Organic electroluminescent element, compound, and electronic device

Abstract

An organic electroluminescent element (1) having a positive electrode (3), a negative electrode (4), and a light-emitting layer (5) included between the positive electrode (3) and the negative electrode (4), the light-emitting layer (5) containing a compound M3 represented by general formula (1-1) or (1-2) and a delayed fluorescence compound M2, the compound M3 and the compound M2 having different structures, and the singlet energy S1 (M3) of the compound M3 and the singlet energy S1 (M2) of the compound M2 satisfying the relationship of the mathematical formula (number 1): S1 (M3) gt; s1 (M2) (number 1). In general formulae (1-1) and (1-2), A is a group represented by general formula (11A) or the like, L1 and L2 are each independently a single bond or a substituted or unsubstituted arylene group, and Y1 is an oxygen atom or a sulfur atom. # imgabs0 #

Description

Technical Field

[0001] The invention relates to an organic electroluminescent element, a compound and an electronic device. Background Art

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

[0003] Fluorescent organic EL devices that use light emission from singlet excitons are being used in full-color displays such as mobile phones and televisions, but internal quantum efficiency of 25% is considered to be the limit. Therefore, research is being conducted to improve the performance of organic EL devices.

[0004] In addition, it is expected that organic EL elements can emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. In this context, efficient fluorescent organic EL elements utilizing thermally activated delayed fluorescence (hereinafter sometimes referred to as "delayed fluorescence") have been proposed and studied.

[0005] For example, the TADF (Thermally Activated Delayed Fluorescence) mechanism has been studied. The TADF mechanism is a mechanism that utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under thermal action when using a material with a small energy difference (ΔST) between the singlet energy level and the triplet energy level. Thermally activated delayed fluorescence is described in, for example, "Device Properties of Organic Semiconductors, edited by Chiba Ya Ando, ​​Kodansha, published on April 1, 2012, pages 261 to 268".

[0006] For example, Patent Document 1 has conducted research to improve the performance of organic EL devices. Patent Document 1 discloses compounds that can be used in organic EL devices and have a benzofuranocarbazole ring or a benzothienylcarbazole ring and a dibenzofuranocarbazole ring at both ends of the para position of a linking group having an elongated structure.

[0007] Examples of the performance of an organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: International Publication No. 2020 / 122118 Summary of the invention

[0011] Technical problem to be solved by the invention

[0012] In organic EL devices utilizing the TADF mechanism, further performance improvement is required.

[0013] An object of the present invention is to provide a high-performance organic electroluminescent element, a compound capable of realizing a high-performance organic electroluminescent element, and an electronic device equipped with the organic EL element.

[0014] Solutions for solving the above technical problems

[0015] According to one embodiment of the present invention, there is provided an organic electroluminescent element having:

[0016] anode;

[0017] a cathode; and

[0018] a light-emitting layer, included between the anode and the cathode,

[0019] The light-emitting layer comprises a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescence compound M2,

[0020] The compound M3 has a different structure from the compound M2.

[0021] The singlet energy S1(M3) of the compound M3 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Formula 1).

[0022] S1(M3)>S1(M2)(number 1)

[0023] [Chemistry 1]

[0024]

[0025] [Chemistry 2]

[0026]

[0027] (In the general formulas (1-1) and (1-2),

[0028] A is a group represented by any of the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0029] L1 and L2 are independently,

[0030] Single key, or

[0031] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[0032] Y1 is an oxygen atom or a sulfur atom,

[0033] By R 21 ~R 28 One or more of the groups of two or more adjacent

[0034] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0035] bonded to each other to form a substituted or unsubstituted fused ring, or

[0036] Not bonded to each other,

[0037] R 100 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Independently,

[0038] Hydrogen atoms,

[0039] Halogen atoms,

[0040] Cyano,

[0041] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0042] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0043] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0044] a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,

[0045] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0046] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0047] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0048] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0049] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0050] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0051] Hydroxyl,

[0052] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0053] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0054] A group represented by -N(Rz)2,

[0055] Thiol group,

[0056] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0057] a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,

[0058] Substituted germanium

[0059] Substituted phosphine oxide groups,

[0060] Nitro,

[0061] Substituted boron, or

[0062] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0063] Rz is

[0064] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0065] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0066] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0067] - The two Rz in N(Rz)2 are the same or different from each other,

[0068] Multiple R 100 Same or different from each other,

[0069] In the general formulas (1-1) and (1-2), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded.)

[0070] [Chemistry 3]

[0071]

[0072] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0073] X1 is an oxygen atom or a sulfur atom,

[0074] By R 11 ~R 20One or more of the groups of two or more adjacent

[0075] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0076] bonded to each other to form a substituted or unsubstituted fused ring, or

[0077] Not bonded to each other,

[0078] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 11 ~R 20 R in the general formula (1-1) and (1-2) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Synonymous, * indicates bonding position. )

[0079] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to one aspect of the present invention.

[0080] According to one embodiment of the present invention, there is provided a compound represented by any one of the following general formulas (100-1) to (100-4).

[0081] [Chemistry 4]

[0082]

[0083] [Chemistry 5]

[0084]

[0085] [Chemistry 6]

[0086]

[0087] [Chemistry 7]

[0088]

[0089] (In the general formulas (100-1) to (100-4),

[0090] A is a group represented by any of the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0091] L1 and L2 are independently,

[0092] Single key, or

[0093] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[0094] Y1 is an oxygen atom or a sulfur atom,

[0095] By R 21 ~R 28 One or more of the groups of two or more adjacent

[0096] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0097] bonded to each other to form a substituted or unsubstituted fused ring, or

[0098] Not bonded to each other,

[0099] R 100 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Independently,

[0100] Hydrogen atoms,

[0101] Halogen atoms,

[0102] Cyano,

[0103] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0104] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0105] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0106] a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,

[0107] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0108] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0109] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0110] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0111] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0112] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0113] Hydroxyl,

[0114] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0115] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0116] A group represented by -N(Rz)2,

[0117] Thiol group,

[0118] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0119] a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,

[0120] Substituted germanium

[0121] Substituted phosphine oxide groups,

[0122] Nitro,

[0123] Substituted boron, or

[0124] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0125] Rz is

[0126] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0127] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0128] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0129] - The two Rz in N(Rz)2 are the same or different from each other,

[0130] Multiple R 100 Same or different from each other,

[0131] Wherein, in the general formula (100-4), R 100 It is not a group represented by -N(Rz)2.

[0132] In the general formula (100-4), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded.)

[0133] [Chemistry 8]

[0134]

[0135] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0136] X1 is an oxygen atom or a sulfur atom,

[0137] By R11 ~R 20 One or more of the groups of two or more adjacent

[0138] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0139] bonded to each other to form a substituted or unsubstituted fused ring, or

[0140] Not bonded to each other,

[0141] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 11 ~R 20 R in the general formula (100-1) to (100-4) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Synonymous, * indicates bonding position. )

[0142] According to one aspect of the present invention, it is possible to provide a high-performance organic electroluminescent element, a compound capable of realizing a high-performance organic electroluminescent element, and an electronic device equipped with the organic EL element. BRIEF DESCRIPTION OF THE DRAWINGS

[0143] Figure 1 This is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to the first embodiment of the present invention.

[0144] Figure 2 This is a schematic diagram of a device for measuring transition PL.

[0145] Figure 3 This is a diagram showing an example of a decay curve of the transition PL.

[0146] Figure 4 This is a diagram showing the relationship between the energy levels of the compound M3 and the compound M2 in the light-emitting layer of an example of the organic electroluminescent element according to the first embodiment of the present invention.

[0147] Figure 5 This is a diagram showing the relationship between the energy levels and energy transfer of the compound M3, the compound M2, and the compound M1 in the light-emitting layer of an example of the organic electroluminescent device according to the second embodiment of the present invention. DETAILED DESCRIPTION

[0148] [definition]

[0149] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0150] In this specification, it is assumed that a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a bondable position in a chemical structural formula where a symbol such as "R" or "D" representing a deuterium atom is not explicitly shown.

[0151] In this specification, the number of ring carbons represents the number of carbon atoms in the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded to form a ring structure. In the case where the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbons. For the "number of ring carbons" described below, the same is true unless otherwise specified. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

[0152] In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

[0153] In this specification, the number of ring atoms represents the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded to form a cyclic structure (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. For the "number of ring atoms" recorded below, the same is true 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 bonded to a pyridine ring or atoms constituting a substituent is not included in the number of ring atoms of the pyridine ring. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, 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. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0154] In the present specification, "the carbon number is XX to YY" in the expression "a substituted or unsubstituted ZZ group having a carbon number of XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0155] In the present specification, "the number of atoms is XX to YY" in the expression "a substituted or unsubstituted ZZ group having a number of atoms of XX to YY" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0156] In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0157] In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

[0158] In addition, in the present specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" in the case of "BB group substituted with AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0159] "Substituents described in this specification"

[0160] The substituents described in the present specification are described below.

[0161] Unless otherwise specified in the present specification, the number of ring carbon atoms in the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0162] Unless otherwise specified in the present specification, the number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0163] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0164] Unless otherwise specified in the present specification, the “unsubstituted alkenyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0165] Unless otherwise specified in the present specification, the “unsubstituted alkynyl group” described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0166] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0167] Unless otherwise specified in the present specification, the number of ring carbon atoms in the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0168] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0169] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0170] "Substituted or unsubstituted aryl"

[0171] As specific examples of "substituted or unsubstituted aryl groups" described in this specification (specific example group G1), the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B) can be cited. (Here, unsubstituted aryl groups refer to the case where "substituted or unsubstituted aryl groups" are "unsubstituted aryl groups", and substituted aryl groups refer to the case where "substituted or unsubstituted aryl groups" are "substituted aryl groups".) In this specification, when simply referred to as "aryl groups", both "unsubstituted aryl groups" and "substituted aryl groups" are included.

[0172] "Substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by a substituent. As a "substituted aryl group", for example, a group in which one or more hydrogen atoms of an "unsubstituted aryl group" in the following specific example group G1A are replaced by a substituent, and an example of a substituted aryl group in the following specific example group G1 B can be cited. In addition, the examples of "unsubstituted aryl group" and "substituted aryl group" cited here are only examples, and the "substituted aryl group" described in this specification also includes: a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the following specific example group G1 B is further replaced by a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" in the following specific example group G1B is further replaced by a substituent.

[0173] Unsubstituted aryl (specific example group G1A):

[0174] Phenyl,

[0175] p-Biphenyl,

[0176] m-Biphenyl,

[0177] o-Biphenyl,

[0178] 4-terphenyl-4-yl,

[0179] 3-Bis(triphenyl)benzene,

[0180] 2-Bis(triphenyl)phenyl,

[0181] 4-terphenyl,

[0182] 3-terphenyl,

[0183] 2-terphenyl-1,

[0184] o-Triphenyl-4-yl,

[0185] o-Triphenyl-3-yl,

[0186] o-Triphenyl-2-yl,

[0187] 1-naphthyl,

[0188] 2-naphthyl,

[0189] Anthracene,

[0190] Benzanthryl,

[0191] Fiki,

[0192] Triphenylene,

[0193] Phenyl,

[0194] Pyrene

[0195] base,

[0196] Benzo base,

[0197] Triphenylene,

[0198] Benzotriphenylene,

[0199] Tetraphenylene (tetraceny l),

[0200] Pentacenyl,

[0201] Fluorene,

[0202] 9,9'-spirobifluorenyl,

[0203] Benzofluorenyl,

[0204] Dibenzofluorenyl,

[0205] Fluoranthene group,

[0206] Benzofluoranthene,

[0207] Perylene, and

[0208] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0209] [Chemistry 9]

[0210]

[0211] [Chemistry 10]

[0212]

[0213] ·Substituted aryl (specific example group G1 B):

[0214] o-Toluyl,

[0215] m-Toluene

[0216] p-Tolyl,

[0217] p-Xylyl,

[0218] m-Xylyl,

[0219] o-Xylyl,

[0220] p-Isopropylphenyl,

[0221] m-isopropylphenyl,

[0222] o-isopropylphenyl,

[0223] 4-tert-Butylphenyl,

[0224] m-tert-butylphenyl,

[0225] o-tert-butylphenyl,

[0226] 3,4,5-Trimethylphenyl,

[0227] 9,9-dimethylfluorenyl,

[0228] 9,9-diphenylfluorenyl,

[0229] 9,9-bis(4-methylphenyl)fluorenyl,

[0230] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0231] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0232] Cyanophenyl,

[0233] Triphenylsilylphenyl,

[0234] Trimethylsilylphenyl,

[0235] Benzene naphthyl,

[0236] Naphthylphenyl, and

[0237] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above-mentioned general formula (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0238] "Substituted or unsubstituted heterocyclic group"

[0239] The "heterocyclic group" described in the present specification 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.

[0240] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0241] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0242] As specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2), the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B) can be cited. (Herein, 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 the present specification, when simply referred to as a "heterocyclic group", both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" are included.

[0243] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are replaced, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. In addition, the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" described in this specification also includes: groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0244] Specific example group G2A includes, for example, the following groups: an unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), an unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3), and a monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0245] Specific example group G2B includes, for example, the following groups: a heterocyclic group containing a nitrogen atom as a substitution (specific example group G2B1), a heterocyclic group containing an oxygen atom as a substitution (specific example group G2B2), a heterocyclic group containing a sulfur atom as a substitution (specific example group G2B3), and a group 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 by a substituent (specific example group G2B4).

