y).

[0469] The compound M3 preferably does not contain a pyridine ring in the molecule.

[0470] The compound M3 is also preferably a compound represented by the following general formula (31a) or general formula (32a).

[0471] [ka]

[0472] (In the general formula (32a), R 35 ~R 37 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (31a) 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 each independently has the same meaning as R3 in general formula (3Y).

[0473] The compound M3 is also preferably a compound represented by the general formula (31a).

[0474] In the general formula (3Y), each R3 is independently hydrogen atoms, 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 (3B) is preferred.

[0475] In the general formula (3Y), each R3 is independently hydrogen atoms, 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 the general formula (3B) is preferred.

[0476] 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).

[0477] [ka]

[0478] [ka]

[0479] (In the general formulae (B31) to (B38), Multiple R 300 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 331 and R 332 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring 300 , R 331 and R332 , and R 333 are each independently, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, 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, In the general formulae (B31) to (B38), * indicates the bonding position to other atoms in the molecule of the compound M3.

[0480] [ka]

[0481] [ka]

[0482] [ka]

[0483] (In the general formulae (B39) to (B44), R 341 ~R 350 One or more pairs of adjacent pairs of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, However, R 341 ~R 351 at least one of the following represents a bonding position to another atom in the molecule of the compound M3; X 31 is a sulfur atom, an oxygen atom, and NR 352 or CR 353 R 354 and R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R that is not a bonding position with another atom in the molecule of the compound M3, does not form the substituted or unsubstituted monocyclic ring, and does 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, independently of each other, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms; -C(=O)R 908 a group represented by -COOR 909 a group represented by halogen atoms, cyano group, nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or It is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0484] 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).

[0485] In the general formula (3Y), Y 31 ~Y 36 At least one of the following is CR3: At least one R3 is a group represented by the general formula (3B), and R B is preferably any one of the groups represented by the general formulae (B31) to (B44).

[0486] In the general formula (3Y), Y 31 ~Y 36 At least one of the following is CR3: At least one R3 is a group represented by the general formula (3B), and R Bis preferably any one of the groups represented by the general formulae (B38) to (B44).

[0487] In the general formulas (3A) and (3B), L 31 teeth, 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, tetravalent group, pentavalent group, or hexavalent group derived from the divalent group; L 32 are each independently, a single bond, or It is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0488] In the general formulas (3A) and (3B), L 31 teeth, a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, n3 is 1, L 32 teeth, a single bond, or It is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[0489] In the general formulas (3A) and (3B), L 31 teeth, single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or 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; n3 is 1, L32 teeth, single bond, a substituted or unsubstituted phenylene group, or A substituted or unsubstituted biphenylene group is preferred.

[0490] In the compounds represented by the general formulas (3X) and (3Y), R 352 teeth, 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0491] In the compounds represented by the general formulas (3X) and (3Y), R 353 and R 354 The set consisting of joined together to form a substituted or unsubstituted monocyclic ring, or linked together to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring 353 and R 354 are 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 It is preferably a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0492] In the compounds represented by the general formulas (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 ) a group represented by 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)2R 938 a group represented by halogen atoms, cyano group, nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are each independently, hydrogen atoms, an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted aryl group having 6 to 25 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0493] In the compounds represented by the general formulas (3X) and (3Y), the substituent in the case of "substituted or unsubstituted" is halogen atoms, an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted aryl group having 6 to 25 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0494] In the compounds represented by the general formulas (3X) and (3Y), the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 10 carbon atoms; an unsubstituted aryl group having 6 to 12 ring carbon atoms, or It is preferably an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0495] 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.

[0496] (Production method of compound M3) The compound M3 according to this embodiment can be produced by a known method.

[0497] (Specific example 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.

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[0538] <Relationship between Compound M3, Compound M2, and Compound M1 in the Light-Emitting Layer> In the organic EL device of this embodiment, it is preferable that the lowest excited singlet energy S1(M2) of the compound M2 and the lowest excited singlet energy S1(M1) of the compound M1 satisfy the relationship of the following mathematical formula (Mathematical Formula 1). S1(M2)>S1(M1)…(Math 1)

[0539] In the organic EL device of this embodiment, the lowest excited singlet energy S1(M2) of the compound M2 and the lowest excited singlet energy S1(M3) of the compound M3 preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M2)…(Math 2)

[0540] Furthermore, the lowest excited singlet energy S1(M3) of the compound M3 is preferably greater than the lowest excited singlet energy S1(M1) of the compound M1. S1(M3)>S1(M1)…(Math 2A)

[0541] It is preferable that the lowest excited singlet energy S1(M3) of compound M3, the lowest excited singlet energy S1(M2) of compound M2, and the lowest excited singlet energy S1(M1) of compound M1 satisfy the relationship of the following mathematical formula (Mathematical Formula 2B). S1(M3)>S1(M2)>S1(M1)…(Number 2B)

[0542] 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).

[0543] 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).

[0544] In the organic EL device of this embodiment, the compounds M3, M2, and M1 preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 5A). T 77K (M3)>T 77K (M2)>T 77K (M1) …(Number 5A)

[0545] 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 element of this embodiment preferably emits red or green light.

[0546] Compound content in the light-emitting layer The contents of the compounds M3, M2, and 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 compounds M3, M2, and M1 in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than compounds M3, M2, and M1. The light-emitting layer may contain only one type of compound M3 or two or more types thereof. 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.

[0547] FIG. 5 shows 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 via this TADF mechanism.

[0548] The organic EL device according to the fourth embodiment contains, in the light-emitting layer, the compound of the first embodiment as compound M2, compound M1 having a lowest excited singlet energy smaller than that of compound M2, and compound M3 having a lowest excited singlet energy larger than that of compound M2. Since the organic EL device according to the fourth embodiment contains the compound of the first embodiment (compound M2) having a high PLQY, the fourth embodiment can provide a high-performance organic EL device that can achieve at least one of high efficiency and long life.

[0549] Fifth Embodiment The configuration of an organic EL element according to the 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.

[0550] The organic EL device according to the fifth embodiment differs from the organic EL device according to the third or fourth embodiment in that the light-emitting layer contains compound M2 and compound M3 but does not contain compound M1, and is otherwise similar to the organic EL device according to the third or fourth embodiment. That is, in the fifth embodiment, the light-emitting layer contains the compound M2 and the 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 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.

[0551] <Compound M2> Compound M2 is a compound according to the first embodiment. The compound M2 is preferably a delayed fluorescent compound.

[0552] <Compound M3> The compound M3 is the same as the compound M3 described in the fourth embodiment.

[0553] <Relationship between Compound M2 and Compound M3 in the Light-Emitting Layer> In the organic EL device of this embodiment, the lowest excited singlet energy S1(M2) of the compound M2 and the lowest excited singlet energy S1(M3) of the compound M3 preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M2)…(Math 2)

[0554] Energy gap T of compound M3 at 77[K] 77K (M3) is the energy gap T of compound M2 at 77[K] 77K It is preferable that it is larger than (M2).

[0555] FIG. 6 is a diagram for explaining the principle of light emission according to an embodiment of the present invention. In Figure 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 Figure 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 the following (i) or (ii) can be observed. (i) When the light-emitting layer does not contain a fluorescent dopant having a lowest excited singlet state S1 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 (fluorescent compound M1 in the third or fourth embodiment) whose lowest excited singlet state S1 is smaller than the lowest excited singlet state S1 (M2) of compound M2, light emission from the fluorescent dopant can be observed. In the organic EL element of this embodiment, the luminescence shown in (i) above can be observed. In the organic EL element of the third or fourth embodiment, the luminescence shown in (ii) above can be observed.

[0556] Compound content in the light-emitting layer The content of the compound M2 and the compound M3 in the light-emitting layer is preferably, for example, in the following range. 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 the compound M2 and the compound M3 in the light-emitting layer is 100% by mass. 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 M3 or two or more types thereof.

[0557] The organic EL device according to the fifth embodiment contains, in the light-emitting layer, the compound according to the first embodiment as compound M2 and compound M3 having a minimum excited singlet energy greater than that of compound M2. Since the organic EL device according to the fifth embodiment contains the compound according to the first embodiment (compound M2) having a high PLQY, the fifth embodiment can provide a high-performance organic EL device that can achieve at least one of high efficiency and long life.

[0558] Sixth Embodiment [Electronic equipment] The 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.

[0559] [Modifications of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0560] 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 due to electron transition from a triplet excited state directly to the ground state. Furthermore, when the organic EL element has a plurality of 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 type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0561] Furthermore, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking 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 blocking layer is disposed adjacent to the cathode side of the light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) located closer to the cathode than the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. Furthermore, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) located closer to the anode than the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers closer to the electrode than the barrier layer (e.g., electron transport layer and hole transport layer). The light-emitting layer and the barrier layer are preferably in contact with each other.

[0562] 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. [Example]

[0563] 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.

