Organic electroluminescent element and electronic apparatus

Abstract

To provide an organic electroluminescent element with an improved element performance.SOLUTION: An organic electroluminescent element 1 includes an anode 3, a cathode 4, and a light-emitting layer 5 disposed between the anode 3 and the cathode 4. The light-emitting layer 5 includes a fluorescent first compound and a delayed fluorescent second compound. The first compound is represented by the following general formula (1), and the second compound is represented by the following general formula (2). The lowest excited singlet energy S1(M1) of the first compound is smaller than the lowest excited singlet energy S1(M2) of the second compound.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to an organic electroluminescence element 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 utilize light emission from singlet excitons are increasingly being applied to full-color displays such as those for mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Therefore, efforts are being made to improve the performance of organic EL devices. Examples of the performance of organic EL devices include brightness, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifetime.

[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) include compounds in which a donor moiety and an acceptor moiety are bonded within the molecule.

[0004] For example, Patent Document 1 can be mentioned as a document relating to organic EL devices and compounds used in organic EL devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] International Publication No. 2021 / 215446 Summary of the Invention [Problem to be solved by the invention]

[0006] Further improvements in the performance of organic EL devices that utilize the TADF mechanism are required. An object of the present invention is to provide an organic electroluminescent element with improved element performance, and an electronic device incorporating the organic EL element. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided an organic electroluminescence device comprising an anode, a cathode, and an emitting layer between the anode and the cathode, the emitting layer comprising a first fluorescent compound and a second delayed fluorescent compound, the first compound being represented by the following general formula (1), the second compound being represented by the following general formula (2), and the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfying the relationship of the following mathematical formula (Mathematical Formula 1). S1(M2)>S1(M1)…(Math 1)

[0008] [ka]

[0009] (In the general formula (1), R 101 ~R 111 are each independently Hydrogen atoms, halogen atoms, cyano groups, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196 ) a group represented by a nitro group, and -Si(R 197 )(R 198 )(R 199 ), wherein R 110 is selected from substituents other than hydrogen atoms, Ring A 1 and Ring B 1 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 50 ring atoms, X 1 -O-, -N(R 131 )- or -S-, R 131 teeth, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted imino 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 131 is a single bond or a linking group L 11 via ring A 1 or Ring B 1 are bonded to each other to form a ring structure, or are not bonded to each other, Linking group L 11 are -O-, -S-, >C(R 186 )(R 187 ) or >Si(R 188 )(R 189 ) and R 186 ~R 189 are each independently hydrogen atoms, halogen 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, and selected from the group consisting of substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms, R 186 and R 187 The pair is a single bond or a linking group L 12 are bonded to each other via an R 188 and R 189 The pair is a single bond or a linking group L 12 are bonded to each other via an Linking group L 12 is -O- or -S-. (In the first compound, R 190 ~R 199each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 190 If there are multiple R 190 are the same or different, and R 191 If there are multiple R 191 are the same or different, and R 192 If there are multiple R 192 are the same or different, and R 193 If there are multiple R 193 are the same or different, and R 194 If there are multiple R 194 are the same or different, and R 195 If there are multiple R 195 are the same or different, and R 196 If there are multiple R 196 are the same or different, and R 197 If there are multiple R 197 are the same or different, and R 198 If there are multiple R 198 are the same or different, and R 199 If there are multiple R 199 are either identical or different.)

[0010] [ka]

[0011] (In the general formula (2), k is 1, 2, 3 or 4; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; k+m+n=4, CN is a cyano group, 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 -C(=O)-O-(R 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, multiple R's are the same or different, D 21 and D 22 are each independently a group represented by the following general formula (21), (22), or (23), D 21 and D 22 are the same or different from each other, Multiple Ds 21 are the same or different from each other, Multiple Ds 22 are either identical or different.)

[0012] [ka]

[0013] [ka]

[0014] (R in the general formula (21) 21 ~R 28 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 (22) 221 ~R 228 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 (23) 231 ~R 238 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 (21) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 21 ~R28 R in the general formula (22) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 221 ~R 228 and R in the general formula (23) that does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 231 ~R 238 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 -C(=O)-O-(R 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 (22) and the general formula (23), ring A2, ring B2, and ring C2 each independently represent a ring structure selected from the group consisting of ring structures represented by the following general formulas (24), (25A), and (25B): ring A2, ring B2, and ring C2 are each fused to one or more adjacent rings at any position; p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, the rings A2 are the same or different from each other; When px is 2, 3 or 4, the rings B2 are the same or different from each other, When py is 2, 3 or 4, the rings C2 are the same or different from each other; However, D 21 and D 22 At least one of the p is 2, 3 or 4, and ring A2 is a group represented by general formula (22) containing both a ring structure represented by general formula (24) below and a ring structure represented by general formula (25B) below, a group represented by the general formula (23) in which at least one of px and py is 2, 3, or 4, and which contains, as ring B2 or ring C2, both a ring structure represented by the following general formula (24) and a ring structure represented by the following general formula (25B), In the general formulae (21) to (23), * indicates the bonding position to the benzene ring in the general formula (2).

[0015] [ka]

[0016] (In the general formula (24), r is 0, 2 or 4; Multiple R 29 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 29 are each independently R in the general formula (21). 21 ~R 28 is equivalent to (In the second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently, 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, and R 902 If there are multiple R 902 are the same or different, and R 903 If there are multiple R 903 are the same or different, and R 904 If there are multiple R 904 are the same or different, and R 905 If there are multiple R 905 are the same or different, and R 906If there are multiple R 906 are the same or different, and R 907 If there are multiple R 907 are the same or different, and R 908 If there are multiple R 908 are the same or different, and R 909 If there are multiple R 909 are the same or different, and R 931 If there are multiple R 931 are the same or different, and R 932 If there are multiple R 932 are the same or different, and R 933 If there are multiple R 933 are the same or different, and R 934 If there are multiple R 934 are the same or different, and R 935 If there are multiple R 935 are the same or different, and R 936 If there are multiple R 936 are the same or different, and 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 an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention. [Effects of the Invention]

[0018] According to one aspect of the present invention, it is possible to provide an organic electroluminescence element with improved element performance, and an electronic device equipped with the organic EL element. [Brief explanation of the drawings]

[0019] [Figure 1] 1 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a first embodiment of the present invention. [Figure 2] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Figure 3] FIG. 10 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 4] FIG. 2 is a diagram showing the energy levels of a first compound and a second compound in an example of an emitting layer of an organic electroluminescence device according to a first embodiment of the present invention, and the relationship between energy transfer. [Figure 5] FIG. 10 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an emitting layer of an example of an organic electroluminescence element according to a second embodiment of the present invention, as well as the relationship between energy transfer. DETAILED DESCRIPTION OF THE INVENTION

[0020] [Definition] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] "Substituents described herein" The substituents described in this specification will be explained below.

[0028] 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.

[0029] "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.

[0030] 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 group, 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).

[0031] [ka]

[0032] [ka]

[0033] 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.

[0034] "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.

[0035] 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).

[0036] 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).

[0037] 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.

[0038] 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.

[0039] Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3): a 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).

[0040] 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):

[0041] [ka]

[0042] [ka]

[0043] 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.

[0044] 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.

[0045] 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].

[0046] 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].

[0047] 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):

[0048] 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.

[0049] "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.

[0050] 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.

[0051] Substituted alkyl groups (specific example group G3B): heptafluoropropyl group (including isomers), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0052] "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.

[0053] Unsubstituted alkenyl groups (specific example group G4A): vinyl groups, Allyl groups, a 1-butenyl group, 2-butenyl group, and 3-butenyl group.

[0054] 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.

[0055] "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.

[0056] Unsubstituted alkynyl groups (specific example group G5A): Ethynyl group.

[0057] "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.

[0058] 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.

[0059] Substituted cycloalkyl groups (specific example group G6B): 4-methylcyclohexyl group.

[0060] -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), 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 -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.

[0061] -O-(R 904 ) a group represented by -O-(R 904 Specific examples (specific example group G8) of the group represented by -O(G1), -O(G2), -O(G3), and -O(G6) is an example. 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.

[0062] -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.

[0063] -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) is an example. 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.

[0064] "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.

[0065] "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.

[0066] "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.

[0067] "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.

[0068] "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.

[0069] "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.

[0070] "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.

[0071] "Substituted or unsubstituted trialkylsilyl group" A specific example of the "substituted or unsubstituted 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. Multiple G3 groups 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 "unsubstituted trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0072] "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.

[0073] 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.

[0074] 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.

[0075] In this specification, a carbazolyl group is specifically any of the following groups, unless otherwise specified in this specification.

[0076] [ka]

[0077] In this specification, unless otherwise specified in this specification, a (9-phenyl)carbazolyl group specifically means any of the following groups:

[0078] [ka]

[0079] In the general formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0080] In this specification, a dibenzofuranyl group and a dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in this specification.

[0081] [ka]

[0082] In the general formulae (TEMP-34) to (TEMP-41), * represents a bonding position.

[0083] 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.

[0084] "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.

[0085] "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.

[0086] "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.

[0087] 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).

[0088] [ka]

[0089] [ka]

[0090] 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.

[0091] [ka]

[0092] 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.

[0093] [ka]

[0094] 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.

[0095] 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).

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-69) to (TEMP-82), * represents a bonding position.

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 each independently represent a hydrogen atom or a substituent. In the general formulae (TEMP-83) to (TEMP-102), * represents a bonding position.

[0105] The above is the explanation of "substituents described in this specification."

[0106] - "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.

[0107] [ka]

[0108] For example, R 921 ~R 930 In the case where "one or more pairs of adjacent two or more groups are bonded to each other to form a ring," the pair of adjacent two groups is R 921 and R 922 Paired with R 922 and R 923 Paired with R 923 and R 924 Paired with R 924 and R 930 Paired with R 930 and R 925 Paired with R 925 and R 926 Paired with R 926 and R 927 Paired with R 927 and R 928 Paired with R 928 and R 929 Pairs with and R 929 and R 921 It is paired with.

[0109] 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).

[0110] [ka]

[0111] 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, R921 and R 922 and are bonded to each other to form ring Q A and R 922 and R 923 and are bonded to each other to form ring Q C and 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.

[0112] [ka]

[0113] 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 Ais a fused ring.

[0114] The "unsaturated ring" is at least one ring selected from the group consisting of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring having an unsaturated bond in its ring structure, and a non-aromatic heterocyclic ring having an unsaturated bond in its ring structure. The unsaturated bond in the ring structure of the unsaturated ring is one or both of a double bond and a triple bond. Examples of aliphatic hydrocarbon rings having an unsaturated bond in their ring structure include cyclohexene and cyclohexadiene. Examples of non-aromatic heterocyclic rings having an unsaturated bond in their ring structure include dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, and isoindoline.

[0115] The "saturated ring" is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bonds and a non-aromatic heterocyclic ring having no unsaturated bonds. The saturated ring has no double or triple bonds in the ring structure. 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 in the main skeleton, or with a plurality of atoms in the main skeleton and one or more additional atoms. For example, R 921 and R 922 and Q are bonded together to form a ring 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 atoms. 921 and R 922 Todekan Q A In the case where R921 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

[0116] Here, unless otherwise specified in this specification, the "arbitrary atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In the arbitrary atom (for example, in the case of a carbon atom or a nitrogen atom), 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 atom other than a carbon atom is included, the formed ring is a heterocycle. Unless otherwise specified in this specification, the "one or more arbitrary atoms" 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 rings" "combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring," unless otherwise specified in this specification, preferably, one or more pairs of adjacent two or more rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0117] 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 "saturated ring" or "unsaturated 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").

[0118] 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, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms, where R901 ~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 903 are 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.

[0119] 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.

[0120] 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.

[0121] 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."

[0122] 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. When a plurality of optional substituents are present, the plurality of optional substituents may be the same or different.

[0123] 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.

[0124] First Embodiment [Organic electroluminescence element] In this embodiment, an organic EL element will be described as a light emitting element. The organic EL device according to this embodiment includes a cathode, an anode, and an organic layer disposed between the cathode and the anode. The organic layer includes at least one layer formed of an organic compound. Alternatively, the organic layer may be formed by stacking multiple layers formed of organic compounds. The organic layer may further include an inorganic substance (at least one of an inorganic compound and a simple substance). In the organic EL device according to this embodiment, at least one of the organic layers is an emitting layer. Therefore, the organic layer may be, for example, a single emitting layer, or may include layers that can be used in an organic EL device. Layers that can be used in an organic EL device are 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 injection layer, an electron transport layer, and a blocking layer. Examples of the blocking layer include an electron blocking layer disposed on the anode side of the emitting layer, and a hole blocking layer disposed on the cathode side of the emitting layer.

[0125] The organic EL device according to this embodiment has an anode, a cathode, and an emitting layer between the anode and the cathode. The emitting layer contains a first fluorescent compound and a second delayed fluorescent compound, wherein the first compound is represented by the following general formula (1), the second compound is represented by the following general formula (2), and the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfy the relationship shown in the following formula (Mathematical Formula 1): S1(M2)>S1(M1)…(Math 1)

[0126] FIG. 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5, an electron transport layer 8, and an electron injection layer 9. The present invention is not limited to the configuration of the organic EL element shown in FIG.

[0127] <Light-emitting layer> In the organic EL element of this embodiment, the first compound is preferably a dopant material (also referred to as a guest material, an emitter, or a light-emitting material), and the second compound is preferably a host material (also referred to as a matrix material).

[0128] In the organic EL device according to this embodiment, the light-emitting layer contains a first fluorescent compound represented by general formula (1) and a second delayed fluorescent compound represented by general formula (2), thereby improving the performance of the organic EL device. The organic EL device according to one aspect of this embodiment improves luminous efficiency (e.g., external quantum efficiency or current efficiency). Furthermore, the organic EL device according to one aspect of this embodiment extends the life of the organic EL device. Furthermore, the organic EL device according to one aspect of this embodiment reduces the driving voltage of the organic EL device. The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0129] In the organic EL device according to this embodiment, the light-emitting layer may contain a metal complex, but preferably does not contain a metal complex. In the organic EL device according to this embodiment, the light-emitting layer preferably does not contain a phosphorescent material. In the organic EL device according to this embodiment, the light-emitting layer preferably does not contain a phosphorescent rare earth metal complex. In the organic EL device according to this embodiment, the light-emitting layer preferably does not contain a heavy metal complex. Here, examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0130] (First Compound) In the organic EL device according to this embodiment, the first compound is a fluorescent compound represented by the following general formula (1): The first compound is preferably a compound that does not exhibit delayed fluorescence.