[0246] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0247] Pyrrolyl,

[0248] Imidazole,

[0249] Pyrazolyl,

[0250] Triazole,

[0251] Tetrazolyl,

[0252] Oxazolyl,

[0253] Isoxazolyl,

[0254] Oxadiazolyl,

[0255] Thiazolyl,

[0256] Isothiazolyl,

[0257] Thiadiazole,

[0258] Pyridyl,

[0259] Pyridazine

[0260] Pyrimidine,

[0261] Pyrazinyl,

[0262] Triazine,

[0263] Indolyl,

[0264] Isoindolyl,

[0265] Indolizinyl,

[0266] Quinolizinyl,

[0267] Quinoline,

[0268] Isoquinolinyl,

[0269] Cinnolyl group,

[0270] Phthalocyanine

[0271] Quinazoline,

[0272] Quinoxaline,

[0273] Benzimidazolyl,

[0274] Indazolyl,

[0275] Phenanthroline,

[0276] Phenanthridinyl,

[0277] Acridinium,

[0278] Phenazine,

[0279] Carbazolyl,

[0280] Benzocarbazolyl,

[0281] Morpholinyl,

[0282] Phenoxazine,

[0283] Phenothiazine,

[0284] Azacarbazolyl, and

[0285] Diazacarbazolyl.

[0286] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0287] Furanyl,

[0288] Oxazolyl,

[0289] Isoxazolyl,

[0290] Oxadiazolyl,

[0291] Xanthyl,

[0292] Benzofuranyl,

[0293] Isobenzofuranyl,

[0294] Dibenzofuranyl,

[0295] Naphthobenzofuranyl,

[0296] Benzoxazolyl,

[0297] Benzisoxazolyl,

[0298] Phenoxazine,

[0299] Morpholinyl,

[0300] dinaphthofuranyl,

[0301] Azadibenzofuranyl,

[0302] Diazadibenzofuranyl,

[0303] Azanaphthobenzofuranyl, and

[0304] naphthyridinylbenzofuranyl.

[0305] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0306] Thienyl,

[0307] Thiazolyl,

[0308] Isothiazolyl,

[0309] Thiadiazole,

[0310] benzothienyl,

[0311] Isobenzothienyl,

[0312] dibenzothienyl,

[0313] naphthobenzothienyl,

[0314] Benzothiazolyl,

[0315] Benzisothiazolyl,

[0316] Phenothiazine,

[0317] dinaphthothienyl,

[0318] azadibenzothienyl,

[0319] diazadibenzothienyl,

[0320] azanaphthobenzothienyl, and

[0321] diazanaphthobenzothienyl group.

[0322] A monovalent heterocyclic group derived by removing one hydrogen atom from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0323] [Chemistry 11]

[0324]

[0325] [Chemistry 12]

[0326]

[0327] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are independently oxygen atoms, sulfur atoms, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0328] In the general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least any one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0329] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0330] (9-phenyl)carbazolyl,

[0331] (9-biphenyl)carbazolyl,

[0332] (9-phenyl)phenylcarbazolyl,

[0333] (9-naphthyl)carbazolyl,

[0334] Diphenylcarbazole-9-yl,

[0335] Phenylcarbazol-9-yl,

[0336] Methylbenzimidazolyl,

[0337] Ethylbenzimidazolyl,

[0338] Phenyl triazine,

[0339] Biphenyl triazine,

[0340] Diphenyltriazine,

[0341] phenylquinazolinyl, and biphenylquinazolinyl.

[0342] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0343] Phenyldibenzofuranyl,

[0344] Methyldibenzofuranyl,

[0345] tert-Butyldibenzofuranyl, and

[0346] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0347] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0348] Phenyldibenzothiophene,

[0349] Methyldibenzothiophene,

[0350] tert-Butyldibenzothienyl, and

[0351] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0352] A group obtained by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the above general formula (TEMP-16) to (TEMP-33) with a substituent (specific example group G2B4):

[0353] The "one or more hydrogen atoms of the monovalent heterocyclic group" refers to the hydrogen atoms bonded to the ring-constituting carbon atoms of the monovalent heterocyclic group, A and Y A When at least one of them is NH, the hydrogen atom bonded to the nitrogen atom, and X A and Y A When one of them is CH2, one or more hydrogen atoms selected from the hydrogen atoms of the methylene group.

[0354] "Substituted or unsubstituted alkyl"

[0355] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when simply referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0356] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced with a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in the "unsubstituted alkyl" refers to a chain alkyl group. Therefore, the "unsubstituted alkyl" includes a straight-chain "unsubstituted alkyl" and a branched "unsubstituted alkyl". In addition, the examples of "unsubstituted alkyl" and "substituted alkyl" cited here are only examples, and the "substituted alkyl" recorded in the present specification also includes: a group in which the hydrogen atom of the alkyl itself in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent.

[0357] Unsubstituted alkyl (specific example group G3A):

[0358] methyl,

[0359] Ethyl,

[0360] n-propyl,

[0361] Isopropyl,

[0362] n-Butyl,

[0363] Isobutyl,

[0364] sec-butyl, and

[0365] Tert-butyl.

[0366] Substituted alkyl (specific example group G3B):

[0367] Heptafluoropropyl (including isomers),

[0368] Pentafluoroethyl,

[0369] 2,2,2-trifluoroethyl, and

[0370] Trifluoromethyl.

[0371] "Substituted or unsubstituted alkenyl"

[0372] As specific examples of "substituted or unsubstituted alkenyl" described in the present specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In the present specification, when simply referred to as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

[0373] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced with a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) having a substituent, and examples of substituted alkenyl (specific example group G4B). In addition, the examples of "unsubstituted alkenyl" and "substituted alkenyl" cited here are only examples, and the "substituted alkenyl" recorded in this specification also includes: a group in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further substituted with a substituent, and a group in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further substituted with a substituent.

[0374] Unsubstituted alkenyl (specific example group G4A):

[0375] Vinyl,

[0376] Allyl,

[0377] 1-Butenyl,

[0378] 2-Butenyl, and

[0379] 3-Butenyl.

[0380] Substituted alkenyl (specific example group G4B):

[0381] 1,3-Butadienyl,

[0382] 1-Methylvinyl,

[0383] 1-methylallyl,

[0384] 1,1-dimethylallyl,

[0385] 2-methylallyl, and

[0386] 1,2-Dimethylallyl.

[0387] "Substituted or unsubstituted alkynyl"

[0388] As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) Hereinafter, when simply referred to as "alkynyl", both "unsubstituted alkynyl" and "substituted alkynyl" are included.

[0389] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0390] Unsubstituted alkynyl (specific example Group G5A): ethynyl.

[0391] "Substituted or unsubstituted cycloalkyl"

[0392] As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when simply referred to as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0393] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced with a substituent. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced with a substituent, and examples of substituted cycloalkyl (specific example group G6B) can be cited. In addition, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" cited here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes: groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced with a substituent, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of the specific example group G6B are further replaced with substituents.

[0394] Unsubstituted cycloalkyl (specific example group G6A):

[0395] Cyclopropyl,

[0396] Cyclobutyl,

[0397] Cyclopentyl,

[0398] Cyclohexyl,

[0399] 1-adamantyl,

[0400] 2-adamantyl,

[0401] 1-Norbornyl, and

[0402] 2-Norborneol.

[0403] Substituted cycloalkyl (specific example group G6B):

[0404] 4-Methylcyclohexyl.

[0405] · "-Si(R 901 )(R 902 )(R 903 )"

[0406] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are represented by (specific example group G7), and include:

[0407] -Si(G1)(G1)(G1),

[0408] -Si(G1)(G2)(G2),

[0409] -Si(G1)(G1)(G2),

[0410] -Si(G2)(G2)(G2),

[0411] -Si(G3)(G3)(G3), and

[0412] -Si(G6)(G6)(G6).

[0413] Here,

[0414] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0415] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0416] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0417] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0418] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0419] Multiple G2 in -Si(G1)(G2)(G2) are the same as or different from each other.

[0420] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0421] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0422] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0423] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0424] · "With -O-(R 904 )"

[0425] As described in this specification, -O-(R 904 ) are represented by (specific example group G8), and include:

[0426] -O(G1),

[0427] -O(G2),

[0428] -O(G3), and

[0429] -O(G6).

[0430] Here,

[0431] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0432] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0433] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0434] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0435] · "With -S-(R 905 )"

[0436] As described in this specification, -S-(R 905 ) are represented by (specific example group G9), and include:

[0437] -S(G1),

[0438] -S(G2),

[0439] -S(G3), and

[0440] -S(G6).

[0441] Here,

[0442] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0443] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0444] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0445] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0446] · "With -N(R 906 )(R 907 )"

[0447] As described in this specification, -N(R 906 )(R 907 ) are represented by (specific example group G10), and the following may be mentioned:

[0448] -N(G1)(G1),

[0449] -N(G2)(G2),

[0450] -N(G1)(G2),

[0451] -N(G3)(G3), and

[0452] -N(G6)(G6).

[0453] Here,

[0454] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0455] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0456] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0457] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0458] - A plurality of G1 in N(G1)(G1) are the same as or different from each other.

[0459] - Multiple G2 in N(G2)(G2) are the same as or different from each other.

[0460] - Multiple G3 in N(G3)(G3) are the same as or different from each other.

[0461] - Multiple G6 in N(G6)(G6) are the same as or different from each other.

[0462] "Halogen atoms"

[0463] Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0464] "Substituted or unsubstituted fluoroalkyl"

[0465] The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl group" are replaced by fluorine atoms (perfluoro group). Unless otherwise specified in the present specification, the carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced by a substituent. In addition, the "substituted fluoroalkyl group" described in the present specification also includes: a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group" are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced by a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are substituted with fluorine atoms.

[0466] "Substituted or unsubstituted haloalkyl"

[0467] The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in the present specification, the carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. In addition, the "substituted haloalkyl group" described in the present specification also includes: a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted haloalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted haloalkyl group" are further substituted with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are substituted with halogen atoms. A haloalkyl group may be referred to as a halogenated alkyl group.

[0468] "Substituted or unsubstituted alkoxy"

[0469] A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in the present specification, the carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0470] "Substituted or unsubstituted alkylthio"

[0471] A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in the present specification, the carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0472] "Substituted or unsubstituted aryloxy group"

[0473] A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in the present specification, the number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0474] "Substituted or unsubstituted arylthio"

[0475] A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in the present specification, the number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0476] "Substituted or unsubstituted trialkylsilyl"

[0477] A specific example of the "substituted or unsubstituted trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Multiple G3's in -Si(G3)(G3)(G3) may be the same or different from each other. Unless otherwise specified in the present specification, the number of carbon atoms of each alkyl group of the "unsubstituted trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0478] "Substituted or unsubstituted aralkyl"

[0479] A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by an "aryl group" as a substituent, and is a form of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and unless otherwise specified in the present specification, the "unsubstituted aralkyl group" has 7 to 50 carbon atoms, preferably 7 to 30, and more preferably 7 to 18 carbon atoms.

[0480] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-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.

[0481] In the case where there is no particular description in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0482] In the case where there is no particular description in the present specification, the substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthroline group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 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 naphthobenzofuranyl group The following examples include benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazol ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazol, (9-phenyl)phenylcarbazol, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophene.

[0483] Unless otherwise specified in the present specification, the carbazolyl group in the present specification is specifically any of the following groups.

[0484] [Chemistry 13]

[0485]

[0486] Unless otherwise specified in the present specification, in the present specification, a (9-phenyl)carbazolyl group is specifically any of the following groups.

[0487] [Chemistry 14]

[0488]

[0489] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0490] Unless otherwise specified in the present specification, in the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups.

[0491] [Chemistry 15]

[0492]

[0493] In the general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0494] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0495] "Substituted or unsubstituted arylene group"

[0496] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aromatic ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aromatic ring.

[0497] · "Substituted or unsubstituted divalent heterocyclic group"

[0498] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

[0499] "Substituted or unsubstituted alkylene"

[0500] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

[0501] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68).

[0502] [Chemistry 16]

[0503]

[0504] [Chemistry 17]

[0505]

[0506] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0507] In the general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0508] [Chemistry 18]

[0509]

[0510] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0511] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0512] In the general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0513] [Chemistry 19]

[0514]

[0515] In the general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0516] In the general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0517] 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 following general formulae (TEMP-69) to (TEMP-102).

[0518] [Chemistry 20]

[0519]

[0520] [Chemistry 21]

[0521]

[0522] [Chemistry 22]

[0523]

[0524] In the general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-69) to (TEMP-82), * represents a bonding position.

[0525] [Chemistry 23]

[0526]

[0527] [Chemistry 24]

[0528]

[0529] [Chemistry 25]

[0530]

[0531] [Chemistry 26]

[0532]

[0533] In the general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulae (TEMP-83) to (TEMP-102), * represents a bonding position.

[0534] The above is the description of the “substituents described in the present specification”.

[0535] ・"When bonding to form a ring"

[0536] In the present specification, the case where “one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other” means the case where “one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring”, the case where “one or more of the groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring”, and the case where “one or more of the groups consisting of two or more adjacent groups are not bonded to each other”.

[0537] The following describes the case in this specification where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring").

[0538] The following description will be given by taking as an example an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring.

[0539] [Chemistry 27]

[0540]

[0541] For example, in R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent groups are bonded to each other to form a ring", the group consisting of two adjacent groups forming one group refers to R 921 With R 922 Group, R 922 With R923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group and R 929 With R 921 group.

[0542] The above “one or more groups” means that two or more groups of the above two or more adjacent groups can simultaneously form a ring. 921 With R 922 Bonded to each other to form ring Q A , while R 925 With R 926 Bonded to each other to form ring Q B In the case of, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0543] [Chemistry 28]

[0544]

[0545] The case where a ring is formed by a group of two or more adjacent groups includes not only the case where a group of two adjacent groups is bonded as in the above example, but also the case where a group of three or more adjacent groups is bonded. 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , so that the three adjacent (R 921 , R 922 and R 923 ) are bonded to each other to form a ring and condensed to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Shared R 922 .

[0546] [Chemistry 29]

[0547]

[0548] The formed "monocyclic ring" or "condensed ring" may be a saturated ring or an unsaturated ring only as the structure of the formed ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and Ring Q B In addition, the ring Q formed in the general formula (TEMP-105) A and Ring Q C is a "condensed ring". A With Ring Q C By RingQ A With Ring Q C If the ring Q of the general formula (TMEP-104) A is a benzene ring, then ring Q A If the ring Q of the general formula (TMEP-104) A is a naphthalene ring, then ring Q A It is a condensed ring.

