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

Abstract

A compound represented by the following general formula (1). In the general formula (1), CN is a cyano group, D 11 and D 12 are independently a group represented by the general formula (11), the general formula (12) or the general formula (13), wherein at least one D 11 It is a group represented by the general formula (12) or (13), wherein R is a hydrogen atom, an aromatic group, or the like.

Description

Technical Field

[0001] The present invention relates to a compound, a material for an organic electroluminescent element, an organic electroluminescent element 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] For example, 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] The TADF (Thermally Activated Delayed Fluorescence) mechanism is a mechanism that utilizes the phenomenon that reverse intersystem crossing from triplet excitons to singlet excitons occurs under the action of heat when a material with a small energy difference (ΔST) between the singlet energy level and the triplet energy level is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors, edited by Chiba Ya Ando, ​​Kodansha, published on April 1, 2012, pages 261-268".

[0006] As a compound exhibiting thermally activated delayed fluorescence (TADF property) (hereinafter also referred to as a TADF property compound), for example, a compound in which a donor site and an acceptor site are bonded in a molecule is known.

[0007] As documents related to organic EL devices and compounds used for organic EL devices, Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4 can be cited.

[0008] Prior art literature

[0009] Patent Literature

[0010] Patent Document 1: International Publication No. 2014 / 208698

[0011] Patent Document 2: International Publication No. 2019 / 195104

[0012] Patent Document 3: International Publication No. 2019 / 190235

[0013] Patent Document 4: International Publication No. 2021 / 066059 Summary of the invention

[0014] Technical problem to be solved by the invention

[0015] In order to improve the performance of electronic devices such as displays, it is expected that the performance of organic EL elements will be further improved. Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. Examples of factors for improving the luminous efficiency of organic EL elements include the use of compounds with high photoluminescence quantum yield (PLQY). In addition, it is expected that the lifespan of organic EL elements will be prolonged.

[0016] The object of the present invention is to provide a compound with high PLQY. In addition, the object of the present invention is to provide a material for an organic electroluminescent element containing a compound with high PLQY, an organic electroluminescent element, and an electronic device equipped with the organic electroluminescent element. In addition, the object of the present invention is to provide a compound capable of achieving at least one of high performance, especially high efficiency and long life of an organic electroluminescent element. In addition, the object of the present invention is to provide an organic electroluminescent element capable of achieving at least one of high performance, especially high efficiency and long life, and an electronic device equipped with the organic electroluminescent element.

[0017] Solutions for solving the above technical problems

[0018] According to one embodiment of the present invention, there is provided a compound represented by the following general formula (1).

[0019] [Chemistry 1]

[0020]

[0021] (In the general formula (1),

[0022] CN is cyano,

[0023] D 11 and D 12 are independently a group represented by the following general formula (11), general formula (12) or general formula (13), wherein at least one D 11 is a group represented by the following general formula (12) or general formula (13),

[0024] R are independently,

[0025] Hydrogen atoms,

[0026] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0027] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0028] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0029] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0030] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0031] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0032] -O-(R 904 ) represents a group,

[0033] -S-(R 905 ) represents a group,

[0034] -N(R 906 )(R 907 ) represents a group,

[0035] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0036] -C(=O)R 908 The groups represented

[0037] -COOR 909 The groups represented

[0038] Cyano,

[0039] Nitro,

[0040] -P(=O)(R 931 )(R 932 ) represents a group,

[0041] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0042] -B(R 936 )(R 937 ) represents a group,

[0043] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0044] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0045] wherein at least one R is a substituent, and at least one R as a substituent is bonded to the benzene ring in the general formula via a carbon-carbon bond,

[0046] k is 1 or 2,

[0047] m is 0, 1 or 2,

[0048] n is 1, 2 or 3,

[0049] k+m+n is 4,

[0050] When k is 2, multiple D 11 Same or different from each other,

[0051] When m is 2, multiple D 12 Same or different from each other,

[0052] When n is 2 or 3, multiple Rs are the same or different from each other.)

[0053] [Chemistry 2]

[0054]

[0055] [Chemistry 3]

[0056]

[0057] [Chemistry 4]

[0058]

[0059] (From the general formula (12) R 11 ~R 18 One or more of the groups of two or more adjacent

[0060] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0061] bonded to each other to form a substituted or unsubstituted fused ring, or

[0062] Not bonded to each other,

[0063] According to the general formula (13), R 111 ~R 118 One or more of the groups of two or more adjacent

[0064] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0065] bonded to each other to form a substituted or unsubstituted fused ring, or

[0066] Not bonded to each other,

[0067] In the general formula (11), R 1 ~R 8 , R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 11 ~R 18 , and R in the general formula (13) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 111 ~R 118 Independently,

[0068] Hydrogen atoms,

[0069] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0070] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0071] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0072] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0073] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0074] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0075] -O-(R 904 ) represents a group,

[0076] -S-(R 905 ) represents a group,

[0077] -N(R 906 )(R 907 ) represents a group,

[0078] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0079] -C(=O)R 908 The groups represented

[0080] -COOR 909 The groups represented

[0081] Halogen atoms,

[0082] Cyano,

[0083] Nitro,

[0084] -P(=O)(R 931 )(R 932 ) represents a group,

[0085] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0086] -B(R 936 )(R 937 ) represents a group,

[0087] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0088] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0089] In the general formula (12) and the general formula (13),

[0090] Ring A, Ring B and Ring C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formula (14) and general formula (15),

[0091] Ring A, Ring B and Ring C are condensed with the adjacent rings at any position,

[0092] p, px and py are independently 1, 2, 3 or 4,

[0093] When p is 2, 3 or 4, the plurality of rings A are identical to or different from each other.

[0094] When px is 2, 3 or 4, the multiple rings B are the same or different from each other,

[0095] When py is 2, 3 or 4, the plurality of ring Cs are the same or different from each other,

[0096] Among them, at least 1 D 11 is a group represented by the general formula (12) or (13), and as D 11 In the general formula (12), p is 4, and the four rings A include two ring structures represented by the following general formula (14) and two ring structures represented by the following general formula (15), and as the D 11 In the general formula (13), px and py are 2, the two rings B include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and the two rings C include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15),

[0097] In the general formulae (11) to (13), * indicates the position of bonding to the benzene ring in the general formula (1).

[0098] [Chemistry 5]

[0099]

[0100] (In the general formula (14),

[0101] r is 0, 2 or 4,

[0102] By multiple R 19 The group composed

[0103] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0104] bonded to each other to form a substituted or unsubstituted fused ring, or

[0105] Not bonded to each other,

[0106] In the general formula (15), X 1 is a sulfur atom or an oxygen atom,

[0107] R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 19 For hydrogen atoms,

[0108] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0109] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0110] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0111] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0112] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0113] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0114] -O-(R 904 ) represents a group,

[0115] -S-(R 905 ) represents a group,

[0116] -N(R 906 )(R 907 ) represents a group,

[0117] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0118] -C(=O)R 908 The groups represented

[0119] -COOR 909 The groups represented

[0120] Halogen atoms,

[0121] Cyano,

[0122] Nitro,

[0123] -P(=O)(R 931 )(R 932 ) represents a group,

[0124] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0125] -B(R 936 )(R 937 ) represents a group,

[0126] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0127] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0128] Multiple R 19 Same or different from each other,

[0129] Multiple X 1 Same or different from each other,

[0130] Among them, D as a group represented by the general formula (13) 11 Satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3).

[0131] Condition (Pv1): When k is 2, X in the ring structure represented by the general formula (15) as ring B is 1 and X in the ring structure represented by the general formula (15) as ring C 1 At least one of them is an oxygen atom.

[0132] Condition (Pv2): When k is 2, 2 D 11 Different from each other.