[0131] [ka]

[0132] (In the general formula (1), R101 ~R 111 are each independently Hydrogen atoms, halogen atoms, cyano groups, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196 ) a group represented by a nitro group, and -Si(R 197 )(R 198 )(R 199 ), wherein R 110 is selected from substituents other than hydrogen atoms, Ring A 1 and Ring B 1 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 50 ring atoms, X 1 -O-, -N(R 131 )- or -S-, R 131 teeth, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted imino 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 131 is a single bond or a linking group L 11 via ring A 1 or Ring B 1 are bonded to each other to form a ring structure, or are not bonded to each other, Linking group L 11 are -O-, -S-, >C(R 186 )(R 187 ) or >Si(R 188 )(R 189 ) and R 186 ~R 189 are each independently hydrogen atoms, halogen 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, and selected from the group consisting of substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms, R 186 and R 187 The pair is a single bond or a linking group L 12 are bonded to each other via an R 188 and R 189 The pair is a single bond or a linking group L 12 are bonded to each other via an Linking group L 12 is -O- or -S-. (In the first compound, R 190 ~R 199each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 190 If there are multiple R 190 are the same or different, and R 191 If there are multiple R 191 are the same or different, and R 192 If there are multiple R 192 are the same or different, and R 193 If there are multiple R 193 are the same or different, and R 194 If there are multiple R 194 are the same or different, and R 195 If there are multiple R 195 are the same or different, and R 196 If there are multiple R 196 are the same or different, and R 197 If there are multiple R 197 are the same or different, and R 198 If there are multiple R 198 are the same or different, and R 199 If there are multiple R 199 are either identical or different.)

[0133] In the organic EL device according to this embodiment, in the general formula (1), R 110 is preferably any group selected from the group consisting of 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0134] In the organic EL device according to this embodiment, in the general formula (1), X 1 -N(R131 )- is preferred.

[0135] In the organic EL device according to this embodiment, the first compound is preferably represented by the following general formula (10).

[0136] [ka]

[0137] (In the general formula (10), R 101 ~R 111 , R 131 , ring A 1 and Ring B 1 are R in the general formula (1), respectively. 101 ~R 111 , R 131 , ring A 1 and Ring B 1 is equivalent to

[0138] In the organic EL device according to this embodiment, in the general formula (1), X 1 -N(R 131 )- and R 131 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, or a substituted or unsubstituted imino group.

[0139] In the organic EL device according to this embodiment, in the general formula (1), X 1 -N(R 131 )- and R 131 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R 131 is connected to ring B via a single bond. 1 and preferably bond to each other to form a ring structure.

[0140] In the organic EL device according to this embodiment, the first compound is preferably represented by the following general formula (101) or general formula (102).

[0141] [ka]

[0142] (In the general formulas (101) and (102), R 101 ~R 111 , L 11 , ring A 1 and Ring B 1 are R in the general formula (1), respectively. 101 ~R 111 , L 11 , ring A 1 and Ring B 1 and ring C 1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 5 to 30 ring atoms.

[0143] In the organic EL device according to this embodiment, in the general formula (1), the general formula (10), the general formula (101), and the general formula (102), the ring A 1 and Ring B 1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 ring carbon atoms.

[0144] In the organic EL device according to this embodiment, in the general formula (101) and the general formula (102), the ring C 1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 ring carbon atoms.

[0145] In the organic EL device according to this embodiment, in the general formula (101) and the general formula (102), the ring A 1 , ring B 1 and Ring C 1 is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 ring carbon atoms.

[0146] In the organic EL device according to this embodiment, the first fluorescent compound is preferably represented by the following general formula (11).

[0147] [ka]

[0148] (In the general formula (11), R 101 ~R 111 are R in the general formula (1), respectively. 101 ~R 111 is synonymous with R 112 ~R 121 are each independently Hydrogen atoms, halogen atoms, cyano groups, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196 ) a group represented by a nitro group, and -Si(R 197 )(R 198 )(R 199 ), wherein R 110is selected from substituents other than hydrogen atoms, R 190 ~R 199 are R in the general formula (1), respectively. 190 ~R 199 is equivalent to

[0149] In the first compound according to this embodiment, R 104 , R 110 , R 117 and R 120 At least one selected from the group consisting of is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0150] In the first compound according to this embodiment, R 110 It is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0151] In the first compound according to this embodiment, R 101 ~R 118 It is also preferred that at least one of the groups is a substituted or unsubstituted N-carbazolyl group.

[0152] In the first compound according to this embodiment, R 112 ~R 114 It is also preferred that at least one of the groups is a substituted or unsubstituted N-carbazolyl group.

[0153] In the first compound according to this embodiment, R 113 It is also preferred that is a substituted or unsubstituted N-carbazolyl group.

[0154] In the first compound according to this embodiment, R 115 ~R 118It is also preferred that at least one of the groups is a substituted or unsubstituted N-carbazolyl group.

[0155] In the first compound according to this embodiment, R 116 It is also preferred that is a substituted or unsubstituted N-carbazolyl group.

[0156] The first compound according to this embodiment preferably has at least one group represented by the following general formula (120).

[0157] [ka]

[0158] (In the general formula (120), R 141 ~R 148 are each independently hydrogen atoms, halogen atoms, cyano group, 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R 190 ) a group represented by -S-(R 191 ) 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, -C(=O)-O-(R 192 ) a group represented by -C(=O)-N(R 193 )(R 194 ) a group represented by -N(R 195 )(R 196) a group represented by a nitro group, and -Si(R 197 )(R 198 )(R 199 ) selected from the group consisting of groups represented by L 13 teeth, single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, m is 0, 1, 2 or 3; When m is 0, -(L 13 )m- is a single bond; When m is 2 or 3, multiple L 13 are the same or different from each other, * indicates the bond position.) (R in the general formula (120) 190 ~R 199 respectively represent R in the compound represented by the general formula (1). 190 ~R 199 is equivalent to

[0159] In the first compound according to this embodiment, the substituted or unsubstituted N-carbazolyl group is preferably a group represented by the general formula (120).

[0160] In the organic EL device according to this embodiment, the first fluorescent compound is preferably represented by the following general formula (121) or (122).

[0161] [ka]

[0162] (In the general formulas (121) and (122), R 101 ~R 121 are R in the general formula (11), respectively. 101 ~R 121 is synonymous with R 141 ~R148 are R in the general formula (120), respectively. 141 ~R 148 is equivalent to

[0163] In the organic EL device according to this embodiment, the first compound has at least one substituted or unsubstituted N-carbazolyl group, thereby improving molecular orientation. Therefore, for example, by including the first compound according to this embodiment and the delayed fluorescent second compound in the light-emitting layer of the organic EL device, the light extraction efficiency is improved, and as a result, the luminous efficiency of the organic EL device is thought to be improved. Furthermore, the first compound according to this embodiment has a structure represented by the general formula (11), which tends to improve molecular orientation, and therefore, it is believed that the lifetime of an organic EL device can be extended by incorporating the first compound according to this embodiment into an emitting layer. The improvement of molecular orientation means that the molecules are aligned in a direction more parallel to the substrate plane of the organic EL element.

[0164] In the first compound according to this embodiment, ring A 1 It is also preferred that at least one cyano group is substituted on the alkyl group.

[0165] In the first compound according to this embodiment, ring C 1 It is also preferred that at least one cyano group is substituted on the alkyl group.

[0166] In the first compound according to this embodiment, R 108 ~R 111 It is also preferred that at least one of the groups is a cyano group.

[0167] In the first compound according to this embodiment, ring B 1 It is also preferred that at least one cyano group is substituted on the alkyl group.

[0168] In the first compound according to this embodiment, R 119 ~R 121 It is also preferred that at least one of the groups is a cyano group.

[0169] In the first compound according to this embodiment, R 108 ~R 111 At least one of the rings B is a cyano group. 1 It is also preferred that at least one cyano group is substituted on the alkyl group.

[0170] In the first compound according to this embodiment, R 108 ~R 111 and R 119 ~R 121 It is also preferred that at least one of the groups is a cyano group.

[0171] In the first compound according to this embodiment, (i) R 108 ~R 111 at least one of the rings B is a cyano group, or 1 and Ring C 1 At least one ring of the formula (iii) R 108 ~R 111 At least one of the rings B is a cyano group. 1 and Ring C 1 By substituting at least one cyano group on at least one ring of the first compound, the ionization potential of the first compound becomes deeper. Therefore, for example, by including the first compound according to this embodiment and the delayed fluorescent second compound in the light-emitting layer of an organic EL device, the efficiency of energy transfer from the second compound to the first compound is improved, and as a result, it is thought that the light-emitting efficiency of the organic EL device is improved.

[0172] In the organic EL device according to this embodiment, the first compound preferably has one or more groups represented by the following general formula (13).

[0173] [ka]

[0174] (In the group represented by the general formula (13), Z 1is a nitrogen atom or CR 151 represents Z 2 is a nitrogen atom or CR 152 represents Z 3 is a nitrogen atom or CR 153 represents Z 4 is a nitrogen atom or CR 154 represents Z 5 is a nitrogen atom or CR 155 represents R 151 ~R 155 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, However, Z 1 ~Z 5 at least one of which represents a nitrogen atom, * represents the bonding position to other atoms in the first compound.

[0175] In the organic EL device according to this embodiment, when the first compound has at least one group represented by the general formula (13), it is considered that intermolecular interactions between the compounds are suppressed, and as a result, intermolecular aggregation is suppressed. Therefore, for example, by including the first compound and the delayed fluorescent second compound in the light-emitting layer of the organic EL device, it is considered that the intermolecular quenching process is suppressed, and as a result, the luminous efficiency of the organic EL device is improved.

[0176] When the first compound according to this embodiment has a plurality of groups represented by the general formula (13), the groups represented by the general formula (13) may be the same or different from each other.

[0177] In the first compound according to this embodiment, R101 ~R 111 It is also preferable that at least one of the above is a group represented by the general formula (13).

[0178] In the first compound according to this embodiment, the group represented by the general formula (13) is ring A 1 It is also preferred that at least one of the following is substituted:

[0179] In the first compound according to this embodiment, the group represented by the general formula (13) is ring B 1 It is also preferred that at least one of the following is substituted:

[0180] In the first compound according to this embodiment, the group represented by the general formula (13) is 1 It is also preferred that at least one of the following is substituted:

[0181] In the first compound according to this embodiment, R 101 ~R 121 It is also preferable that at least one of the above is a group represented by the general formula (13). In the first compound according to this embodiment, R 101 ~R 121 It is also preferable that at least one or two of the above be a group represented by the general formula (13).

[0182] In the first compound according to this embodiment, R 115 ~R 118 It is also preferable that at least one of the above is a group represented by the general formula (13). In the first compound according to this embodiment, R 115 ~R 118 It is also preferable that at least one or two of the above be a group represented by the general formula (13).

[0183] In the first compound according to this embodiment, Z 1 ~Z 5 one, two or three of which are nitrogen atoms, and Z 1 ~Z 5It is preferred that the remainder of the group is not a nitrogen atom. In the first compound according to this embodiment, R 151 ~R 155 It is preferred that at least one of the groups be independently selected from substituents other than a hydrogen atom. In the first compound according to this embodiment, Z 3 is preferably a nitrogen atom.

[0184] In the first compound according to this embodiment, Z 1 ~Z 5 is a nitrogen atom, and R is bonded to a carbon atom at the ortho position relative to the nitrogen atom. 151 ~R 155 It is preferred that at least one of the groups be independently selected from substituents other than a hydrogen atom. In the first compound according to this embodiment, R 152 and R 154 At least one of the groups is preferably selected from substituents other than a hydrogen atom. In the first compound according to this embodiment, R 152 and R 154 are preferably each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. In the first compound according to this embodiment, R 152 and R 154 are each independently preferably a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and more preferably a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms.

[0185] In the first compound according to this embodiment, the group represented by the general formula (13) is preferably a group represented by the following general formula (131), (132), or (133).

[0186] [ka]

[0187] (In the general formulae (131) to (133), R 151 ~R 155 are R in the general formula (13), respectively. 151 ~R 155 and * has the same meaning as * in the general formula (13).

[0188] In the first compound according to this embodiment, the group represented by the general formula (13) is also preferably a group represented by the following general formula (134), (135), (136), (137), (138), or (139).

[0189] [ka]

[0190] (In the general formulae (134) to (139), R 151 ~R 155 are R in the general formula (13), respectively. 151 ~R 155 and * has the same meaning as * in the general formula (13).

[0191] In the general formulae (131) to (139), R 151 ~R 155 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms. In the general formulae (134) to (139), R 151 ~R 154 are each independently preferably a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, and more preferably a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0192] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms and having at least one double bond in the ring but not having aromaticity. Unless otherwise specified in this specification, the number of ring carbon atoms in the cycloalkenyl group described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6. Specific examples of the cycloalkenyl group described in this specification include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.

[0193] In the first compound according to this embodiment, the substituent ("optional substituent") in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 50 carbon atoms; an unsubstituted alkenyl group having 2 to 50 carbon atoms; an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; an unsubstituted cycloalkenyl 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 Halogen atoms, nitro groups, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and It is preferably a group selected from the group consisting of unsubstituted heterocyclic groups having 5 to 50 ring atoms. In the first compound according to this embodiment, 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, 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. 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 903 are 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.

[0194] In the first compound according to the present embodiment, the substituent in the "substituted or unsubstituted" case is preferably a group selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.

[0195] In the first compound according to the present embodiment, the substituent in the "substituted or unsubstituted" case is more preferably a group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.

[0196] In the first compound according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups. "Unsubstituted" in the case of "substituted or unsubstituted" means that a hydrogen atom is bonded to the group.

[0197] (Method for producing the first compound) The compound according to this embodiment (first compound) 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.

[0198] (Specific Examples of the First Compound) Specific examples of the compound (first 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 omitted. In this specification, a methyl group may be represented as Me, and a phenyl group may be represented as Ph.

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[0226] (Maximum peak wavelength) The maximum peak wavelength of the first compound according to this embodiment (a compound having a structure represented by the general formula (1)) is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 550 nm or less, and more preferably 515 nm or more and 540 nm or less. The first compound according to this embodiment preferably exhibits green emission. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 500 nm or more and 560 nm or less.

[0227] In this specification, the method for measuring the maximum peak wavelength of a compound is as follows. -6 mol / L or more, 10 -5 A toluene solution containing the compound dissolved at a concentration of 100 mol / L or less is prepared and placed in a quartz cell. The emission spectrum of this sample (toluene solution) is measured at room temperature (300 K) using a spectrofluorometer. The vertical axis of the emission spectrum represents emission intensity, and the horizontal axis represents wavelength. The emission spectrum can be measured, for example, using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measurement device is not limited to the device used here. In the emission spectrum, the peak wavelength at which the emission intensity is greatest is defined as the maximum peak wavelength. Note that in this specification, the maximum peak wavelength of fluorescent emission may also be referred to as the maximum fluorescent emission peak wavelength. The emission spectrum half width FWHM is the full width at half maximum at the maximum peak of the emission spectrum.

[0228] (Second Compound) In the organic EL device according to this embodiment, the second compound is a delayed fluorescent compound represented by the following general formula (2).

[0229] [ka]

[0230] (In the general formula (2), k is 1, 2, 3 or 4; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; k+m+n=4, CN is a cyano group, 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 -C(=O)-O-(R 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, multiple R's are the same or different, D 21 and D 22 are each independently a group represented by the following general formula (21), (22), or (23), D 21 and D 22 are the same or different from each other, Multiple Ds 21 are the same or different from each other, Multiple Ds 22 are either identical or different.)