[0549] 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 the ring structure, and a non-aromatic heterocyclic ring having an unsaturated bond in the 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 the ring structure include cyclohexene and cyclohexadiene. Examples of non-aromatic heterocyclic rings having an unsaturated bond in the ring structure include dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, and isoindoline.

[0550] The "saturated ring" is at least one ring selected from an aliphatic hydrocarbon ring having no unsaturated bond and a non-aromatic heterocyclic ring having no unsaturated bond. In a saturated ring, there is no double bond or triple bond in the ring structure.

[0551] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with a hydrogen atom.

[0552] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with a hydrogen atom.

[0553] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with a hydrogen atom.

[0554] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more arbitrary atoms. For example, R 921 With R 922 The ring Q formed by bonding A Represented by R 921 The carbon atom of the anthracene skeleton bonded to R 922 As a specific example, in the case where R 921 With R 922 Ring Q A In the case of R 921 The carbon atom of the anthracene skeleton bonded to R 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The ring formed is a benzene ring.

[0555] Here, in the case where no particular description is given in this specification, "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a bond that does not form a ring may be terminated by a hydrogen atom or the like, or may be substituted by an "any substituent" described later. In the case of any atom other than a carbon atom, the formed ring is a heterocycle.

[0556] Unless otherwise specified in the present specification, the number of "one or more arbitrary atoms" constituting a monocyclic or condensed 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.

[0557] Unless otherwise specified in the present specification, of "monocyclic ring" and "condensed ring", "monocyclic ring" is preferred.

[0558] Unless otherwise specified in the present specification, of "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0559] Unless otherwise specified in the present specification, the "monocyclic ring" is preferably a benzene ring.

[0560] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0561] Unless otherwise specified in the present specification, in the case of "one or more groups consisting of two or more adjacent groups" "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", it is preferred that one or more groups consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted "unsaturated ring", and the substituted or unsubstituted "unsaturated ring" is composed of multiple atoms of the parent skeleton and at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0562] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0563] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "saturated ring" or "unsaturated ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0564] The above is an explanation of the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0565] ·Substituents in the case of "substituted or unsubstituted"

[0566] 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) is, for example,

[0567] An unsubstituted alkyl group having 1 to 50 carbon atoms,

[0568] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0569] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0570] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0571] -Si(R 901 )(R 902 )(R 903 ),

[0572] -O-(R 904 ),

[0573] -S-(R 905 ),

[0574] -N(R 906 )(R 907 ),

[0575] Halogen atoms, cyano, nitro,

[0576] unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0577] a group selected from the group consisting of an unsubstituted heterocyclic group having 5 to 50 ring atoms, etc.,

[0578] Here, R 901 ~R 907 Independently,

[0579] Hydrogen atoms,

[0580] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0581] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0582] 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.

[0583] In the presence of two or more R 901 In the case of 2 or more R 901 Same or different from each other,

[0584] In the presence of two or more R 902 In the case of 2 or more R 902 Same or different from each other,

[0585] In the presence of two or more R 903 In the case of 2 or more R 903 Same or different from each other,

[0586] In the presence of two or more R 904 In the case of 2 or more R 904 Same or different from each other,

[0587] In the presence of two or more R 905 In the case of 2 or more R 905 Same or different from each other,

[0588] In the presence of two or more R 906 In the case of 2 or more R 906 Same or different from each other,

[0589] In the presence of two or more R 907 In the case of 2 or more R 907 The same as or different from each other.

[0590] In one embodiment, the substituent in the case of "substituted or unsubstituted" is

[0591] An alkyl group having 1 to 50 carbon atoms,

[0592] an aryl group having 6 to 50 ring carbon atoms, and

[0593] A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0594] In one embodiment, the substituent in the case of "substituted or unsubstituted" is

[0595] An alkyl group having 1 to 18 carbon atoms,

[0596] an aryl group having 6 to 18 ring carbon atoms, and

[0597] A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0598] Specific examples of each group of the above-mentioned optional substituent are the specific examples of the substituent described in the above-mentioned section of "substituent described in the present specification".

[0599] Unless otherwise specified in the present specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0600] Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0601] When a plurality of arbitrary substituents exist, the plurality of arbitrary substituents may be the same as or different from each other.

[0602] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[0603] [First embodiment]

[0604] The structure of the organic EL element according to the first embodiment of the present invention will be described.

[0605] The organic EL element has an organic layer between two electrodes, the anode and the cathode. The organic layer includes at least one layer composed of an organic compound. Alternatively, the organic layer is composed of a plurality of layers composed of organic compounds stacked together. The organic layer may further include an inorganic compound. In the organic EL element of this embodiment, at least one layer of the organic layer is a light-emitting layer. Therefore, the organic layer may, for example, be composed of a light-emitting layer, or may include a layer that can be used in an organic EL element. There is no particular limitation on the layer that can be used in the organic EL element, and for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer and a blocking layer can be cited.

[0606] The organic EL element of this embodiment has a light-emitting layer included between an anode and a cathode.

[0607] The organic EL element of this embodiment has an anode, a cathode, and a light-emitting layer contained between the anode and the cathode, wherein the light-emitting layer contains a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescence compound M2, wherein the compound M3 has a different structure from the compound M2, and the singlet energy S1(M3) of the compound M3 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (number 1).

[0608] S1(M3)>S1(M2)(number 1)

[0609] The present inventors have found that a high-performance organic EL device can be realized by including a compound M3 represented by the general formula (1-1) or (1-2) (compound M3 of this embodiment) in a light-emitting layer together with a delayed fluorescence compound M2.

[0610] The compound M3 of this embodiment is a compound obtained by bonding benzofuranocarbazole or benzothiophenocarbazole, which supplies an appropriate amount of holes to the light-emitting layer, to dibenzofuran or dibenzothiophene with high durability via a meta-bonded biphenylene or ortho-bonded biphenylene with a short conjugated length. The compound M3 of this embodiment shows a high triplet energy, and thus the triplet energy of the compound with delayed fluorescence can be fully blocked.

[0611] Therefore, according to this embodiment, a high-performance organic EL element can be realized.

[0612] According to one aspect of this embodiment, the organic EL element emits light with high efficiency.

[0613] According to one aspect of this embodiment, the life of the organic EL element is prolonged.

[0614] Figure 1Schematic diagram of an example of the structure of the organic EL element in this embodiment is shown in FIG.

[0615] 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 composed of a hole injection layer 6, a hole transport layer 7, a light-emitting layer 5, an electron transport layer 8, and an electron injection layer 9 stacked in this order from the anode 3 side.

[0616] The light-emitting layer 5 may contain a metal complex.

[0617] The light-emitting layer 5 preferably does not contain a phosphorescent material (dopant material).

[0618] It is preferred that the light-emitting layer 5 does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.

[0619] Furthermore, the light-emitting layer 5 preferably does not contain a metal complex.

[0620] In the organic EL device 1 of this embodiment, the light-emitting layer 5 contains the compound M2 having delayed fluorescence and the compound M3 represented by the general formula (1-1) or (1-2).

[0621] In the case of this embodiment, compound M2 is preferably a dopant material (sometimes also referred to as a guest material, an emitter, or a light-emitting material), and compound M3 is preferably a host material (sometimes also referred to as a matrix material).

[0622] The compound M3 may be a compound having delayed fluorescence or a compound not having delayed fluorescence.

[0623] Hereinafter, the structure of the organic EL element of this embodiment will be described in detail. Hereinafter, description of reference numerals may be omitted.

[0624] <Luminous Layer>

[0625] (Compound M3)

[0626] The light-emitting layer in this embodiment includes a compound M3 represented by the following general formula (1-1) or (1-2).

[0627] The compound M3 in this embodiment may be a compound that exhibits thermally activated delayed fluorescence or a compound that does not exhibit thermally activated delayed fluorescence, but is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0628] [Chemistry 30]

[0629]

[0630] [Chemistry 31]

[0631]

[0632] (In the general formulas (1-1) and (1-2),

[0633] A is a group represented by any of the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0634] L1 and L2 are independently,

[0635] Single key, or

[0636] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[0637] Y1 is an oxygen atom or a sulfur atom,

[0638] By R 21 ~R 28 One or more of the groups of two or more adjacent

[0639] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0640] bonded to each other to form a substituted or unsubstituted fused ring, or

[0641] Not bonded to each other,

[0642] R 100 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Independently,

[0643] Hydrogen atoms,

[0644] Halogen atoms,

[0645] Cyano,

[0646] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0647] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0648] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0649] a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,

[0650] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0651] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[0652] a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,

[0653] a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,

[0654] a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,

[0655] a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms,

[0656] Hydroxyl,

[0657] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[0658] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[0659] A group represented by -N(Rz)2,

[0660] Thiol group,

[0661] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[0662] a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms,

[0663] Substituted germanium

[0664] Substituted phosphine oxide groups,

[0665] Nitro,

[0666] Substituted boron, or

[0667] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[0668] Rz is

[0669] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0670] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0671] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0672] - The two Rz in N(Rz)2 are the same or different from each other,

[0673] Multiple R 100 Same or different from each other,

[0674] In the general formulas (1-1) and (1-2), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded.)

[0675] [Chemistry 32]

[0676]

[0677] (In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0678] X1 is an oxygen atom or a sulfur atom,

[0679] By R 11 ~R 20 One or more of the groups of two or more adjacent

[0680] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0681] bonded to each other to form a substituted or unsubstituted fused ring, or

[0682] Not bonded to each other,

[0683] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 11 ~R 20 R in the general formula (1-1) and (1-2) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Synonymous, * indicates bonding position. )

[0684] In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F),

[0685] When L1 is a single bond and L2 is an arylene group, * indicates the position of bonding to L2.

[0686] When L1 is an arylene group and L2 is a single bond, * indicates the position of bonding to L1.

[0687] When L1 and L2 are arylene groups, * indicates the position of bonding to L1.

[0688] When L1 and L2 are single bonds, * indicates the position of bonding to the carbon atom of the six-membered ring.

[0689] In this embodiment, the compound M3 is preferably a compound represented by the general formula (1-1).

[0690] In this embodiment, the compound represented by the general formula (1-1) as the compound M3 is represented by the following general formula (100-1), (100-2), (100-3) or (100-5).

[0691] [Chemistry 33]

[0692]

[0693] [Chemistry 34]

[0694]

[0695] (In the general formulas (100-1), (100-2), (100-3) and (100-5), A, L1, L2, Y1, R 21 ~R 28 and R 100 A, L1, L2, Y1, R in the general formula (1-1) are independently 21 ~R 28 and R 100 Synonymous.)

[0696] In this embodiment, the compound represented by the general formula (1-2) as the compound M3 is represented by the following general formula (100-4A), (100-4B), (100-4C) or (100-4D).

[0697] [Chemistry 35]

[0698]

[0699] [Chemistry 36]

[0700]

[0701] (In the general formulas (100-4A), (100-4B), (100-4C) and (100-4D), A, L1, L2, Y1, R 21 ~R 28 and R 100 A, L1, L2, Y1, R in the general formula (1-2) are independently 21 ~R 28 and R 100 Synonymous.)

[0702] In the compound M3 of one embodiment, L1 and L2 are each independently a single bond or a substituted or unsubstituted phenylene group.

[0703] In one embodiment of compound M3, L1 and L2 are single bonds.

[0704] In compound M3 according to one embodiment, A is a group represented by the general formula (11F).

[0705] In the compound M3 according to one embodiment, A is a group represented by the general formula (11D).

[0706] In one embodiment of compound M3, X1 is a sulfur atom.

[0707] In compound M3 according to one embodiment, X1 is an oxygen atom.

[0708] In one embodiment of compound M3, Y1 is an oxygen atom.

[0709] In one embodiment of compound M3, X1 is a sulfur atom and Y1 is an oxygen atom. In one embodiment of compound M3, X1 and Y1 are oxygen atoms.

[0710] In one embodiment of compound M3, R 21 ~R 28 A group of two or more adjacent ones in is not bonded to each other.

[0711] In one embodiment of compound M3, R 21 ~R 28 Each independently represents a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[0712] In one embodiment of compound M3, R 21 ~R 28 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0713] In one embodiment of compound M3, R 21 ~R 28 A hydrogen atom.

[0714] In one embodiment of compound M3, R 21 ~R 28 At least one of them is a deuterium atom.

[0715] In one embodiment of compound M3, R 11 ~R 20 A group of two or more adjacent ones in is not bonded to each other.

[0716] In one embodiment of compound M3, R 11 ~R 20 Each independently represents a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[0717] In one embodiment of compound M3, R 11 ~R20 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group.

[0718] In one embodiment of compound M3, R 11 ~R 20 A hydrogen atom.

[0719] In one embodiment of compound M3, R 11 ~R 20 At least one of them is a deuterium atom.

[0720] In one embodiment of compound M3, R 100 Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[0721] In one embodiment of compound M3, R 100 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a trimethylsilyl group.

[0722] In one embodiment of compound M3, R 100 A hydrogen atom.

[0723] In one embodiment of compound M3, a plurality of R 100 At least one of them is a deuterium atom.

[0724] In one embodiment of compound M3, R 100 It is not a group represented by -N(Rz)2.

[0725] Compound M3 of one embodiment is

[0726] From the compounds represented by the general formulae (100-1) to (100-3), and

[0727] Any compound selected from the group consisting of compounds represented by the general formulae (100-4A) to (100-4D). Among them, preferably, R 100 It is not a group represented by -N(Rz)2.

[0728] The compounds represented by the general formulae (100-1) to (100-3) have the same meanings as the compounds represented by the general formulae (100-1) to (100-3) in the fourth embodiment.

[0729] Represented by the general formula (100-4A) to (100-4D) and R 100 The compound which is not a group represented by -N(Rz)2 has the same meaning as the compound represented by the general formula (100-4) among the compounds of the fourth embodiment.

[0730] In the light-emitting layer of one embodiment, the compound having a singlet energy S1 larger than the singlet energy S1 (M2) of the delayed fluorescence compound M2 is only the compound M3.