[0564] <Compound> 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 1-5, 2-1 to 2-11, 3-1 to 3-24, and 4-1 to 4-25 are shown below.

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[0573] The structures of the compounds used in the production of the organic EL devices according to Comparative Examples 1-1, 2-1, 3-1, and 4-1 are shown below.

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[0575] The structures of other compounds used in the production of organic EL devices according to Examples 1-1 to 1-5, 2-1 to 2-11, 3-1 to 3-24, 4-1 to 4-25, Comparative Example 1-1, Comparative Example 2-1, Comparative Example 3-1 and Comparative Example 4-1 are shown below.

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[0579] <Fabrication of Organic EL Devices (1)> An organic EL device was fabricated and evaluated as follows.

[0580] (Example 1-1) A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode lines was mounted on a substrate holder of 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, thereby forming a hole injection layer with a 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, the compound HT-1 was vapor-deposited on this hole injection layer to form a first hole transport layer having a thickness of 110 nm. Next, the compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, the compound CBP was vapor-deposited on this second hole transport layer to form an electron blocking layer with a thickness of 5 nm. Next, on this electron blocking layer, a compound M3-1 as compound M3 and a compound A-1 as compound M2 were co-deposited to form an emitting layer having a thickness of 25 nm. The concentration of compound M3-1 in the emitting layer was 75 mass %, and the concentration of compound A-1 was 25 mass %. Next, the compound ET-1 was vapor-deposited on this light-emitting layer to form a hole-blocking layer having a thickness of 5 nm. Next, the compound ET-2 was vapor-deposited on this hole-blocking layer to form an electron-transporting layer with a thickness of 50 nm. Next, LiF was vapor-deposited on this electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injection layer to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 1-1 is shown in outline below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(110) / HT-2(5) / CBP(5) / M3-1:A-1(25,75%:25%) / ET-1(5) / ET-2(50) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in parentheses, the percentages (97%:3%) indicate the ratios (mass%) of Compound HT-1 and Compound HA in the hole injection layer, and the percentages (75%:25%) indicate the ratios (mass%) of Compound M3-1 and Compound A-1 in the light-emitting layer. The same notation is used hereinafter.

[0581] (Examples 1-2 to 1-5) The organic EL devices of Examples 1-2 to 1-5 were each produced in the same manner as in Example 1-1, except that the compound A-1 used as the compound M2 in the light-emitting layer of Example 1-1 was changed to the compound M2 shown in Table 1.

[0582] (Comparative Example 1-1) The organic EL device of Comparative Example 1-1 was produced in the same manner as in Example 1-1, except that the compound A-1 used as the compound M2 in the emitting layer of Example 1-1 was changed to the compound M2 shown in Table 1.

[0583] Example 2-1 The organic EL device 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, a compound A-1 as compound M2, and a compound GD as compound M1 were co-deposited to form an emitting layer with a thickness of 25 nm, and the concentration of compound M3-1 in the emitting layer was set to 74 mass %, the concentration of compound A-1 was set to 25 mass %, and the concentration of compound GD was set to 1 mass %. The device configuration of the organic EL device according to Example 2-1 is shown in outline below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(110) / HT-2(5) / CBP(5) / M3-1:A-1:GD(25,74%:25%:1%) / ET-1(5) / ET-2(50) / LiF(1) / Al(80)

[0584] (Examples 2-2 to 2-11) The organic EL devices of Examples 2-2 to 2-11 were each produced in the same manner as in Example 2-1, except that the compound A-1 used as the compound M2 in the emitting layer of Example 2-1 was changed to the compound M2 shown in Table 2.

[0585] (Comparative Example 2-1) The organic EL device of Comparative Example 2-1 was produced in the same manner as in Example 2-1, except that the compound A-1 used as the compound M2 in the light-emitting layer of Example 2-1 was changed to the compound M2 shown in Table 2.

[0586] <Evaluation of Organic EL Devices (1)> The fabricated organic EL devices were evaluated as follows. The evaluation results are shown in Tables 1 and 2. Although the comparative compound Ref-1 used in Comparative Examples 1-1 and 2-1 does not correspond to compound M2, it is listed in the same column as compound M2 for convenience. The evaluation results of the compounds used in the emitting layer of each example are also shown in Tables 1 and 2.

[0587] (Life span LT95) The organic EL device was fabricated with a current density of 50 mA / cm 2 A voltage was applied so that the voltage was such that the luminance reached 95% of the initial luminance (LT95 (unit: hours)), and the lifespan was measured as the time it took for the luminance to reach 95% of the initial luminance. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). Table 1 shows the "LT95 (relative value)" (unit: %). The "LT95 (relative value)" shown in Table 1 was calculated based on the measured LT95 value of each example (Examples 1-1 to 1-5 and Comparative Example 1-1) and the following formula (Math 1X). LT95 (relative value) = (LT95 of each example / LT95 of comparative example 1-1) × 100 (equation 1X)

[0588] (External quantum efficiency EQE) The organic EL device was fabricated with a current density of 10.00 mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the value was 0.05 was measured using a spectroradiometer CS-2000 (Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated, assuming that Lambertian radiation was used. Table 2 shows the "EQE (relative value)" (unit: %). The "EQE (relative value)" shown in Table 2 was calculated based on the measured EQE value of each example (Examples 2-1 to 2-11 and Comparative Example 2-1) and the following formula (Mathematical formula 2X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) × 100 (2X)

[0589] (Maximum peak wavelength λ p and emission half-width FWHM) The current density of the organic EL element is 10.00mA / 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 calculated. FWHM is an abbreviation for Full Width at Half Maximum.

[0590] (CIE1931 chromaticity) The current density of the organic EL element is 10.00mA / 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.).

[0591] [Table 1]

[0592] [Table 2]

[0593] <Fabrication of Organic EL Devices (2)> Example 3-1 A 25mm x 75mm x 1.1mm thick glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the cleaned transparent electrode lines was mounted on a substrate holder of a vacuum deposition apparatus, and first, compound HT-3 and compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The concentration of compound HT-3 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, the compound HT-3 was vapor-deposited on this hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, the compound HT-4 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 30 nm. Next, on the second hole transport layer, compound M3-2 as compound M3 and compound A-1 as compound M2 were co-deposited to form an emitting layer having a thickness of 25 nm. The concentration of compound M3-2 in the emitting layer was 75 mass %, and the concentration of compound A-1 was 25 mass %. Next, the compound ET-3 was vapor-deposited on this light-emitting layer to form a hole-blocking layer with a thickness of 5 nm. Next, compound ET-4 and compound Liq were co-deposited on the hole blocking layer to form an electron transport layer with a thickness of 50 nm. The concentration of compound ET-4 in the electron transport layer was 50 mass %, and the concentration of compound Liq was 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was vapor deposited on this electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injection layer to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 3-1 is shown in outline below. ITO(130) / HT-3:HA(10,97%:3%) / HT-3(90) / HT-4(30) / M3-2:A-1(25,75%:25%) / ET-3(5) / ET-4:Liq(50,50%:50%) / Yb(1) / Al(80)

[0594] (Examples 3-2 to 3-20) The organic EL devices of Examples 3-2 to 3-20 were each produced in the same manner as in Example 3-1, except that the compound A-1 used as the compound M2 in the emitting layer of Example 3-1 was changed to the compound M2 shown in Table 3.

[0595] (Examples 3-21 to 3-24) The organic EL devices of Examples 3-21 to 3-24 were each produced in the same manner as in Example 3-1, except that the compound A-1 used as the compound M2 in the emitting layer of Example 3-1 was changed to the compound M2 shown in Table 4.

[0596] (Comparative Example 3-1) The organic EL device of Comparative Example 3-1 was prepared in the same manner as in Example 3-1, except that the compound A-1 used as the compound M2 in the light-emitting layer of Example 3-1 was changed to the compound M2 shown in Table 3.

[0597] Example 4-1 The organic EL device of Example 4-1 was fabricated in the same manner as in Example 3-1, except that instead of the emitting layer of Example 3-1, a compound M3-2 as compound M3, a compound A-40 as compound M2, and a compound GD2 as compound M1 were co-deposited to form an emitting layer with a thickness of 25 nm, and the concentration of compound M3-2 in the emitting layer was set to 74.4 mass%, the concentration of compound A-40 was set to 25 mass%, and the concentration of compound GD2 was set to 0.6 mass%. The device configuration of the organic EL device according to Example 4-1 is shown in outline below. ITO(130) / HT-3:HA(10,97%:3%) / HT-3(90) / HT-4(30) / M3-2:A-40:GD2(25,74.4%:25%:0.6%) / ET-3(5) / ET-4:Liq(50,50%:50%) / Yb(1) / Al(80)

[0598] (Example 4-2) The organic EL device of Example 4-2 was produced in the same manner as in Example 4-1, except that the compound A-40 used as the compound M2 in the light-emitting layer of Example 4-1 was changed to the compound M2 shown in Table 5.