[0231] [ka]

[0232] [ka]

[0233] (R in the general formula (21) 21 ~R 28 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 (22) 221 ~R 228 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 (23) 231 ~R 238 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 (21) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 21 ~R 28 R in the general formula (22) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 221 ~R 228 and R in the general formula (23) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 231 ~R 238 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 -C(=O)-O-(R 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 (22) and the general formula (23), ring A2, ring B2, and ring C2 each independently represent a ring structure selected from the group consisting of ring structures represented by the following general formulas (24), (25A), and (25B): ring A2, ring B2, and ring C2 are each fused to one or more adjacent rings at any position; p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, the rings A2 are the same or different from each other; When px is 2, 3 or 4, the rings B2 are the same or different from each other, When py is 2, 3 or 4, the rings C2 are the same or different from each other; However, D 21 and D 22 At least one of the p is 2, 3 or 4, and ring A2 is a group represented by general formula (22) containing both a ring structure represented by general formula (24) below and a ring structure represented by general formula (25B) below, a group represented by the general formula (23) in which at least one of px and py is 2, 3, or 4, and which contains, as ring B2 or ring C2, both a ring structure represented by the following general formula (24) and a ring structure represented by the following general formula (25B), In the general formulae (21) to (23), * indicates the bonding position to the benzene ring in the general formula (2).

[0234] [ka]

[0235] (In the general formula (24), r is 0, 2 or 4; Multiple R 29 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 29 are each independently R in the general formula (21). 21 ~R 28 is equivalent to (In the second compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 are each independently, 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, and R 902 If there are multiple R 902 are the same or different, and R 903 If there are multiple R 903 are the same or different, and R 904If there are multiple R 904 are the same or different, and R 905 If there are multiple R 905 are the same or different, and R 906 If there are multiple R 906 are the same or different, and R 907 If there are multiple R 907 are the same or different, and R 908 If there are multiple R 908 are the same or different, and R 909 If there are multiple R 909 are the same or different, and R 931 If there are multiple R 931 are the same or different, and R 932 If there are multiple R 932 are the same or different, and R 933 If there are multiple R 933 are the same or different, and R 934 If there are multiple R 934 are the same or different, and R 935 If there are multiple R 935 are the same or different, and R 936 If there are multiple R 936 are the same or different, and R 937 If there are multiple R 937 are either identical or different.)

[0236] In the second compound according to this embodiment, for example, "a group represented by general formula (22), in which p is 3 or 4 and which contains, as ring A, both a ring structure represented by general formula (24) and a ring structure represented by general formula (25B)" may contain, as ring A, a ring structure represented by general formula (25A). Furthermore, in the second compound according to this embodiment, "the group represented by general formula (23), in which px is 3 or 4 and which contains, as ring B, both the ring structure represented by general formula (24) and the ring structure represented by general formula (25B)" may contain, as ring B, the ring structure represented by general formula (25A). Furthermore, in the second compound according to this embodiment, "the group represented by general formula (23), in which py is 3 or 4 and which contains, as ring C, both the ring structure represented by general formula (24) and the ring structure represented by general formula (25B)" may contain, as ring C, the ring structure represented by general formula (25A).

[0237] In the second compound according to this embodiment, the benzene ring of the general formula (2) to which the groups represented by the general formulae (21) to (23) are bonded is the benzene ring explicitly shown in the general formula (2), and R, D 21 and D 22 It is not a benzene ring contained in

[0238] In the organic EL device according to this embodiment, in the general formula (2), k is 1, 2, or 3, m is 0, 1, or 2, and n is 1, 2, or 3, provided that at least one R is a substituent, and that at least one R as the substituent is preferably bonded to the benzene ring in the general formula (2) via a carbon-carbon bond.

[0239] In the organic EL device according to this embodiment, the compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), (202), or (203).

[0240] [ka]

[0241] (In the general formulas (201), (202) and (203), D 21 , D 22 , R, k, m and n are each the D in the general formula (2). 21, D 22 , R, k, m, and n.)

[0242] In the second compound according to this embodiment, n is preferably 2 or 3.

[0243] In the second compound according to this embodiment, it is preferred that k is 1, m is 1, and n is 2.

[0244] In the organic EL device according to this embodiment, the compound represented by the general formula (2) is preferably a compound represented by the following general formula (211).

[0245] [ka]

[0246] (In the general formula (211), D 21 and D 22 are D in the general formula (2), respectively. 21 and D 22 is synonymous with R 201 and R 202 are each independently defined as R in the general formula (2).

[0247] In the second compound according to this embodiment, at least one D 21 is preferably a group represented by the following general formula (221), (222) or (231).

[0248] [ka]

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[0251] (In the general formulas (221) and (222), R 221 ~R 228 are R in the general formula (22), respectively. 221 ~R 228 is synonymous with Ring A 21、 Ring A 22 , ring A 23 and Ring A 24 two of which are ring structures represented by the general formula (24) and the remaining two are ring structures represented by either the general formula (25A) or (25B), However, ring A 21、 Ring A 22 , ring A 23 and Ring A 24 at least one of the ring structures represented by general formula (25B) In the general formula (231), R 231 ~R 238 are R in the general formula (23), respectively. 231 ~R 238 is synonymous with Ring B 21 and Ring B 22 one of the ring structures represented by the general formula (24) is a ring structure represented by the general formula (24), and ring B 21 and Ring B 22 the other is a ring structure represented by any one of the general formulas (25A) and (25B), Ring C 21 and Ring C 22 one of the ring structures represented by the general formula (24) is a ring structure represented by the general formula (24), and ring C 21 and Ring C 22 the other is a ring structure represented by any one of the general formulas (25A) and (25B), However, ring B 21 , ring B 22 , ring C 21 and Ring C 22 at least one of the ring structures represented by general formula (25B) In the general formulae (221), (222), and (231), * indicates the bonding position.

[0252] In the second compound according to this embodiment, ring A 21 and Ring A 23 is a ring structure represented by the general formula (24), and ring A 22 and Ring A 24 are each independently a ring structure represented by the general formula (25A) or (25B), and ring A 22 and Ring A 24 At least one of these is preferably a ring structure represented by the general formula (25B). In the second compound according to this embodiment, ring A 21 and Ring A 23 is a ring structure represented by the general formula (24), and ring A 22 and Ring A 24 is also preferably a ring structure represented by the general formula (25B). In the second compound according to this embodiment, ring B 21 and Ring C 21 is a ring structure represented by the general formula (24), and ring B 22 and Ring C 22 are each independently a ring structure represented by the general formula (25A) or (25B), and ring B 22 and Ring C 22 At least one of these is preferably a ring structure represented by the general formula (25B). In the second compound according to this embodiment, ring B 21 is a ring structure represented by the general formula (24), ring 2B2 is a ring structure represented by the general formula (25B), and ring C 21 is a ring structure represented by the general formula (24), and ring C 22 is also preferably a ring structure represented by the general formula (25B).

[0253] In the second compound according to this embodiment, ring A 21 and Ring A 23 is a ring structure represented by the general formula (24), and ring A 22 and Ring A 24 is a ring structure represented by the general formula (25B), and ring B 21 is a ring structure represented by the general formula (24), and ring B 22is a ring structure represented by the general formula (25B), and ring C 21 is a ring structure represented by the general formula (24), and ring C 22 is preferably a ring structure represented by the general formula (25B).

[0254] In the second compound according to this embodiment, at least one D 21 is preferably a group represented by the general formula (231).

[0255] In the second compound according to this embodiment, at least one D 21 is preferably a group represented by the following general formula (223), (224), (225) or (232).

[0256] [ka]

[0257] [ka]

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[0259] (In the general formulae (223), (224) and (225), R 221 ~R 228 are R in the general formula (22), respectively. 221 ~R 228 is synonymous with R 291 ~R 294 are each independently R in the general formula (24). 29 is synonymous with In the general formula (232), R 231 ~R 238 are R in the general formula (23), respectively. 231 ~R 238 is synonymous with R 295 ~R 298are each independently R in the general formula (24). 29 is synonymous with In the general formulae (223), (224), (225) and (232), X 21 and X 22 are each independently an oxygen atom or a sulfur atom, provided that X 21 and X 22 At least one of the groups is a sulfur atom, and * indicates the bonding position.

[0260] In the second compound according to this embodiment, X 21 is preferably a sulfur atom. In the second compound according to this embodiment, X 22 and X 21 is preferably a sulfur atom.

[0261] In the second compound according to this embodiment, at least one D 21 is preferably a group represented by the general formula (232).

[0262] In the second compound according to this embodiment, D 22 is a group represented by the general formula (21) or (22), and m is preferably an integer of 1 or more.

[0263] In the second compound according to this embodiment, m is preferably 1, 2 or 3, more preferably 1 or 2, and even more preferably 1.

[0264] In the second compound according to this embodiment, D 22 is preferably a group represented by the general formula (22). In the second compound according to this embodiment, D 22 is also preferably a group represented by the general formula (21).

[0265] In the second compound according to this embodiment, the group represented by the general formula (22) is preferably a group represented by the following general formula (22A), (22B), (22C), (22D), (22E), or (22F).

[0266] [ka]

[0267] [ka]

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[0269] (In the general formulae (22A), (22B), (22C), (22D), (22E) and (22F), R 221 ~R 228 are R in the general formula (22), respectively. 221 ~R 228 is synonymous with R 229 and R 230 are each independently R in the general formula (24). 29 is synonymous with X 23 is an oxygen atom or a sulfur atom, and * in the general formulae (22A), (22B), (22C), (22D), (22E) and (22F) indicates the bonding position.

[0270] In the second compound according to this embodiment, X 23 is preferably a sulfur atom.

[0271] In the second compound according to this embodiment, R 21 ~R 28 It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other. In the second compound according to this embodiment, R 221 ~R 228It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other. In the second compound according to this embodiment, R 231 ~R 238 It is also preferred that any pair of two or more adjacent groups of the above is not bonded to each other.

[0272] In the second compound according to the present embodiment, it is preferable that R in the general formula (2) each independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0273] In the second compound according to the present embodiment, it is preferable that R in the general formula (2) are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0274] In the second compound according to this embodiment, R 21 ~R 28 , R in the general formula (22) 221 ~R 228 , R in the general formula (23) 231 ~R 238 and R in the general formula (24) 29 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0275] In the second compound according to this embodiment, R 21 ~R 28 , R in the general formula (22) 221 ~R 228 , R in the general formula (23) 231 ~R 238 and R in the general formula (24)29 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0276] In the second compound according to this embodiment, R in the general formula (2) is each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and R in the general formula (21) is 21 ~R 28 , R in the general formula (22) 221 ~R 228 , R in the general formula (23) 231 ~R 238 and R in the general formula (24) 29 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0277] In the second compound according to this embodiment, R in the general formula (2) is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, and R in the general formula (21) is 21 ~R 28 , R in the general formula (22) 221 ~R 228 , R in the general formula (23) 231 ~R 238 and R in the general formula (24) 29 are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

[0278] In the second compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms; an unsubstituted alkenyl group having 2 to 25 carbon atoms; an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms; -Si(R 901 )(R 902 )(R 903 ) a group represented by -O-(R 904 ) a group represented by -S-(R 905 ) a group represented by -N(R 906 )(R 907 ) 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.

[0279] In the second compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0280] In the second compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0281] In the second compound according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0282] As used herein, —O—(R 904 ) is a group represented by R 904 When is a hydrogen atom, it is a hydroxy group. As used herein, -S-(R 905 ) is a group represented by R 905 When is a hydrogen atom, it is a thiol group. As used herein, -P(=O)(R 931 )(R 932 ) is a group represented by R 931 and R 932 is a substituent, it is a substituted phosphine oxide group, and R 931 and R 932 When is an aryl group, it is an arylphosphoryl group. As used herein, -Ge(R 933 )(R 934 )(R 935 ) is a group represented by R 933 , R 934 and R 935 is a substituent, it is a substituted germanium group. As used herein, -B(R 936 )(R 937 ) is a group represented by R 936 and R 937 is a substituent, it is a substituted boryl group.

[0283] (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 to the excited singlet state, which normally has a low transition probability, 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 second compound according to this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0284] Generally, delayed fluorescence can be confirmed by transient PL (photoluminescence) measurement.

[0285] 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.

[0286] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Figure 2. An example of a method for measuring transient PL and an analysis of the behavior of delayed fluorescence will be described below using Figure 2.

[0287] 2 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. 2.

[0288] 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 %.

[0289] 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.

[0290] For example, a thin film sample A was prepared as described above using the following compound HX1 as the matrix material and the following compound DX1 as the doping material, and transient PL measurement was carried out.

[0291] [ka]

[0292] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following compound HX2 as a matrix material and the above-mentioned compound DX1 as a doping material.

[0293] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0294] [ka]

[0295] 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.

[0296] 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.

[0297] 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. 2.

[0298] Furthermore, to measure the delayed fluorescence of the second compound according to this embodiment, a sample prepared by the following method is used. For example, the second 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 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 intensities of both spectra according to equation (1) in Morris et al., J. Phys. Chem. 80 (1976) 969.

[0299] 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 of prompt luminescence and delayed luminescence and their ratio for compounds other than the second compound according to this embodiment are measured in the same manner as the amounts of prompt luminescence and delayed luminescence and their ratio for the second compound according to this embodiment.

[0300] (ΔST) In this embodiment, the lowest excited singlet energy S1 and the energy gap T at 77 [K] 77K The difference between (S1-T77K ) is defined as ΔST.

[0301] The lowest excited singlet energy S1(M2) of the second compound according to this embodiment and the energy gap T at 77 [K] of the second compound according to this embodiment 77K The difference ΔST(M2) from (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies any of the relationships of the following mathematical formulas (10), (11), (12), and (13). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV …(Math. 11) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV …(Math. 12) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV…(Math 13)

[0302] (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. Here, the second compound according to this embodiment is preferably a thermally activated delayed fluorescent compound having 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 believed 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

[0303] 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.

[0304] (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 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. The vertical axis of the absorption spectrum represents absorption intensity, and the horizontal axis represents wavelength. 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.

[0305] 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.

[0306] (Method for producing the second compound) The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0307] (Specific Example of the Second Compound) Specific examples of the second compound according to this embodiment include the following compounds, however, the present invention is not limited to these specific examples.

[0308] [ka]

[0309] [ka]

[0310] [ka]

[0311] [ka]

[0312] [ka]

[0313] [ka]

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[0315]

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[0316]

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[0317]

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[0318]

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[0319]

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[0320]

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[0321]

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[0322]

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[0323]

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[0326] [ka]

[0327] [ka]

[0328] (Relationship between the first compound and the second compound in the light-emitting layer) In the organic EL device according to this embodiment, the light-emitting layer contains a fluorescent first compound and a delayed fluorescent second compound, and it is preferable that the lowest excited singlet energy S1(M1) of the first compound and the lowest excited singlet energy S1(M2) of the second compound satisfy the relationship shown in the following mathematical formula (Mathematical Formula 1). S1(M2)>S1(M1)…(Math 1)

[0329] Energy gap T of the first compound at 77[K] 77K (M1) is the energy gap T at 77[K] of the second compound 77K It is preferable that the value is smaller than (M2). In other words, it is preferable that the relationship of the following mathematical formula (Mathematical Formula 5) is satisfied. T 77K (M2)>T 77K (M1) ... (Number 5)

[0330] When the organic EL device of this embodiment is caused to emit light, it is preferable that the first compound mainly emits light in the light-emitting layer.