[0133] Condition (Pv3): When n is 3, X in the ring structure represented by the general formula (15) as ring B is 1and X in the ring structure represented by the general formula (15) as ring C 1 are independently a sulfur atom or an oxygen atom. )

[0134] (In the general formula, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 Independently,

[0135] Hydrogen atoms,

[0136] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0137] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0138] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0139] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0140] In the presence of multiple R 901 In the case of multiple R 901 Same or different from each other,

[0141] In the presence of multiple R 902 In the case of multiple R 902 Same or different from each other,

[0142] In the presence of multiple R 903 In the case of multiple R 903 Same or different from each other,

[0143] In the presence of multiple R 904 In the case of multiple R 904 Same or different from each other,

[0144] In the presence of multiple R 905 In the case of multiple R 905 Same or different from each other,

[0145] In the presence of multiple R 906 In the case of multiple R 906 Same or different from each other,

[0146] In the presence of multiple R 907 In the case of multiple R 907 Same or different from each other,

[0147] In the presence of multiple R 908 In the case of multiple R 908 Same or different from each other,

[0148] In the presence of multiple R 909 In the case of multiple R 909 Same or different from each other,

[0149] In the presence of multiple R 931 In the case of multiple R 931 Same or different from each other,

[0150] In the presence of multiple R 932 In the case of multiple R 932 Same or different from each other,

[0151] In the presence of multiple R 933 In the case of multiple R 933 Same or different from each other,

[0152] In the presence of multiple R 934 In the case of multiple R 934 Same or different from each other,

[0153] In the presence of multiple R 935 In the case of multiple R 935 Same or different from each other,

[0154] In the presence of multiple R 936 In the case of multiple R 936 Same or different from each other,

[0155] In the presence of multiple R 937 In the case of multiple R 937 The same or different from each other.)

[0156] According to one aspect of the present invention, there is provided a material for an organic electroluminescent device comprising the compound according to one aspect of the present invention.

[0157] According to one embodiment of the present invention, there is provided an organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer contains a compound M2 as a compound according to one embodiment of the present invention.

[0158] 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.

[0159] According to one embodiment of the present invention, a compound with high PLQY can be provided. In addition, according to one embodiment of the present invention, a material for an organic electroluminescent element or an organic electroluminescent element containing the compound with high PLQY can be provided. In addition, according to one embodiment of the present invention, an electronic device equipped with the organic electroluminescent element can be provided. In addition, according to one embodiment of the present invention, a compound capable of achieving at least one of high performance, especially high efficiency and long life of an organic electroluminescent element can be provided. In addition, according to one embodiment of the present invention, an organic electroluminescent element capable of achieving at least one of high performance, especially high efficiency and long life, and an electronic device equipped with the organic electroluminescent element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0160] Figure 1 This is a schematic diagram of a device for measuring transition PL.

[0161] Figure 2 This is a diagram showing an example of a decay curve of the transition PL.

[0162] Figure 3 It is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0163] Figure 4 This is a diagram showing the relationship between the energy levels and energy transfer of the compound M1 and the compound M2 in the light-emitting layer of an example of the organic electroluminescent device according to the third embodiment of the present invention.

[0164] Figure 5 This is a diagram showing the relationship between the energy levels and energy transfer of the compound M1, the compound M2, and the compound M3 in the light-emitting layer of an example of the organic electroluminescent device according to the fourth embodiment of the present invention.

[0165] Figure 6 This is a diagram showing the relationship between the energy levels and energy transfer of the compound M2 and the compound M3 in the light-emitting layer of an example of the organic electroluminescent element according to the fifth embodiment of the present invention. DETAILED DESCRIPTION

[0166] [definition]

[0167] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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 ring, 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.

[0172] In this 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" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0173] In this 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" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0174] 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".

[0175] 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.

[0176] 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 by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0177] "Substituents described in this specification"

[0178] The substituents described in the present specification are described below.

[0179] 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.

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] "Substituted or unsubstituted aryl"

[0189] 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.

[0190] "Substituted aryl group" means 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" of the following specific example group G1A are replaced by a substituent, and an example of a substituted aryl group of the following specific example group G1B 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 an aryl group itself in the "substituted aryl group" of the following specific example group G1B is further replaced by a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further replaced by a substituent.

[0191] Unsubstituted aryl (specific example group G1A):

[0192] Phenyl,

[0193] p-Biphenyl,

[0194] m-Biphenyl,

[0195] o-Biphenyl,

[0196] 4-terphenyl-4-yl,

[0197] 3-Bis(triphenyl)phenyl,

[0198] 2-Bis(triphenyl)benzene,

[0199] 4-terphenyl,

[0200] 3-terphenyl,

[0201] 2-terphenyl-1,

[0202] o-Triphenyl-4-yl,

[0203] o-Triphenyl-3-yl,

[0204] o-Triphenyl-2-yl,

[0205] 1-naphthyl,

[0206] 2-naphthyl,

[0207] Anthracene,

[0208] Benzanthryl,

[0209] Fiki,

[0210] Triphenylene,

[0211] Phenyl,

[0212] Pyrene

[0213] base,

[0214] Benzo base,

[0215] Triphenylene,

[0216] Benzotriphenylene,

[0217] Tetracenyl,

[0218] Pentacenyl,

[0219] Fluorene,

[0220] 9,9'-spirobifluorenyl,

[0221] Benzofluorenyl,

[0222] Dibenzofluorenyl,

[0223] Fluoranthene group,

[0224] Benzofluoranthene,

[0225] Perylene, and

[0226] 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).

[0227] [Chemistry 6]

[0228]

[0229] [Chemistry 7]

[0230]

[0231] Substituted aryl (specific example group G1B):

[0232] o-Toluyl,

[0233] m-Toluene

[0234] p-Tolyl,

[0235] p-Xylyl,

[0236] m-Xylyl,

[0237] o-Xylyl,

[0238] p-Isopropylphenyl,

[0239] m-isopropylphenyl,

[0240] o-isopropylphenyl,

[0241] 4-tert-Butylphenyl,

[0242] m-tert-butylphenyl,

[0243] o-tert-butylphenyl,

[0244] 3,4,5-Trimethylphenyl,

[0245] 9,9-dimethylfluorenyl,

[0246] 9,9-diphenylfluorenyl,

[0247] 9,9-bis(4-methylphenyl)fluorenyl,

[0248] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0249] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0250] Cyanophenyl,

[0251] Triphenylsilylphenyl,

[0252] Trimethylsilylphenyl,

[0253] Benzene naphthyl,

[0254] Naphthylphenyl, and

[0255] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0256] "Substituted or unsubstituted heterocyclic group"

[0257] 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.

[0258] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0259] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0260] 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.

[0261] "Substituted heterocyclic group" means 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.

[0262] 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).

[0263] 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).

[0264] Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

[0265] Pyrrolyl,

[0266] Imidazole,

[0267] Pyrazolyl,

[0268] Triazole,

[0269] Tetrazolyl,

[0270] Oxazolyl,

[0271] Isoxazolyl,

[0272] Oxadiazolyl,

[0273] Thiazolyl,

[0274] Isothiazolyl,

[0275] Thiadiazole,

[0276] Pyridyl

[0277] Pyridazine

[0278] Pyrimidine,

[0279] Pyrazinyl,

[0280] Triazine,

[0281] Indolyl,

[0282] Isoindolyl,

[0283] Indolizinyl,

[0284] Quinolizinyl,

[0285] Quinoline,

[0286] Isoquinolinyl,

[0287] Cinnolyl group,

[0288] Phthalocyanine

[0289] Quinazoline,

[0290] Quinoxaline,

[0291] Benzimidazolyl,

[0292] Indazolyl,

[0293] Phenanthroline,

[0294] Phenanthridinyl,

[0295] Acridinium,

[0296] Phenazine,

[0297] Carbazolyl,

[0298] Benzocarbazolyl,

[0299] Morpholinyl,

[0300] Phenoxazine,

[0301] Phenothiazine,

[0302] Azacarbazolyl, and

[0303] Diazacarbazolyl.

[0304] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0305] Furanyl,

[0306] Oxazolyl,

[0307] Isoxazolyl,

[0308] Oxadiazolyl,

[0309] Xanthyl,

[0310] Benzofuranyl,

[0311] Isobenzofuranyl,

[0312] Dibenzofuranyl,

[0313] Naphthobenzofuranyl,

[0314] Benzoxazolyl,

[0315] Benzisoxazolyl,

[0316] Phenoxazine,

[0317] Morpholinyl,

[0318] Dinaphthofuranyl,

[0319] Azadibenzofuranyl,

[0320] Diazadibenzofuranyl,

[0321] Azanaphthobenzofuranyl, and

[0322] Phthaloquinone benzofuranyl.