[0731] ·Method for producing compound M3 according to this embodiment

[0732] The compound M3 of this embodiment can be produced, for example, by the method described in Examples described below. The compound M3 of this embodiment can be produced by following the reaction described in Examples described below, using a known substitution reaction and a raw material that matches the target compound.

[0733] Specific examples of the compound M3 according to the present embodiment include the following compounds, but the present invention is not limited to these specific examples of the compounds.

[0734] [Chemistry 37]

[0735]

[0736] [Chemistry 38]

[0737]

[0738] [Chemistry 39]

[0739]

[0740] [Chemistry 40]

[0741]

[0742] [Chemistry 41]

[0743]

[0744] [Chemistry 42]

[0745]

[0746] [Chemistry 43]

[0747]

[0748] [Chemistry 44]

[0749]

[0750] [Chemistry 45]

[0751]

[0752] [Chemistry 46]

[0753]

[0754] [Chemistry 47]

[0755]

[0756] [Chemistry 48]

[0757]

[0758] [Chemistry 49]

[0759]

[0760] [Chemistry 50]

[0761]

[0762] [Chemistry 51]

[0763]

[0764] [Chemistry 52]

[0765]

[0766] [Chemistry 53]

[0767]

[0768] [Chemistry 54]

[0769]

[0770] [Chemistry 55]

[0771]

[0772] [Chemistry 56]

[0773]

[0774] [Chemistry 57]

[0775]

[0776] [Chemistry 58]

[0777]

[0778] [Chemistry 59]

[0779]

[0780] [Chemistry 60]

[0781]

[0782] [Chemistry 61]

[0783]

[0784] [Chemistry 62]

[0785]

[0786] [Chemistry 63]

[0787]

[0788] [Chemistry 64]

[0789]

[0790] [Chemistry 65]

[0791]

[0792] [Chemistry 66]

[0793]

[0794] [Chemistry 67]

[0795]

[0796] [Chemistry 68]

[0797]

[0798] [Chemistry 69]

[0799]

[0800] [Chemistry 70]

[0801]

[0802] (Compound M2)

[0803] The light-emitting layer of this embodiment contains the delayed fluorescence compound M2.

[0804] Delayed fluorescence

[0805] Delayed fluorescence is explained in "Device Properties of Organic Semiconductors" (edited by Chiba Ya Adachi, published by Kodansha) on pages 261 to 268. This document states that if the energy difference ΔE between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, 13 , then the reverse energy transfer from the excited triplet state to the excited singlet state, which usually has a low migration probability, occurs efficiently, generating thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence is illustrated in Figure 10.38 in the document. The compound M2 in this embodiment is preferably a compound that shows thermally activated delayed fluorescence generated by such a mechanism.

[0806] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[0807] It is also possible to analyze the behavior of delayed fluorescence based on the decay curve obtained by transition PL measurement. Transition PL measurement refers to a method of irradiating a sample with a pulsed laser to excite it and measuring the decay behavior (transition characteristics) of the PL luminescence after stopping the irradiation. The PL luminescence in the TADF material is divided into a luminescence component from a singlet exciton generated by the initial PL excitation and a luminescence component from a singlet exciton generated via a triplet exciton. The lifetime of the singlet exciton generated by the initial PL excitation is in the nanosecond range, which is very short. Therefore, the luminescence from the singlet exciton decays rapidly after irradiation with the pulsed laser.

[0808] On the other hand, delayed fluorescence is the emission of singlet excitons generated via triplet excitons with a long lifetime, and therefore decays slowly. Thus, there is a large time difference between the emission of singlet excitons generated by the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity from delayed fluorescence can be obtained.

[0809] Figure 2 A schematic diagram of an example apparatus for measuring transition PL is shown in FIG. Figure 2 An example of the transition PL measurement method and delayed fluorescence behavior analysis is described.

[0810] Figure 2 The transient PL measurement device 100 comprises: a pulse laser unit 101, which can irradiate light of a predetermined wavelength; a sample chamber 102, which stores the measurement sample; a spectrometer 103, which splits the light emitted from the measurement sample; a streak camera 104, which is used to form a two-dimensional image; and a personal computer 105, which reads the two-dimensional image for analysis. In addition, the measurement of transient PL is not limited to Figure 2 The device described.

[0811] The sample accommodated in the sample chamber 102 can be obtained by forming a thin film in which a host material is doped with a doping material at a concentration of 12% by mass on a quartz substrate.

[0812] The thin film sample housed in the sample chamber 102 is irradiated with a pulse laser from the pulse laser unit 101 to excite the doping material. The luminescence is extracted in a direction of 90 degrees relative to the irradiation direction of the excitation light, the extracted light is split by the spectrometer 103, and a two-dimensional image is formed 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 the bright spot corresponds to the luminescence intensity. If the two-dimensional image is cut out along a specified time axis, a luminescence spectrum can be obtained in which the vertical axis is the luminescence intensity and the horizontal axis is the wavelength. In addition, if the two-dimensional image is cut out along the wavelength axis, an attenuation curve (transition PL) can be obtained in which the vertical axis is the logarithm of the luminescence intensity and the horizontal axis is time.

[0813] For example, a thin film sample A was prepared as described above using the reference compound H1 described below as a host material and the reference compound D1 described below as a dopant material, and transition PL measurement was performed.

[0814] [Chemistry 71]

[0815]

[0816] Here, the attenuation curves were analyzed using the thin film sample A and the thin film sample B. The thin film sample B was prepared as described above using the reference compound H2 described below as a host material and the reference compound D1 described above as a dopant material.

[0817] Figure 3 2 shows the decay curves obtained from the transition PL measured for the film sample A and the film sample B.

[0818] [Chemistry 72]

[0819]

[0820] As described above, by transient PL measurement, a luminescence decay curve with luminescence intensity as the vertical axis and time as the horizontal axis can be obtained. Based on the luminescence decay curve, the fluorescence intensity ratio of the fluorescence emitted from the singlet excited state generated by light excitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be calculated. In delayed fluorescent materials, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the rapidly decaying fluorescence is larger to a certain extent.

[0821] Specifically, as luminescence from delayed fluorescent materials, there are prompt luminescence and delay luminescence. Prompt luminescence refers to luminescence observed immediately from the excited state after being excited by pulsed light (light irradiated by pulsed laser) of a wavelength absorbed by the delayed fluorescent material. Delay luminescence refers to luminescence that cannot be observed immediately after being excited by the pulsed light but is observed later.

[0822] The amount of prompt luminescence and delay luminescence and the ratio of the two can be calculated by the same method as described in "Nature" 492, 234-238, 2012 (reference 1). In addition, the device used for calculating the amount of prompt luminescence and delay luminescence is not limited to the device described in reference 1 or Figure 2 The device described in .

[0823] In addition, in the present specification, in the measurement of the delayed fluorescence of compound M2, a sample prepared by the method shown below is used. For example, compound M2 is dissolved in toluene, and in order to eliminate the influence of self-absorption, a dilute solution having an absorbance of 0.05 or less at the excitation wavelength is prepared. In addition, in order to prevent extinction caused by oxygen, the sample solution is frozen and exhausted, and then sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[0824] The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of the ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of the two spectra according to the formula (1) in Morris et al., J. Phys. Chem., 80 (1976) 969.

[0825] In this embodiment, the amount of prompt luminescence (immediate luminescence) of the compound to be measured (compound M2) is denoted as X. P , the amount of Delay luminescence is recorded as X D When X D / X P The value of is preferably 0.05 or more.

[0826] The measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio thereof of compounds other than Compound M2 in this specification is also the same as the measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio thereof of Compound M2.

[0827] ·Method for producing compound M2 according to this embodiment

[0828] The compound M2 of this embodiment can be produced by a known method.

[0829] Specific examples of the compound M2 according to the present embodiment include the following compounds, but the present invention is not limited to these specific examples of the compounds.

[0830] [Chemistry 73]

[0831]

[0832] [Chemistry 74]

[0833]

[0834] [Chemistry 75]

[0835]

[0836] <Relationship between Compound M3 and Compound M2 in the Emitting Layer>

[0837] In the organic EL device of this embodiment, the singlet energy S1(M2) of the compound M2 and the singlet energy S1(M3) of the compound M3 satisfy the relationship of the following mathematical formula (Formula 1).

[0838] S1(M3)>S1(M2)(number 1)

[0839] The energy gap T of the preferred compound M3 at 77[K] 77K (M3) is larger than the energy gap T of compound M2 at 77[K] 77K (M2) That is, it is preferable to satisfy the relationship of the following mathematical formula (Formula 11).

[0840] T 77K (M3)>T 77K (M2)…(number 11)

[0841] When the organic EL device of this embodiment is made to emit light, it is preferred that the light emitting layer does not mainly emit light from the compound M3.

[0842] Relationship between triplet energy and energy gap at 77[K]

[0843] Here, the relationship between the triplet energy and the energy gap at 77 [K] is described. In the present embodiment, the energy gap at 77 [K] is different from the triplet energy generally defined.

[0844] The triplet energy is measured as follows. First, the compound to be measured is dissolved in an appropriate solvent, and the resulting solution is sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum is measured at a low temperature (77 [K]) (with a vertical axis: phosphorescence intensity and a horizontal axis: wavelength), and a tangent is drawn to the rising edge of the short wavelength side of the phosphorescence spectrum. Based on the wavelength value of the intersection of the tangent and the horizontal axis, the triplet energy is calculated according to a prescribed conversion formula.

[0845] Here, the compound of thermally activated delayed fluorescence in the compound of the present embodiment is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at a low temperature (77 [K]), and the excited singlet state and the excited triplet state coexist. As a result, it can be considered that the spectrum measured in the same manner as above includes luminescence from both the excited singlet state and the excited triplet state. Although it is difficult to distinguish which state the luminescence comes from, the value of the triplet energy is basically dominant.

[0846] Therefore, in this embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to distinguish the difference in a strict sense, the value measured as follows is referred to as the energy gap T 77K The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as a measurement sample. For the measurement sample, the phosphorescence spectrum was measured at a low temperature (77 [K]) (with the vertical axis: phosphorescence emission intensity and the horizontal axis: wavelength), and a tangent was drawn to the rising edge of the short-wavelength side of the phosphorescence spectrum. The wavelength value λ based on the intersection of the tangent and the horizontal axis was calculated. edge [nm], the energy calculated by the following conversion formula (F1) is taken as the energy gap T at 77 [K] 77K .

[0847] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0848] The tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum is drawn as shown below. Consider that the tangent line is a tangent line at each point on the long wavelength side curve when moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side of the spectrum maximum value. The slope of the tangent line increases as the curve rises (i.e., as the vertical axis value increases). The tangent line drawn at the point where the slope value takes the maximum value (i.e., the tangent line at the inflection point) is used as the tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum.

[0849] In addition, the maximum point with a peak intensity of less than 15% 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 closest to the maximum value on the shortest wavelength side and where the slope value takes the maximum value is used as the tangent to the rising edge of the short wavelength side of the phosphorescence spectrum.

[0850] Phosphorescence can be measured using a spectrofluorophotometer model F-4500 manufactured by Hitachi High-Technologies Corporation. The measuring device is not limited thereto, and measurement can be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0851] Singlet energy S1

[0852] As a measurement method of the singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be mentioned.

[0853] 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 the sample is measured at room temperature (300 K) (with a vertical axis: absorption intensity and a horizontal axis: wavelength). A tangent is drawn to the falling edge on the long wavelength side of the absorption spectrum, and the wavelength value λedge [nm] of the intersection of the tangent and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the singlet energy.

[0854] Conversion formula (F2): S1[eV]=1239.85 / λedge

[0855] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310) can be mentioned, but the present invention is not limited to this.

[0856] The tangent line for the falling edge on the long wavelength side of the absorption spectrum is drawn as shown below. Consider that the tangent line is the tangent line at each point on the curve when moving along the long wavelength direction on the spectrum curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum. As the curve descends (i.e., as the vertical axis value decreases), the slope of the tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope value takes the minimum value on the longest wavelength side (excluding the case where the absorbance reaches 0.1 or less) is used as the tangent line for the falling edge on the long wavelength side of the absorption spectrum.

[0857] In addition, the maximum point where the absorbance value is 0.2 or less is not included in the above-mentioned maximum value on the longest wavelength side.

[0858] In this embodiment, the singlet energy S1 is compared with the energy gap T at 77 [K]. 77K The difference (S1-T 77K ) is defined as △ST.

[0859] In this embodiment, the singlet energy S1(M2) of the compound M2 and the energy gap T at 77[K] of the compound M2 are 77K The difference ΔST(M2) between (M2) and (M2) is preferably less than 0.3 eV, more preferably less than 0.2 eV, further preferably less than 0.1 eV, and further preferably less than 0.01 eV. That is, ΔST(M2) preferably satisfies any of the following mathematical formulas (Equation 1A) to (Equation 1D).

[0860] △ST(M2)=S1(M2)-T 77K (M2) <0.3eV (several 1A)

[0861] △ST(M2)=S1(M2)-T 77K (M2) < 0.2eV (number 1B)

[0862] △ST(M2)=S1(M2)-T 77K (M2) <0.1eV (several 1C)

[0863] △ST(M2)=S1(M2)-T 77K (M2) <0.01eV (number 1D)

[0864] Thickness of the light-emitting layer

[0865] The film thickness of the light-emitting layer in the organic EL element of the present embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. If it is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity become easy, and if it is 50 nm or less, it is easy to suppress the increase of the driving voltage.

[0866] ·Content ratio of the compound in the light-emitting layer

[0867] The content of the compound M2 and the compound M3 contained in the light-emitting layer is preferably within the following ranges, for example.

[0868] The content of the compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[0869] The content of the compound M3 is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and even more preferably 40% by mass or more and 80% by mass or less.

[0870] In addition, this embodiment does not exclude the inclusion of materials other than the compound M2 and the compound M3 in the light-emitting layer.