[0331] (TADF mechanism) Figure 4 shows an example of the relationship between the energy levels of the second compound and the first compound in the light-emitting layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound. T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound. T1(M2) represents the lowest excited triplet state of the second compound. 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 the second compound to the first compound. As shown in Figure 4, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound 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.

[0332] 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 maximum 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 maximum 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 maximum peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0333] The maximum peak wavelength of light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2A 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).

[0334] (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.

[0335] (Compound content in the light-emitting layer) In the organic EL device of this embodiment, the contents of the first compound and the second compound contained in the light-emitting layer are preferably within the following ranges, for example. In the organic EL element of this embodiment, the content of the first compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. In the organic EL element of this embodiment, the content of the second compound is preferably from 10% to 80% by mass, more preferably from 10% to 60% by mass, and even more preferably from 20% to 60% by mass. In addition, in the organic EL element of this embodiment, the content of the second compound may be from 90% to 99.9% by mass, from 95% to 99.9% by mass, or from 99% to 99.9% by mass. The present embodiment does not exclude the case where the light-emitting layer contains materials other than the first compound and the second compound. In the organic EL device of the present embodiment, the light-emitting layer may contain only one type of first compound or two or more types. The light-emitting layer may contain only one type of second compound or two or more types.

[0336] The structure of the organic EL element according to this embodiment will be further described.

[0337] (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.

[0338] (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 thereof, 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 can be used to form the anode using alkali metals, alkaline earth metals, and alloys containing these metals. Furthermore, when using silver paste, coating and inkjet printing can be used.

[0339] When the organic EL element is a bottom-emission type, the anode is a light-transmitting electrode having light-transmitting properties. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. In this specification, light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the anode section. The light-transmitting or semi-transmitting metal material may be a material listed as a material used for the conductive layer (or transparent conductive layer) described below.

[0340] When the organic EL device is a top-emission type, the anode is a light-reflective electrode having a light-reflective layer. The light-reflective layer is preferably formed of a metal material having light reflectivity. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metal material having light reflectivity can be appropriately selected from the materials listed in the above section on the anode. Examples of metal materials used for the light-reflecting layer include a simple metal material selected from the group consisting of Al, Ag, Ta, Zn, Mo, W, Ni, and Cr, or an alloy material containing a metal selected from this group as the main component (preferably 50% by mass or more of the total); an amorphous alloy selected from the group consisting of NiP, NiB, CrP, and CrB; and a microcrystalline alloy selected from the group consisting of NiAl and silver alloys. The metal material used for the light-reflecting layer may be at least one alloy selected from the group consisting of APC (an alloy of silver, palladium, and copper), ARA (an alloy of silver, rubidium, and gold), MoCr (an alloy of molybdenum and chromium), and NiCr (an alloy of nickel and chromium). The light-reflecting layer may be a single layer or multiple layers.

[0341] The anode as a light-reflective electrode may be composed of only a light-reflecting layer, or may have a multilayer structure including a light-reflecting layer and a conductive layer (preferably a transparent conductive layer). When the anode has a light-reflecting layer and a conductive layer, the conductive layer is preferably disposed between the reflective layer and a layer including a hole-transporting region (e.g., a hole-injection layer or a hole-transporting layer). The anode may also have a multilayer structure in which a light-reflecting layer is disposed between two conductive layers (a first conductive layer and a second conductive layer). In such a multilayer structure, the first conductive layer and the second conductive layer may be formed of the same material or different materials. The material used for the conductive layer can be appropriately selected from the materials listed in the anode section. In addition, the conductive layer (transparent conductive layer) serving as a transparent electrode can also be made of a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Furthermore, the conductive layer may be made of, for example, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing at least one selected from the group consisting of alkali metals and alkaline earth metals (e.g., MgAg and AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing at least one selected from rare earth metals.

[0342] (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.

[0343] When the organic EL element is a bottom-emission type, the cathode is a light-reflective electrode. The light-reflective electrode is preferably formed of a metal material having light reflectivity. The light-reflective metal material can be appropriately selected from the materials listed in the cathode section. In addition, the light-reflective metal material may be the material listed as the metal material used for the light-reflecting layer.

[0344] When the organic EL element is a top-emission type, the cathode is a light-transmitting electrode having light-transmitting properties. The light-transmitting electrode is preferably formed of a light-transmitting or semi-transmitting metal material that transmits light emitted from the light-emitting layer. Light-transmitting or semi-transmitting means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-transmitting or semi-transmitting metal material can be appropriately selected from the materials listed in the section on the cathode. The light-transmitting or semi-transmitting metal material may be the material listed above as the material used for the conductive layer (or transparent conductive layer).

[0345] (capping layer) When the organic EL device is a top-emission type, the organic EL device usually has a capping layer on the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). The capping layer may also contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, and dibenzofuran derivatives. A laminate obtained by stacking layers containing these substances can also be used as the capping layer.

[0346] The organic EL element according to this embodiment may be a bottom-emission type organic EL element, or may be a top-emission type organic EL element. When the organic EL element is a bottom-emission type, it is preferable that the anode is a light-transmitting electrode having light transparency, and the cathode is a light-reflective electrode having light reflection. When the organic EL element is a top-emission type, it is preferable that the anode is a light-reflective electrode having light reflectivity, and the cathode is a light-transmitting electrode having light transmittance.

[0347] (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.

[0348] (Hole transport layer) The organic EL device of this embodiment preferably includes a hole transport layer between the anode and the light-emitting layer. The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. 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- ... Aromatic amine compounds such as phenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) 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-transporting layer may be formed using 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 also be used as long as they have a higher hole-transporting capacity than electron-transporting capacity. The layer containing the substance with a high hole-transporting capacity may be a single layer or a layer in which two or more layers made of the above-mentioned substances are stacked.

[0349] (electron barrier layer) The electron blocking layer is preferably a layer that transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) closer to the anode than the electron blocking layer. The compound contained in the electron blocking layer is, for example, a compound used in known electron blocking layers, and is preferably at least one compound selected from the group consisting of aromatic amine compounds and carbazole derivatives. The compound contained in the electron blocking layer may also be a monoamine compound having only one substituted or unsubstituted amino group in the molecule. The compound contained in the electron blocking layer may also be a compound having a substituted or unsubstituted carbazolyl group and one substituted or unsubstituted amino group in the molecule. In the organic EL device according to this embodiment, the compound contained in the electron blocking layer is also preferably a monoamine compound containing one or more rings selected from the group consisting of a substituted or unsubstituted carbazole ring, a substituted or unsubstituted dibenzofuran ring, and a substituted or unsubstituted fluorene ring. The electron blocking layer may be a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the anode than the electron blocking layer (e.g., a hole transport layer and a hole injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0350] (hole blocking layer) The hole blocking layer is preferably a layer that transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) closer to the cathode than the hole blocking layer. The compound contained in the hole blocking layer is, for example, a compound used in known hole blocking layers. The compound contained in the hole blocking layer is preferably at least one compound selected from the group consisting of metal complexes, heteroaromatic compounds, and polymer compounds, similar to the compounds that can be used in the electron transport layer described below. The compound contained in the hole blocking layer may also be, for example, at least one compound selected from the group consisting of imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives. In the organic EL device according to this embodiment, the compound contained in the hole blocking layer is preferably a compound having an azine ring and a carbazole ring, or a compound having an azine ring and a dibenzofuran ring. It is also preferable that the hole blocking layer is a layer that prevents excitons generated in the light-emitting layer from migrating to a layer closer to the cathode than the hole blocking layer (for example, an electron transport layer or an electron injection layer) so that excitation energy does not leak from the light-emitting layer to a peripheral layer.

[0351] (electron transport layer) The organic EL device of this embodiment also preferably includes an electron transport layer between the cathode and the light-emitting layer. The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can be made of 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; or 3) polymer compounds. Specifically, 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 can be used as low-molecular-weight organic compounds. 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).

[0352] (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 in 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.

[0353] (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.

[0354] (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.

[0355] Second Embodiment [Organic electroluminescence element] The configuration of an organic EL element according to a second embodiment will be described. In the description of the second embodiment, the same components as those in the first embodiment will be denoted by the same reference numerals or names, and the description thereof will be omitted or simplified. Furthermore, in the second embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the first embodiment can be used.

[0356] The organic EL device according to the second embodiment differs from the organic EL device according to the first embodiment in that the light-emitting layer further contains a third compound, but is otherwise similar to the organic EL device according to the first embodiment. In a second embodiment, the light-emitting layer includes a first compound, a second compound, and a third compound. In this embodiment, the first compound is preferably a dopant material, the second compound is preferably a host material, and the third compound is preferably a host material. The third compound is preferably not a dopant material.

[0357] The organic EL device according to this embodiment has an anode, a cathode, and an emitting layer between the anode and the cathode. The emitting layer contains a first fluorescent compound, a second delayed fluorescent compound, and a third compound. The first compound is represented by general formula (1), the second compound is represented by general formula (2), and the third compound is represented by general formula (3):

[0358] In the organic EL device according to this embodiment, the light-emitting layer contains a first fluorescent compound represented by general formula (1), a second delayed fluorescent compound represented by general formula (2), and a third compound represented by general formula (3), thereby improving the performance of the organic EL device. The organic EL device according to one aspect of this embodiment improves luminous efficiency (e.g., external quantum efficiency or current efficiency). Furthermore, the organic EL device according to one aspect of this embodiment extends the life of the organic EL device. Furthermore, the organic EL device according to one aspect of this embodiment reduces the driving voltage of the organic EL device. The organic EL device according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0359] (Third Compound) In the organic EL device according to this embodiment, the third compound is a compound represented by the following general formula (3).

[0360] [ka]

[0361] (In the general formula (3), Y3 is an oxygen atom or a sulfur atom, R 31 ~R 38 One of the is a single bond that binds to *3, 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, n3 is 0 or 1, m3 is 0 or 1, R 310 , R 320 and R which is not a single bond bonded to *3, 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, halogen atoms, cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated 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 alkenyl group having 2 to 50 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 50 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 -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 -P(=O)(OR 938 )(OR 939 ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or is a nitro group, Multiple R 310 are identical to or different from each other, Multiple R 320 are identical to or different from each other, A 30 is a group represented by any one of the formulae selected from the group consisting of the following general formulae (31A), (31B), (31C), (31D), (31E), and (31F).

[0362] [ka]

[0363] [ka]

[0364] [ka]

[0365] (In the general formulae (31A), (31B), (31C), (31D), (31E) and (31F), X3 is an oxygen atom or a sulfur atom, R 331 ~R 340 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 331 ~R 340 R each independently does not form the substituted or unsubstituted monocyclic ring in the general formula (3) and does not form the substituted or unsubstituted fused ring. 31 ~R 38 *a is equivalent to A 30 ) (In the third compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 , R 937 , R 938 and R 939 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 906 and R907 are each independently, 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 substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R 901 If there are multiple R 901 are the same or different, and R 902 If there are multiple R 902 are the same or different, and R 903 If there are multiple R 903 are the same or different, and R 904 If there are multiple R 904 are the same or different, and R 905 If there are multiple R 905 are the same or different, and R 906 If there are multiple R 906 are the same or different, and R 907 If there are multiple R 907 are the same or different, and R 908 If there are multiple R 908 are the same or different, and R 909 If there are multiple R 909 are the same or different, and R 931 If there are multiple R 931 are the same or different, and R 932 If there are multiple R 932 are the same or different, and R 933 If there are multiple R 933 are the same or different, and R 934 If there are multiple R 934 are the same or different, and R 935 If there are multiple R 935 are the same or different, and R 936 If there are multiple R936 are the same or different, and R 937 If there are multiple R 937 are the same or different, and R 938 If there are multiple R 938 are the same or different, and R 939 If there are multiple R 939 are either identical or different.)

[0366] In the general formula (3), when n3 is 0 and m3 is 1, *a in the general formulae (31A), (31B), (31C), (31D), (31E) and (31F) is R 320 represents the bonding position of any one of the carbon atoms of the benzene ring to which it is attached. In the general formula (3), when n3 is 1 and m3 is 0 or 1, *a in the general formulae (31A), (31B), (31C), (31D), (31E) and (31F) is R 310 represents the bonding position of any one of the carbon atoms of the benzene ring to which it is attached. In the general formula (3), when n3 is 0 and m3 is 0, *a in the general formulae (31A), (31B), (31C), (31D), (31E) and (31F) is R 31 ~R 34 represents the bonding position of any one of the carbon atoms of the six-membered ring to which the group is bonded.

[0367] In the third compound according to this embodiment, R 31 ~R 34 It is preferable that any one of R is a single bond bonded to *3, 32 is more preferably a single bond bonded to *3. In the third compound according to this embodiment, R 32 When is a single bond bonded to *3, the general formula (3) is represented by the following general formula (30).

[0368] [ka]

[0369] (In the general formula (30), A 30 , R 310 , R 320 , n3, m3, R 31 , R 33 ~R 38 and Y3 are each A in the general formula (3). 30 , R 310 , R 320 , n3, m3, R 31 , R 33 ~R 38 and Y3.)

[0370] In the third compound according to this embodiment, it is preferred that n3 is 1 and m3 is 0 or 1.

[0371] In the third compound according to this embodiment, n3 and m3 are 0, or n3 is 1, m3 is 0, and R 310 It is also preferred that is a hydrogen atom.

[0372] In the third compound according to this embodiment, n3 and m3 are also preferably 0.

[0373] In the third compound according to this embodiment, R 31 is a single bond bonded to *3, n3 is 1, and m3 is 0, the general formula (3) is represented by the following general formula (301). In the third compound according to this embodiment, R 32 is a single bond bonded to *3, n3 is 1, and m3 is 0, the general formula (3) is represented by the following general formula (302). In the third compound according to this embodiment, R 33 is a single bond bonded to *3, n3 is 1, and m3 is 0, the general formula (3) is represented by the following general formula (303). In the third compound according to this embodiment, R 34 is a single bond bonded to *3, n3 is 1, and m3 is 0, the general formula (3) is represented by the following general formula (304).

[0374] [ka]

[0375] [ka]

[0376] (In the general formulae (301) to (304), A 30 , R 310 , R 31 ~R 38 and Y3 are each A in the general formula (3). 30 , R 310 , R 31 ~R 38 and Y3.)

[0377] In the organic EL device according to this embodiment, the third compound is preferably a compound represented by the following general formula (32A).

[0378] [ka]

[0379] (In the general formula (32A), A 30 , Y3, R 31 ~R 38 and *3 respectively represent A in the general formula (3). 30 , Y3, R 31 ~R 38 and *3, R 311 ~R 314 are each independently R in the general formula (3). 310 is equivalent to

[0380] In the organic EL device according to this embodiment, the third compound is also preferably a compound represented by the following general formula (32B).