[0323] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

[0324] Thienyl,

[0325] Thiazolyl,

[0326] Isothiazolyl,

[0327] Thiadiazole,

[0328] benzothienyl,

[0329] Isobenzothienyl,

[0330] dibenzothienyl,

[0331] naphthobenzothienyl,

[0332] Benzothiazolyl,

[0333] Benzisothiazolyl,

[0334] Phenothiazine,

[0335] Dinaphthothienyl,

[0336] azadibenzothienyl,

[0337] diazadibenzothienyl,

[0338] azanaphthobenzothienyl, and

[0339] Diazanaphthobenzothienyl group.

[0340] 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):

[0341] [Chemistry 8]

[0342]

[0343] [Chemistry 9]

[0344]

[0345] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A are independently an oxygen atom, a sulfur atom, NH or CH 2 Among them, X A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0346] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A At least one of them is NH or CH 2 In the case of the monovalent heterocyclic group derived from the ring structure represented by the general formula (TEMP-16) to (TEMP-33), the monovalent heterocyclic group derived from these NH or CH 2 A monovalent group obtained by removing one hydrogen atom from a

[0347] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0348] (9-phenyl)carbazolyl,

[0349] (9-biphenyl)carbazolyl,

[0350] (9-phenyl)phenylcarbazolyl,

[0351] (9-naphthyl)carbazolyl,

[0352] Diphenylcarbazole-9-yl,

[0353] Phenylcarbazol-9-yl,

[0354] Methylbenzimidazolyl,

[0355] Ethylbenzimidazolyl,

[0356] Phenyl triazine,

[0357] Biphenyl triazine,

[0358] Diphenyltriazine,

[0359] Phenylquinazolinyl, and

[0360] Biphenylquinazolinyl.

[0361] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0362] Phenyldibenzofuranyl,

[0363] Methyldibenzofuranyl,

[0364] tert-Butyldibenzofuranyl, and

[0365] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0366] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0367] Phenyldibenzothiophene,

[0368] Methyldibenzothiophene,

[0369] tert-Butyldibenzothienyl, and

[0370] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0371] 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):

[0372] 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 One of them is CH 2 In the case of , one or more hydrogen atoms are selected from the hydrogen atoms of the methylene group.

[0373] "Substituted or unsubstituted alkyl"

[0374] 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.

[0375] "Substituted alkyl" means 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" represents 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.

[0376] Unsubstituted alkyl (specific example group G3A):

[0377] methyl,

[0378] Ethyl,

[0379] n-propyl,

[0380] Isopropyl,

[0381] n-Butyl,

[0382] Isobutyl

[0383] sec-butyl, and

[0384] Tert-butyl.

[0385] Substituted alkyl (specific example group G3B):

[0386] Heptafluoropropyl (including isomers),

[0387] Pentafluoroethyl,

[0388] 2,2,2-trifluoroethyl, and

[0389] Trifluoromethyl.

[0390] "Substituted or unsubstituted alkenyl"

[0391] 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.

[0392] "Substituted alkenyl" means 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 atom of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent.

[0393] Unsubstituted alkenyl (specific example group G4A):

[0394] Vinyl,

[0395] Allyl,

[0396] 1-Butenyl,

[0397] 2-Butenyl, and

[0398] 3-Butenyl.

[0399] Substituted alkenyl (specific example group G4B):

[0400] 1,3-Butadienyl,

[0401] 1-Methylvinyl,

[0402] 1-methylallyl,

[0403] 1,1-dimethylallyl,

[0404] 2-methylallyl, and

[0405] 1,2-Dimethylallyl.

[0406] "Substituted or unsubstituted alkynyl"

[0407] 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.

[0408] "Substituted alkynyl" means 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.

[0409] Unsubstituted alkynyl (specific example group G5A):

[0410] Ethynyl.

[0411] "Substituted or unsubstituted cycloalkyl"

[0412] 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.

[0413] "Substituted cycloalkyl" means 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 substituent in the "substituted cycloalkyl" of the specific example group G6B are further replaced with a substituent.

[0414] Unsubstituted cycloalkyl (specific example group G6A):

[0415] Cyclopropyl,

[0416] Cyclobutyl,

[0417] Cyclopentyl,

[0418] Cyclohexyl,

[0419] 1-adamantyl,

[0420] 2-adamantyl,

[0421] 1-Norbornyl, and

[0422] 2-Norborneol.

[0423] Substituted cycloalkyl (specific example group G6B):

[0424] 4-Methylcyclohexyl.

[0425] · "-Si(R 901 )(R 902 )(R 903 )"

[0426] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are represented by (specific example group G7), and include:

[0427] -Si(G1)(G1)(G1),

[0428] -Si(G1)(G2)(G2),

[0429] -Si(G1)(G1)(G2),

[0430] -Si(G2)(G2)(G2),

[0431] -Si(G3)(G3)(G3), and

[0432] -Si(G6)(G6)(G6).

[0433] Here,

[0434] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0435] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0436] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0437] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0438] A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

[0439] Multiple G2 in -Si(G1)(G2)(G2) are the same as or different from each other.

[0440] A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

[0441] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0442] Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

[0443] Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0444] · "With -O-(R 904 )"

[0445] As described in this specification, -O-(R 904 ) are represented by (specific example group G8), and include:

[0446] -O(G1),

[0447] -O(G2),

[0448] -O(G3), and

[0449] -O(G6).

[0450] Here,

[0451] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0452] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0453] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0454] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0455] · "With -S-(R 905 )"

[0456] As described in this specification, -S-(R 905 ) are represented by (specific example group G9), and include:

[0457] -S(G1),

[0458] -S(G2),

[0459] -S(G3), and

[0460] -S(G6).

[0461] Here,

[0462] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0463] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0464] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0465] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0466] · "With -N(R 906 )(R 907 )"

[0467] As described in this specification, -N(R 906 )(R 907 ) are represented by (specific example group G10), and the following may be mentioned:

[0468] -N(G1)(G1),

[0469] -N(G2)(G2),

[0470] -N(G1)(G2),

[0471] -N(G3)(G3), and

[0472] -N(G6)(G6).

[0473] Here,

[0474] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0475] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0476] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0477] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0478] - A plurality of G1 in N(G1)(G1) are the same as or different from each other.

[0479] - Multiple G2 in N(G2)(G2) are the same as or different from each other.

[0480] - Multiple G3 in N(G3)(G3) are the same as or different from each other.

[0481] - Multiple G6 in N(G6)(G6) are the same as or different from each other.

[0482] "Halogen atoms"

[0483] 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.

[0484] "Substituted or unsubstituted fluoroalkyl"

[0485] The "substituted or unsubstituted fluoroalkyl group" described in the present specification means 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" means 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 an 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.

[0486] "Substituted or unsubstituted haloalkyl"

[0487] The "substituted or unsubstituted haloalkyl group" described in the present specification means 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" means 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.

[0488] "Substituted or unsubstituted alkoxy"

[0489] 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.

[0490] "Substituted or unsubstituted alkylthio"

[0491] 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.

[0492] "Substituted or unsubstituted aryloxy group"

[0493] 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.

[0494] "Substituted or unsubstituted arylthio"

[0495] 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.

[0496] "Substituted or unsubstituted trialkylsilyl"

[0497] A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. Multiple G3s 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 "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0498] "Substituted or unsubstituted aralkyl"

[0499] 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.

[0500] 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.

[0501] 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.

[0502] 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 naphthylbenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthylbenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0503] Unless otherwise specified in the present specification, the carbazolyl group in the present specification is specifically any of the following groups.

[0504] [Chemistry 10]

[0505]

[0506] Unless otherwise specified in the present specification, in the present specification, a (9-phenyl)carbazolyl group is specifically any of the following groups.

[0507] [Chemistry 11]

[0508]

[0509] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0510] 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.

[0511] [Chemistry 12]

[0512]

[0513] In the general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0514] 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.

[0515] "Substituted or unsubstituted arylene group"

[0516] 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.

[0517] · "Substituted or unsubstituted divalent heterocyclic group"

[0518] 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.