[0599] (Examples 4-3 to 4-25) The organic EL devices of Examples 4-3 to 4-25 were prepared in the same manner as in Example 4-1, except that compound A-40 used as compound M2 in the emitting layer of Example 4-1 was changed to compound M2 shown in Tables 6 and 7.

[0600] (Comparative Example 4-1) The organic EL device of Comparative Example 4-1 was prepared in the same manner as in Example 4-1, except that the compound A-40 used as the compound M2 in the light-emitting layer of Example 4-1 was replaced with the compound M2 shown in Table 5.

[0601] <Evaluation of Organic EL Devices (2)> The organic EL devices fabricated in Examples 3-1 to 3-24, Examples 4-1 to 4-25, Comparative Example 3-1, and Comparative Example 4-1 were evaluated for the items shown in Tables 3, 4, 5, 6, and 7 by the methods described in <Evaluation of Organic EL Devices (1)>. The evaluation results are shown in Tables 3, 4, 5, 6, and 7.

[0602] The "EQE (relative value)" shown in Tables 3 and 4 was calculated based on the measured EQE values ​​of each example (Examples 3-1 to 3-24 and Comparative Example 3-1) and the following formula (Formula 3X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 3-1) × 100 (3X)

[0603] The "EQE (relative value)" shown in Tables 5, 6 and 7 was calculated based on the measured EQE values ​​of each example (Examples 4-1 to 4-25 and Comparative Example 4-1) and the following formula (Formula 4X). EQE (relative value) = (EQE of each example / EQE of Comparative Example 4-1) × 100 (4X)

[0604] [Table 3]

[0605] [Table 4]

[0606] [Table 5]

[0607] [Table 6]

[0608] [Table 7]

[0609] The organic EL devices according to the examples using the compound represented by general formula (1) exhibited improved device performance compared to the organic EL devices according to the comparative examples.

[0610] <Compound evaluation> The compounds used in the production of the examples and the following compounds were evaluated.

[0611] [ka]

[0612] [ka]

[0613] (Fluorescence quantum yield (PLQY) measurement) A compound to be measured was dissolved in toluene to a concentration of 5 μmol / L to prepare a toluene solution. After that, the prepared solution was bubbled with nitrogen for 5 minutes and sealed to prevent the inclusion of outside air. The prepared toluene solution of the compound to be measured was subjected to PLQY measurement using an absolute PL (photoluminescence) quantum yield measurement device, Quantaurus-QY (manufactured by Hamamatsu Photonics KK).

[0614] (Maximum peak wavelength of the compound) The maximum peak wavelength λ of the 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 of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ.

[0615] (Delayed fluorescence of the compound) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 1. Compound A-1 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 produce an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of both spectra 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-1, there are two types of emission: prompt emission (immediate emission) that is observed immediately from the excited state, and delayed emission (delayed emission) that is not observed immediately after the excitation but is observed later. In this example, delayed fluorescence emission means that the amount of delayed emission (delayed emission) is 5% or more of the amount of prompt emission (immediate emission). Specifically, when the amount of prompt emission (immediate emission) is X P and the amount of delay light emission is X D When X D / X P This means 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). 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. Compounds A-2 to A-42 and comparative compound Ref-1 were also measured in the same manner as compound A-1. It was confirmed that the amount of delay luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (prompt luminescence) for Compounds A-1 to A-42 and Comparative Compound Ref-1. Specifically, for Compounds A-1 to A-42 and Comparative Compound Ref-1, X D / X P The value was 0.05 or higher.

[0616] (Lowest excited singlet energy S1) The lowest excited singlet energy S1 of the compound to be measured was measured by the solution method described above.

[0617] (energy gap T 77K and ΔST) Energy gap T of the compound to be measured 77K is the energy gap T 77K The measurement was carried out by the following method. For compounds A-1 to A-42 and comparative compound Ref-1, the energy gap T 77K ΔST was confirmed from the value of and the value of the lowest excited singlet energy S1 above. "<0.01" in the table indicates that ΔST is less than 0.01 eV.

[0618] [Table 8]

[0619] <Synthesis example>

[0620] (Synthesis of Compound A-1) The synthesis method of compound A-1 is described below.

[0621] [ka]

[0622] 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 (yield 58%) by GC-MS (Gas Chromatograph Mass Spectrometry). NMP is an abbreviation for N-methyl-2-pyrrolidone.

[0623] 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 to yield 12 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate Mb (yield 31%).

[0624] [ka]

[0625] Under a nitrogen atmosphere, a 500 mL three-neck flask was charged with 3-bromodibenzothiophene (26.3 g, 100 mmol), chlorotrimethylsilane (33 g, 300 mmol), and THF (150 mL). 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, followed by the dropwise addition of iodine monochloride (49 g, 300 mmol) at 0 °C, and the mixture was stirred at 40 °C for 6 hours. The mixture was cooled to room temperature, saturated aqueous sodium hydrogen sulfite solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to give intermediate Mc (28 g, 72 mmol, 72% yield).

[0626] 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. The mixture was heated and stirred at 60 °C for 8 hours, 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 Md by GC-MS analysis (86% yield).

[0627] Under a nitrogen atmosphere, intermediate Md (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. The mixture was 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 Me by ASAP-MS analysis (86% yield). ASAP-MS stands for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0628] [ka]

[0629] Under a nitrogen atmosphere, intermediate Mb (3.0 g, 9.48 mmol), intermediate Me (3.6 g, 9.5 mmol), potassium carbonate (2.6 g, 19 mmol), and 50 mL of DMF 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 resulting yellow solid was identified as intermediate Mf by ASAP-MS analysis (yield 64%). DMF is an abbreviation for N,N-dimethylformamide.

[0630] Under a nitrogen atmosphere, 12H-[1]Benzothieno[2,3-a]carbazole (0.809 g, 2.96 mmol), sodium hydride (40% by weight oil content) (0.14 g, 3.55 mmol), and 15 mL of DMF were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 min. Next, intermediate Mf (2 g, 2.96 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 h. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.6 g of a yellow solid. The resulting yellow solid was identified as compound A-1 by ASAP-MS analysis (yield 58%).

[0631] (Synthesis of Compound A-2) The synthesis method of compound A-2 is described below.

[0632] [ka]

[0633] Under a nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (0.971 g, 3.55 mmol), sodium hydride (40% by weight oil content) (0.14 g, 3.55 mmol), and 15 mL of DMF were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 min. Next, intermediate Mf (2 g, 2.96 mmol) was added to the reaction mixture and stirred at room temperature for 2 h. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.2 g of a yellow solid. The resulting yellow solid was identified as compound A-2 by ASAP-MS analysis (yield 80%).

[0634] (Synthesis of Compound A-3) The synthesis method of compound A-3 is described below.

[0635] [ka]

[0636] Under a nitrogen atmosphere, intermediate Mc (20 g, 51.4 mmol), dibenzo[b,d]furan-4-amine (9.42 g, 51.4 mmol), Pd2dba3 (0.706 g, 0.771 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(triphenyl-l-phosphane) (1.130 g, 1.542 mmol), NaOt-Bu (7.41 g, 77 mmol), and toluene (171 mL) were added to a 500 mL three-neck flask. The mixture was heated and stirred at 60 °C for 8 hours, then cooled to room temperature (25 °C). The precipitated solid was collected by filtration and washed with 200 mL of toluene to obtain 19 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate Mg (yield 83%).

[0637] Under a nitrogen atmosphere, intermediate Mg (15 g, 33.8 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.430 g, 1.013 mmol), palladium(II) acetate (0.114 g, 0.506 mmol), potassium carbonate (9.80 g, 70.9 mmol), and DMAc (169 mL) were added to a 300 mL three-neck flask. The mixture was stirred at 140 °C for 6 hours and then cooled to room temperature (25 °C). The precipitated solid was collected by filtration and washed with acetone to obtain 8.4 g of a white solid. The resulting white solid was identified as intermediate Mh by ASAP-MS analysis (yield 69%).

[0638] [ka]

[0639] Under a nitrogen atmosphere, intermediate Mh (0.532 g, 1.465 mmol), sodium hydride (40% by mass oil content) (0.064 g, 1.598 mmol), and 15 mL of DMF were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 minutes. Next, intermediate Mf (0.9 g, 1.332 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 0.7 g of a yellow solid. The resulting yellow solid was identified as compound A-3 by ASAP-MS analysis (yield 52%).

[0640] (Synthesis of Compound A-4) The synthesis method of compound A-4 is explained below.

[0641] [ka]

[0642] Under a nitrogen atmosphere, intermediate Mb (3 g, 9.48 mmol), tripotassium phosphate (4.03 g, 18.97 mmol), intermediate Mh (3.45 g, 9.48 mmol), and DMF (47.4 ml) were placed in a 200 ml three-neck flask and stirred at 60°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 4.9 g of a yellow solid. ASAP-MS analysis identified the product as intermediate Mi (yield 78%).