[0381] [ka]

[0382] (In the general formula (32B), A 30 , Y3, R 31 ~R 38 and *3 respectively represent A in the general formula (3). 30 , Y3, R 31 ~R 38 and *3, R 311 ~R 314 are each independently R in the general formula (3). 310 is equivalent to

[0383] In the organic EL device according to this embodiment, the third compound is also preferably a compound represented by the following general formula (32C).

[0384] [ka]

[0385] (In the general formula (32C), A 30 , Y3, R 31 ~R 38 and *3 respectively represent A in the general formula (3). 30 , Y3, R 31 ~R 38 and *3, R 311 ~R 314 are each independently R in the general formula (3). 310 is equivalent to

[0386] In the third compound according to this embodiment, A 30 is preferably a group represented by the general formula (31D), (31E) or (31F), and A 30 is more preferably a group represented by the general formula (31D) or (31F).

[0387] In the third compound according to this embodiment, A 30 is also preferably a group represented by the general formula (31D).

[0388] In the third compound according to this embodiment, A 30 is also preferably a group represented by the general formula (31F).

[0389] In the third compound according to this embodiment, X3 is also preferably an oxygen atom.

[0390] In the third compound according to this embodiment, X3 is also preferably a sulfur atom.

[0391] In the third compound according to this embodiment, Y3 is preferably an oxygen atom. In the third compound according to this embodiment, X3 and Y3 are preferably oxygen atoms. In the third compound according to this embodiment, it is also preferable that X3 is a sulfur atom and Y3 is an oxygen atom.

[0392] In the organic EL device according to this embodiment, the third compound is preferably a compound represented by the following general formula (321A).

[0393] [ka]

[0394] (In the general formula (321A), Y3, R 31 ~R 38 and *3 respectively represent Y and R in the general formula (3). 31 ~R 38 and *3, R 311 ~R 314 are each independently R in the general formula (3). 310 is synonymous with A 32 is a group represented by any one of the formulae selected from the group consisting of the following general formulae (33A), (33B), (33C), (33D), (33E), (33F), (34A), (34B), (34C), (34D), (34E) and (34F).

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] [ka]

[0399] [ka]

[0400] [ka]

[0401] (In the general formulae (33A), (33B), (33C), (33D), (33E), (33F), (34A), (34B), (34C), (34D), (34E) and (34F), R 331 ~R 340 and *a are R in the general formulae (31A), (31B), (31C), (31D), (31E), and (31F), respectively. 331 ~R 340 and *a.)

[0402] In the third compound according to this embodiment, A 32 is preferably a group represented by the general formula (33D) or (34F).

[0403] In the third compound according to this embodiment, A 30is preferably a group represented by any one of the formulae selected from the group consisting of the general formulae (33A), (33B), (33C), (33D), (33E), (33F), (34A), (34B), (34C), (34D), (34E) and (34F). In the third compound according to this embodiment, A 30 is preferably a group represented by the general formula (33D) or (34F).

[0404] In the third compound according to this embodiment, R 331 ~R 340 is preferably a hydrogen atom.

[0405] In the third compound according to this embodiment, R 31 ~R 38 is preferably a hydrogen atom.

[0406] In the third compound according to this embodiment, the substituent in the term "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 a group represented by -COOR 909 a group represented by -P(=O)(R 931 )(R 932 ), a group represented by -Ge(R 933 )(R 934 )(R 935 ), a group represented by -B(R 936 )(R 937 ), a group represented by -S(=O)R 938a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms, R 901 ~R 909 , and R 931 ~R 938 are preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0407] In the third compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[0408] In the third compound according to the present embodiment, the substituent in the term "substituted or unsubstituted" is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[0409] In the organic EL device according to this embodiment, it is also preferable that all of the groups described as "substituted or unsubstituted" in the third compound are "unsubstituted" groups.

[0410] In the organic EL device according to this embodiment, it is also preferable that the only compound in the light-emitting layer having a minimum excited singlet energy S1 greater than the minimum excited singlet energy S1(M2) of the second compound is the third compound.

[0411] (Method for producing the third compound) The third compound according to this embodiment can be produced by a known method. Alternatively, the third compound can be produced by following a known method and using known alternative reactions and raw materials suited to the target compound.

[0412] (Specific Example of the Third Compound) Specific examples of the third compound according to this embodiment include the following compounds, however, the present invention is not limited to these specific examples of compounds.

[0413] [ka]

[0414] [ka]

[0415] [ka]

[0416] [ka]

[0417] [ka]

[0418] [ka]

[0419] [ka]

[0420] [ka]

[0421] [ka]

[0422] [ka]

[0423] [ka]

[0424] [ka]

[0425] [ka]

[0426] [ka]

[0427] (Relationship between the first compound, the second compound, and the third compound in the light-emitting layer) In the organic EL device according to this embodiment, when the light-emitting layer contains a first compound, a second compound, and a third compound, it is preferable that the lowest excited singlet energy S1(M2) of the second compound and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship shown in the following mathematical formula (Mathematical Formula 2A). S1(M3)>S1(M2) ... (Mathematics 2A)

[0428] In the organic EL device according to this embodiment, it is preferable that the lowest excited singlet energy S1(M1) of the first compound, the lowest excited singlet energy S1(M2) of the second compound, and the lowest excited singlet energy S1(M3) of the third compound satisfy the relationship of the following mathematical formula (Mathematical Formula 2). S1(M3)>S1(M2)>S1(M1)…(Number 2)

[0429] In the organic EL device according to this embodiment, the energy gap T 77K (M3) is the energy gap T of the first compound at 77[K].77K It is preferable that it is larger than (M1). In the organic EL device according to this embodiment, the energy gap T 77K (M3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (M2).

[0430] In the organic EL device according to this embodiment, the energy gap T 77K (M1) and the energy gap T at 77[K] of the second compound 77K (M2) and the energy gap T at 77[K] of the third compound 77K It is preferable that (M3) satisfies the relationship of the following mathematical formula (Mathematical Formula 2B). T 77K (M3)>T 77K (M2)>T 77K (M1) ... (Math 2B)

[0431] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent first compound mainly emits light in the light-emitting layer. The organic EL element of this embodiment preferably emits red or green light, similarly to the organic EL element of the first embodiment. The maximum peak wavelength of the light emitted from the organic EL element can be measured in the same manner as in the organic EL element of the first embodiment.

[0432] (Compound content in the light-emitting layer) In the organic EL device according to this embodiment, when the light-emitting layer contains the first compound, the second compound, and the third compound, the contents of the first compound, the second compound, and the third compound in the light-emitting layer are preferably, for example, in the following ranges. In the organic EL element according to this embodiment, the content of the first compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. In the organic EL element according to this embodiment, the content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. In the organic EL device according to this embodiment, the content of the third compound is preferably 10% by mass or more and 80% by mass or less. In the organic EL device according to this embodiment, the upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the case where the light-emitting layer contains materials other than the first compound, the second compound, and the third compound. In the organic EL device according to this embodiment, the light-emitting layer may contain only one type of first compound or two or more types thereof. The light-emitting layer may contain only one type of second compound or two or more types thereof. The light-emitting layer may contain only one type of third compound or two or more types thereof.

[0433] FIG. 5 shows an example of the relationship between the energy levels of a first compound, a second compound, and a third compound in an emitting layer. In FIG. 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. The dashed arrow from S1(M2) to S1(M1) in FIG. 5 represents Förster energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound. As shown in Figure 5, when a compound with a small ΔST(M2) is used as the second compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound 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.

[0434] Third Embodiment (electronic equipment) The electronic device according to this embodiment is equipped with the organic electroluminescence element according to the above-described embodiment. Examples of the electronic device include a display device and a light-emitting device. Examples of the display device include display components (e.g., an organic EL panel module), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lighting fixtures. The light-emitting device can be used in a display device, for example, as a backlight for a display device.

[0435] [Modification 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.

[0436] 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.

[0437] 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.

[0438] In addition, the specific structure and shape in carrying out the present invention may be other structures within the scope that the object of the present invention can be achieved. [Example]

[0439] 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.

[0440] <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 1-17 and Examples 2-1 to 2-7 are shown below.

[0441] [ka]

[0442] The structures of the comparative compounds used in the production of the organic EL devices according to Comparative Examples 1-1 to 1-4 are shown below.

[0443] [ka]

[0444] The structures of the compounds represented by general formula (2) used in the production of the organic EL devices according to Examples 1-1 to 1-17 and Examples 2-1 to 2-7 or Comparative Examples 1-1 to 1-4 are shown below.

[0445] [ka]

[0446] The structures of the compounds represented by general formula (3) used in the production of the organic EL devices according to Examples 1-1 to 1-17 and Examples 2-1 to 2-7 or Comparative Examples 1-1 to 1-4 are shown below.

[0447] [ka]

[0448] The structures of other compounds used in the production of the organic EL devices according to Examples 1-1 to 1-17 and Examples 2-1 to 2-7 or Comparative Examples 1-1 to 1-4 are shown below.

[0449] [ka]

[0450] [ka]

[0451] [ka]

[0452] [ka]

[0453] [ka]

[0454] <Fabrication of Organic EL Devices (1)> (Example 1-1) The organic EL device of Example 1-1 was produced as follows. 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-1-1 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-1-1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass. Next, the compound HT-1-1 was vapor-deposited on the hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compound HT-2-1 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 30 nm. This second hole transport layer may be referred to as an electron blocking layer. Next, a 40 nm thick light-emitting layer was formed on the second hole transport layer by co-depositing a fluorescent compound GD-1 as a first compound, a delayed fluorescent compound TADF-1 as a second compound, and a compound Matrix-2 as a third compound. The concentrations of compound GD-1, TADF-1, and Matrix-2 in the light-emitting layer were 0.6 mass %, 35 mass %, and 64.4 mass %, respectively. Next, the compound ET-1-1 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 5 nm. This first electron-transporting layer may be referred to as a hole-blocking layer. Next, the compound ET-2-1 and Liq were co-deposited on the first electron-transporting layer to form a second electron-transporting layer with a thickness of 50 nm. The concentration of the compound ET-2-1 in the second electron-transporting layer was 50 mass %, and the concentration of Liq was 50 mass %. Liq is an abbreviation for (8-quinolinolato)lithium. Next, ytterbium (Yb) was vapor deposited on this second electron transport layer to form an electron injecting electrode (cathode) with a film thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injecting electrode to form a metallic Al cathode with a film thickness of 50 nm. The device configuration of the organic EL device of Example 1-1 is shown in outline below. ITO(130) / HT-1-1:HA(10,97%:3%) / HT-1-1(90) / HT-2-1(30) / Matrix-2:TADF-1: GD-1(40,64.4%:35%:0.6%) / ET-1-1(5) / ET-2-1:Liq(50,50%:50%) / Yb(1) / Al(50) The numbers in parentheses indicate film thickness (unit: nm). Also in parentheses, the percentages (97%:3%) indicate the concentrations (mass%) of compound HT-1-1 and compound HA in the hole injection layer, the percentages (64.4%:35%:0.6%) indicate the concentrations (mass%) of the third compound, second compound, and first compound in the light-emitting layer, and the percentages (50%:50%) indicate the concentrations (mass%) of compound ET-2-1 and Liq in the second electron transport layer.

[0455] (Examples 1-2 to 1-15) The organic EL devices of Examples 1-2 to 1-15 were fabricated in the same manner as the organic EL device of Example 1-1, except that the third compound, Martinx-2, the second compound, TADF-1, and the first compound, Compound GD-1, in the emitting layer of the organic EL device of Example 1-1 were replaced with the third compound, second compound, and first compound, respectively, shown in Table 1, and that the concentrations of the third compound (64.4% by mass) and the second compound (35% by mass) in the emitting layer of Examples 1-3 to 1-11 and 1-13 to 1-15 were replaced with the third compound (59.4% by mass) and the second compound (40% by mass), respectively. Note that in the following tables, the unit of concentration represented as [%] means % by mass.

[0456] (Comparative Examples 1-1 to 1-4) The organic EL devices of Comparative Examples 1-1 to 1-4 were produced in the same manner as the organic EL device of Example 1-1, except that the third compound, Martinx-2, the second compound, TADF-1, and the first compound, GD-1, in the emitting layer of the organic EL device of Example 1-1 were changed to the third compound, the second compound, and the first compound, respectively, shown in Table 1, and that in Comparative Examples 1-3 to 1-4, the concentration of the third compound (64.4% by mass) and the concentration of the second compound (35% by mass) in the emitting layer were changed to the concentration of the third compound (59.4% by mass) and the concentration of the second compound (40% by mass), respectively.

[0457] <Evaluation of Organic EL Devices (1)> The produced organic EL devices were evaluated as follows. The evaluation results are shown in Table 1.

[0458] (driving voltage) Between the anode and cathode of the organic EL element, the current density is 10 mA / cm 2 The voltage (unit: V) was measured when electricity was applied so that

[0459] (External quantum efficiency EQE, maximum peak wavelength λ EL and emission spectrum half width FWHM) Current density is 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the maximum peak wavelength λ was obtained was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. In addition, from the obtained spectral radiance spectrum, the maximum peak wavelength λ EL The full width at half maximum (FWHM) of the emission spectrum (unit: nm) was measured. FWHM is an abbreviation for full width at half maximum.

[0460] (CIE1931 chromaticity) Current density is 10mA / cm 2 The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the organic EL element so that the chromaticity was as follows:

[0461] (Life span LT95) The current density of the organic EL element is 50mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0462] [Table 1]

[0463] <Fabrication of Organic EL Devices (2)> (Examples 1-16) The organic EL devices according to Examples 1 to 16 were produced as follows. 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-1-4 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-1-4 in the hole injection layer was 94 mass %, and the concentration of compound HA was 6 mass %. Next, the compound HT-1-4 was vapor-deposited on this hole injection layer to form a first hole transport layer having a thickness of 90 nm. Next, the compound HT-2-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm. Next, a 28 nm thick light-emitting layer was formed on the second hole transport layer by co-depositing a fluorescent compound GD-4 as a first compound, a delayed fluorescent compound TADF-2 as a second compound, and a compound Matrix-1 as a third compound. The concentrations of compound GD-4, TADF-2, and Matrix-1 in the light-emitting layer were 0.6 mass %, 35 mass %, and 64.4 mass %, respectively. Next, the compound ET-1-2 was vapor-deposited on the light-emitting layer to form a first electron-transporting layer having a thickness of 18 nm. This first electron-transporting layer may be referred to as a hole-blocking layer. Next, on the first electron-transporting layer, the compound ET-2-1 and Liq were co-deposited to form a second electron-transporting layer having a thickness of 18 nm, in which the concentration of the compound ET-2-1 in the second electron-transporting layer was 50% by mass, and the concentration of Liq in the second electron-transporting layer was 50% by mass. Next, ytterbium (Yb) was vapor deposited on the second 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 50 nm. The device configuration of the organic EL device according to Examples 1-16 is shown in outline below. ITO(130) / HT-1-4:HA(10,94%:6%) / HT-1-4(90) / HT-2-3(10) / Matrix-1:TADF-2:G D-4(28,64.4%:35%:0.6%) / ET-1-2(18) / ET-2-1:Liq(18,50%:50%) / Yb(1) / Al(50)

[0464] (Examples 1-17) The organic EL device of Example 1-17 was produced in the same manner as in Example 1-16, except that the compound ET-1-2 (first electron transport material) used in the first electron transport layer (hole blocking layer) of Example 1-16 was changed to a compound shown in Table 2.