[0871] The light-emitting layer may contain only one type of compound M2, or may contain two or more types of compound M2. The light-emitting layer may contain only one type of compound M3, or may contain two or more types of compound M3.

[0872] Figure 4 : is a diagram showing an example of the relationship between the energy levels of the compound M3 and the compound M2 in the light-emitting layer. Figure 4 In , S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. Figure 4 As shown, if a material with a small ΔST(M2) is used as compound M2, the lowest excited triplet state T1 of compound M2 can reversely intersystem cross to the lowest excited singlet state S1 through thermal energy.

[0873] By utilizing the reverse intersystem crossing generated in the compound M2, when the light-emitting layer does not contain a fluorescent dopant whose lowest excited singlet state S1 is less than the lowest excited singlet state S1(M2) of the compound M2, light emission from the lowest excited singlet state S1(M2) of the compound M2 can be observed. It is believed that by utilizing the delayed fluorescence based on the TADF mechanism, the internal quantum efficiency can be increased to 100% in theory.

[0874] The organic EL device of this embodiment contains, in the light-emitting layer, a compound M2 having delayed fluorescence and a compound M3 having a larger singlet energy than the compound M2 (compound M3 represented by the general formula (1-1) or (1-2)).

[0875] According to this embodiment, a high-performance organic EL element can be realized.

[0876] According to one aspect of this embodiment, an organic EL element that emits light with high efficiency can be realized.

[0877] According to one aspect of this embodiment, an organic EL element that emits light with a long life can be realized.

[0878] The organic EL element of this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0879] The structure of the organic EL element will be further described.

[0880] (Substrate)

[0881] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, and plastic can be used. In addition, a flexible substrate can also be used. A flexible substrate refers to a (flexible) substrate that can be bent, for example, a plastic substrate can be mentioned. As the material forming the plastic substrate, for example, polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

[0882] (anode)

[0883] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or more). Specifically, examples thereof include indium oxide-tin oxide (ITO: Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, examples thereof include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[0884] These materials are usually formed into films by sputtering. For example, for indium oxide-zinc oxide, it can be formed by sputtering by using a target to which zinc oxide of 1 mass % or more and 10 mass % or less is added relative to indium oxide. In addition, for example, for indium oxide containing tungsten oxide and zinc oxide, it can be formed by sputtering by using a target containing 0.5 mass % or more and 5 mass % of tungsten oxide and 0.1 mass % or more and 1 mass % of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[0885] In the EL layer formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that is independent of the work function of the anode and easily injects holes (cavities). Therefore, materials that can be used as electrode materials (for example, metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0886] It is also possible to use an element belonging to Group 1 or Group 2 of the periodic table, i.e., an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr) and an alloy containing them (e.g., MgAg, AlLi), a rare earth metal such as europium (Eu) and ytterbium (Yb) and an alloy containing them, etc., as a material with a smaller work function. In addition, when an alkali metal, an alkaline earth metal and an alloy containing them are used to form an anode, a vacuum evaporation method or a sputtering method can be used. Furthermore, when a silver paste is used, a coating method or an inkjet method can be used.

[0887] (cathode)

[0888] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof with a relatively small work function (specifically, less than 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[0889] When an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste is used, a coating method or an inkjet method can be used.

[0890] In addition, by providing an electron injection layer, the cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[0891] (Hole Injection Layer)

[0892] The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc. can be used.

[0893] In addition, as a substance with high hole injection property, there can be mentioned 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), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl}-N-phenylamino]biphenyl (abbreviation: DNTPD), Aromatic amine compounds such as 3-[(1-phenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

[0894] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD) and other polymer compounds can be mentioned. In addition, a polymer compound to which an acid is added, such as poly (3, 4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (PAni / PSS) and the like can also be used.

[0895] (Hole Transport Layer)

[0896] The hole transport layer is a layer containing a substance with high hole transport properties. The hole transport layer can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N -phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and other aromatic amine compounds. The substances mentioned here are mainly aromatic amine compounds with 10 -6 cm 2 / (V·s) or more.

[0897] In the hole transport layer, carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA) or anthracene derivatives such as t-BuDNA, DNA, and DPAnth can also be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as: PVK) or poly(4-vinyltriphenylamine) (abbreviated as: PVTPA) can also be used.

[0898] However, any substance other than these may be used as long as it has a higher hole transport property than electrons. In addition, the layer containing a substance having a high hole transport property may be not only a single layer but also a layer in which two or more layers formed of the above substances are stacked.

[0899] When two or more hole transport layers are provided, it is preferred that a material having a larger energy gap be provided on the side close to the light emitting layer. As such a material, HT-2 used in the examples described below can be mentioned.

[0900] (Electron Transport Layer)

[0901] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use 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, 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as: Almq3), bis (10-hydroxybenzo [h] quinoline) beryllium (abbreviated as: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), bathophenanthroline (abbreviated as BPhen), bathocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviated as BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly those having 10 -6 cm 2 / (V·s) or more. In addition, as long as the electron transport property is higher than the hole transport property, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can be composed of a single layer, or it can be composed of two or more layers formed by the above substances.

[0902] In addition, the electron transport layer can also use a polymer compound, for example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), etc. can be used.

[0903] (Electron Injection Layer)

[0904] The electron injection layer is a layer containing a substance with high electron injection. In the electron injection layer, alkali metals, alkaline earth metals or their compounds such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx) can be used. In addition, it is also possible to use a substance obtained by making a substance with electron transportability contain an alkali metal, an alkaline earth metal or their compounds, specifically a substance obtained by making Alq contain magnesium (Mg). In addition, in this case, electron injection can be performed more efficiently from the cathode.

[0905] Alternatively, the electron injection layer can also use a composite material mixed with an organic compound and an electron donor (donor). Such a composite material generates electrons in an organic compound through an electron donor, so the electron injection and electron transport properties are excellent. In this case, as an organic compound, it is preferably a material with excellent transmission of the generated electrons, and specifically, it is possible to use, for example, a substance (metal complex or heteroaromatic compound, etc.) constituting the above-mentioned electron transport layer. As an electron donor, as long as it is a substance that shows electron donation for an organic compound. Specifically, it is preferably an alkali metal, an alkaline earth metal or a rare earth metal, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be exemplified. In addition, it is preferably an alkali metal oxide or an alkaline earth metal oxide, and lithium oxide, calcium oxide, barium oxide, etc. can be exemplified. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[0906] (Layer Formation Method)

[0907] The method for forming each layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above, and can adopt a dry film-forming method such as vacuum evaporation, sputtering, plasma method, ion plating method, or a wet film-forming method such as spin coating, immersion method, flow coating, inkjet method, or other well-known methods.

[0908] (film thickness)

[0909] The film thickness of each organic layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above. However, if the film thickness is too thin, defects such as pinholes are likely to occur. On the contrary, if it is too thick, a higher applied voltage is required and the efficiency becomes poor. Therefore, it is usually preferably in the range of several nm to 1 μm.

[0910] [Second embodiment]

[0911] The structure of the organic EL element of the second embodiment is described. In the description of the second embodiment, the same components as those of the first embodiment are given the same reference numerals and names, and the description is omitted or simplified. In addition, 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.

[0912] The organic EL device of the second embodiment is different from the organic EL device of the first embodiment in that the light-emitting layer further contains a fluorescent compound M1. The other aspects are the same as those of the first embodiment.

[0913] In one mode of the second embodiment, the light-emitting layer contains the compound M3 represented by the general formula (1-1) or (1-2), the delayed fluorescent compound M2, and the fluorescent compound M1.

[0914] In one aspect of the second embodiment, compound M1 is preferably a dopant material, compound M2 is preferably a host material, and compound M3 is preferably a host material. Sometimes, one of compound M2 and compound M3 is referred to as a first host material, and the other is referred to as a second host material.

[0915] (Compound M1)

[0916] The light-emitting layer of this embodiment contains the fluorescent compound M1.

[0917] The compound M1 of this embodiment is not a phosphorescent metal complex. The compound M1 of this embodiment is preferably not a heavy metal complex. In addition, the compound M1 of this embodiment is preferably not a metal complex.

[0918] Furthermore, the compound M1 according to the present embodiment is preferably a compound that does not exhibit thermally activated delayed fluorescence.

[0919] As the compound M1 of this embodiment, a fluorescent material can be used. Specifically, for example, the fluorescent material includes diarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, diarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, diarylaminopyrene derivatives, aryl-substituted pyrene derivatives, diarylamino Derivatives, aryl substitution Derivatives, diarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthenefluoranthene derivatives, compounds containing boron atoms, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives and tetracene derivatives, etc.

[0920] When the compound M1 is a fluorescent compound, the compound M1 preferably emits light with a maximum peak wavelength of 400 nm to 700 nm.

[0921] In this specification, the maximum peak wavelength refers to the wavelength at which the compound to be measured is 10 -6 mol / L or more 10 -5 The peak wavelength of the fluorescence spectrum at which the emission intensity in the fluorescence spectrum of the toluene solution dissolved at a concentration of mol / L or less is measured is the maximum. A spectrofluorophotometer (F-7000 manufactured by Hitachi High-Technologies Corporation) is used as the measuring device.

[0922] Preferably, compound M1 emits red light or green light.

[0923] In this specification, red light emission refers to light emission having a maximum peak wavelength in a fluorescence spectrum within a range of 600 nm to 660 nm.

[0924] When compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably from 600 nm to 660 nm, more preferably from 600 nm to 640 nm, and even more preferably from 610 nm to 630 nm.

[0925] In this specification, green light emission refers to light emission having a maximum peak wavelength in a fluorescence spectrum within a range of 500 nm to 560 nm.

[0926] When compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm.

[0927] In this specification, blue light emission refers to light emission having a maximum peak wavelength in a fluorescence spectrum within a range of 430 nm to 480 nm.

[0928] When the compound M1 is a blue fluorescent compound, the maximum peak wavelength of the compound M1 is preferably from 430 nm to 480 nm, and more preferably from 440 nm to 480 nm.

[0929] The measurement of the maximum peak wavelength of light emitted from the organic EL element is performed as follows.

[0930] The organic EL element was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta Inc.) by applying a voltage so that the current density reached 10 mA / cm 2 Spectral emission brightness spectrum at .

[0931] In the obtained spectroscopic emission brightness spectrum, the peak wavelength of the emission spectrum where the emission intensity reaches the maximum is measured and is taken as the maximum peak wavelength (unit: nm).

[0932] (Compound represented by general formula (2A))

[0933] In this embodiment, the compound M1 is preferably a compound represented by the following general formula (2A): The compound M1 is preferably a compound that emits light with a maximum peak wavelength of 500 nm to 560 nm.

[0934] [Chemistry 76]

[0935]

[0936] (In the general formula (2A),

[0937] The Za ring, the Zb ring and the Zc ring are each independently,

[0938] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[0939] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[0940] Ra is bonded to the Za ring or the Zb ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

[0941] Rb is bonded to the Za ring or the Zc ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

[0942] Ra and Rb which do not form the substituted or unsubstituted heterocyclic ring are each independently,

[0943] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0944] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0945] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0946] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0947] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0948] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0949] (Compound represented by general formula (D11))

[0950] In the present embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (D11). It is also preferred that the compound represented by the general formula (2A) is a compound represented by the following general formula (D11).

[0951] [Chemistry 77]

[0952]

[0953] (In the general formula (D11), Rb has the same meaning as Rb in the general formula (2A),

[0954] X1 is CR1 or a nitrogen atom,

[0955] X2 is CR2 or a nitrogen atom,

[0956] X3 is CR3 or a nitrogen atom,

[0957] X4 is CR4 or a nitrogen atom,

[0958] X5 is CR5 or a nitrogen atom,

[0959] X6 is CR6 or a nitrogen atom,

[0960] X7 is CR7 or a nitrogen atom, or a carbon atom bonded to X8 via a single bond,

[0961] X8 is CR8 or a nitrogen atom, or a carbon atom bonded to X7 via a single bond,

[0962] X9 is CR9 or a nitrogen atom,

[0963] X 10 CR 10 or nitrogen atoms,

[0964] X 11 CR 11 or nitrogen atoms,

[0965] X 12 CR 12 or nitrogen atoms,

[0966] Q is CR Q or nitrogen atoms,

[0967] From R1 to R6 and R9 to R 11 One or more of the groups of two or more adjacent

[0968] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0969] bonded to each other to form a substituted or unsubstituted fused ring, or

[0970] Not bonded to each other,

[0971] One or more of the groups consisting of two or more adjacent ones of R3, R4 and Rb

[0972] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0973] bonded to each other to form a substituted or unsubstituted fused ring, or

[0974] Not bonded to each other,

[0975] At least one hydrogen atom in a monocyclic ring or condensed ring formed by two or more adjacent groups of R3, R4 and Rb being bonded to each other is removed from

[0976] An alkyl group having 1 to 50 carbon atoms,

[0977] An aryl group having 6 to 50 ring carbon atoms,

[0978] a heterocyclic group having 5 to 50 ring atoms,

[0979] -O-(R 920 ) represented by, and

[0980] -N(R 921 )(R 922 ) is substituted or unsubstituted with at least one substituent selected from the group consisting of the groups represented by

[0981] At least one hydrogen in the substituent is substituted with an aryl group having 6 to 50 ring carbon atoms or an alkyl group having 1 to 50 ring carbon atoms, or is unsubstituted,

[0982] R1 to R2 that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring 11 and R 12 ~R 13 and R Q Independently,

[0983] Hydrogen atoms,

[0984] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0985] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0986] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0987] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0988] -Si(R 911 )(R 912 )(R 913) represents a group,

[0989] -O-(R 914 ) represents a group,

[0990] -S-(R 915 ) represents a group,

[0991] -N(R 916 )(R 917 ) represents a group,

[0992] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0993] -C(=O)R 918 The groups represented

[0994] -COOR 919 The groups represented

[0995] Halogen atoms,

[0996] Cyano,

[0997] Nitro,

[0998] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0999] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1000] Rb which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring is

[1001] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1002] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1003] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1004] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1005] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1006] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1007] R 911 ~R 922 Independently,

[1008] Hydrogen atoms,

[1009] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1010] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1011] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1012] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1013] In the presence of multiple R 911 In the case of multiple R 911 Same or different from each other,

[1014] In the presence of multiple R 912 In the case of multiple R 912 Same or different from each other,

[1015] In the presence of multiple R 913 In the case of multiple R 913 Same or different from each other,

[1016] In the presence of multiple R 914 In the case of multiple R 914 Same or different from each other,

[1017] In the presence of multiple R 915 In the case of multiple R 915 Same or different from each other,

[1018] In the presence of multiple R 916 In the case of multiple R 916 Same or different from each other,

[1019] In the presence of multiple R 917 In the case of multiple R 917 Same or different from each other,

[1020] In the presence of multiple R 918 In the case of multiple R 918 Same or different from each other,

[1021] In the presence of multiple R 919 In the case of multiple R 919 Same or different from each other,

[1022] In the presence of multiple R 920 In the case of multiple R 920 Same or different from each other,

[1023] In the presence of multiple R 921 In the case of multiple R 921 Same or different from each other,

[1024] In the presence of multiple R 922In the case of multiple R 922 The same or different from each other.)