[0643] Under a nitrogen atmosphere, 12H-[1]Benzothieno[2,3-a]carbazole (0.912 g, 3.33 mmol), sodium hydride (40% by mass oil content) (0.133 g, 3.33 mmol), and DMF (15.16 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 minutes. Intermediate Mi (2 g, 3.03 mmol) was then added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.1 g of a yellow solid. The resulting yellow solid was identified as compound A-4 by ASAP-MS analysis (yield 40%).

[0644] (Synthesis of Compound A-5) The synthesis method of compound A-5 is described below.

[0645] [ka]

[0646] Under a nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (0.646 g, 2.365 mmol), sodium hydride (40% by weight oil content) (0.095 g, 2.365 mmol), and DMF (19.70 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 min. Intermediate Mi (1.3 g, 1.970 mmol) was then added to the reaction mixture and stirred at room temperature for 2 h. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.4 g of a yellow solid. The resulting yellow solid was identified as compound A-5 by ASAP-MS analysis (78% yield).

[0647] (Synthesis of Compound A-6) The synthesis method of compound A-6 is explained below.

[0648] [ka]

[0649] Under a nitrogen atmosphere, intermediate Mh (1 g, 3.16 mmol), sodium hydride (40% by mass oil content) (0.278 g, 6.96 mmol), and DMF (15.8 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 minutes. Next, intermediate Mb (2.53 g, 6.96 mmol) was added to the reaction mixture, and the mixture was stirred at 100 °C for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.1 g of a yellow solid. The resulting yellow solid was identified as compound A-6 by ASAP-MS analysis (yield 66%).

[0650] (Synthesis of Compound A-7) The synthesis method of compound A-7 is described below.

[0651] [ka]

[0652] Under a nitrogen atmosphere, 1,3-dibromo-2,5-difluorobenzene (35 g, 129 mmol), cyanocopper (25.4 g, 283 mmol), and NMP (257 mL) were placed in a 1 L three-neck flask and stirred at 150 °C for 5 hours. 500 mL 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 and recrystallized from ethanol to yield 12 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate Mj (yield 57%).

[0653] Under a nitrogen atmosphere, 2,5-difluoroisophthalonitrile (6.3 g, 38.4 mmol), potassium carbonate (11.67 g, 84 mmol), diacetoxypalladium (0.431 g, 1.919 mmol), tricyclohexylphosphonium tetrafluoroborate (2.120 g, 5.76 mmol), bromobenzene (12.05 mL, 115 mmol), 2-ethylhexanoic acid (2.460 mL, 15.36 mmol), and xylene (80 mL) were placed in a 300 mL three-neck flask and stirred at 100 °C for 5 hours. 100 mL of methylene chloride was added to the reaction solution, which was then passed through Celite. The methylene chloride in the resulting solution was concentrated, and the precipitated solid was filtered. The resulting solid was purified by silica gel column chromatography to yield 5.2 g of a white solid. The resulting white solid was identified as intermediate Mk by GC-MS analysis (yield 43%).

[0654] [ka]

[0655] Under a nitrogen atmosphere, intermediate Mk (1.5 g, 4.74 mmol), intermediate Me (1.8 g, 4.74 mmol), tripotassium phosphate (3.02 g, 14.23 mmol), and DMF (23.71 ml) were placed in a 200 mL three-neck flask and stirred at 60 °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 2 g of a yellow solid. The resulting yellow solid was identified as intermediate ML by ASAP-MS analysis (yield 62%).

[0656] Under a nitrogen atmosphere, 12H-[1]Benzothieno[2,3-a]carbazole (0.922 g, 3.37 mmol), sodium hydride (40% by mass oil content) (0.124 g, 3.09 mmol), and DMF (14.06 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 min. Intermediate ML (1.9 g, 2.81 mmol) was then added to the reaction mixture and stirred at 70 °C for 8 h. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.8 g of a yellow solid. The resulting yellow solid was identified as compound A-7 by ASAP-MS analysis (yield 69%).

[0657] (Synthesis of Compound A-8) The synthesis method of compound A-8 is described below.

[0658] [ka]

[0659] Under a nitrogen atmosphere, intermediate Mk (2.4 g, 7.59 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (2.074 g, 7.59 mmol), tripotassium phosphate (4.83 g, 22.76 mmol), and DMF (37.9 ml) were placed in a 200 ml three-neck flask and stirred at 50 °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 g of a yellow solid. The resulting yellow solid was identified as intermediate M-k2 by ASAP-MS analysis (yield 93%).

[0660] Under a nitrogen atmosphere, intermediate Me (1.332 g, 3.51 mmol), sodium hydride (40% by mass oil content) (0.154 g, 3.86 mmol), and DMF (14.06 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 minutes. Next, intermediate M-k2 (2 g, 3.51 mmol) was added to the reaction mixture, and the mixture was stirred at 170 °C for 14 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 0.98 g of a yellow solid. The resulting yellow solid was identified as compound A-8 by ASAP-MS analysis (yield 30%).

[0661] (Synthesis of Compound A-9) The synthesis method of compound A-9 is described below.

[0662] [ka]

[0663] Under a nitrogen atmosphere, 9H-carbazole (2.313 g, 13.84 mmol), sodium hydride (40% by mass oil content) (0.488 g, 12.21 mmol), and DMF (40.7 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 minutes. Intermediate Mf (5.5 g, 8.14 mmol) was then 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 6.3 g of a yellow solid. The resulting yellow solid was identified as compound A-9 by ASAP-MS analysis (yield 94%).

[0664] (Synthesis of Compound A-10) The synthesis method of compound A-10 is explained below.

[0665] [ka]

[0666] Under a nitrogen atmosphere, 12H-benzofuro[2,3-a]carbazole (1.466 g, 5.70 mmol), sodium hydride (40% by weight oil content) (0.228 g, 5.70 mmol), and DMF (17.26 mL) were placed in a 100 mL three-neck flask and stirred at 0 °C for 30 min. Next, intermediate Mf (3.5 g, 5.18 mmol) was added to the reaction mixture and stirred at room temperature for 2 h. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.7 g of a yellow solid. The resulting yellow solid was identified as compound A-10 by ASAP-MS analysis (yield 78%).

[0667] (Synthesis of Compound A-11) The synthesis method of compound A-11 is explained below.

[0668] [ka]

[0669] Under a nitrogen atmosphere, 5-bromo-1,3-difluoro-2-iodobenzene (4.00 g, 12.54 mmol), o-tolylboronic acid (3.75 g, 27.60 mmol), potassium carbonate (10.40 g, 75.00 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium (0.266 g, 0.376 mmol), DME (66.9 mL), and ion-exchanged water (16.7 mL) were placed in a 200 mL three-neck flask and stirred at 90 °C for 5 hours. 100 mL of ion-exchanged water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine. The washed organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mm (3.50 g, 11.9 mmol, yield 95%).

[0670] [ka]

[0671] Under a nitrogen atmosphere, 2,2,6,6-Tetramethylpiperidine (2.428 ml, 14.27 mmol) and THF (20 ml) were added to a 200 ml three-neck flask. The contents of the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and 14.3 ml of n-butyllithium (1.6 M, hexane solution) was added dropwise. The mixture was stirred at 0 °C for 20 minutes, cooled to -78 °C, and then a solution of intermediate Mm (3.5 g, 11.89 mmol) in 20 ml of THF was added and stirred for 15 minutes. After stirring, bromine (1.218 ml, 23.78 mmol) was added to the solution, which was then returned to room temperature and stirred for 20 minutes. After stirring, saturated aqueous sodium bisulfite solution (100 mL) was added to the solution, and the organic layer was extracted with hexane. 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 on a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure on a rotary evaporator. The resulting liquid was dissolved in 20 mL of THF to prepare a solution. This solution was added dropwise to the prepared LiTMP THF solution at -78 °C and stirred for 15 minutes. Bromine (0.77 mL, 15.0 mmol) was added to the solution, and the mixture was returned to room temperature and stirred for 20 minutes. Saturated aqueous sodium bisulfite solution (100 mL) was added to the stirred solution, and the organic layer was extracted with hexane. 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 on a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mn (2.75 g, 6.07 mmol, 51% yield). LiTMP is the abbreviation for lithium 2,2,6,6-tetramethylpiperidide.

[0672] Under a nitrogen atmosphere, intermediate Mn (2.75 g, 6.07 mmol), cyanocopper (1.31 g, 14.6 mmol), and DMF (66 mL) were placed in a 1 L three-neck flask and stirred at 150 °C for 5 hours. 500 mL 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 1.0 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate Mo (yield 44%).