[0465] <Evaluation of Organic EL Devices (2)> The produced organic EL devices were evaluated in the same manner as in <Evaluation of organic EL devices (1)>. The evaluation results are shown in Table 2.

[0466] [Table 2]

[0467] <Fabrication of Organic EL Devices (3)> Example 2-1 The organic EL device according to Example 2-1 was produced as follows. A 200 nm thick silver alloy layer, APC (Ag-Pd-Cu) layer, and a 10 nm thick indium oxide-zinc oxide (IZO) layer were deposited in this order by sputtering on a glass substrate (25 mm x 75 mm x 0.7 mm) for device fabrication. This resulted in a conductive material layer consisting of an APC layer and an IZO layer. The APC layer is a reflective layer, and the IZO layer is a transparent conductive layer. IZO is a registered trademark. Subsequently, using ordinary lithography techniques, this conductive material layer was patterned by etching using a resist pattern as a mask to form a lower electrode (anode). Next, on the lower electrode (anode), Compound HT-1-5 and Compound HA were co-deposited to form a hole injection layer with a thickness of 10 nm, in which the concentration of Compound HT-1-5 was 97% by mass and the concentration of Compound HA was 3% by mass. Next, the compound HT-1-5 was vapor-deposited on this hole injection layer to form a first hole transport layer having a thickness of 195 nm. Next, the compound HT-2-4 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm. Next, a 40 nm thick light-emitting layer was formed on the second hole transport layer by co-depositing a fluorescent compound GD-1 as a first compound, a delayed fluorescent compound TADF-2 as a second compound, and a compound Matrix-1 as a third compound. The concentrations of compound GD-1, TADF-2, and Matrix-1 in the light-emitting layer were 0.6 mass %, 25 mass %, and 74.4 mass %, respectively. Next, the compound ET-1-4 was vapor-deposited on this light-emitting layer to form a first electron-transporting layer (hole-blocking layer) having a thickness of 5 nm. Next, a second electron-transporting layer having a thickness of 30 nm was formed on the first electron-transporting layer by co-deposition of the compound ET-2-3 and Liq, in which the concentration of the compound ET-2-3 was 50% by mass and the concentration of Liq was 50% by mass. Next, ytterbium (Yb) was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Next, Mg and Ag were co-deposited on the electron injection layer at a mixing ratio (mass % ratio) of 10%:90% to form an upper electrode (cathode) made of a semi-transparent MgAg alloy with a total thickness of 14 nm. Next, a film of the compound CAP was formed on the entire surface of the upper electrode to form a capping layer with a thickness of 80 nm. The device configuration of the organic EL device according to Example 2-1 is shown in outline below. APC(200) / IZO(10) / HT-1-5:HA(10,97%:3%) / HT-1-5(195) / HT-2-4(5) / Matrix-1:TADF-2:GD-1(4 0,74.4%:25%:0.6%) / ET-1-4(5) / ET-2-3:Liq(30,50%:50%) / Yb(1) / Mg:Ag(14,10%:90%) / CAP(80)

[0468] (Examples 2-2 to 2-4) The organic EL devices of Examples 2-2 to 2-4 were manufactured in the same manner as the organic EL device of Example 2-1, except that the concentration of the third compound (74.4% by mass) and the concentration of the second compound (25% by mass) in the light-emitting layer were changed to the concentrations shown in Table 3.

[0469] <Evaluation of Organic EL Devices (3)> The produced organic EL elements were evaluated in the same manner as in <Evaluation of organic EL elements (1)>. The evaluation results are shown in Table 3. The lifetime LT95 and current efficiency were measured by the following methods.

[0470] (Life span LT95) The current density of the organic EL element is 30mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0471] (Current efficiency L / J) The current density of the organic EL element is 10.00mA / cm 2 The spectral radiance spectrum when a voltage was applied so that the value was 1 / 2 was measured using a spectroradiometer CS-1000 (manufactured by Konica Minolta, Inc.) The current efficiency L / J (unit: cd / A) was calculated from the obtained spectral radiance spectrum.

[0472] [Table 3]

[0473] <Fabrication of Organic EL Devices (4)> (Examples 2-5) The organic EL device according to Example 2-5 was produced as follows. A substrate for device fabrication was prepared by laminating a 100 nm thick metallic Ag layer as a reflective layer and a 10 nm thick ITO layer as a transparent conductive layer in that order on a glass substrate (25 mm x 75 mm x 0.7 mm). In this substrate for device fabrication, the conductive material layer consisted of a metallic Ag layer and an ITO layer. Next, using conventional lithography techniques, this conductive material layer was patterned by etching using a resist pattern as a mask to form a lower electrode (anode). The compound HT-1-4 and the compound HA were co-deposited on the lower electrode (anode) to form a hole injection layer having a thickness of 10 nm. The concentration of the compound HT-1-4 in the hole injection layer was 94% by mass, and the concentration of the compound HA was 6% by mass. The compound HT-1-4 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 140 nm. Next, the compound HT-2-3 was vapor-deposited on the first hole transport layer to form a second hole transport layer (electron blocking layer) having a thickness of 10 nm. On the second hole transport layer, a fluorescent compound GD-4 as a first compound, a delayed fluorescent compound TADF-2 as a second compound, and a compound Matrix-1 as a third compound were co-deposited to form an emitting layer with a thickness of 28 nm. The concentrations of compound GD-4, compound TADF-2, and compound Matrix-1 in the emitting layer were 0.6 mass %, 35 mass %, and 64.4 mass %, respectively. Next, the compound ET-1-2 was vapor-deposited on this light-emitting layer to form a first electron transporting layer (hole blocking layer) having a thickness of 40 nm. Next, on the first electron-transporting layer, the compound ET-2-1 and Liq were co-deposited to form a second electron-transporting layer having a thickness of 10 nm, in which the concentration of the compound ET-2-1 in the second electron-transporting layer was 50% by mass, and the concentration of Liq in the second electron-transporting layer was 50% by mass. Next, ytterbium (Yb) was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Next, Mg and Ag were co-deposited on the electron injection layer in a mixture ratio (mass % ratio) of 10%:90% to form an upper electrode (cathode) made of a semi-transparent MgAg alloy with a total thickness of 14 nm. Next, a film of the compound CAP was formed on the entire surface of the upper electrode to form a capping layer with a thickness of 85 nm. The device configuration of the organic EL device according to Example 2-5 is shown in outline below. Ag(100) / ITO(10) / HT-1-4:HA(10,94%:6%) / HT-1-4(140) / HT-2-3(10) / Matrix-1:TADF-2:GD-4(2 8,64.4%:35%:0.6%) / ET-1-2(40) / ET-2-1:Liq(10,50%:50%) / Yb(1) / Mg:Ag(14,10%:90%) / CAP(85)

[0474] (Examples 2-6) The organic EL device of Example 2-6 was produced in the same manner as in Example 2-5, except that the compound ET-1-2 (first electron transport material) used in the first electron transport layer (hole blocking layer) of Example 2-5 was changed to a compound shown in Table 4.

[0475] <Evaluation of Organic EL Devices (4)> The produced organic EL elements were evaluated in the same manner as in <Evaluation of organic EL elements (1)> and <Evaluation of organic EL elements (3)>, except for the following lifespan LT95. The evaluation results are shown in Table 4.

[0476] (Life span LT95) The current density of the organic EL element is 30mA / cm 2 The time required for the luminance to reach 95% of the initial luminance (LT95 (unit: hours)) was measured as the lifetime. The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.).

[0477] [Table 4]

[0478] <Fabrication of Organic EL Devices (5)> (Examples 2-7) The organic EL device according to Example 2-7 was produced as follows. A substrate for device fabrication was prepared by laminating a 100 nm thick metallic Ag layer as a reflective layer and a 10 nm thick ITO layer as a transparent conductive layer in that order on a glass substrate (25 mm x 75 mm x 0.7 mm). In this substrate for device fabrication, the conductive material layer consisted of a metallic Ag layer and an ITO layer. Next, using conventional lithography techniques, this conductive material layer was patterned by etching using a resist pattern as a mask to form a lower electrode (anode). The compound HT-2-2 and the compound HA were co-deposited on the lower electrode (anode) to form a hole injection layer having a thickness of 10 nm. The concentration of the compound HT-2-2 in the hole injection layer was 97% by mass, and the concentration of the compound HA was 3% by mass. The compound HT-2-2 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 138 nm. Next, the compound HT-2-4 was vapor-deposited on the first hole transport layer to form a second hole transport layer (electron blocking layer) having a thickness of 5 nm. On the second hole transport layer, a fluorescent compound GD-3 as a first compound, a delayed fluorescent compound TADF-4 as a second compound, and a compound Matrix-1 as a third compound were co-deposited to form an emitting layer with a thickness of 40 nm. The concentrations of compound GD-3, compound TADF-4, and compound Matrix-1 in the emitting layer were 0.8 mass %, 35 mass %, and 64.2 mass %, respectively. Next, the compound ET-1-1 was vapor-deposited on this light-emitting layer to form a first electron transporting layer (hole blocking layer) with a thickness of 5 nm. Next, on the first electron-transporting layer, the compound ET-2-1 and Liq were co-deposited to form a second electron-transporting layer having a thickness of 35 nm, in which the concentration of the compound ET-2-1 was 50% by mass and the concentration of Liq was 50% by mass. Next, ytterbium (Yb) was vapor deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm. Next, Mg and Ag were co-deposited on the electron injection layer in a mixture ratio (mass % ratio) of 10%:90% to form an upper electrode (first cathode) made of a semi-transparent MgAg alloy with a total thickness of 14 nm. Next, a film of the compound CAP was formed on the entire surface of the upper electrode to form a capping layer with a thickness of 85 nm. The device configuration of the organic EL device according to Example 2-7 is shown in outline below. Ag(100) / ITO(10) / HT-2-2:HA(10,97%:3%) / HT-2-2(138) / HT-2-4(5) / Matrix-1:TADF-4:GD-3(4 0,64.2%:35%:0.8%) / ET-1-1(5) / ET-2-1:Liq(35,50%:50%) / Yb(1) / Mg:Ag(14,10%:90%) / CAP(85)

[0479] <Evaluation of Organic EL Devices (5)> The lifespan LT95 of the fabricated organic EL devices was measured at a current density of 30 mA / cm, in the same manner as in the method described in <Evaluation of organic EL devices (4)>. 2 The other evaluation items were evaluated in the same manner as in <Evaluation of organic EL element (1)> and <Evaluation of organic EL element (3)>. The evaluation results are shown in Table 5.

[0480] [Table 5]

[0481] <Compound evaluation> (Delayed fluorescence of the compound) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound TADF-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 create 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) of a wavelength absorbed by the compound TADF-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. 2. Compounds TADF-2, TADF-3, TADF-4 and TADF-5 were also measured in the same manner as compound TADF-1. It was confirmed that the amount of delayed luminescence (delayed luminescence) was 5% or more of the amount of prompt luminescence (prompt luminescence) for compounds TADF-1, TADF-2, TADF-3, TADF-4, and TADF-5. Specifically, for compounds TADF-1, TADF-2, TADF-3, TADF-4, and TADF-5, X D / X P The value was 0.05 or higher.

[0482] (Maximum peak wavelength of the compound) Maximum peak wavelength λ of the compoundP 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 is referred to as the maximum peak wavelength λ P It was decided.

[0483] (Lowest excited singlet energy S1) The lowest excited singlet energy S1 was measured by the solution method described above.

[0484] [Table 6]

[0485] <Synthesis example> [Synthesis of Compound GD-3] (Synthesis of Intermediate M-1)

[0486] [ka]

[0487] Under a nitrogen atmosphere, 1-bromo-4-t-butyl-2-nitrobenzene (110 g, 427 mmol), 1-pyreneboronic acid (100 g, 406 mmol), tetrakis(triphenylphosphine)palladium(0) (14.1 g, 12.2 mmol), sodium carbonate (86 g, 813 mmol), 1,2-dimethoxyethane (900 mL), and ion-exchanged water (450 mL) were placed in a three-neck flask and heated under reflux with stirring for 4 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by filtration. The resulting solid was purified by silica gel column chromatography to yield 122 g of an orange solid. Mass spectrometry identified the orange solid as intermediate M-1 (yield 79%).

[0488] (Synthesis of intermediate M-2)

[0489] [ka]

[0490] Under a nitrogen atmosphere, intermediate M-1 (50 g, 143 mmol), triphenylphosphine (94 g, 358 mmol), and orthodichlorobenzene (286 mL) were placed in a three-neck flask and stirred at 180°C for 10 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by recrystallization to obtain 39.3 g of a white solid. Mass spectrometry identified the white solid as intermediate M-2 (yield 79%).

[0491] (Synthesis of intermediate M-3)

[0492] [ka]

[0493] Under a nitrogen atmosphere, intermediate M-2 (95 g, 273 mmol), 1-bromo-2,6-difluorobenzene (185 g, 957 mmol), tripotassium phosphate (290 g, 1367 mmol), and N,N-dimethylformamide (DMF) (1367 mL) were placed in a three-neck flask and stirred at 100 °C for 10 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 82.7 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate M-3 (yield 58%).

[0494] (Synthesis of intermediate M-4)

[0495] [ka]

[0496] Under a nitrogen atmosphere, 1-bromo-2-nitrobenzene (10 g, 49.5 mmol), 4-(9H-carbazol-9-yl)phenylboronic acid (14 g, 49.5 mmol), Pd(PPh3)4 (1.1 g, 1.0 mmol), sodium carbonate (13 g, 124 mmol), 165 mL of DME, and 80 mL of ion-exchanged water were placed in a three-neck flask and stirred at 80 °C for 6 hours. The precipitated solid was separated by vacuum filtration and washed with methanol. The resulting solid was dried under reduced pressure (60 °C) for 4 hours to obtain 14.5 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate M-4 (yield 81%).

[0497] (Synthesis of intermediate M-5)

[0498] [ka]

[0499] Under a nitrogen atmosphere, intermediate M-4 (14 g, 38.5 mmol), triphenylphosphine (25 g, 96.3 mmol), and 77 mL of ortho-dichlorobenzene were placed in a three-neck flask and stirred at 180 °C for 12 hours. The ortho-dichlorobenzene was removed by vacuum distillation, and the residue was purified by silica gel chromatography (dichloromethane, hexane 1:1). The resulting solid was dried under reduced pressure (60 °C) for 3 hours to obtain 8.1 g of a white solid. Mass spectrometry identified the white solid as intermediate M-5 (yield 63%).

[0500] (Synthesis of intermediate M-6)

[0501] [ka]

[0502] Under a nitrogen atmosphere, intermediate M-3 (11 g, 21 mmol), intermediate M-5 (7.0 g, 21 mmol), tripotassium phosphate (14 g, 64 mmol), and N,N-dimethylformamide (DMF) (45 mL) were placed in a three-neck flask and stirred for 12 hours at 100° C. After the reaction solution was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 14 g of a pale yellow solid, which was identified by mass spectrometry as intermediate M-6 (yield 79%). .