[1025] It is also preferred that the compound represented by the general formula (D11) is represented by the following general formula (D13).

[1026] [Chemistry 78]

[1027]

[1028] (In the general formula (D13),

[1029] R1~R3、R5~R 13 and R Q R1 to R3, R5 to R6 in the general formula (D11) are independently 13 and R Q Synonymous,

[1030] By R A1 ~R A4 One or more of the groups of two or more adjacent

[1031] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1032] bonded to each other to form a substituted or unsubstituted fused ring, or

[1033] Not bonded to each other,

[1034] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring A1 ~R A4 Independently,

[1035] Hydrogen atoms,

[1036] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1037] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1038] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1039] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1040] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1041] -Si(R 931 )(R 932 )(R 933 ) represents a group,

[1042] -O-(R 934 ) represents a group,

[1043] -S-(R 935 ) represents a group,

[1044] -N(R 936 )(R 937 ) represents a group,

[1045] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1046] -C(=O)R 938 The groups represented

[1047] -COOR 939 The groups represented

[1048] Halogen atoms,

[1049] Cyano,

[1050] Nitro,

[1051] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1052] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1053] R 931 ~R 939 Independently,

[1054] Hydrogen atoms,

[1055] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1056] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1057] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1058] In the presence of multiple R 931 In the case of multiple R 931 Same or different from each other,

[1059] In the presence of multiple R 932 In the case of multiple R 932 Same or different from each other,

[1060] In the presence of multiple R 933 In the case of multiple R 933 Same or different from each other,

[1061] In the presence of multiple R 934 In the case of multiple R 934 Same or different from each other,

[1062] In the presence of multiple R 935 In the case of multiple R 935 Same or different from each other,

[1063] In the presence of multiple R 936 In the case of multiple R 936 Same or different from each other,

[1064] In the presence of multiple R 937 In the case of multiple R 937 Same or different from each other,

[1065] In the presence of multiple R 938 In the case of multiple R 938 Same or different from each other,

[1066] In the presence of multiple R 939 In the case of multiple R 939 The same or different from each other.)

[1067] It is also preferred that the compound represented by the general formula (D11) is represented by the following general formula (D13A).

[1068] [Chemistry 79]

[1069]

[1070] (In the general formula (D13A), R1, R3, R5 to R 13 , R Q and R A1 ~R A4 R1, R3, R5 to R 13 , R Q and R A1 ~R A4 Synonymous,

[1071] By R A5 ~R A9 One or more of the groups of two or more adjacent

[1072] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1073] bonded to each other to form a substituted or unsubstituted fused ring, or

[1074] Not bonded to each other,

[1075] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring A5 ~R A9are independently connected to the R in the general formula (D13) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring A1 ~R A4 Synonymous.)

[1076] In the general formulae (D13) and (D13A), for example, the group consisting of R5 and R6 may bond to each other to form a substituted or unsubstituted monocyclic ring, may bond to each other to form a substituted or unsubstituted condensed ring, or may not bond to each other.

[1077] Among the compounds represented by the general formula (D11), R1 to R 13 and R Q Independently,

[1078] Hydrogen atoms,

[1079] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1080] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1081] A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[1082] Among the compounds represented by the general formula (D11), R1 to R 13 and R Q Independently,

[1083] Hydrogen atoms,

[1084] a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

[1085] a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1086] A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[1087] In the compounds represented by the general formula (D13) and (D13A), R1 to R3, R5 to R 13 , R Q and R A1 ~R A9 Independently,

[1088] Hydrogen atoms,

[1089] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1090] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1091] A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[1092] In the compounds represented by the general formula (D13) and (D13A), R1 to R3, R5 to R 13 , R Q and R A1 ~R A9 Independently,

[1093] Hydrogen atoms,

[1094] a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

[1095] a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1096] A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[1097] It is also preferred that the compound represented by the general formula (D11) is represented by the following general formula (D14).

[1098] [Chemistry 80]

[1099]

[1100] (In the compound represented by the general formula (D14), R2, R6, R 13 , R Q and R A2 Independently,

[1101] Hydrogen atoms,

[1102] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[1103] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or

[1104] A substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[1105] In the general formula (D14), preferably R 13 and R Q Independently,

[1106] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[1107] Substituted or unsubstituted phenyl,

[1108] Substituted or unsubstituted naphthyl, or

[1109] A substituted or unsubstituted dibenzofuranyl group.

[1110] Preferably, in the compound represented by the general formula (D14), R6 and R A2Each independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[1111] (Compound represented by general formula (16))

[1112] In this embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (16). It is also preferred that the compound represented by the general formula (2A) is a compound represented by the following general formula (16).

[1113] [Chemistry 81]

[1114]

[1115] (In the compound represented by the general formula (16),

[1116] By R 161 ~R 177 One or more of the groups of two or more adjacent

[1117] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1118] bonded to each other to form a substituted or unsubstituted fused ring, or

[1119] Not bonded to each other,

[1120] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 161 ~R 177 Independently,

[1121] Hydrogen atoms,

[1122] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1123] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1124] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1125] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1126] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1127] -Si(R 961 )(R 962 )(R 963 ) represents a group,

[1128] -O-(R 964 ) represents a group,

[1129] -S-(R965 ) represents a group,

[1130] -N(R 966 )(R 967 ) represents a group,

[1131] -C(=O)R 968 The groups represented

[1132] -COOR 969 The groups represented

[1133] Halogen atoms,

[1134] Cyano,

[1135] Nitro,

[1136] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1137] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1138] R 961 ~R 969 Independently,

[1139] Hydrogen atoms,

[1140] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1141] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1142] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1143] In the presence of multiple R 961 In the case of multiple R 961 Same or different from each other,

[1144] In the presence of multiple R 962 In the case of multiple R 962 Same or different from each other,

[1145] In the presence of multiple R 963 In the case of multiple R 963 Same or different from each other,

[1146] In the presence of multiple R 964 In the case of multiple R 964 Same or different from each other,

[1147] In the presence of multiple R 965 In the case of multiple R 965 Same or different from each other,

[1148] In the presence of multiple R 966 In the case of multiple R 966 Same or different from each other,

[1149] In the presence of multiple R 967 In the case of multiple R 967 Same or different from each other,

[1150] In the presence of multiple R 968 In the case of multiple R 968 Same or different from each other,

[1151] In the presence of multiple R 969 In the case of multiple R 969 The same or different from each other.)

[1152] Among the compounds represented by the general formula (16), R 161 ~R 177 Independently,

[1153] Hydrogen atoms,

[1154] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1155] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[1156] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1157] Among the compounds represented by the general formula (16), R 168 ~R 170 At least one of

[1158] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1159] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1160] Among the compounds represented by the general formula (16), R 161 ~R 177 Independently,

[1161] Hydrogen atoms, or

[1162] A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

[1163] Among the compounds represented by the general formula (16), R 161 ~R 177 A hydrogen atom.

[1164] Among the compounds represented by the general formula (16), it is also preferred that R 161 ~R 177 At least one of the two or more adjacent groups in the formula (16A) is bonded to each other to form a ring represented by the following general formula (16A).

[1165] [Chemistry 82]

[1166]

[1167] (The dotted line in the general formula (16A) indicates the junction site,

[1168] R X1 ~R X4 Independently,

[1169] Hydrogen atoms,

[1170] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1171] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1172] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1173] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1174] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1175] -Si(R 961 )(R 962 )(R 963 ) represents a group,

[1176] -O-(R 964 ) represents a group,

[1177] -S-(R 965 ) represents a group,

[1178] -N(R 966 )(R 967 ) represents a group,

[1179] -C(=O)R 968 The groups represented

[1180] -COOR 969 The groups represented

[1181] Halogen atoms,

[1182] Cyano,

[1183] Nitro,

[1184] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1185] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1186] In the presence of multiple R X1 In the case of multiple R X1 Same or different from each other,

[1187] In the presence of multiple R X2 In the case of multiple R X2 Same or different from each other,

[1188] In the presence of multiple R X3 In the case of multiple R X3 Same or different from each other,

[1189] In the presence of multiple R X4 In the case of multiple R X4 The same as or different from each other.

[1190] In the general formula (16),

[1191] It is also preferred that R 161 and R 162 The group composed of

[1192] By R 165 and R 166 The group composed of

[1193] By R 172 and R 173 The groups formed, and

[1194] By R 176 and R 177 At least one of the constituting groups is bonded to each other to form a ring represented by the general formula (16A).

[1195] In the general formula (16), preferably R 161 and R 162 The group composed of R 176 and R 177 The constituted groups do not simultaneously form a ring represented by the general formula (16A).

[1196] In the general formula (16), it is also preferred that R 165 and R 166 The groups formed are bonded to each other to form a ring represented by the general formula (16A), and R 172 and R 173 The constituent groups are bonded to each other to form a ring represented by the general formula (16A). In this case, the compound M1 is represented by the following general formula (161).

[1197] It is also preferred that the compound represented by the general formula (16) is a compound represented by the following general formula (161).

[1198] [Chemistry 83]

[1199]

[1200] (In the general formula (161), R 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R X1 ~R X4 are independently connected to R in the general formula (16) 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R in the general formula (16A) X1 ~R X4 Synonymous.)

[1201] It is also preferred that the compound represented by the general formula (16) is a compound represented by the following general formula (162).

[1202] [Chemistry 84]

[1203]

[1204] (In the general formula (162), R 161 ~R 163 , R 168 ~R 170 and R 175 ~R 177 are independently connected to R in the general formula (16) 161 ~R 163 , R 168 ~R 170 and R 175 ~R 177 Synonymous.)

[1205] It is also preferred that the compound represented by the general formula (16) is a compound represented by the following general formula (163).

[1206] [Chemistry 85]

[1207]

[1208] (In the general formula (163), R 162 , R169 and R 176 are independently connected to R in the general formula (16) 162 , R 169 and R 176 Synonymous.)

[1209] It is also preferred that, in compound M1, all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[1210] ·Method for producing compound M1

[1211] Compound M1 can be produced by a known method.

[1212] Specific examples of the compound M1 according to the present embodiment are shown below, but the present invention is not limited to these specific examples of the compound.

[1213] In addition, the coordination bonds between the boron atom and the nitrogen atom in the pyrromethene skeleton are indicated by various methods such as solid lines, dotted lines, arrows, or abbreviations. In this specification, they are indicated by solid lines, dotted lines, or omitted.

[1214] [Chemistry 86]

[1215]

[1216] [Chemistry 87]

[1217]

[1218] [Chemistry 88]

[1219]

[1220] [Chemistry 89]

[1221]

[1222] [Chemistry 90]

[1223]

[1224] [Chemistry 91]

[1225]

[1226] [Chemistry 92]

[1227]

[1228] [Chemistry 93]

[1229]

[1230] [Chemistry 94]

[1231]

[1232] [Chemistry 95]

[1233]

[1234] [Chemistry 96]

[1235]

[1236] [Chemistry 97]

[1237]

[1238] [Chemistry 98]

[1239]

[1240] [Chemistry 99]

[1241]

[1242] [Chemical 100]

[1243]

[1244] [Chemistry 101]

[1245]

[1246] [Chemistry 102]

[1247]

[1248] [Chemistry 103]

[1249]

[1250] [Chemistry 104]

[1251]

[1252] [Chemistry 105]

[1253]

[1254] <Relationship among Compound M3, Compound M2, and Compound M1 in the Emitting Layer>

[1255] In the organic EL device of this embodiment, it is preferred that the singlet energy S1(M1) of the compound M1 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Formula 2).

[1256] S1(M2)>S1(M1)(number 2)

[1257] Furthermore, it is preferred that the singlet energy S1(M3) of the compound M3 is greater than the singlet energy S1(M1) of the compound M1.

[1258] It is preferred that the singlet energy S1(M3) of the compound M3, the singlet energy S1(M2) of the compound M2, and the singlet energy S1(M1) of the compound M1 satisfy the relationship of the following mathematical formula (Formula 2A).

[1259] S1(M3)>S1(M2)>S1(M1)…(Number 2A)

[1260] When the organic EL device of this embodiment is made to emit light, it is preferred that the fluorescent compound M1 mainly emits light in the light-emitting layer.

[1261] The organic EL element of this embodiment preferably emits red light or green light.

[1262] ·Content ratio of the compound in the light-emitting layer

[1263] The contents of the compound M3, the compound M2, and the compound M1 contained in the light-emitting layer are preferably within the following ranges, for example.

[1264] The content of the compound M3 is preferably 10% by mass or more and 80% by mass or less.

[1265] The content of the compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[1266] The content of the compound M1 is preferably 0.01 mass % to 10 mass %, more preferably 0.01 mass % to 5 mass %, and even more preferably 0.01 mass % to 1 mass %.

[1267] The upper limit of the total content of the compound M3, the compound M2, and the compound M1 in the light-emitting layer is 100 mass %. In addition, the light-emitting layer of this embodiment may contain materials other than the compound M3, the compound M2, and the compound M1.