[0673] [ka]

[0674] Under a nitrogen atmosphere, intermediate Mo (1.0 g, 2.90 mmol), cesium fluoride (1.32 g, 8.71 mmol), intermediate Me (1.1 g, 2.90 mmol), and DMF (10.0 ml) were placed in a 100 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. The collected solid was purified by silica gel column chromatography to obtain 1.5 g of a yellow solid. The resulting yellow solid was identified as intermediate Mp by ASAP-MS analysis (yield 75%).

[0675] Under a nitrogen atmosphere, intermediate Mp (1.54 g, 2.20 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (0.718 g, 2.63 mmol), cesium fluoride (1.00 g, 6.56 mmol), and DMF (11.0 mL) were placed in a 100 mL recovery flask and stirred at 50 °C for 1 hour. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.62 g of a yellow solid. The resulting yellow solid was identified as compound A-11 by ASAP-MS analysis (77% yield).

[0676] (Synthesis of Compound A-12) The synthesis method of compound A-12 is described below.

[0677] [ka]

[0678] Under a nitrogen atmosphere, 5-bromo-1,3-difluoro-2-iodobenzene (5.00 g, 15.68 mmol), o-tolylboronic acid (2.13 g, 15.68 mmol), potassium phosphate (9.98 g, 47.00 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.128 g, 0.157 mmol), DME (84.1 mL), and ion-exchanged water (20.9 mL) were placed in a 200 mL three-neck flask and stirred at room temperature for 1 hour. 100 mL of ion-exchanged water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine. The washed organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mq (3.47 g, 12.3 mmol, yield 78%).

[0679] Under a nitrogen atmosphere, a 200 mL three-neck flask was charged with intermediate Mq (3.47 g, 12.3 mmol), phenylboronic acid (2.26 g, 18.54 mmol), potassium phosphate (7.87 g, 37.1 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium (0.101 g, 0.124 mmol), DME (65.9 mL), and ion-exchanged water (16.5 mL) and stirred at 60 °C for 2 hours. 100 mL of ion-exchanged water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine. The washed organic layer was dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mr (3.15 g, 11.2 mmol, 90% yield).

[0680] [ka]

[0681] Under a nitrogen atmosphere, 2,2,6,6-Tetramethylpiperidine (3.19 ml, 18.73 mmol) and THF (40 ml) were added to a 200 ml three-neck flask. The contents of the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and 18.7 ml of n-butyllithium (1.6 M, hexane solution) was added dropwise. The mixture was stirred at 0 °C for 20 minutes, cooled to -78 °C, and then a solution of intermediate Mr (3.15 g, 11.2 mmol) in 20 ml of THF was added and stirred for 15 minutes. After stirring, bromine (1.28 ml, 25.0 mmol) was added to the solution, returned to room temperature, and stirred for 20 minutes. After stirring, saturated aqueous sodium bisulfite solution (100 ml) was added to the solution, and the organic layer was extracted with hexane. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated on a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure using a rotary evaporator. The resulting liquid was dissolved in 20 mL of THF to prepare a solution. This solution was added dropwise to the prepared LiTMP THF solution at -78 °C and stirred for 15 minutes. Bromine (1.28 mL, 25.0 mmol) was added, and the mixture was allowed to return to room temperature and stirred for 20 minutes. After stirring, saturated aqueous sodium bisulfite solution (100 mL) was added to the solution, and the organic layer was extracted with hexane. 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 using silica gel column chromatography to obtain intermediate Ms (4.16 g, 9.51 mmol, 85% yield).

[0682] Under a nitrogen atmosphere, intermediate Ms (4.16 g, 9.51 mmol), cyanocopper (2.20 g, 24.6 mmol), and DMF (112 mL) were placed in a 1 L three-neck flask and stirred at 160 °C for 10 hours. 500 mL 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 1.57 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate Mt (yield 42%).

[0683] [ka]

[0684] Under a nitrogen atmosphere, intermediate Mt (1.0 g, 3.03 mmol), cesium fluoride (1.38 g, 9.08 mmol), intermediate Me (1.15 g, 3.03 mmol), and DMF (15.0 mL) were placed in a 100 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. The collected solid was purified by silica gel column chromatography to obtain 1.55 g of a yellow solid. The resulting yellow solid was identified as intermediate Mu by ASAP-MS analysis (74% yield).

[0685] Under a nitrogen atmosphere, intermediate Mu (1.55 g, 2.25 mmol), 12H-[1]Benzothieno[2,3-a]carbazole (0.737 g, 2.70 mmol), cesium fluoride (1.02 g, 6.74 mmol), and DMF (11.0 mL) were placed in a 100 mL recovery flask and stirred at 50 °C for 1 hour. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.6 g of a yellow solid. The resulting yellow solid was identified as compound A-12 by ASAP-MS analysis (yield 75%).

[0686] (Synthesis of Compound A-13) The synthesis method of compound A-13 is described below.

[0687] [ka]

[0688] Under a nitrogen atmosphere, intermediate Ma (20 g, 122 mmol), diacetoxypalladium (1.368 g, 6.09 mmol), tricyclohexylphosphine (5.13 g, 18.28 mmol), potassium carbonate (42.1 g, 305 mmol), and xylene (244 mL) were added to a 500 mL three-neck flask and stirred at room temperature for 30 minutes. Then, 2-ethylhexanoic acid (7.81 mL, 48.7 mmol) and 1-bromo-4-(tert-butyl)benzene (45.7 mL, 268 mmol) were added and stirred at 100 °C for 5 hours. The reaction solution was returned to room temperature, 200 mL of methylene chloride was added, and the mixture was 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 to yield 36 g of a white solid. The resulting white solid was identified as intermediate Mv by GC-MS analysis (yield 69%).

[0689] [ka]

[0690] Under a nitrogen atmosphere, intermediate Mv (7.2 g, 16.80 mmol), intermediate Me (6.38 g, 16.80 mmol), potassium carbonate (4.64 g, 33.6 mmol), and DMF (56.0 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 12 g of a yellow solid. The obtained yellow solid was identified as intermediate Mw by ASAP-MS analysis (yield 91%).

[0691] Under a nitrogen atmosphere, a 100 mL three-neck flask was charged with the intermediate Mw (3 g, 3.81 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (1.249 g, 4.57 mmol), potassium carbonate (0.789 g, 5.71 mmol), and DMF (12.69 mL) and stirred at 120 °C for 4 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.5 g of a yellow solid. The resulting yellow solid was identified as compound A-13 by ASAP-MS analysis (yield 88%).

[0692] (Synthesis of Compound A-14) The synthesis method of compound A-14 is explained below.

[0693] [ka]

[0694] Under a nitrogen atmosphere, 5H-pyrido[3,2-b]indole (0.684 g, 4.07 mmol), potassium carbonate (0.614 g, 4.44 mmol), intermediate Mf (2.5 g, 3.70 mmol), and DMF (12.33 mL) were placed in a 100 mL three-neck flask and stirred at 140 °C for 4 hours. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.1 g of a yellow solid. The resulting yellow solid was identified as compound A-14 by ASAP-MS analysis (yield 88%).

[0695] (Synthesis of Compound A-15) The synthesis method of compound A-15 is described below.

[0696] [ka]

[0697] Under a nitrogen atmosphere, 4-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 Mf (2.5 g, 3.70 mmol) was added at 0 °C, and the mixture was slowly warmed to room temperature and stirred at room temperature for an additional 1 hour. After stirring, 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-15 by ASAP-MS analysis (yield 72%).

[0698] (Synthesis of Compound A-16) The synthesis method of compound A-16 is explained below.

[0699] [ka]

[0700] 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 Mf (2.5 g, 3.70 mmol) was added at 0 °C, and the mixture was slowly heated to room temperature and stirred for an additional 1 hour at room temperature. 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%).

[0701] (Synthesis of Compound A-17) The synthesis method of compound A-17 is described below.

[0702] [ka]

[0703] Under a nitrogen atmosphere, a 1000 mL three-neck flask was charged with Boronic acid, B-(6-phenyl-4-dibenzothienyl)- (40 g, 132 mmol), sulfamic acid (29.7 g, 263 mmol), acetonitrile (658 mL), and sodium hydroxide (1 M) (881 mL, 881 mmol) 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. GC-MS analysis identified the resulting white solid as intermediate M-1 (yield 48%).

[0704] 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. The mixture was heated and stirred at 100 °C for 8 hours, then cooled to room temperature (25 °C). After cooling, the resulting solution was purified by silica gel chromatography to yield 25 g of a white solid. The resulting white solid was identified as intermediate M-2 by ASAP-MS analysis (77% yield).

[0705] 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 added to a 200 mL three-neck flask. The mixture was 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 methanol to obtain 7.2 g of a white solid. The resulting white solid was identified as intermediate M-3 by ASAP-MS analysis (73% yield).

[0706] [ka]

[0707] Under a nitrogen atmosphere, intermediate M-3 (4.0 g, 8.8 mmol), cesium fluoride (2.7 g, 17.6 mmol), intermediate Mb (2.9 g, 9.22 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 5.5 g of a yellow solid. The resulting yellow solid was identified as intermediate M-4 by ASAP-MS analysis (yield 83%).