[0519] "Substituted or unsubstituted alkylene"

[0520] 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.

[0521] 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).

[0522] [Chemistry 13]

[0523]

[0524] [Chemistry 14]

[0525]

[0526] In the general formulas (TEMP-42) to (TEMP-52), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0527] In the general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0528] [Chemistry 15]

[0529]

[0530] In the general formulas (TEMP-53) to (TEMP-62), Q 1 ~Q 10 are each independently a hydrogen atom or a substituent.

[0531] Formula Q 9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0532] In the general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0533] [Chemistry 16]

[0534]

[0535] In the general formulas (TEMP-63) to (TEMP-68), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0536] In the general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0537] 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).

[0538] [Chemistry 17]

[0539]

[0540] [Chemistry 18]

[0541]

[0542] [Chemistry 19]

[0543]

[0544] In the general formulas (TEMP-69) to (TEMP-82), Q 1 ~Q 9 are each independently a hydrogen atom or a substituent.

[0545] [Chemistry 20]

[0546]

[0547] [Chemistry 21]

[0548]

[0549] [Chemistry 22]

[0550]

[0551] [Chemistry 23]

[0552]

[0553] In the general formulas (TEMP-83) to (TEMP-102), Q 1 ~Q 8 are each independently a hydrogen atom or a substituent.

[0554] The above is the description of the “substituents described in the present specification”.

[0555] ・"When bonding to form a ring"

[0556] 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”.

[0557] The following describes 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" and 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" (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring") in this specification. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring is described as an example.

[0558] [Chemistry 24]

[0559]

[0560] 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 R 923 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.

[0561] The above-mentioned "one or more groups" means that two or more groups of the above-mentioned groups consisting of 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).

[0562] [Chemistry 25]

[0563]

[0564] 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. For example, R 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 .

[0565] [Chemistry 26]

[0566]

[0567] 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.

[0568] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0569] 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.

[0570] 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.

[0571] 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.

[0572] "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 elements. 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.

[0573] Here, in the case where no particular explanation is given in this specification, "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur. In any element (for example, in the case of carbon or nitrogen), the bond that does not form a ring may be terminated by a hydrogen atom or the like, or may be substituted by an "arbitrary substituent" described later. In the case of containing any element other than carbon, the formed ring is a heterocyclic ring.

[0574] Unless otherwise specified in the present specification, the number of "one or more arbitrary elements" 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.

[0575] Unless otherwise specified in the present specification, of "monocyclic ring" and "condensed ring", "monocyclic ring" is preferred.

[0576] Unless otherwise specified in the present specification, of "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0577] Unless otherwise specified in the present specification, the "monocyclic ring" is preferably a benzene ring.

[0578] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0579] 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 single 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 one or more and less than 15 elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0580] 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".

[0581] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0582] 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").

[0583] ·Substituents in the case of "substituted or unsubstituted"

[0584] 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,

[0585] An unsubstituted alkyl group having 1 to 50 carbon atoms,

[0586] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0587] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0588] unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

[0589] -Si(R 901 )(R 902 )(R 903 ),

[0590] -O-(R 904 ),

[0591] -S-(R 905 ),

[0592] -N(R 906 )(R 907 ),

[0593] Halogen atoms, cyano, nitro,

[0594] a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms, etc.

[0595] Here, R 901 ~R 907 Independently,

[0596] Hydrogen atoms,

[0597] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0598] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0599] 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.

[0600] In the presence of two or more R 901 In the case of 2 or more R 901 Same or different from each other,

[0601] In the presence of two or more R 902 In the case of 2 or more R 902 Same or different from each other,

[0602] In the presence of two or more R 903 In the case of 2 or more R 903 Same or different from each other,

[0603] In the presence of two or more R 904 In the case of 2 or more R 904 Same or different from each other,

[0604] In the presence of two or more R 905 In the case of 2 or more R 905 Same or different from each other,

[0605] In the presence of two or more R 906 In the case of 2 or more R 906 Same or different from each other,

[0606] In the presence of two or more R 907In the case of 2 or more R 907 The same as or different from each other.

[0607] In one embodiment, the substituent in the case of "substituted or unsubstituted" is

[0608] An alkyl group having 1 to 50 carbon atoms,

[0609] A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.

[0610] In one embodiment, the substituent in the case of "substituted or unsubstituted" is

[0611] Alkyl having 1 to 18 carbon atoms,

[0612] A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.

[0613] 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".

[0614] 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.

[0615] 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.

[0616] 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.

[0617] [First embodiment]

[0618] <Compound>

[0619] The compound of the present embodiment is a compound represented by the following general formula (1).

[0620] [Chemistry 27]

[0621]

[0622] (In the general formula (1),

[0623] CN is cyano,

[0624] D 11 and D 12 are independently a group represented by the following general formula (11), general formula (12) or general formula (13), wherein at least one D 11 is a group represented by the following general formula (12) or general formula (13),

[0625] R are independently,

[0626] Hydrogen atoms,

[0627] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0628] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0629] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0630] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0631] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0632] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0633] -O-(R 904 ) represents a group,

[0634] -S-(R 905 ) represents a group,

[0635] -N(R 906 )(R 907 ) represents a group,

[0636] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0637] -C(=O)R 908 The groups represented

[0638] -COOR 909 The groups represented

[0639] Cyano,

[0640] Nitro,

[0641] -P(=O)(R 931 )(R 932 ) represents a group,

[0642] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0643] -B(R 936 )(R 937 ) represents a group,

[0644] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0645] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0646] wherein at least one R is a substituent, and at least one R as a substituent is bonded to the benzene ring in the general formula (1) via a carbon-carbon bond.

[0647] k is 1 or 2,

[0648] m is 0, 1 or 2,

[0649] n is 1, 2 or 3,

[0650] k+m+n is 4,

[0651] When k is 2, multiple D 11 Same or different from each other,

[0652] When m is 2, multiple D 12 Same or different from each other,

[0653] When n is 2 or 3, multiple Rs are the same or different from each other.)

[0654] [Chemistry 28]

[0655]

[0656] [Chemistry 29]

[0657]

[0658] [Chemistry 30]

[0659]

[0660] (From the general formula (12) R 11 ~R 18 One or more of the groups of two or more adjacent

[0661] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0662] bonded to each other to form a substituted or unsubstituted fused ring, or

[0663] Not bonded to each other,

[0664] According to the general formula (13), R 111 ~R 118 One or more of the groups of two or more adjacent

[0665] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0666] bonded to each other to form a substituted or unsubstituted fused ring, or

[0667] Not bonded to each other,

[0668] In the general formula (11), R 1 ~R 8 , R in the general formula (12) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 11 ~R 18 , and R in the general formula (13) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 111 ~R 118 Independently,

[0669] Hydrogen atoms,

[0670] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0671] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0672] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0673] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0674] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0675] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0676] -O-(R 904 ) represents a group,

[0677] -S-(R 905 ) represents a group,

[0678] -N(R 906 )(R 907 ) represents a group,

[0679] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0680] -C(=O)R 908 The groups represented

[0681] -COOR 909 The groups represented

[0682] Halogen atoms,

[0683] Cyano,

[0684] Nitro,

[0685] -P(=O)(R 931 )(R 932 ) represents a group,

[0686] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0687] -B(R 936 )(R 937 ) represents a group,

[0688] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0689] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0690] In the general formula (12) and the general formula (13),

[0691] Ring A, Ring B and Ring C are each independently any ring structure selected from the group consisting of ring structures represented by the following general formula (14) and general formula (15),

[0692] Ring A, Ring B and Ring C are condensed with the adjacent rings at any position,

[0693] p, px and py are independently 1, 2, 3 or 4,

[0694] When p is 2, 3 or 4, the plurality of rings A are identical to or different from each other.

[0695] When px is 2, 3 or 4, the multiple rings B are the same or different from each other,

[0696] When py is 2, 3 or 4, the plurality of ring Cs are the same or different from each other,

[0697] Among them, at least 1 D 11 is a group represented by the general formula (12) or (13), and as D 11In the general formula (12), p is 4, and the four rings A include two ring structures represented by the following general formula (14) and two ring structures represented by the following general formula (15), and as the D 11 In the general formula (13), px and py are 2, the two rings B include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15), and the two rings C include one ring structure represented by the following general formula (14) and one ring structure represented by the following general formula (15),

[0698] In the general formulae (11) to (13), * indicates the position of bonding to the benzene ring in the general formula (1).