[1268] The light-emitting layer may contain only one compound M3 or two or more compounds M3. The light-emitting layer may contain only one compound M2 or two or more compounds M2. The light-emitting layer may contain only one compound M1 or two or more compounds M1.

[1269] Figure 5 : is a diagram showing an example of the relationship between the energy levels of compound M3, compound M2, and compound M1 in the light-emitting layer. Figure 5In the formula, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1, and T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. Figure 5 The dashed arrow from S1(M2) to S1(M1) in represents the Förster-type energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1.

[1270] like Figure 5 As shown, if a compound with a smaller ΔST(M2) is used as compound M2, the lowest excited triplet state T1(M2) can reversely intersystem cross to the lowest excited singlet state S1(M2) through thermal energy. In addition, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of compound M2 to compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of compound M1 can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1271] The organic EL element of the second embodiment contains in the light-emitting layer a compound M2 having delayed fluorescence, a compound M3 having a larger singlet energy than the compound M2 (compound M3 represented by the general formula (1-1) or (1-2)), and a compound M1 having a smaller singlet energy than the compound M2 having delayed fluorescence.

[1272] According to the second embodiment, a high-performance organic EL element can be realized.

[1273] According to one aspect of the second embodiment, an organic EL element that emits light with high efficiency can be realized.

[1274] According to one aspect of the second embodiment, an organic EL element that emits light with a long lifetime can be realized.

[1275] The organic EL element of the second embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1276] [Third embodiment]

[1277] [Electronic equipment]

[1278] The electronic device of this embodiment is equipped with any one of the organic EL elements in the above-mentioned embodiments. As the electronic device, for example, a display device and a light-emitting device can be cited. As the display device, for example, a display component (such as an organic EL panel module, etc.), a television, a mobile phone, a tablet computer and a personal computer can be cited. As the light-emitting device, for example, lighting and vehicle lamps can be cited.

[1279] [Fourth embodiment]

[1280] [Compound]

[1281] The compound of the fourth embodiment is a compound represented by any one of the following general formulae (100-1) to (100-4).

[1282] The compounds represented by the following general formulae (100-1) to (100-3) in the compounds of the fourth embodiment are one embodiment of the compounds represented by the general formula (1-1) described in the first embodiment, and are synonymous with the compounds represented by the general formulae (100-1) to (100-3) described in the first embodiment.

[1283] The compound represented by the following general formula (100-4) among the compounds of the fourth embodiment is one embodiment of the compound represented by the general formula (1-2) described in the first embodiment, and is different from the compounds represented by the general formulas (100-4A) to (100-4D) described in the first embodiment (wherein R 100 is not synonymous with the group represented by -N(Rz)2).

[1284] [Chemistry 106]

[1285]

[1286] [Chemistry 107]

[1287]

[1288] [Chemistry 108]

[1289]

[1290] [Chemistry 109]

[1291]

[1292] (In the general formulas (100-1) to (100-3), A, L1, L2, Y1, R 21 ~R 28 and R 100 A, L1, L2, Y1, R in the general formula (1-1) are independently 21 ~R 28 and R100 Synonymous.)

[1293] (In the general formula (100-4), A, L1, L2, Y1, R 21 ~R 28 and R 100 A, L1, L2, Y1, R in the general formula (1-2) are independently 21 ~R 28 and R 100 The same meaning, wherein R in the general formula (100-4) 100 It is not a group represented by -N(Rz)2. In the general formula (100-4), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded.)

[1294] As described below, L1, L2, A, X1, Y1, R in the above-mentioned "compound M3 of one embodiment" 21 ~R 28 , R 11 ~R 20 and R 100 The conditions of and the like can also be applied to the compound of the fourth embodiment.

[1295] The compound of the fourth embodiment is preferably a compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3).

[1296] In one aspect of the compound of the fourth embodiment, L1 and L2 are each independently a single bond or a substituted or unsubstituted phenylene group.

[1297] In one aspect of the compound of the fourth embodiment, L1 and L2 are single bonds.

[1298] In one aspect of the compound of the fourth embodiment, A is a group represented by the general formula (11F).

[1299] In one aspect of the compound of the fourth embodiment, A is a group represented by the general formula (11D).

[1300] In one aspect of the compound of the fourth embodiment, X1 is a sulfur atom.

[1301] In one aspect of the compound of the fourth embodiment, X1 is an oxygen atom.

[1302] In one aspect of the compound of the fourth embodiment, Y1 is an oxygen atom.

[1303] In one embodiment of the compound of the fourth embodiment, X1 is a sulfur atom and Y1 is an oxygen atom. In one embodiment of the compound of the fourth embodiment, X1 and Y1 are oxygen atoms.

[1304] In one embodiment of the compound of the fourth embodiment, R 21 ~R 28 A group consisting of two or more adjacent ones in is not bonded to each other.

[1305] In one embodiment of the compound of the fourth embodiment, R 21 ~R 28 Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[1306] In one embodiment of the compound of the fourth embodiment, R 21 ~R 28 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzofuranyl group.

[1307] In one embodiment of the compound of the fourth embodiment, R 21 ~R 28 A hydrogen atom.

[1308] In one embodiment of the compound of the fourth embodiment, R 21 ~R 28 At least one of them is a deuterium atom.

[1309] In one embodiment of the compound of the fourth embodiment, R 11 ~R 20 A group consisting of two or more adjacent ones in is not bonded to each other.

[1310] In one embodiment of the compound of the fourth embodiment, R 11 ~R 20 Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[1311] In one embodiment of the compound of the fourth embodiment, R 11 ~R 20 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted carbazolyl group.

[1312] In one embodiment of the compound of the fourth embodiment, R 11 ~R 20 A hydrogen atom.

[1313] In one embodiment of the compound of the fourth embodiment, R 11 ~R 20 At least one of them is a deuterium atom.

[1314] In one embodiment of the compound of the fourth embodiment, R 100 Each independently represents a hydrogen atom, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (preferably a substituted or unsubstituted phenyl group).

[1315] In one embodiment of the compound of the fourth embodiment, R 100 Each independently represents a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a trimethylsilyl group.

[1316] In one embodiment of the compound of the fourth embodiment, R 100 A hydrogen atom.

[1317] In one embodiment of the compound of the fourth embodiment, a plurality of R 100 At least one of them is a deuterium atom.

[1318] According to the fourth embodiment, a high-performance organic EL element can be realized.

[1319] According to one aspect of the fourth embodiment, an organic EL element that emits light with high efficiency can be realized. According to one aspect of the fourth embodiment, an organic EL element that emits light with a long life can be realized. The compound of the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1320] [Organic EL element]

[1321] An organic EL device as one mode of the fourth embodiment is an organic EL device in which the compound of the fourth embodiment (a compound represented by any one of the general formulae (100-1) to (100-4)) is contained in any one of the organic layers disposed between the anode and the cathode.

[1322] An organic EL element as one scheme of the fourth embodiment is an organic EL element in which the compound represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3) is contained in any layer of the organic layer arranged between the anode and the cathode.

[1323] The compound of the fourth embodiment is a compound capable of realizing a high-performance organic EL element. Therefore, the organic EL element as one scheme of the fourth embodiment is a high-performance organic EL element. The organic EL element as one scheme of the fourth embodiment emits light with high efficiency. The organic EL element as one scheme of the fourth embodiment emits light with a long life.

[1324] Specific examples of the compound of the fourth embodiment include the same compounds as those exemplified as the compound M3 in the first embodiment. However, the present invention is not limited to these specific examples of the compound.

[1325] [Fifth embodiment]

[1326] [Materials for organic EL devices]

[1327] The organic EL device material according to the fifth embodiment contains the compound according to the fourth embodiment.

[1328] According to the material for an organic EL device of the fifth embodiment, a high-performance organic EL device and electronic equipment can be realized.

[1329] In addition, the organic EL device material of the sixth embodiment may further contain other compounds. When the organic EL device material of the sixth embodiment further contains other compounds, the other compounds may be solid or liquid.

[1330] [Variations of Embodiments]

[1331] In addition, the present invention is not limited to the above-mentioned embodiment, and changes, improvements, etc. within the scope that can achieve the purpose of the present invention are included in the present invention.

[1332] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be stacked. In the case where the organic EL element has multiple light-emitting layers, at least one light-emitting layer satisfies the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission caused by electron migration directly from a triplet excited state to a ground state.

[1333] When the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem organic EL element in which a plurality of light-emitting units are stacked with an intermediate layer interposed therebetween may be used.

[1334] In addition, 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 to block at least any one of holes, electrons, and excitons.

[1335] For example, when a blocking layer is disposed in contact with 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) on the cathode side of the blocking layer. When the organic EL element includes an electron transport layer, the blocking layer is preferably included between the light-emitting layer and the electron transport layer.

[1336] In addition, when a blocking layer is disposed in contact with the anode side of the light-emitting layer, the blocking layer transports holes and prevents electrons from reaching the layer on the anode side of the blocking layer (e.g., a hole transport layer). When the organic EL element includes a hole transport layer, it is preferred that the blocking layer is included between the light-emitting layer and the hole transport layer.

[1337] In addition, a blocking layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. A layer (such as an electron transport layer and a hole transport layer) that prevents excitons generated in the light-emitting layer from moving to the electrode side of the blocking layer.

[1338] It is preferred that the light-emitting layer is in contact with the blocking layer.

[1339] In addition, the specific structure and shape in the implementation of the present invention may adopt other structures and the like within the scope that can achieve the purpose of the present invention.

[1340] Example

[1341] The present invention is further described in detail with reference to the following examples, but the present invention is not limited to these examples.

[1342] <Compound>

[1343] The compound M3 represented by the general formula (1-1) used for the production of the organic EL device of the example is shown below.

[1344] [Chemistry 110]

[1345]

[1346] The compounds used for producing the organic EL device of Comparative Example are shown below.

[1347] [Chemistry 111]

[1348]

[1349] Other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[1350] [Chemistry 112]

[1351]

[1352] [Chemistry 113]

[1353]

[1354] [Chemistry 114]

[1355]

[1356] [Chemistry 115]

[1357]

[1358] [Manufacturing of organic EL elements]

[1359] (Example 1)

[1360] A 25 mm×75 mm×1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Gioma Technology Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 1 minute. The ITO film thickness was 130 nm.

[1361] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device, and compound HT-1 and compound HA were co-evaporated to form a hole injection layer with a thickness of 10 nm in a manner that the transparent electrode line was covered on the surface of the side where the transparent electrode lines were formed. The concentration of compound HT-1 in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[1362] Next, compound HT-1 was deposited on the hole injection layer to form a hole transport layer with a thickness of 90 nm.

[1363] Next, compound HT-2 was vapor-deposited on the hole transport layer to form an electron blocking layer with a thickness of 30 nm.

[1364] Next, on the electron blocking layer, a fluorescent compound GD-1 as compound M1, a delayed fluorescent compound TADF-1 as compound M2, and a compound M3-1 as compound M3 were co-evaporated to form a light-emitting layer with a film thickness of 40 nm. The concentration of compound GD-1 in the light-emitting layer was set to 0.6% by mass, the concentration of compound TADF-1 was set to 25% by mass, and the concentration of compound M3-1 was set to 74.4% by mass.

[1365] Next, compound ET-1 was vapor-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 5 nm.

[1366] Next, compound ET-2 and compound Liq were co-evaporated on the hole blocking layer to form an electron transport layer with a thickness of 35 nm. The concentration of compound ET-2 in the electron transport layer was set to 50% by mass, and the concentration of compound Liq was set to 50% by mass. In addition, Liq is the abbreviation of (8-quinolinolato)lithium.

[1367] Next, ytterbium (Yb) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) with a film thickness of 1 nm.

[1368] Then, metal aluminum (Al) was vapor-deposited on the electron injecting electrode to form a metal Al cathode with a film thickness of 80 nm.

[1369] The device configuration of the organic EL device of Example 1 is schematically shown as follows.

[1370] ITO (130) / HT-1: HA (10, 97%: 3%) / HT-1 (90) / HT-2 (30) / M3-1: TADF-1: GD-1 (40, 74.4%: 25%: 0.6%) / ET-1 (5) / ET-2: Liq (35, 50%: 50%) / Yb (1) / Al (80)

[1371] In addition, the numbers in parentheses indicate the film thickness (unit: nm).

[1372] In the same bracket, the number expressed as a percentage (97%:3%) shows the ratio (mass %) of compound HT-1 and compound HA in the hole injection layer, the number expressed as a percentage (74.4%:25%:0.6%) shows the ratio (mass %) of compound M3, compound M2 and compound M1 in the light-emitting layer, and the number expressed as a percentage (50%:50%) shows the ratio (mass %) of compound ET-2 and compound Liq in the electron transport layer.

[1373] [Examples 2-3]

[1374] Organic EL devices of Examples 2 and 3 were prepared in the same manner as in Example 1 except that the compound M3-1 used in Example 1 was changed to the compounds described in Table 1, respectively.

[1375] [Comparative Example 1]

[1376] An organic EL device of Comparative Example 1 was prepared in the same manner as in Example 1 except that the compound M3-1 used in Example 1 was changed to a compound described in Table 1.

[1377] [Example 4]

[1378] An organic EL device of Example 4 was prepared in the same manner as in Example 1 except that the concentration of the compound TADF-1 in the light-emitting layer of Example 1 was changed to the concentration shown in Table 1 and the concentration of the compound M3-1 was changed to 69.4 mass % (wt %).

[1379] [Examples 5-6]

[1380] Organic EL devices of Examples 5 and 6 were prepared in the same manner as in Example 4 except that the compound M3-1 used in Example 4 was changed to the compounds described in Table 1, respectively.

[1381] [Comparative Example 2]

[1382] An organic EL device of Comparative Example 2 was prepared in the same manner as in Example 4 except that the compound M3-1 used in Example 4 was changed to a compound described in Table 1.

[1383] [Evaluation of organic EL elements]

[1384] The following evaluations were performed on the produced organic EL device. The measurement results are shown in Table 1.