[0708] [ka]

[0709] Under a nitrogen atmosphere, 9H-carbazole (1.0 g, 45.98 mmol), sodium hydride (40% by mass oil content) (0.24 g, 5.98 mmol), and DMF (40 ml) were placed in a 100 ml three-neck flask and stirred at 0°C for 1 hour. Next, intermediate M-4 (3.0 g, 3.99 mmol) was added at 0°C, and the mixture was slowly warmed to room temperature and stirred at room temperature for an additional 1 hour. After stirring, 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 2.9 g of a yellow solid. The resulting yellow solid was identified as compound A-17 by ASAP-MS analysis (yield 81%).

[0710] (Synthesis of Compound A-18) The synthesis method of compound A-18 is described below.

[0711] [ka]

[0712] Under a nitrogen atmosphere, a 1000 mL three-neck flask was charged with Boronic acid, B-(6-phenyl-4-dibenzothienyl)- (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) and stirred at 50 °C for 6 hours. 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%).

[0713] 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 reaction solution. After the 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 the reaction was completed, 100 mL of 10% hydrochloric acid was added dropwise. After the 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%).

[0714] 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. The resulting solution was concentrated. The resulting solid was purified by silica gel column chromatography to yield 28 g of a white solid. The resulting white solid was identified as intermediate M-7 by ASAP-MS analysis (72% yield).

[0715] [ka]

[0716] Under a nitrogen atmosphere, a 100 mL three-neck flask was charged with 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). The mixture was heated and stirred at 60 °C for 8 hours, then cooled to room temperature (25 °C). The resulting solution was purified by silica gel chromatography to yield 5 g of a white solid. The resulting white solid was identified as intermediate M-8 by ASAP-MS analysis (70% yield).

[0717] 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 added to a 500 mL three-neck flask. The mixture was 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 methanol to obtain 18 g of a white solid. The resulting white solid was identified as intermediate M-9 by ASAP-MS analysis (77% yield).

[0718] [ka]

[0719] Under a nitrogen atmosphere, intermediate M-9 (18 g, 8.8 mmol), cesium fluoride (7.7 g, 51 mmol), intermediate Mb (11 g, 35.5 mmol), and DMF (230 ml) were placed in a 500 ml recovery flask and stirred at room temperature for 12 hours. 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 20 g of a yellow solid. The resulting yellow solid was identified as intermediate M-10 by ASAP-MS analysis (yield 71%).

[0720] [ka]

[0721] Under a nitrogen atmosphere, 2-phenyl-9h-carbazole (1.4 g, 5.80 mmol), sodium hydride (40% by mass oil content) (0.23 g, 5.80 mmol), and DMF (50 ml) were placed in a 100 ml three-neck flask and stirred at 0 °C for 1 hour. Next, intermediate M-10 (4.0 g, 4.83 mmol) was added at 0 °C, and the mixture was slowly warmed to room temperature and stirred for an additional hour at room temperature. 30 ml of ion-exchanged water was added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to obtain 2.9 g of a yellow solid. The resulting yellow solid was identified as compound A-18 by ASAP-MS analysis (yield 89%).

[0722] (Synthesis of Compound A-19) The synthesis method of compound A-19 is described below.

[0723] [ka]

[0724] Under a nitrogen atmosphere, 4-bromo-9H-carbazole (66.6 g, 271 mmol), (2-chlorophenyl)boronic acid (44.4 g, 284 mmol), potassium carbonate (56.1 g, 406 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.1 g, 1.35 mmol), THF (200 mL), and ion-exchanged water (65 mL) were placed in a 500 mL three-neck flask and stirred at room temperature for 8 hours. After stirring, the reaction solution was concentrated. 100 mL of ion-exchanged water was added to the concentrated reaction solution, and the organic layer was extracted with toluene. 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. The compound obtained after removing the solvent under reduced pressure was purified by silica gel column chromatography to obtain a white solid. The resulting white solid was identified as intermediate M-11 using ASAP-MS (yield 96%).

[0725] Under a nitrogen atmosphere, intermediate M-11 (6 g, 21.6 mmol), diazabicycloundecene (DBU) (9.67 mL, 64.8 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.552 g, 1.080 mmol), and N,N-dimethylacetamide (DMAc) (22 mL) were added to a 100 mL three-neck flask and refluxed with stirring for 20 hours. After the reaction was complete, 100 mL of ion-exchanged water was added, and the organic layer was extracted with toluene. The extracted organic layer was washed with water and brine, dried over sodium sulfate, and 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 to yield 2.8 g of a white solid. The resulting white solid was identified as intermediate M-12 using ASAP-MS (54% yield).

[0726] [ka]

[0727] Under a nitrogen atmosphere, intermediate M-12 (1.29 g, 5.33 mmol), sodium hydride (40% by mass oil content) (0.21 g, 5.33 mmol), and DMF (45 ml) were placed in a 200 mL three-neck flask and stirred at 0 °C for 1 hour. Next, intermediate Mf (3.0 g, 4.44 mmol) was added at 0 °C, and the mixture was slowly warmed to room temperature and stirred at room temperature for an additional 1 hour. 50 ml of ethyl acetate was added to the reaction mixture, and the solid was filtered. The resulting solid was purified by silica gel column chromatography to obtain 3.4 g of a yellow solid. The resulting yellow solid was identified as compound A-19 by ASAP-MS analysis (yield 85%).

[0728] (Synthesis of Compound A-20) The synthesis method of compound A-20 is described below.

[0729] [ka]

[0730] Under a nitrogen atmosphere, a 200 mL three-neck flask was charged with 2-bromo-1,3-difluoro-5-iodobenzene (7.00 g, 21.95 mmol), [1,1'-biphenyl]-2-ylboronic acid (4.78 g, 24.15 mmol), potassium phosphate (13.98 g, 65.90 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.359 g, 0.439 mmol), DME (117 mL), and ion-exchanged water (29 mL) and stirred at room temperature for 8 hours. After concentrating the reaction solution, 20 mL of ion-exchanged water was added. The organic layer was extracted with dichloromethane. 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. After removing the solvent under reduced pressure, the resulting compound was purified by silica gel column chromatography to obtain intermediate T-1 (6.97 g, 20.05 mmol, yield 91%).

[0731] Under a nitrogen atmosphere, a 200 mL three-neck flask was charged with intermediate T-1 (6.97 g, 20.05 mmol), phenylboronic acid (2.95 g, 24.23 mmol), potassium carbonate (12.86 g, 60.6 mmol), 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.330 g, 0.404 mmol), DME (108 mL), and ion-exchanged water (26.9 mL) and stirred at 60 °C for 4 hours. After concentrating the reaction solution, 20 mL of ion-exchanged water was added. The organic layer was extracted with dichloromethane. 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. The compound obtained after removing the solvent under reduced pressure was purified by silica gel column chromatography to obtain intermediate T-2 (6.23 g, 18.1 mmol, 90% yield).

[0732] [ka]

[0733] Under a nitrogen atmosphere, 2,2,6,6-Tetramethylpiperidine (6.16 ml, 36.2 mmol) and THF (60 ml) were added to a 200 ml three-neck flask. The contents of the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and 22.6 ml of n-butyllithium (1.6 M, hexane solution) was added dropwise. The mixture was stirred at 0 °C for 20 minutes and cooled to -78 °C. A solution of intermediate T-2 (6.2 g, 18.1 mmol) in 60 ml of THF was added to the three-neck flask and stirred for 20 minutes. Bromine (2.32 ml, 45.0 mmol) was added to the reaction solution, and the mixture was allowed to return to room temperature and stirred for 20 minutes. Saturated aqueous sodium bisulfite solution (100 ml) was added to the reaction solution, and the organic layer was extracted with ethyl acetate. 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 on a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure using a rotary evaporator. The resulting liquid was dissolved in 60 mL of THF and added dropwise to a reconstituted THF solution of LiTMP at -78 °C and stirred for 15 minutes. Bromine (2.32 mL, 45.0 mmol) was added to the reaction solution, and the mixture was allowed to return to room temperature and stirred for 20 minutes. A saturated aqueous solution of sodium bisulfite (100 mL) was added to the reaction solution, and the organic layer was extracted with hexane. The extracted organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated using a rotary evaporator. The compound obtained after concentration was purified using silica gel column chromatography to obtain intermediate T-3 (8.1 g, 16.2 mmol, 89% yield).

[0734] Under a nitrogen atmosphere, intermediate T-3 (8.1 g, 16.2 mmol), cyanocopper (3.19 g, 35.6 mmol), and NMP (162 mL) were placed in a 1 L three-neck flask and stirred at 180 °C for 10 hours. 500 mL of methylene chloride was added to the reaction mixture, which was then filtered through Celite. The filtrate was concentrated using an evaporator. The resulting solid was purified by silica gel chromatography to yield 1.74 g of a white solid. GC-MS analysis identified the resulting white solid as intermediate T-4 (yield 27%).