[0503] (Synthesis of compound GD-3)

[0504] [ka]

[0505] Under a nitrogen atmosphere, intermediate M-6 (14 g, 17 mmol) and t-butylbenzene (170 mL) were placed in a three-neck flask and cooled to -40 °C. A 1.2 mol / L (28 mL, 34 mmol) sec-butyllithium solution (solvent: cyclohexane and n-hexane) was added dropwise and stirred for 2 hours. The reaction mixture was cooled to -70 °C, and boron tribromide (6.4 mL, 67 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was cooled to 0 °C, and N,N-diisopropylethylamine (29 mL, 168 mmol) was added dropwise. The mixture was warmed to 130 °C and stirred for 3 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The collected solid was washed with acetone to obtain 6.5 g of an orange solid. Mass spectrometry identified the orange solid as compound GD-3 (yield: 51%).

[0506] [Synthesis of Compound GD-4] (Synthesis of intermediate M-7)

[0507] [ka]

[0508] Under a nitrogen atmosphere, 4-chloro-2-iodonitrobenzene (70 g, 247 mmol), 4-(9H-carbazol-9-yl)phenylboronic acid (71 g, 247 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (4.0 g, 4.95 mmol), potassium phosphate tripotassium (115 g, 544 mmol), 1,4-dioxane (500 mL), and ion-exchanged water (250 mL) were placed in a three-neck flask and stirred at room temperature for 4 hours. After cooling to room temperature, the organic layer was extracted using a separatory funnel. The extracted organic layer was concentrated and purified by silica gel column chromatography to obtain 93 g of a yellow solid. Mass spectrometry identified the yellow solid as intermediate M-7 (yield 94%).

[0509] (Synthesis of intermediate M-8)

[0510] [ka]

[0511] Under a nitrogen atmosphere, intermediate M-7 (93 g, 233 mmol), triphenylphosphine (153 g, 582.7 mmol), and orthodichlorobenzene (ODCB) (500 mL) were placed in a three-neck flask and heated under reflux with stirring for 12 hours. The reaction mixture was concentrated and purified by silica gel column chromatography to obtain 42 g of a white solid. Mass spectrometry identified the white solid as intermediate M-8 (yield 49%).

[0512] (Synthesis of intermediate M-9)

[0513] [ka]

[0514] Under a nitrogen atmosphere, intermediate M-3 (50 g, 96 mmol), intermediate M-8 (4.36 g, 98 mmol), tripotassium phosphate (102 g, 481 mmol), and N,N-dimethylformamide (DMF) (200 mL) were placed in a three-neck flask and stirred at 100 °C for 12 hours. After cooling the reaction mixture to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 73 g of a pale yellow solid. Mass spectrometry identified the pale yellow solid as intermediate M-9 (yield 88%).

[0515] (Synthesis of intermediate M-10)

[0516] [ka]

[0517] Under a nitrogen atmosphere, intermediate M-9 (73 g, 84 mmol) and t-butylbenzene (842 mL) were placed in a three-neck flask and cooled to -40 °C. A 1.2 mol / L (140 mL, 168 mmol) sec-butyllithium solution (solvent: cyclohexane and n-hexane) was then added dropwise and stirred for 2 hours. The reaction mixture was cooled to -70 °C, and boron tribromide (24 mL, 253 mmol) was added dropwise. The mixture was then warmed to room temperature and stirred for 2 hours. The reaction mixture was then cooled to 0 °C, and N,N-diisopropylethylamine (117 mL, 674 mmol) was added dropwise. The mixture was then warmed to 130 °C and stirred for 3 hours. The reaction mixture was then cooled to room temperature, and the precipitated solid was collected by suction filtration to obtain 44 g of an orange solid. Mass spectrometry identified the orange solid as intermediate M-10 (yield: 66%).

[0518] (Synthesis of Compound GD-4)

[0519] [ka]

[0520] Under a nitrogen atmosphere, intermediate M-10 (2.4 g, 3.0 mmol), potassium hexacyanoferrate(II) (2.2 g, 6.0 mmol), dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.21 g, 0.30 mmol), sodium carbonate (0.06 g, 0.6 mmol), and 1-methyl-2-pyrrolidone (60 mL) were placed in a three-neck flask and stirred at 135 °C for 4 hours. The reaction mixture was cooled to room temperature, and 60 mL of dichloromethane and silica gel were added and suction filtered. The resulting solution was concentrated, methanol was added, and the resulting solid was purified by silica gel column chromatography to yield 1.1 g of an orange solid. Mass spectrometry identified the orange solid as compound GD-4 (46% yield).

[0521] [Synthesis of Compound GD-5] (Synthesis of intermediate M-11)

[0522] [ka]

[0523] Under a nitrogen atmosphere, 2-bromocarbazole (8.0 g, 32.5 mmol), 2,6-di-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (11.3 g, 35.8 mmol), PdXphosG3 (0.28 g, 0.33 mmol), tripotassium phosphate (9.7 g, 45.5 mmol), 1,2-dimethoxyethane (DME) (160 mL), and ion-exchanged water (20 mL) were placed in a three-neck flask and heated under reflux with stirring for 3 hours. After cooling to room temperature, water and toluene were added and the mixture was separated. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to yield 9.7 g of a white solid. The white solid was identified as intermediate M-11 by LC-MS (Liquid Chromatography-Mass Spectrometry) (yield 83%).

[0524] (Synthesis of intermediate M-12)

[0525] [ka]

[0526] Under a nitrogen atmosphere, 2,9-di-tert-butyl-7H-phenaleno[1,9-bc]carbazole (14.3 g, 35.4 mmol), 1-bromo-2,6-difluorobenzene (17.1 g, 88.5 mmol), tripotassium phosphate (7.5 g, 35.4 mmol), and N,N-dimethylformamide (DMF) (354 mL) were placed in a three-neck flask and stirred at 150 °C for 4 hours. After cooling to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to yield 11.1 g of a yellow solid. LC-MS identified the yellow solid as intermediate M-12 (yield 54%).

[0527] (Synthesis of intermediate M-13)

[0528] [ka]

[0529] Under a nitrogen atmosphere, intermediate M-12 (5.0 g, 8.67 mmol), intermediate M-11 (3.4 g, 9.54 mmol), tripotassium phosphate (2.0 g, 9.54 mmol), and DMF (43 mL) were placed in a three-neck flask and stirred at 150 °C for 3 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 5.2 g of a yellow solid. LC-MS identified the yellow solid as intermediate M-13 (yield 66%).

[0530] (Synthesis of Compound GD-5)

[0531] [ka]

[0532] Under a nitrogen atmosphere, intermediate M-13 (5.2 g, 5.7 mmol) and xylene (57 mL) were placed in a three-neck flask and cooled to -50 °C. A 1.6 mol / L n-butyllithium solution (solvent: cyclohexane) (4.3 mL, 6.8 mmol) was added dropwise and the mixture was stirred at 0 °C for 1 hour. After cooling the reaction mixture to -50 °C, boron tribromide (0.65 mL, 6.8 mmol) was added dropwise, the mixture was warmed to room temperature, and the mixture was stirred for 1 hour. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (DIPEA) (2.0 mL, 11.4 mmol) was added dropwise, the mixture was warmed to 150 °C, and the mixture was stirred for 6 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to yield 1.9 g of an orange solid. The orange solid was identified as compound GD-5 by LC-MS (yield 40%).

[0533] [Synthesis of Compound GD-6] (Synthesis of intermediate M-14)

[0534] [ka]

[0535] Under a nitrogen atmosphere, 3-bromocarbazole (8.0 g, 32.5 mmol), 2,6-di-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (11.3 g, 35.8 mmol), PdXphosG3 (0.28 g, 0.33 mmol), tripotassium phosphate (9.7 g, 45.5 mmol), 1,2-dimethoxyethane (160 mL), and ion-exchanged water (20 mL) were placed in a three-neck flask and heated under reflux with stirring for 3 hours. The reaction mixture was cooled to room temperature, and then water and toluene were added. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 9.6 g of a white solid. LC-MS identified the white solid as intermediate M-14 (yield 80%).

[0536] (Synthesis of intermediate M-15)

[0537] [ka]

[0538] Under a nitrogen atmosphere, intermediate M-12 (6.1 g, 10.6 mmol), intermediate M-14 (4.2 g, 11.7 mmol), tripotassium phosphate (2.5 g, 11.7 mmol), and DMF (53 mL) were placed in a three-neck flask and stirred at 150 °C for 4 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 6.7 g of a yellow solid. LC-MS identified the yellow solid as intermediate M-15 (yield 69%).

[0539] (Synthesis of Compound GD-6)

[0540] [ka]

[0541] Under a nitrogen atmosphere, intermediate M-15 (6.7 g, 7.3 mmol) and xylene (73 mL) were placed in a three-neck flask and cooled to -50 °C. A 1.6 mol / L n-butyllithium solution (solvent: cyclohexane) (5.5 mL, 8.8 mmol) was added dropwise and the mixture was stirred at 0 °C for 1 hour. After cooling the reaction mixture to -50 °C, boron tribromide (0.83 mL, 8.8 mmol) was added dropwise, the mixture was warmed to room temperature, and the mixture was stirred for 1 hour. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (2.6 mL, 14.6 mmol) was added dropwise, the mixture was warmed to 150 °C, and the mixture was stirred for 6 hours. The reaction mixture was cooled to room temperature, and water and dichloromethane were added, followed by separation. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 0.42 g of an orange solid, which was identified by LC-MS as compound GD-6 (yield 6.8%).

[0542] [Synthesis of Compound GD-7] (Synthesis of intermediate M-16)

[0543] [ka]

[0544] Under a nitrogen atmosphere, 9-tert-butyl-7H-phenaleno[1,9-bc]carbazole (35.0 g, 100 mmol), 1-bromo-2,6-difluorobenzene (48.6 g, 250 mmol), tripotassium phosphate (23.5 g, 110 mmol), and DMF (1000 mL) were placed in a three-neck flask and stirred at 150 °C for 4 hours. After cooling to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to yield 23.6 g of a yellow solid. LC-MS identified the yellow solid as intermediate M-16 (yield 45%).

[0545] (Synthesis of intermediate M-17)

[0546] [ka]

[0547] Under a nitrogen atmosphere, intermediate M-16 (4.2 g, 8.01 mmol), intermediate M-11 (3.0 g, 8.41 mmol), tripotassium phosphate (1.8 g, 8.41 mmol), and DMF (27 mL) were placed in a three-neck flask and stirred at 150 °C for 8 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 4.5 g of a yellow solid. LC-MS identified the yellow solid as intermediate M-17 (yield 65%).

[0548] (Synthesis of Compound GD-7)

[0549] [ka]

[0550] Under a nitrogen atmosphere, intermediate M-17 (4.5 g, 5.2 mmol) and xylene (52 mL) were placed in a three-neck flask and cooled to -50 °C. A 1.6 mol / L n-butyllithium solution (solvent: cyclohexane) (3.9 mL, 6.3 mmol) was added dropwise and the mixture was stirred at 0 °C for 1 hour. After cooling the reaction mixture to -50 °C, boron tribromide (0.60 mL, 6.3 mmol) was added dropwise, the mixture was warmed to room temperature, and the mixture was stirred for 1 hour. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (1.8 mL, 10.5 mmol) was added dropwise, the mixture was warmed to 150 °C, and the mixture was stirred for 6 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to yield 1.6 g of an orange solid. The orange solid was identified as compound GD-7 by LC-MS (yield 39%).

[0551] [Synthesis of Compound GD-8] (Synthesis of intermediate M-18)

[0552] [ka]

[0553] Under a nitrogen atmosphere, intermediate M-16 (10.0 g, 19.2 mmol), 2,4-dichlorocarbazole (4.1 g, 17.5 mmol), tripotassium phosphate (3.7 g, 17.5 mmol), and DMF (58 mL) were placed in a three-neck flask and stirred at 150 °C for 4 hours. After the reaction mixture was cooled to room temperature, water was added and the precipitated solid was collected by suction filtration. The resulting solid was purified by silica gel column chromatography to obtain 10.7 g of a yellow solid. LC-MS identified the product as intermediate M-18 (yield 75%).

[0554] (Synthesis of intermediate M-19)

[0555] [ka]

[0556] Under a nitrogen atmosphere, intermediate M-18 (10.7 g, 14.5 mmol) and xylene (145 mL) were placed in a three-neck flask and cooled to -50 °C. A 1.6 mol / L n-butyllithium solution (solvent: cyclohexane) (10.9 mL, 17.4 mmol) was added dropwise and the mixture was stirred at 0 °C for 1 hour. After cooling the reaction mixture to -50 °C, boron tribromide (1.65 mL, 4.4 mmol) was added dropwise, the mixture was warmed to room temperature, and the mixture was stirred for 1 hour. After cooling the reaction mixture to 0 °C, N,N-diisopropylethylamine (5.1 mL, 29.0 mmol) was added dropwise, the mixture was warmed to 150 °C, and the mixture was stirred for 6 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration to obtain 4.7 g of an orange solid. LC-MS identified the orange solid as intermediate M-19 (yield: 49%).

[0557] (Synthesis of Compound GD-8)

[0558] [ka]

[0559] Under a nitrogen atmosphere, intermediate M-19 (4.3 g, 6.5 mmol), 2,6-di-tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.6 g, 14.4 mmol), PdXphosG3 (0.11 g, 0.13 mmol), tripotassium phosphate (3.9 g, 18.3 mmol), 1,2-dimethoxyethane (33 mL), and ion-exchanged water (4 mL) were added and heated under reflux with stirring for 4 hours. The reaction mixture was cooled to room temperature, and then water and dichloromethane were added and the mixture was separated. The resulting organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 4.9 g of an orange solid. LC-MS identified the orange solid as compound GD-8 (77% yield). [Explanation of symbols]

[0560] 1... organic EL element, 2... substrate, 3... anode, 4... cathode, 5... light-emitting layer, 6... hole injection layer, 7... hole transport layer, 8... electron transport layer, 9... electron injection layer.