[0699] [Chemistry 31]

[0700]

[0701] (In the general formula (14),

[0702] r is 0, 2 or 4,

[0703] By multiple R 19 The group composed

[0704] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[0705] bonded to each other to form a substituted or unsubstituted fused ring, or

[0706] Not bonded to each other,

[0707] In the general formula (15), X 1 is a sulfur atom or an oxygen atom,

[0708] R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 19 For hydrogen atoms,

[0709] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0710] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[0711] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0712] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0713] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0714] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[0715] -O-(R 904 ) represents a group,

[0716] -S-(R 905 ) represents a group,

[0717] -N(R 906 )(R 907 ) represents a group,

[0718] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[0719] -C(=O)R 908 The groups represented

[0720] -COOR 909 The groups represented

[0721] Halogen atoms,

[0722] Cyano,

[0723] Nitro,

[0724] -P(=O)(R 931 )(R 932 ) represents a group,

[0725] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[0726] -B(R 936 )(R 937 ) represents a group,

[0727] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0728] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0729] Multiple R 19 Same or different from each other,

[0730] Multiple X 1 Same or different from each other,

[0731] Among them, D as a group represented by the general formula (13) 11 Satisfies at least one of the following conditions (Pv1), (Pv2) and (Pv3).

[0732] Condition (Pv1): When k is 2, X in the ring structure represented by the general formula (15) as ring B is 1and X in the ring structure represented by the general formula (15) as ring C 1 At least one of them is an oxygen atom.

[0733] Condition (Pv2): When k is 2, 2 D 11 Different from each other.

[0734] Condition (Pv3): When n is 3, X in the ring structure represented by the general formula (15) as ring B is 1 and X in the ring structure represented by the general formula (15) as ring C 1 are independently a sulfur atom or an oxygen atom. )

[0735] (In the general formula, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 Independently,

[0736] Hydrogen atoms,

[0737] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0738] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0739] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0740] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0741] In the presence of multiple R 901 In the case of multiple R 901 Same or different from each other,

[0742] In the presence of multiple R 902 In the case of multiple R 902 Same or different from each other,

[0743] In the presence of multiple R 903 In the case of multiple R 903 Same or different from each other,

[0744] In the presence of multiple R 904In the case of multiple R 904 Same or different from each other,

[0745] In the presence of multiple R 905 In the case of multiple R 905 Same or different from each other,

[0746] In the presence of multiple R 906 In the case of multiple R 906 Same or different from each other,

[0747] In the presence of multiple R 907 In the case of multiple R 907 Same or different from each other,

[0748] In the presence of multiple R 908 In the case of multiple R 908 Same or different from each other,

[0749] In the presence of multiple R 909 In the case of multiple R 909 Same or different from each other,

[0750] In the presence of multiple R 931 In the case of multiple R 931 Same or different from each other,

[0751] In the presence of multiple R 932 In the case of multiple R 932 Same or different from each other,

[0752] In the presence of multiple R 933 In the case of multiple R 933 Same or different from each other,

[0753] In the presence of multiple R 934 In the case of multiple R 934 Same or different from each other,

[0754] In the presence of multiple R 935 In the case of multiple R 935 Same or different from each other,

[0755] In the presence of multiple R 936 In the case of multiple R 936 Same or different from each other,

[0756] In the presence of multiple R 937 In the case of multiple R 937 The same or different from each other.)

[0757] According to this embodiment, a compound having a high PLQY can be provided.

[0758] In the compound of this embodiment, D 11 and D 12 When the groups are different from each other, or when multiple D 11 When the compound of this embodiment is used in the organic layer of an organic EL element, the hole injection property is improved, and at least one of the luminous efficiency and the life span is improved. Specifically, the reason is that D 11 and D 12 Since the oxidation potentials are different, holes are injected into the organic layer in stages.

[0759] In the compounds of this embodiment, all D 11 and D 12 Except X 1 In the case of groups with the same chemical structure, at least one X 1 If X is an oxygen atom, the life of the organic EL device will be prolonged. 1 The group of oxygen atoms and all X 1 Since the bonding angle with respect to the benzene ring represented by the general formula (1) is smaller than that of the group consisting of sulfur atoms, the life of the compound of this embodiment can be prolonged by using the compound in the organic layer.

[0760] In the compounds of this embodiment, the benzene ring of the general formula (1) to which the groups represented by the general formulae (11) to (13) are bonded refers to the benzene ring itself explicitly shown in the general formula (1), not R, D 11 and D 12 The benzene ring contained in .

[0761] In the compounds represented by the general formulae (110), (120), (130), (126), (127), (126A), (127A), (127B), (111), (112) and (113) described later, as in the case of the general formula (1), the benzene rings clearly shown in these general formulae are bonded to groups represented by the general formulae (11) to (13) etc.

[0762] In the compound of this embodiment, preferably at least one D 11 It is a group represented by the following general formula (121), general formula (122) or general formula (131).

[0763] [Chemistry 32]

[0764]

[0765] [Chemistry 33]

[0766]

[0767] [Chemistry 34]

[0768]

[0769] (In the general formula (121) and the general formula (122), R 11 ~R 18 and R in the general formula (12) 11 ~R 18 Synonymous,

[0770] Ring A 1 , Ring A 2 , Ring A 3 and Ring A 4 Two of them are ring structures represented by the general formula (14), and the remaining two are ring structures represented by the general formula (15),

[0771] In the general formula (131), R 111 ~R 118 and R in the general formula (13) 111 ~R 118 Synonymous,

[0772] Ring B 1 and Ring B 2 One of them is a ring structure represented by the general formula (14), and ring B 1 and Ring B 2 The other one is a ring structure represented by the general formula (15),

[0773] Ring C 1 and Ring C 2 One of them is a ring structure represented by the general formula (14), and ring C 1 and Ring C 2 The other one is a ring structure represented by the general formula (15),

[0774] The * in the general formula (121), the general formula (122) and the general formula (131) indicates the position of bonding to the benzene ring in the general formula (1).

[0775] In the compounds of this embodiment, ring A is preferably 1 and Ring A 3 is a ring structure represented by the general formula (14), wherein ring A 2 and Ring A 4 It is a ring structure represented by the general formula (15).

[0776] In the compounds of this embodiment, ring B is preferably 1 is a ring structure represented by the general formula (14), wherein ring B 2is a ring structure represented by the general formula (15), wherein ring C 1 is a ring structure represented by the general formula (14), wherein ring C 2 It is a ring structure represented by the general formula (15).

[0777] In the compound of this embodiment, preferably at least one D 11 It is a group represented by the general formula (131).

[0778] In the compound of this embodiment, preferably at least one D 11 It is a group represented by the following general formula (123), general formula (124), general formula (125) or general formula (132).

[0779] [Chemistry 35]

[0780]

[0781] [Chemistry 36]

[0782]

[0783] [Chemistry 37]

[0784]

[0785] [Chemistry 38]

[0786]

[0787] (In the general formula (123), the general formula (124) and the general formula (125), R 11 ~R 18 and R in the general formula (12) 11 ~R 18 Synonymous, R 191 ~R 194 are independently connected to R in the general formula (14) 19 Synonymous,

[0788] In the general formula (132), R 111 ~R 118 and R in the general formula (13) 111 ~R 118 Synonymous, R 195 ~R 198 are independently connected to R in the general formula (14) 19 Synonymous,

[0789] In the general formula (123), the general formula (124), the general formula (125) and the general formula (132), X 11 and X 12are independently and respectively 1 In the same way, * indicates the position of bonding to the benzene ring in the general formula (1).

[0790] In the compounds of this embodiment, preferably R 191 ~R 194 The groups of two or more adjacent ones in are not bonded to each other.

[0791] In the compounds of this embodiment, preferably R 195 ~R 198 The groups of two or more adjacent ones in are not bonded to each other.

[0792] In the compounds of this embodiment, preferably X 11 A sulfur atom.