[0735] [ka]

[0736] Under a nitrogen atmosphere, intermediate T-4 (1.95 g, 4.97 mmol), cesium fluoride (2.27 g, 14.9 mmol), intermediate Me (1.89 g, 4.97 mmol), and DMF (49.7 ml) were placed in a 100 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. The collected solid was purified by silica gel column chromatography to obtain 2.9 g of a yellow solid. The resulting yellow solid was identified as intermediate T-5 (78% yield) by ASAP-MS analysis.

[0737] Under a nitrogen atmosphere, intermediate T-5 (1.5 g, 2.00 mmol), 9H-carbazole (0.567 g, 3.39 mmol), cesium fluoride (0.909 g, 5.98 mmol), and DMF (20 mL) were placed in a 100 mL recovery flask and stirred at 80 °C for 4 hours. 200 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by column chromatography to obtain 0.9 g of a yellow solid. The resulting yellow solid was identified as compound A-20 by ASAP-MS analysis (yield 50%).

[0738] (Synthesis of Compound A-21) The synthesis method of compound A-21 is described below.

[0739] [ka]

[0740] Under a nitrogen atmosphere, 3-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 Mf (2.5 g, 3.70 mmol) was added to the reaction solution at 0°C, and the mixture was slowly heated to room temperature and stirred for an additional 1 hour at room temperature. 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 2.7 g of a yellow solid. The resulting yellow solid was identified as compound A-21 by ASAP-MS analysis (yield 81%).

[0741] (Synthesis of Compound A-22) The synthesis method of compound A-22 is described below.

[0742] [ka]

[0743] Under a nitrogen atmosphere, 1-bromo-9H-carbazole (10 g, 40.6 mmol), phenylboronic acid (7.43 g, 60.9 mmol), potassium carbonate (16.85 g, 122 mmol), tetrakistriphenylphosphine palladium (0.939 g, 0.813 mmol), toluene (135 mL), THF (67.7 mL), and ion-exchanged water (67.7 mL) were placed in a 500 mL three-neck flask and stirred at 100 °C for 5 hours. After cooling to room temperature, ion-exchanged water was added to the reaction solution, and the organic layer was extracted with toluene. The organic layer was dried over sodium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography (hexane / dichloromethane = 80%:20%) to obtain intermediate X-1 (8.50 g, 34.9 mmol, 86% yield).

[0744] [ka]

[0745] Under a nitrogen atmosphere, intermediate Mf (1.58 g, 2.34 mmol), intermediate X-1 (0.683 g, 2.81 mmol), cesium fluoride (1.776 g, 11.69 mmol), and DMF (23.4 ml) were placed in a 100 mL three-neck flask and stirred at 130 °C for 5 hours and then at 150 °C for 4 hours. After cooling to room temperature, water was added to the reaction mixture, and the precipitated solid was washed with methanol. The solid was purified by column chromatography to obtain 0.339 g of a yellow solid. The resulting yellow solid was identified as compound A-22 by ASAP-MS analysis (yield 16%).

[0746] (Synthesis of Compound A-23) The synthesis method of compound A-23 is described below.

[0747] [ka]

[0748] Under a nitrogen atmosphere, 3,6-diphenylcarbazole (1.418 g, 4.44 mmol) and DMF (37.0 ml) were placed in a 100 ml three-neck flask and cooled on ice to 0°C. After cooling on ice, sodium hydride (40% by mass oil content) (0.178 g, 4.44 mmol) was added to the reaction solution, which was then stirred at 0°C for 1 hour. Intermediate Mf (2.5 g, 3.70 mmol) was added to the reaction solution at 0°C, and the mixture was slowly warmed 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 3.3 g of a yellow solid. The resulting yellow solid was identified as compound A-23 by ASAP-MS analysis (yield: 91%).

[0749] (Synthesis of Compound A-24) The synthesis method of compound A-24 is described below.

[0750] [ka]

[0751] Under a nitrogen atmosphere, 2,7-diphenylcarbazole (1.418 g, 4.44 mmol) and DMF (37.0 ml) were placed in a 100 ml three-neck flask and cooled on ice to 0°C. After cooling, sodium hydride (40% by mass oil content) (0.178 g, 4.44 mmol) was added to the reaction solution, which was then stirred at 0°C for 1 hour. Intermediate Mf (2.5 g, 3.70 mmol) was added to the reaction solution at 0°C, and the mixture was slowly warmed 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 2.8 g of a yellow solid. The resulting yellow solid was identified as compound A-24 by ASAP-MS analysis (yield 78%).

[0752] (Synthesis of Compound A-25) The synthesis method of compound A-25 is described below.

[0753] [ka]

[0754] Under a nitrogen atmosphere, 2-bromocarbazole (10 g, 40.6 mmol), 2-biphenylboronic acid (8.45 g, 42.7 mmol), potassium carbonate (8.42 g, 60.9 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.1 g, 1.35 mmol), THF (30 mL), and ion-exchanged water (10 mL) were placed in a 100 mL three-neck flask and stirred at room temperature for 8 hours. After concentrating the reaction solution, 30 mL of ion-exchanged water was added. The organic layer was extracted with toluene. 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. After removing the solvent under reduced pressure, the resulting compound was purified by silica gel column chromatography to obtain 11 g of a white solid. The resulting white solid was identified as intermediate M-13 using ASAP-MS (85% yield).

[0755] [ka]

[0756] Under a nitrogen atmosphere, intermediate M-13 (1.42 g, 4.44 mmol) and DMF (40 ml) were placed in a 100 ml three-neck flask and ice-cooled to 0 °C. After ice-cooling, sodium hydride (40% oil content) (0.18 g, 4.44 mmol) was added to the reaction solution, which was then stirred at 0 °C for 1 hour. Intermediate Mf (2.5 g, 3.70 mmol) was added at 0 °C, and the mixture was slowly warmed 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 1.9 g of a yellow solid. The resulting yellow solid was identified as compound A-25 by ASAP-MS analysis (yield 78%).

[0757] (Synthesis of Compound A-26) The synthesis method of compound A-26 is described below.

[0758] [ka]

[0759] Under a nitrogen atmosphere, intermediate T-5 (1.4 g, 1.86 mmol), 2-phenyl-9H-carbazole (0.770 g, 3.17 mmol), cesium fluoride (0.849 g, 5.59 mmol), and DMF (18.6 mL) were placed in a 100 mL recovery flask and stirred at 80 °C for 5 hours. 200 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by column chromatography to obtain 0.8 g of a yellow solid. The resulting yellow solid was identified as compound A-26 by ASAP-MS analysis (yield 44%).

[0760] (Synthesis of Compound A-27) The synthesis method of compound A-27 is described below.

[0761] [ka]

[0762] Under a nitrogen atmosphere, 3,9'-bi[9H-carbazole] (1.77 g, 5.33 mmol), sodium hydride (40% by mass oil content) (0.21 g, 5.33 mmol), and DMF (45 ml) were placed in a 100 mL three-neck flask and stirred at 0 °C for 1 hour. Next, intermediate Mf (3.0 g, 4.44 mmol) was added to the reaction solution at 0 °C, and the mixture was slowly heated to room temperature and stirred for an additional hour at room temperature. 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 2.7 g of a yellow solid. The resulting yellow solid was identified as compound A-27 by ASAP-MS analysis (yield 62%).

[0763] (Synthesis of Compound A-28) The synthesis method of compound A-28 is described below.

[0764] [ka]

[0765] Under a nitrogen atmosphere, 4,9'-bi[9H-carbazole] (0.83 g, 2.49 mmol), sodium hydride (40% by mass oil content) (0.11 g, 2.84 mmol), and DMF (24 ml) were placed in a 100 mL three-neck flask and stirred at 0 °C for 1 hour. Next, intermediate Mf (1.6 g, 2.37 mmol) was added to the reaction solution at 0 °C, and the mixture was slowly warmed to room temperature and stirred for an additional hour at room temperature. 20 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 1.7 g of a yellow solid. The resulting yellow solid was identified as compound A-28 by ASAP-MS analysis (yield 73%).

[0766] (Synthesis of Compound A-29) The synthesis method of compound A-29 is described below.

[0767] [ka]

[0768] Under a nitrogen atmosphere, 1-bromo-4,5-dichloro-2-nitrobenzene (8 g, 29.5 mmol), phenylboronic acid (36 g, 295 mmol), tripotassium phosphate (16.85 g, 122 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.30 g, 1.420 mmol), SPhos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) (2.40 g, 5.85 mmol), and toluene (135 mL) were added to a 1000 mL recovery flask and stirred at 110 °C for 6 hours. After cooling to room temperature, 20 mL of ion-exchanged water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and 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 (hexane / ethyl acetate=90%:10%-70%:30%) to obtain intermediate X-2 (1.15 g, 3.23 mmol, yield 11%).