[1385] (External quantum efficiency EQE)

[1386] The device was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.) by applying a voltage to the device so that the current density reached 10 mA / cm 2 The spectral emission brightness spectrum at the time of . Based on the obtained spectral emission brightness spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian emission was performed. Table 1 shows "EQE (relative value)" (unit: %).

[1387] The "EQE (relative value)" of Examples 1 to 3 was calculated based on the measured value of EQE of each example and the following mathematical formula (numeral 1X).

[1388] The "EQE (relative value)" of Examples 4 to 6 was calculated based on the measured value of EQE of each example and the following mathematical formula (numeral 2X).

[1389] EQE (relative value) = (EQE of each example / EQE of Comparative Example 1) × 100 ... (number 1 ×)

[1390] EQE (relative value) = (EQE of each example / EQE of Comparative Example 2) × 100 ... (number 2X)

[1391] (Maximum peak wavelength λp)

[1392] The device was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.) by applying a voltage to the device so that the current density reached 10 mA / cm 2 The maximum peak wavelength λp (unit: nm) is determined from the obtained spectral emission brightness spectrum.

[1393] (Lifespan LT95)

[1394] A voltage was applied to the organic EL element so that the current density reached 50 mA / cm 2 The time until the brightness reaches 95% of the initial brightness (LT95 (unit: hr)) was measured as the life. The brightness was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.). "LT95 (relative value)" (unit: %) is shown in Table 1.

[1395] The "LT95 (relative value)" of Examples 1 to 3 was calculated based on the measured value of LT95 of each example and the following mathematical formula (Equation 1Y).

[1396] The "LT95 (relative value)" of Examples 4 to 6 was calculated based on the measured value of LT95 of each example and the following mathematical formula (Equation 2Y).

[1397] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 ... (number 1Y)

[1398] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 2) × 100 ... (number 2Y)

[1399] (CIE1931 chromaticity)

[1400] The current density of the organic EL element was measured by applying a voltage to the element to reach 10 mA / cm using a spectrophotometer CS-2000 (manufactured by Konica Minolta). 2 CIE1931 chromaticity coordinates (x, y) at .

[1401] [Table 1]

[1402]

[1403] The organic EL elements of Examples 1 to 3 containing the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light-emitting layer emit light with higher efficiency than the organic EL element of Comparative Example 1 in which the compound M3 is replaced by the compound Ref-1.

[1404] In addition, the organic EL elements of Examples 4 to 6, which contain the compound M3 represented by the general formula (1-1), the delayed fluorescent compound M2, and the fluorescent compound M1 in the light-emitting layer, emit light with high efficiency and have a longer life compared to the organic EL element of Comparative Example 2 in which the compound M3 is replaced by the compound Ref-1.

[1405] <Evaluation of Compounds>

[1406] The physical property values ​​of the compounds listed in Table 1 were measured by the following methods.

[1407] Delayed fluorescence of compound TADF-1

[1408] Delayed fluorescence is achieved by utilizing Figure 2 The transition PL was measured by the device shown in the figure. The compound TADF-1 was dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength was prepared to eliminate the influence of self-absorption. In addition, in order to prevent extinction caused by oxygen, the sample solution was frozen and exhausted and then sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[1409] The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of the ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensity of the two spectra according to the formula (1) in Morris et al., J. Phys. Chem., 80 (1976) 969.

[1410] After being excited by pulsed light (light irradiated by pulsed laser) of a wavelength absorbed by the compound TADF-1, there is prompt luminescence (immediate luminescence) observed immediately from the excited state and delay luminescence (delayed luminescence) observed after the excitation. The delayed fluorescence luminescence in this embodiment means that the amount of delay luminescence (delayed luminescence) is 5% or more relative to the amount of prompt luminescence (immediate luminescence). Specifically, it means that the amount of prompt luminescence (immediate luminescence) is set to X P , set the amount of Delay light emission to X D When X D / X P The value of is 0.05 or more.

[1411] The amount of prompt luminescence and delay luminescence and the ratio of the two can be calculated by the same method as described in "Nature" 492, 234-238, 2012 (reference 1). In addition, the device used for calculating the amount of prompt luminescence and delay luminescence is not limited to the device described in reference 1 or Figure 2 The device described in .

[1412] In the case of the compound TADF-1, it was confirmed that the amount of Delay luminescence was 5% or more relative to the amount of Prompt luminescence.

[1413] Specifically, for compound TADF-1, X D / X P The value of is 0.05 or more.

[1414] Singlet energy S1

[1415] The singlet energy S1 of the compound to be measured was measured by the above-mentioned solution method.

[1416] Energy gap T at 77[K] 77K

[1417] Using the energy gap T described in the above “Relationship between triplet energy and energy gap at 77 [K]” 77K The measurement method measures the T of the compound to be measured. 77K In addition, by T 77K The measurement result confirms △ST with the value of the singlet energy S1 mentioned above.

[1418] The ΔST of compound GD-1 is 0.40 eV.

[1419] The maximum peak wavelength of the compound

[1420] The maximum peak wavelength λ of the compound was measured by the following method.

[1421] A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (set as the vertical axis: luminescence intensity, the horizontal axis: wavelength). In this embodiment, the luminescence spectrum is measured by a spectrophotometer (device name: F-7000) manufactured by Hitachi. In addition, the luminescence spectrum measuring device is not limited to the device used here. In the luminescence spectrum, the peak wavelength of the luminescence spectrum with the maximum luminescence intensity is taken as the maximum peak wavelength λ.

[1422] <Synthesis of Compounds>

[1423] Compounds M3-1 to M3-3 were synthesized.

[1424] [Synthesis Example 1: Synthesis of Compound M3-1]

[1425] (1-1) Synthesis of intermediate M-1

[1426] [Chemistry 116]

[1427]

[1428] Under nitrogen atmosphere, dimethoxyethane (150 mL) and water (30 mL) were added to a mixture of 3-chlorophenylboronic acid (4.63 g, 29.6 mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (9.56 g, 29.6 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.623 g, 0.888 mmol) and sodium carbonate (4.71 g, 44.4 mmol), and the mixture was stirred at 90°C for 3 hours. After the reaction was completed, water and toluene were added to extract the organic layer, which was then washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off. The obtained reaction product was purified by silica gel chromatography to obtain intermediate M-1 (8.71 g, yield 83%). It was identified as intermediate M-1 by LC-MS (Liquid Chromatography-Mass spectrometry) analysis.

[1429] (1-2) Synthesis of Compound M3-1

[1430] [Chemistry 117]

[1431]

[1432] Under nitrogen atmosphere, xylene (30 mL) was added to a mixture of 12H-benzo[4,5]thieno[2,3-a]carbazole (1.70 g, 6.21 mmol), intermediate M-1 (2.10 g, 5.91 mmol), dibenzylideneacetone palladium (0.68 g, 0.118 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (Xphos) (0.113 g, 0.236 mmol) and sodium tert-butoxide (0.852 g, 8.87 mmol), and the mixture was stirred at 140°C for 2 hours. After the reaction was completed, water and toluene were added to extract the organic layer, which was then washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off. The reaction product was purified by silica gel chromatography and recrystallized using toluene to obtain compound M3-1 (0.85 g, yield 24%). The product was identified as compound M3-1 by LC-MS analysis.

[1433] [Synthesis Example 2: Synthesis of Compound M3-2]

[1434] (2-1) Synthesis of Compound M3-2

[1435] [Chemistry 118]

[1436]

[1437] Under a nitrogen atmosphere, xylene (30 mL) was added to a mixture of 5H-benzofurano[3,2-c]carbazole (1.64 g, 6.38 mmol), intermediate M-1 (2.16 g, 6.08 mmol), dibenzylideneacetone palladium (0.699 g, 0.122 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.116 g, 0.243 mmol) and sodium tert-butoxide (0.877 g, 9.12 mmol), and the mixture was stirred at 140°C for 2 hours. After the reaction was completed, water and toluene were added to extract the organic layer, which was then washed with saturated brine. The organic layer was dried over magnesium sulfate, filtered, and the solvent was distilled off. Heptane was added to the obtained reaction product, filtered, and the filtrate was recrystallized with toluene to obtain compound M3-2 (0.92 g, yield 26%). The product was identified as compound M3-2 by LC-MS analysis.

[1438] [Synthesis Example 3: Synthesis of Compound M3-3]

[1439] (3-1) Synthesis of Compound M3-3

[1440] [Chemistry 119]

[1441]

[1442] Under nitrogen atmosphere, xylene (30 mL) was added to a mixture of 12H-benzofuran [2,3-a] carbazole (1.64 g, 6.38 mmol), intermediate M-1 (2.16 g, 6.08 mmol), dibenzylideneacetone palladium (0.699 g, 0.122 mmol), 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (0.116 g, 0.243 mmol) and sodium tert-butoxide (0.877 g, 9.12 mmol), and stirred at 140 ° C for 2 hours. After the reaction was completed, the solid was filtered, washed with methanol, and recrystallized with toluene to obtain compound M3-3 (2.45 g, yield 70%). It was identified as compound M3-3 by LC-MS analysis.

[1443] Description of Reference Numerals

[1444] 1 Organic EL elements

[1445] 2 substrate

[1446] 3 Anode

[1447] 4 Cathode

[1448] 5. Luminous layer

[1449] 6 Hole injection layer

[1450] 7 Hole Transport Layer

[1451] 8 Electron transport layer

[1452] 9 Electron injection layer.

Claims

1. An organic electroluminescent element, characterized in that: have: anode; a cathode; and a light-emitting layer, included between the anode and the cathode, The light-emitting layer comprises a compound M3 represented by the following general formula (1-1) or (1-2) and a delayed fluorescence compound M2, The compound M3 has a different structure from the compound M2. The singlet energy S1(M3) of the compound M3 and the singlet energy S1(M2) of the compound M2 satisfy the relationship of the following mathematical formula (Formula 1): S1(M3)>S1(M2)(number 1) [Chemistry 1] [Chemistry 2] In the general formulas (1-1) and (1-2), A is a group represented by any of the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F), L1 and L2 are independently, Single key, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Y1 is an oxygen atom or a sulfur atom, By R 21 ~R 28 One or more of the groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 100 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Independently, Hydrogen atoms, Halogen atoms, Cyano, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxyl, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A group represented by -N(Rz)2, Thiol group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, Substituted germanium Substituted phosphine oxide groups, Nitro, Substituted boron, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, - The two Rz in N(Rz)2 are the same or different from each other, Multiple R 100 Same or different from each other, In the general formulas (1-1) and (1-2), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded, [Chemistry 3] In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X1 is an oxygen atom or a sulfur atom, By R 11 ~R 20 One or more of the groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 11 ~R 20 R in the general formula (1-1) and (1-2) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Synonymically, * indicates bonding position.

2. The organic electroluminescent element according to claim 1, wherein The compound M3 is a compound represented by the general formula (1-1).

3. The organic electroluminescent element according to claim 1 or 2, characterized in that: L1 and L2 are single bonds.

4. The organic electroluminescent device according to any one of claims 1 to 3, wherein: A is a group represented by the above-mentioned general formula (11F).

5. The organic electroluminescent element according to any one of claims 1 to 4, characterized in that: Y1 is an oxygen atom.

6. The organic electroluminescent element according to any one of claims 1 to 5, wherein: X1 is a sulfur atom.

7. The organic electroluminescent device according to any one of claims 1 to 6, wherein: R 21 ~R 28 A hydrogen atom.

8. The organic electroluminescent device according to any one of claims 1 to 7, wherein: R 11 ~R 20 A hydrogen atom.

9. The organic electroluminescent device according to any one of claims 1 to 8, wherein: R 100 A hydrogen atom.

10. The organic electroluminescent device according to any one of claims 1 to 9, wherein: The light-emitting layer does not contain a metal complex.

11. An electronic device, characterized in that: The organic electroluminescent element according to any one of claims 1 to 10 is mounted.

12. A compound, characterized in that It is represented by any one of the following general formulas (100-1) to (100-4), [Chemistry 4] [Chemistry 5] [Chemistry 6] [Chemistry 7] In the general formulas (100-1) to (100-4), A is a group represented by any of the following general formulae (11A), (11B), (11C), (11D), (11E) and (11F), L1 and L2 are independently, Single key, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, Y1 is an oxygen atom or a sulfur atom, By R 21 ~R 28 One or more of the groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 100 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Independently, Hydrogen atoms, Halogen atoms, Cyano, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxyl, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A group represented by -N(Rz)2, Thiol group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, Substituted germanium Substituted phosphine oxide groups, Nitro, Substituted boron, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, - The two Rz in N(Rz)2 are the same or different from each other, Multiple R 100 Same or different from each other, Wherein, in the general formula (100-4), R 100 is not a group represented by -N(Rz)2, In the general formula (100-4), * represents 21 ~R 24 Any one bonding position of the carbon atom of the six-membered ring to which it is bonded, [Chemistry 8] In the general formulae (11A), (11B), (11C), (11D), (11E) and (11F), X1 is an oxygen atom or a sulfur atom, By R 11 ~R 20 One or more of the groups of two or more adjacent bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 11 ~R 20 R in the general formula (100-1) to (100-4) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 21 ~R 28 Synonymically, * indicates bonding position.

13. The compound according to claim 12, characterized in that It is represented by the general formula (100-1), the general formula (100-2), or the general formula (100-3).

14. The compound according to claim 12 or 13, characterized in that L1 and L2 are single bonds.

15. The compound according to any one of claims 12 to 14, characterized in that A is a group represented by the above-mentioned general formula (11F).

16. The compound according to any one of claims 12 to 15, characterized in that Y1 is an oxygen atom.

17. The compound according to any one of claims 12 to 16, characterized in that X1 is a sulfur atom.

18. The compound according to any one of claims 12 to 17, characterized in that R 21 ~R 28 A hydrogen atom.

19. The compound according to any one of claims 12 to 18, characterized in that R 11 ~R 20 A hydrogen atom.

20. The compound according to any one of claims 12 to 19, characterized in that R 100 A hydrogen atom.

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