[0793] In the compounds of this embodiment, X in the groups represented by the general formula (123), the general formula (124) and the general formula (125) is preferably 11 A sulfur atom.

[0794] In the compound of this embodiment, preferably at least one D 11 It is a group represented by the general formula (132).

[0795] In the compound of this embodiment, X in the group represented by the general formula (132) is preferably 11 In the compounds of this embodiment, it is more preferred that X in the group represented by the general formula (132) is 11 is a sulfur atom, X 12 is a sulfur atom or an oxygen atom.

[0796] In the compounds of this embodiment, D 12 It is a group represented by the general formula (11) or the general formula (12).

[0797] In the compounds of this embodiment, D 12 It is a group represented by the general formula (12).

[0798] In the compound of this embodiment, the group represented by the general formula (12) is preferably any group selected from the group consisting of groups represented by the following general formulae (12A), (12B), (12C), (12D), (12E) and (12F).

[0799] [Chemistry 39]

[0800]

[0801] [Chemistry 40]

[0802]

[0803] [Chemistry 41]

[0804]

[0805] [Chemistry 42]

[0806]

[0807] [Chemistry 43]

[0808]

[0809] [Chemistry 44]

[0810]

[0811] (In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F),

[0812] R 11 ~R 18 are independently connected to R in the general formula (12) 11 ~R 18 Synonymous,

[0813] R 19 and R 20 are independently connected to R in the general formula (14) 19 Synonymous,

[0814] X 1 and X in the general formula (15) 1 Synonymous,

[0815] In the general formulae (12A), (12B), (12C), (12D), (12E) and (12F), * indicates the position of bonding to the benzene ring in the general formula (1).

[0816] Among the compounds of this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (110), general formula (120) or general formula (130).

[0817] [Chemistry 45]

[0818]

[0819] (In the general formula (110), the general formula (120) and the general formula (130), D 11 , D 12 , R, k, m and n are respectively the same as D in the general formula (1) 11 , D 12, R, k, m, and n are synonymous. )

[0820] In the compound of this embodiment, n in the general formula (1) is preferably 2 or 3.

[0821] In the compound of this embodiment, it is also preferred that n is 2 in the general formula (1).

[0822] Among the compounds of this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (126) or (127).

[0823] [Chemistry 46]

[0824]

[0825] (In the general formula (126) and the general formula (127), D 11 and D in the general formula (1) 11 Synonymous, D 12 and D in the general formula (1) 12 Synonymous, R 101 ~R 104 Each of them is independently synonymous with R in the general formula (1), k is 1 or 2, m is 0 or 1, and k+m is 2.)

[0826] In the compound of this embodiment, it is also preferred that k is 2, 2 D 11 One of the D 11 is a group represented by the general formula (12), and another D 11 It is a group represented by the general formula (13).

[0827] In the compound of this embodiment, it is also preferred that k is 2, 2 D 11 is a group represented by the general formula (13), as D 11 The two groups represented by the general formula (13) are different from each other.

[0828] In the compound of this embodiment, it is also preferred that k and m are 1, D 11 and D 12 One of them is a group represented by the general formula (12), and the other is a group represented by the general formula (13).

[0829] Among the compounds of this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (126A), general formula (127A) or general formula (127B).

[0830] [Chemistry 47]

[0831]

[0832] (In the general formula (126A), the general formula (127A) and the general formula (127B), D 11 and D in the general formula (1) 11 Synonymous, D 12 and D in the general formula (1) 12 Synonymous, R 101 ~R 104 Each independently has the same meaning as R in the general formula (1).

[0833] Preferably, in the general formula (126A), the general formula (127A) and the general formula (127B), D 11 and D 12 are different groups from each other.

[0834] In the compound of this embodiment, it is also preferred that n is 3 in the general formula (1).

[0835] Among the compounds of this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (111), general formula (112) or general formula (113).

[0836] [Chemistry 48]

[0837]

[0838] (In the general formula (111), the general formula (112) and the general formula (113), D 11 and D in the general formula (1) 11 Synonymous, R 101 ~R 104 Each independently has the same meaning as R in the general formula (1).

[0839] In the compound of the present embodiment, groups consisting of two or more adjacent Rs are not bonded to each other.

[0840] In the compounds of this embodiment, R 101 ~R 104 The groups of two or more adjacent ones in are not bonded to each other.

[0841] In the compound of this embodiment, it is preferred that R in the general formula (1) is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

[0842] In the compound of this embodiment, it is preferred that R in the general formula (1) is independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted heterocyclic group having 6 ring atoms.

[0843] In the compounds of this embodiment, preferably R 101 ~R 104 Each of them is independently a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms.

[0844] In the compounds of this embodiment, preferably R 101 ~R 104 Each independently represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group having 6 ring atoms.

[0845] Among the compounds of this embodiment, it is also preferred that the compound represented by the general formula (1) is represented by the following general formula (126C) or (127C).

[0846] [Chemistry 49]

[0847]

[0848] (In the general formula (126C) and the general formula (127C), D 11 and D in the general formula (1) 11 Synonymous, D 12 and D in the general formula (1) 12 Synonymous, R 131 ~R 140 and R 141 ~R 150 Each of them is independently synonymous with R in the general formula (1), k is 1 or 2, m is 0 or 1, and k+m is 2.)

[0849] Among the compounds of this embodiment, the compound represented by the general formula (1) is preferably represented by the following general formula (126D) or (127D).

[0850] [Chemistry 50]

[0851]

[0852] (In the general formulae (126D) and (127D), D 11 and D in the general formula (1) 11 Synonymous, D 12 and D in the general formula (1) 12 Synonymous, R 131 ~R 140 and R 141 ~R 150 Each independently has the same meaning as R in the general formula (1).

[0853] In the compounds of this embodiment, D 11is a group represented by the general formula (132), D 12 It is a group represented by any one of the general formulae (12A) to (12F).

[0854] In the compounds of this embodiment, R 131 ~R 140 and R 141 ~R 150 Preferably, each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring carbon atoms, and more preferably each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0855] In the compounds of this embodiment, R 1 ~R 8 The groups of two or more adjacent ones in are not bonded to each other.

[0856] In the compounds of this embodiment, preferably R 11 ~R 18 The groups of two or more adjacent ones in are not bonded to each other.

[0857] In the compounds of this embodiment, preferably R 11 ~R 20 The groups of two or more adjacent ones in are not bonded to each other.

[0858] In the compounds of this embodiment, preferably R 111 ~R 118 The groups of two or more adjacent ones in are not bonded to each other.

[0859] In the compounds of this embodiment, it is preferred that R in the general formula (11) 1 ~R 8 , R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 And R in the general formula (14) 19 Each of them is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0860] In the compounds of this embodiment, it is preferred that R in the general formula (11) 1 ~R 8, R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 And R in the general formula (14) 19 Each of them is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0861] In the compounds of this embodiment, R 191 ~R 198 Preferably, they are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably, they are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or an unsubstituted aryl group having 6 to 50 ring carbon atoms.

[0862] The compound of this embodiment is preferably a delayed fluorescence compound.

[0863] Delayed fluorescence

[0864] 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 of this embodiment is preferably a compound that shows thermally activated delayed fluorescence generated by such a mechanism.

[0865] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[0866] 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.

[0867] 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.

[0868] Figure 1 A schematic diagram of an example apparatus for measuring transition PL is shown in FIG. Figure 1 An example of the transition PL measurement method and delayed fluorescence behavior analysis is described.

[0869] Figure 1 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 1 The device described.

[0870] 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.

[0871] 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.

[0872] 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.

[0873] [Chemistry 51]

[0874]

[0875] 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.

[0876] Figure 2 2 shows the decay curves obtained from the transition PL measured for the film sample A and the film sample B.

[0877] [Chemistry 52]

[0878]

[0879] 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.

[0880] 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.

[0881] 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 for calculating the amount of prompt luminescence and delay luminescence is not limited to the device described in reference 1 or Figure 1 The device described in .

[0882] In addition, in the measurement of the delayed fluorescence of the compound of the present embodiment, a sample prepared by the method shown below is used. For example, the compound of the present embodiment 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.