[0769] Under a nitrogen atmosphere, intermediate X-2 (1 g, 2.85 mmol), triphenylphosphine (3 g, 11.44 mmol), and o-dichlorobenzene (10 ml) were added to a 100 mL recovery flask and stirred at 180 °C for 6 hours. After cooling to room temperature, the reaction solution was concentrated by vacuum distillation. The compound obtained after concentration was purified by silica gel column chromatography (hexane / ethyl acetate = 95%:5%-50%:50%) to obtain intermediate X-3 (0.66 g, 2.08 mmol, 73% yield).

[0770] [ka]

[0771] Under a nitrogen atmosphere, sodium hydride (60% by mass, 0.056 g, 1.40 mmol) was added to a DMF (8.0 mL) solution of intermediate X-3 (0.446 g, 1.40 mmol) in a 50 mL three-neck flask under ice cooling. The mixture was stirred at the same temperature for 30 minutes. A DMF (5.4 mL) solution of intermediate Mf (0.94 g, 1.40 mmol) was added dropwise to the reaction mixture, and the mixture was warmed to room temperature and stirred for 6 hours. Water was added to the reaction mixture, and the precipitated solid was washed with methanol. The solid was purified by column chromatography to obtain 0.339 g of a yellow solid. The resulting yellow solid was identified as compound A-29 by ASAP-MS analysis (yield 16%).

[0772] (Synthesis of Compound A-30) The synthesis method of compound A-30 is described below.

[0773] [ka]

[0774] 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 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 yield 13.2 g of a white solid. The resulting white solid was identified as intermediate X-4 by GC-MS analysis (yield 44%).

[0775] 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 placed in a 200 mL three-neck flask and stirred at room temperature for 10 minutes. Then, 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 evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 2.20 g of a white solid, which was identified as intermediate X-5 by ASAP-MS analysis (yield 56%).

[0776] [ka]

[0777] 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 resulting yellow solid was identified as intermediate X-6 (yield 65%) by ASAP-MS analysis.

[0778] Under a nitrogen atmosphere, sodium hydride (60% by mass, 0.080 g, 2.00 mmol) was added to a DMF (7 mL) solution of carbazole (0.36 g, 2.51 mmol) in a 100 mL recovery flask under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. A DMF (7 mL) solution of intermediate X-6 (1.50 g, 1.812 mmol) was added dropwise to the reaction mixture, 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 solid was purified by column chromatography to obtain 0.925 g of a yellow solid. The resulting yellow solid was identified as compound A-30 by ASAP-MS analysis (yield 52%).

[0779] (Synthesis of Compound A-31) The synthesis method of compound A-31 is described below.

[0780] [ka]

[0781] 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. A solution of dibenzo[b,d]thiophene-3-amine (15 g, 75 mmol) was dissolved in acetonitrile (90 mL) to prepare a solution, which was then added dropwise to the reaction mixture over 15 minutes. The reaction mixture was stirred for 1 hour, allowed to cool, and then 6N hydrochloric acid (150 mL) was added and stirred. The reaction mixture was extracted with toluene, washed with brine, and concentrated. The resulting compound was purified by silica gel column chromatography to yield 12 g of a white solid. The resulting white solid was identified as intermediate T-6 by ASAP-MS analysis (73% yield).

[0782] Under a nitrogen atmosphere, a 500 mL three-neck flask was charged with intermediate T-6 (12.0 g, 54.9 mmol), chlorotrimethylsilane (17.5 g, 110 mmol), and THF (180 mL). The contents of the three-neck flask were cooled to -78 °C in a dry ice / acetone bath, and then 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...

Claims

1. A compound represented by the following general formula (126D): 【Chemical 1】 (In the general formula (126D), CN is a cyano group; D １１ is a group represented by the following general formula (13): D １２ is a group represented by the following general formula (11) or general formula (12): R 131 to R 140 each independently represent 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. 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 (R in the general formula (12) １１ ~R １８ adjacent pairs of two or more of R in the general formula (13) １１１ ~R １１８ adjacent pairs of two or more of R in the general formula (11) １ ~R ８ , R in the general formula (12) １１ ~R １８ and R in the general formula (13) １１１ ~R １１８ are each independently, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ a group represented by -COOR ９０９ a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R ９３１ ) (R ９３２ ) a group represented by -Ge(R ９３３ ) (R ９３４ ) (R ９３５ ) a group represented by -B(R ９３６ ) (R ９３７ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, In the general formula (12) and the general formula (13), Ring A, ring B, and ring C each independently represent a 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 the adjacent ring at any position; p, px, and py are each independently 1, 2, 3, or 4; when p is 2, 3 or 4, the rings A are the same or different from each other; when px is 2, 3 or 4, the rings B are the same or different from each other; when py is 2, 3 or 4, the rings C are the same or different from each other; However, this D １１ In the group represented by the general formula (13), px and py are 2, 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 general formulas (11) to (13), * indicates a bonding position. 【Chemistry 5】 (In the general formula (14), r is 0, 2 or 4; Multiple R １９ are not mutually bonded, In the general formula (15), X １ is a sulfur atom or an oxygen atom, R １９ teeth, hydrogen atoms, 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 group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ９０８ a group represented by -COOR ９０９ a group represented by halogen atoms, cyano group, nitro group, -P(=O)(R ９３１ ) (R ９３２ ) a group represented by -Ge(R ９３３ ) (R ９３４ ) (R ９３５ ) a group represented by -B(R ９３６ ) (R ９３７ ) a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, Multiple R １９ are the same or different from each other, Multiple Xs １ are the same or different from each other.) (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 atoms, 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, 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.)

2. R １３１ ~R １４０ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; The compound of claim 1.

3. The group represented by the general formula (12) is any group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E), and (12F): The compound of claim 1. 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 (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 is synonymous with X １ represents X in the general formula (15). １ is synonymous with In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), * indicates a bonding position.

4. D １１ is a group represented by the following general formula (131): A compound according to any one of claims 1 to 3. 【Chemistry 14】 (In the general formula (131), R １１１ ~R １１８ is R in the general formula (13). １１１ ~R １１８ is synonymous with 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 general formula (15), 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 general formula (15), In the general formula (131), * indicates a bonding position.

5. R 1 to R 8 in the general formula (11), R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ and R in the general formula (14) １９ each independently represents 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; A compound according to any one of claims 1 to 3.

6. D 12 is a group represented by the general formula (12). A compound according to any one of claims 1 to 3.

7. D 12 is a group represented by the general formula (11). A compound according to any one of claims 1 to 3.

8. Contains a compound according to any one of claims 1 to 3 Materials for organic electroluminescence devices.

9. an anode, a cathode, and an organic layer; The organic layer comprises a compound according to any one of claims 1 to 3 as compound M2. Organic electroluminescent element.

10. the organic layer has at least one light-emitting layer; the light-emitting layer contains the compound M2; The organic electroluminescence device according to claim 9 .

11. the light-emitting layer contains the compound M2 and further contains a compound M1, The compound M1 is a fluorescent compound, The lowest excited singlet energy S of the compound M1 １ (M1) and the lowest excited singlet energy S of the compound M2 １ (M2) satisfies the relationship of the following formula (Formula 1), The organic electroluminescence device according to claim 10 . S １ (M2)>S １ (M1)…(Number 1)

12. The compound M1 is a compound represented by the following general formula (D1): The organic electroluminescence device according to claim 11 . 【Chemical 27】 (In the general formula (D1), Ring A, ring B, ring D, ring E and ring F each independently represent a substituted or unsubstituted aryl ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of substituted or unsubstituted heterocycles 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 is Ring B, when present, is a nitrogen atom or a carbon atom; When ring B does not exist, an oxygen atom, a 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 Ring D, when present, is a nitrogen atom or a carbon atom; When ring D does not exist, it is an oxygen atom, a sulfur atom, or NRd. Ze is Ring E, when present, is a nitrogen atom or a carbon atom; When ring E does not exist, it is an oxygen atom, a sulfur atom, or NRe; Zf is a nitrogen atom or a carbon atom; Zg is Ring F, when present, is a nitrogen atom or a carbon atom; When ring F does not exist, an oxygen atom, a 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 each independently represent a hydrogen atom or a substituent; Rb and Rb as substituents １ , 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 ) a group represented by -N(R ９１６ ) (R ９１７ ) is a group represented by However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.) (In the compound M1, R ９１１ ~R ９１７ are each independently, hydrogen atoms, 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, 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.)

13. the light-emitting layer contains the compound M2 and further contains a compound M3, The lowest excited singlet energy S of the compound M2 １ (M2) and the lowest excited singlet energy S of the compound M3 １ (M3) satisfies the relationship of the following formula (Formula 2): The organic electroluminescence device according to claim 10 . S １ (M3)>S １ (M2) …(number 2)

14. An electronic device equipped with the organic electroluminescence element according to claim 9.

Images