Claims

1. an anode; A cathode; a light-emitting layer between the anode and the cathode, the light-emitting layer comprises a fluorescent first compound and a delayed fluorescent second compound, The first compound is represented by the following general formula (1): The second compound is represented by the following general formula (2): The lowest excited singlet energy S of the first compound １ (M1) and the lowest excited singlet energy S of the second compound １ (M2) satisfies the relationship of the following formula (Formula 1), Organic electroluminescent element. S １ (M2)>S １ (M1)…(Number 1) 【Chemical Formula 1】 (In the general formula (1), R １０１ ~R １１１ are each independently Hydrogen atoms, halogen atoms, cyano groups, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R １９０ ) a group represented by -S-(R １９１ ) 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, -C(=O)-O-(R １９２ ) a group represented by -C(=O)-N(R １９３ ) (R １９４ ) a group represented by -N(R １９５ ) (R １９６ ) a group represented by a nitro group, and -Si(R １９７ ) (R １９８ ) (R １９９ ) wherein R １１０ is selected from substituents other than hydrogen atoms, Ring A １ and Ring B １ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocycle having 5 to 50 ring atoms, X １ is -O-, -N(R １３１ )- or -S-; R １３１ teeth, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted imino 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 １３１ represents a single bond or a linking group L １１ via ring A １ or Ring B １ are bonded to each other to form a ring structure, or are not bonded to each other, Linking group L １１ is -O-, -S-, >C(R １８６ ) (R １８７ ) or >Si(R １８８ ) (R １８９ ) and R １８６ ~R １８９ are each independently hydrogen atoms, halogen 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, and selected from the group consisting of substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms, R １８６ and R １８７ The pair is a single bond or a linking group L １２ are bonded to each other via an R １８８ and R １８９ The pair is a single bond or a linking group L １２ are bonded to each other via an Linking group L １２ is —O— or —S—. (In the first compound, R １９０ ~R １９９ each independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R １９０ If there are multiple R １９０ are the same or different from each other, R １９１ If there are multiple R １９１ are the same or different from each other, R １９２ If there are multiple R １９２ are the same or different from each other, R １９３ If there are multiple R １９３ are the same or different from each other, R １９４ If there are multiple R １９４ are the same or different from each other, R １９５ If there are multiple R １９５ are the same or different from each other, R １９６ If there are multiple R １９６ are the same or different from each other, R １９７ If there are multiple R １９７ are the same or different from each other, R １９８ If there are multiple R １９８ are the same or different from each other, R １９９ If there are multiple R １９９ are the same or different from each other.) 【Chemistry 2】 (In the general formula (2), k is 1, 2, 3 or 4; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; k+m+n=4, CN is a cyano group; Each 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 -C(=O)-O-(R 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, multiple R's are the same or different, D ２１ and D ２２ are each independently a group represented by the following general formula (21), (22), or (23): D ２１ and D ２２ are the same or different from each other, Multiple D ２１ are the same or different from each other, Multiple D ２２ are the same or different from each other.) 【Chemistry 3】 【Chemistry 4】 (R in the general formula (21) ２１ ~R ２８ 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 (22) ２２１ ~R ２２８ 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 (23) ２３１ ~R ２３８ 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 (21) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ２１ ~R ２８ R in the general formula (22) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ２２１ ~R ２２８ and R in the general formula (23) which does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. ２３１ ~R ２３８ 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 -C(=O)-O-(R 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 (22) and the general formula (23), ring A ２ , ring B ２ and Ring C ２ are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (24), (25A), and (25B): Ring A ２ , ring B ２ and Ring C ２ are each fused to one or more adjacent rings at any position, p, px, and py are each independently 1, 2, 3, or 4; When p is 2, 3 or 4, a plurality of rings A ２ are identical to or different from each other, When px is 2, 3 or 4, a plurality of rings B ２ are identical to or different from each other, When py is 2, 3 or 4, a plurality of rings C ２ are identical to or different from each other, However, D ２１ and D ２２ At least one of the p is 2, 3 or 4, and ring A ２ is a group represented by the general formula (22) containing both a ring structure represented by the following general formula (24) and a ring structure represented by the following general formula (25B), At least one of px and py is 2, 3, or 4, and ring B ２ Or Ring C ２ is a group represented by the general formula (23) containing both a ring structure represented by the following general formula (24) and a ring structure represented by the following general formula (25B), * in the general formulas (21) to (23) indicates the bonding position to the benzene ring in the general formula (2). 【Chemistry 5】 (In the general formula (24), r is 0, 2 or 4; Multiple R ２９ 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 ２９ are each independently R in the general formula (21). ２１ ~R ２８ is synonymous with (In the second compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０６ , R ９０７ , R ９０８ , R ９０９ , R ９３１ , R ９３２ , R ９３３ , R ９３４ , R ９３５ , R ９３６ and R ９３７ are each independently, 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. 2. The organic electroluminescent device according to claim 1, the light-emitting layer contains a third compound, The third compound is represented by the following general formula (3): The lowest excited singlet energy S of the first compound １ (M1) and the lowest excited singlet energy S of the second compound １ (M2) and the lowest excited singlet energy S of the third compound １ (M3) satisfies the relationship of the following formula (Formula 2): Organic electroluminescent element. S １ (M3)>S １ (M2)>S １ (M1)…(Number 2) 【Chemistry 6】 (In the general formula (3), Y ３ is an oxygen atom or a sulfur atom, R ３１ ~R ３８ Any one of the following is a single bond that bonds to *3; 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, n3 is 0 or 1; m3 is 0 or 1; R ３１０ , R ３２０ and R which is not a single bond bonded to *3, does not form the substituted or unsubstituted monocycle, and does not form the substituted or unsubstituted fused ring. ３１ ~R ３８ are each independently, hydrogen atoms, halogen atoms, cyano group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted halogenated 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 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 -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 -P(=O)(OR ９３８ ) (OR ９３９ ) a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, or is a nitro group, Multiple R ３１０ are identical to or different from each other, Multiple R ３２０ are identical to or different from each other, A ３０ is a group represented by any one of the formulae selected from the group consisting of the following general formulae (31A), (31B), (31C), (31D), (31E), and (31F): 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 (In the general formulae (31A), (31B), (31C), (31D), (31E) and (31F), X ３ is an oxygen atom or a sulfur atom, R ３３１ ~R ３４０ 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 ３３１ ~R ３４０ each independently represents R that does not form the substituted or unsubstituted monocyclic ring in the general formula (3) and does not form the substituted or unsubstituted fused ring. ３１ ~R ３８ *a is the same as A ３０ represents the bonding position of (In the third compound, R ９０１ , R ９０２ , R ９０３ , R ９０４ , R ９０５ , R ９０８ , R ９０９ , R ９３１ , R ９３２ , R ９３３ , R ９３４ , R ９３５ , R ９３６ , R ９３７ , R ９３８ and R ９３９ 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 ９０６ and R ９０７ are each independently, 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 substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, R ９０１ If there are multiple R ９０１ are the same or different from each other, R ９０２ If there are multiple R ９０２ are the same or different from each other, R ９０３ If there are multiple R ９０３ are the same or different from each other, R ９０４ If there are multiple R ９０４ are the same or different from each other, R ９０５ If there are multiple R ９０５ are the same or different from each other, R ９０６ If there are multiple R ９０６ are the same or different from each other, R ９０７ If there are multiple R ９０７ are the same or different from each other, R 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, R ９３８ If there are multiple R ９３８ are the same or different from each other, R ９３９ If there are multiple R ９３９ are the same or different from each other.)

3. 3. The organic electroluminescence device according to claim 2, n3 is 1 and m3 is 0 or 1; Organic electroluminescent element.

4. 4. The organic electroluminescent device according to claim 2, The third compound is a compound represented by the following general formula (32A): Organic electroluminescent element. 【Chemistry 10】 (In the general formula (32A), A ３０ , Y ３ , R ３１ ~R ３８ and *3 respectively represent A in the general formula (3). ３０ , Y ３ , R ３１ ~R ３８ and *3, R ３１１ ~R ３１４ are each independently R in the general formula (3). ３１０ is synonymous with

5. 4. The organic electroluminescent device according to claim 2, The third compound is a compound represented by the following general formula (32B): Organic electroluminescent element. 【Chemistry 11】 (In the general formula (32B), A ３０ , Y ３ , R ３１ ~R ３８ and *3 respectively represent A in the general formula (3). ３０ , Y ３ , R ３１ ~R ３８ and *3, R ３１１ ~R ３１４ are each independently R in the general formula (3). ３１０ is synonymous with

6. 4. The organic electroluminescent device according to claim 2, The third compound is a compound represented by the following general formula (32C): Organic electroluminescent element. 【Chemistry 12】 (In the general formula (32C), A ３０ , Y ３ , R ３１ ~R ３８ and *3 respectively represent A in the general formula (3). ３０ , Y ３ , R ３１ ~R ３８ and *3, R ３１１ ~R ３１４ are each independently R in the general formula (3). ３１０ is synonymous with

7. 3. The organic electroluminescence device according to claim 2, n3 and m3 are 0, or n3 is 1, m3 is 0, and R ３１０ is a hydrogen atom, Organic electroluminescent element.

8. The organic electroluminescence device according to claim 7, n3 and m3 are 0; Organic electroluminescent element.

9. The organic electroluminescence device according to any one of claims 2 to 8, A ３０ is a group represented by the general formula (31D), (31E) or (31F), Organic electroluminescent element.

10. The organic electroluminescence device according to claim 9, A ３０ is a group represented by the general formula (31D) or (31F), Organic electroluminescent element.

11. The organic electroluminescence device according to claim 9 or 10, A ３０ is a group represented by the general formula (31D). Organic electroluminescent element.

12. The organic electroluminescence device according to claim 9 or 10, A ３０ is a group represented by the general formula (31F), Organic electroluminescent element.

13. The organic electroluminescent device according to any one of claims 2 to 12, X ３ is an oxygen atom, Organic electroluminescent element.

14. The organic electroluminescent device according to any one of claims 2 to 12, X ３ is a sulfur atom, Organic electroluminescent element.

15. The organic electroluminescent device according to any one of claims 2 to 4, The third compound is a compound represented by the following general formula (321A): Organic electroluminescent element. 【Chemistry 13】 (In the general formula (321A), Y ３ , R ３１ ~R ３８ and *3 respectively represent Y in the general formula (3). ３ , R ３１ ~R ３８ and *3, R ３１１ ~R ３１４ are each independently R in the general formula (3). ３１０ is synonymous with A ３２ is a group represented by any one of the formulae selected from the group consisting of the following general formulae (33D) and (34F): 【Chemistry 14】 (In the general formulas (33D) and (34F), R ３３１ ~R ３４０ and *a are R in the general formulas (31D) and (31F), respectively. ３３１ ~R ３４０ and *a.)

16. The organic electroluminescent device according to any one of claims 2 to 15, Y ３ is an oxygen atom, Organic electroluminescent element.

17. The organic electroluminescent device according to any one of claims 1 to 16, In the general formula (1), R １１０ is any group selected from the group consisting of 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, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; Organic electroluminescent element.

18. The organic electroluminescence device according to any one of claims 1 to 17, In the general formula (1), X １ -N (R １３１ )- and R １３１ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, or a substituted or unsubstituted imino group, Organic electroluminescent element.

19. The organic electroluminescent device according to any one of claims 1 to 17, In the general formula (1), X １ -N (R １３１ )- and R １３１ 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 １３１ is connected to ring B via a single bond １ and Organic electroluminescent element.

20. 20. The organic electroluminescence device according to claim 1, In the general formula (1), ring A １ and Ring B １ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 ring carbon atoms; Organic electroluminescent element.

21. The organic electroluminescent device according to any one of claims 1 to 20, The first fluorescent compound is represented by the following general formula (11): Organic electroluminescent element. 【Chemistry 15】 (In the general formula (11), R １０１ ~R １１１ are R in the general formula (1), respectively. １０１ ~R １１１ is synonymous with R １１２ ~R １２１ are each independently Hydrogen atoms, halogen atoms, cyano groups, 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 alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, -O-(R １９０ ) a group represented by -S-(R １９１ ) 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, -C(=O)-O-(R １９２ ) a group represented by -C(=O)-N(R １９３ ) (R １９４ ) a group represented by -N(R １９５ ) (R １９６ ) a group represented by a nitro group, and -Si(R １９７ ) (R １９８ ) (R １９９ ) wherein R １１０ is selected from substituents other than hydrogen atoms, R １９０ ~R １９９ are R in the general formula (1), respectively. １９０ ~R １９９ is equivalent to

22. The organic electroluminescent device according to any one of claims 1 to 21, In the general formula (2), k is 1, 2, or 3, m is 0, 1, or 2, and n is 1, 2, or 3; 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 (2) via a carbon-carbon bond; Organic electroluminescent element.

23. The organic electroluminescent device according to any one of claims 1 to 22, At least one D ２１ is a group represented by the following general formula (221), (222) or (231): Organic electroluminescent element. 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 (In the general formulas (221) and (222), R ２２１ ~R ２２８ are R in the general formula (22), respectively. ２２１ ~R ２２８ is synonymous with Ring A ２１、 Ring A ２２ , ring A ２３ and Ring A ２４ Among these, two are ring structures represented by the general formula (24), and the remaining two are ring structures represented by either the general formula (25A) or (25B), However, ring A ２１、 Ring A ２２ , ring A ２３ and Ring A ２４ at least one of which is a ring structure represented by general formula (25B), In the general formula (231), R ２３１ ~R ２３８ are R in the general formula (23), respectively. ２３１ ~R ２３８ is synonymous with Ring B ２１ and Ring B ２２ one of the ring structures represented by the general formula (24) is a ring structure represented by the general formula (24), and ring B ２１ and Ring B ２２ the other is a ring structure represented by any one of general formulas (25A) and (25B), Ring C ２１ and Ring C ２２ is a ring structure represented by the general formula (24), and ring C ２１ and Ring C ２２ the other is a ring structure represented by any one of general formulas (25A) and (25B), However, ring B ２１ , ring B ２２ , ring C ２１ and Ring C ２２ at least one of which is a ring structure represented by general formula (25B), In the general formulae (221), (222) and (231), * indicates a bonding position.

24. 24. The organic electroluminescence device according to claim 23, Ring A ２１ and Ring A ２３ is a ring structure represented by the general formula (24), and ring A ２２ and Ring A ２４ is a ring structure represented by the general formula (25B), Ring B ２１ is a ring structure represented by the general formula (24), and ring B ２２ is a ring structure represented by the general formula (25B), Ring C ２１ is a ring structure represented by the general formula (24), and ring C ２２ is a ring structure represented by the general formula (25B). Organic electroluminescent element.

25. 25. The organic electroluminescence device according to claim 23 or 24, At least one D ２１ is a group represented by the general formula (231), Organic electroluminescent element.

26. 24. The organic electroluminescence device according to claim 23, At least one D ２１ is a group represented by the following general formula (223), (224), (225) or (232): Organic electroluminescent element. 【Chemistry 19】 【Chemistry 20】 【Chemical Formula 21】 (In the general formulae (223), (224) and (225), R ２２１ ~R ２２８ are R in the general formula (22), respectively. ２２１ ~R ２２８ is synonymous with R ２９１ ~R ２９４ are each independently R in the general formula (24). ２９ is synonymous with In the general formula (232), R ２３１ ~R ２３８ are R in the general formula (23), respectively. ２３１ ~R ２３８ is synonymous with R ２９５ ~R ２９８ are each independently R in the general formula (24). ２９ is synonymous with In the general formulae (223), (224), (225) and (232), X ２１ and X ２２ are each independently an oxygen atom or a sulfur atom, provided that X ２１ and X ２２ At least one of the groups is a sulfur atom, and * indicates the bonding position.

27. 27. The organic electroluminescence device according to claim 26, X ２１ is a sulfur atom, Organic electroluminescent element.

28. 28. The organic electroluminescence device according to claim 26 or 27, At least one D ２１ is a group represented by the general formula (232), Organic electroluminescent element.

29. 29. The organic electroluminescence device according to claim 1, The light-emitting layer does not contain a heavy metal complex. Organic electroluminescent element.

30. An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 29.

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