[0883] 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.

[0884] In this embodiment, the amount of prompt luminescence (immediate luminescence) of the compound to be measured 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.

[0885] In this specification, the measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio thereof of compounds other than the compound of this embodiment is the same as the measurement of the amounts of Prompt luminescence and Delay luminescence and the ratio thereof of the compound of this embodiment.

[0886] ·△ST

[0887] In this embodiment, the lowest excited singlet energy S 1 and the energy gap T at 77[K] 77K The difference (S 1 -T 77K ) is defined as △ST.

[0888] The lowest excited singlet energy S of the compound of this embodiment is 1 (M1) and the energy gap T at 77 [K] of the compound of this embodiment 77K The difference ΔST(M1) between (M1) and (M1) 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(M1) preferably satisfies the relationship of the following mathematical formula (Equation 10), (Equation 11), (Equation 12), or (Equation 13).

[0889] △ST(M1)=S 1 (M1)-T77K (M1)<0.3eV…(Number 10)

[0890] △ST(M1)=S 1 (M1)-T 77K (M1)<0.2eV…(Number 11)

[0891] △ST(M1)=S 1 (M1)-T 77K (M1)<0.1eV…(Number 12)

[0892] △ST(M1)=S 1 (M1)-T 77K (M1)<0.01eV…(Number 13)

[0893] Relationship between triplet energy and energy gap at 77[K]

[0894] 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.

[0895] 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 emission intensity and a horizontal axis: wavelength), a tangent is drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy is calculated based on the wavelength value of the intersection of the tangent and the horizontal axis according to a prescribed conversion formula.

[0896] Here, among the compounds of the present embodiment, the compound with thermally activated delayed fluorescence is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at 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 way 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.

[0897] 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 77KThe 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 .

[0898] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0899] 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 the maximum value on the short wavelength side of the spectrum moves from the short wavelength side of the phosphorescence spectrum to the maximum value of the spectrum on the short wavelength side. 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.

[0900] 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.

[0901] 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.

[0902] ·Lowest excited singlet state energy S 1

[0903] The lowest excited singlet energy S of the solution was used. 1 The following method can be mentioned as a measurement method (sometimes called a solution method).

[0904] 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 (300K) (with the vertical axis: absorption intensity and the 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 lowest excited singlet energy.

[0905] Conversion formula (F2): S 1 [eV] = 1239.85 / λedge

[0906] 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.

[0907] 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.

[0908] 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.

[0909] (Method for producing the compound of this embodiment)

[0910] The compound of the present embodiment can be produced by following the synthesis method described in the Examples described below, or by imitating the synthesis method, using known substitution reactions and raw materials that match the target product.

[0911] (Specific examples of the compound of this embodiment)

[0912] As specific examples of the compounds of this embodiment, the following compounds can be cited. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is marked as D in a chemical formula, and a protium atom is marked as H or omitted.

[0913] [Chemistry 53]

[0914]

[0915] [Chemistry 54]

[0916]

[0917] [Chemistry 55]

[0918]

[0919] [Chemistry 56]

[0920]

[0921] [Chemistry 57]

[0922]

[0923] [Chemistry 58]

[0924]

[0925] [Chemistry 59]

[0926]

[0927] [Chemistry 60]

[0928]

[0929] [Chemistry 61]

[0930]

[0931] [Chemistry 62]

[0932]

[0933] [Chemistry 63]

[0934]

[0935] [Chemistry 64]

[0936]

[0937] [Chemistry 65]

[0938]

[0939] [Chemistry 66]

[0940]

[0941] [Chemistry 67]

[0942]

[0943] [Chemistry 68]

[0944]

[0945] [Chemistry 69]

[0946]

[0947] [Chemistry 70]

[0948]

[0949] [Chemistry 71]

[0950]

[0951] [Chemistry 72]

[0952]

[0953] [Chemistry 73]

[0954]

[0955] [Chemistry 74]

[0956]

[0957] [Chemistry 75]

[0958]

[0959] [Chemistry 76]

[0960]

[0961] [Chemistry 77]

[0962]

[0963] [Chemistry 78]

[0964]

[0965] [Chemistry 79]

[0966]

[0967] [Chemistry 80]

[0968]

[0969] [Chemistry 81]

[0970]

[0971] [Chemistry 82]

[0972]

[0973] [Chemistry 83]

[0974]

[0975] [Chemistry 84]

[0976]

[0977] [Chemistry 85]

[0978]

[0979] [Chemistry 86]

[0980]

[0981] [Chemistry 87]

[0982]

[0983] [Chemistry 88]

[0984]

[0985] [Chemistry 89]

[0986]

[0987] [Chemistry 90]

[0988]

[0989] [Chemistry 91]

[0990]

[0991] [Chemistry 92]

[0992]

[0993] [Chemistry 93]

[0994]

[0995] [Chemistry 94]

[0996]

[0997] [Chemistry 95]

[0998]

[0999] [Chemistry 96]

[1000]

[1001] [Chemistry 97]

[1002]

[1003] [Chemistry 98]

[1004]

[1005] [Chemistry 99]

[1006]

[1007] [Chemical 100]

[1008]

[1009] [Chemistry 101]

[1010]

[1011] [Chemistry 102]

[1012]

[1013] [Chemistry 103]

[1014]

[1015] [Chemistry 104]

[1016]

[1017] [Chemistry 105]

[1018]

[1019] [Chemistry 106]

[1020]

[1021] [Chemistry 107]

[1022]

[1023] [Chemistry 108]

[1024]

[1025] [Chemistry 109]

[1026]

[1027] [Chemistry 110]

[1028]

[1029] [Chemistry 111]

[1030]

[1031] [Chemistry 112]

[1032]

[1033] [Chemistry 113]

[1034]

[1035] [Chemistry 114]

[1036]

[1037] [Chemistry 115]

[1038]

[1039] [Chemistry 116]

[1040]

[1041] [Chemistry 117]

[1042]

[1043] [Chemistry 118]

[1044]

[1045] [Chemistry 119]

[1046]

[1047] [Chemistry 120]

[1048]

[1049] [Chemistry 121]

[1050]

[1051] [Chemistry 122]

[1052]

[1053] [Chemistry 123]

[1054]

[1055] [Chemistry 124]

[1056]

[1057] [Chemistry 125]

[1058]

[1059] [Chemistry 126]

[1060]

[1061] [Chemistry 127]

[1062]

[1063] [Chemistry 128]

[1064]

[1065] [Chemistry 129]

[1066]

[1067] [Chemistry 130]

[1068]

[1069] [Chemistry 131]

[1070]

[1071] [Chemistry 132]

[1072]

[1073] [Chemistry 133]

[1074]

[1075] [Chemistry 134]

[1076]

[1077] [Chemistry 135]

[1078]

[1079] [Chemistry 136]

[1080]

[1081] [Chemistry 137]

[1082]

[1083] [Chemistry 138]

[1084]

[1085] [Chemistry 139]

[1086]

[1087] [Chemistry 140]

[1088]

[1089] [Chemistry 141]

[1090]

[1091] [Second embodiment]

[1092] <Materials for organic electroluminescent devices>

[1093] The organic electroluminescent element material of this embodiment contains the compound of the first embodiment. As one embodiment, an organic electroluminescent element material containing only the compound of the first embodiment can be exemplified, and as another embodiment, an organic electroluminescent element material containing the compound of the first embodiment and other compounds different from the compound in the first embodiment can be exemplified.

[1094] In the organic electroluminescent device material of this embodiment, the compound of the first embodiment is preferably used as a host material. In this case, the organic electroluminescent device material may contain the compound of the first embodiment as a host material and other compounds such as a dopant material.

[1095] In the organic electroluminescent device material of this embodiment, it is preferred that the compound of the first embodiment is a delayed fluorescence material.

[1096] [Third embodiment]

[1097] <Organic electroluminescent element>

[1098] The organic EL element of this embodiment will be described.

[1099] The organic EL element of this embodiment has an organic layer between the 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 also include an inorganic compound.

[1100] In the organic EL device of this embodiment, the organic layer contains the compound of Embodiment 1. That is, the organic EL device of this embodiment has an anode, a cathode, and an organic layer, and the organic layer contains the compound of Embodiment 1 as the compound M2.

[1101] In the organic EL device of this embodiment, it is preferred that the organic layer has at least one light-emitting layer, and the light-emitting layer contains the compound of the first embodiment as the compound M2.

[1102] The organic layer may be composed of, for example, a light-emitting layer, or may include a layer that can be used in an organic EL element. The layer that can be used in an organic EL element is not particularly limited, and for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer may be cited.

[1103] In one embodiment, the light-emitting layer may also include a metal complex.

[1104] Furthermore, in one embodiment, the light-emitting layer preferably does not contain a metal complex.

[1105] In one embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material).

[1106] In one embodiment, the light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy metal complex include iridium complexes, osmium complexes, and platinum complexes.

[1107] exist Figure 3 Schematic diagram of an example of the structure of the organic EL element of this embodiment is shown in FIG.

[1108] 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. Figure 3 The structure of the organic EL element shown.

[1109] (Luminous layer)

[1110] In the organic EL element of this embodiment, the light-emitting layer includes compound M1 and compound M2. Compound M2 in the light-emitting layer is preferably a compound of the first embodiment. In the case of this embodiment, compound M2 is preferably a host material (sometimes also referred to as a matrix material), and compound M1 is preferably a dopant material (sometimes also referred to as a guest material, a luminescent substance, or a luminescent material).

[1111] In this embodiment, when the light-emitting layer contains the compound of the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain a metal complex other than the phosphorescent metal complex.

[1112] (Compound M2)

[1113] The compound M2 is preferably the compound of Embodiment 1. The compound M2 of this embodiment is preferably a thermally activated delayed fluorescence compound.

[1114] (Compound M1)

[1115] The compound M1 is preferably a fluorescent compound. The compound M1 is preferably a compound that does not exhibit delayed fluorescence.

[1116] The compound M1 of this embodiment is not a phosphorescent metal complex. The compound M1 is preferably not a heavy metal complex. In addition, the compound M1 is preferably not a metal complex.

[1117] 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.

[1118] The compound M1 is preferably a compound that emits light having a maximum peak wavelength of 400 nm to 700 nm.

[1119] 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 peak wavelength of the fluorescence spectrum at which the emission intensity in the fluorescence spectrum is the maximum. A spectrofluorophotometer (F-7000, manufactured by Hitachi High-Technologies Corporation) was used as the measuring device.

[1120] Preferably, compound M1 emits red light or green light.

[1121] 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.

[1122] 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.

[1123] 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.

[1124] 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.

[1125] 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.

[1126] 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.

[1127] The measurement of the maximum peak wavelength of light emitted from the organic EL element is performed as follows.

[1128] 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 In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum at which the luminescence intensity reaches the maximum is measured and taken as the maximum peak wavelength (unit: nm).

[1129] (Compound represented by general formula (D1))

[1130] In the present embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (D1).

[1131] [Chemistry 142]

[1132]

[1133] (In the general formula (D1),

[1134] Ring A, Ring B, Ring D, Ring E and Ring F are each independently

[1135] A substituted or unsubstituted aromatic ring having 6 to 30 ring carbon atoms, and

[1136] a ring structure selected from the group consisting of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms,

[1137] Only one of ring B and ring D exists, or both ring B and ring D exist.

[1138] When both ring B and ring D are present, ring B and ring D share the bond connecting Zc and Zh.

[1139] Only one of the ring E and the ring F is present, or both the ring E and the ring F are present,

[1140] When both ring E and ring F are present, ring E and ring F share the bond connecting Zf and Zi.

[1141] Za is a nitrogen atom or a carbon atom,

[1142] When ring B is present, Zb is a nitrogen atom or a carbon atom,

[1143] When ring B is absent, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ),

[1144] Zc is a nitrogen atom or a carbon atom,

[1145] When ring D is present, Zd is a nitrogen atom or a carbon atom,

[1146] In the absence of ring D, Zd is an oxygen atom, a sulfur atom or NRd,

[1147] When ring E is present, Ze is a nitrogen atom or a carbon atom,

[1148] In the absence of ring E, Ze is an oxygen atom, a sulfur atom or NRe,

[1149] Zf is a nitrogen atom or a carbon atom,

[1150] When ring F is present, Zg is a nitrogen atom or a carbon atom,

[1151] In the absence of ring F, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ),

[1152] Zh is a nitrogen atom or a carbon atom,

[1153] Zi is a nitrogen atom or a carbon atom,

[1154] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S,

[1155] Rb, Rb 1 , Rb 2 , Rb3 , Rb 4 、Rd、Re、Rg、Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are each independently a hydrogen atom or a substituent,

[1156] Rb, Rb as a substituent 1 , Rb 2 , Rb 3 , Rb 4 、Rd、Re、Rg、Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are independently,

[1157] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1158] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[1159] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1160] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1161] -Si(R 911 )(R 912 )(R 913 ) represents a group,

[1162] -O-(R 914 ) represents a group,

[1163] -S-(R 915 ) or

[1164] -N(R 916 )(R 917 ) represents a group,

[1165] Among them, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.)

[1166] (In the compound M1, R 911 ~R 917 Independently,

[1167] Hydrogen atoms,

[1168] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1169] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1170] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1171] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1172] In the presence of multiple R 911 In the case of multiple R 911 Same or different from each other,

[1173] In the presence of multiple R 912 In the case of multiple R 912 Same or different from each other,

[1174] In the presence of multiple R 913 In the case of multiple R 913 Same or different from each other,

[1175] In the presence of multiple R 914 In the case of multiple R 914 Same or different from each other,

[1176] In the presence of multiple R 915 In the case of multiple R 915 Same or different from each other,

[1177] In the presence of multiple R 916 In the case of multiple R 916 Same or different from each other,

[1178] In the presence of multiple R 917 In the case of multiple R 917 The same or different from each other.)

[1179] The bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds, which are covalent bonds rather than coordination bonds.

[1180] In the present specification, examples of heterocycles include ring structures (heterocycles) obtained by removing chemical bonds from the "heterocyclic groups" exemplified in the above "substituents described in the present specification." These heterocycles may have a substituent or may be unsubstituted.

[1181] In the present specification, examples of aromatic rings include ring structures (aromatic rings) obtained by removing chemical bonds from the "aryl groups" exemplified in the above-mentioned "substituents described in the present specification." These aromatic rings may have a substituent or may be unsubstituted.

[1182] In the present embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (D11).

[1183] [Chemistry 143]

[1184]

[1185] (In the general formula (D11),

[1186] Ring A, Ring D and Ring E are each independently

[1187] A substituted or unsubstituted aromatic ring having 6 to 30 ring carbon atoms, and

[1188] a ring structure selected from the group consisting of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms,

[1189] Za is a nitrogen atom or a carbon atom,

[1190] Zb is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ),

[1191] Zc is a nitrogen atom or a carbon atom,

[1192] Zd is a nitrogen atom or a carbon atom,

[1193] Ze is a nitrogen atom or a carbon atom,

[1194] Zf is a nitrogen atom or a carbon atom,

[1195] Zg is an oxygen atom, a sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ),

[1196] Zh is a nitrogen atom or a carbon atom,

[1197] Zi is a nitrogen atom or a carbon atom,

[1198] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S,

[1199] Rb, Rb 1 , Rb 2 , Rb 3 , Rb 4 , Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are independently Rb, Rb 1 , Rb 2 , Rb 3 , Rb4 , Rg, Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh.)

[1200] In the present embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (D16).

[1201] [Chemistry 144]

[1202]

[1203] (In the general formula (D16),

[1204] By R 161 ~R 177 One or more of the groups of two or more adjacent

[1205] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1206] bonded to each other to form a substituted or unsubstituted fused ring, or

[1207] Not bonded to each other,

[1208] 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,

[1209] Hydrogen atoms,

[1210] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1211] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1212] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1213] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1214] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1215] -Si(R 961 )(R 962 )(R 963 ) represents a group,

[1216] -O-(R 964 ) represents a group,

[1217] -S-(R 965 ) represents a group,

[1218] -N(R 966 )(R 967 ) represents a group,

[1219] -C(=O)R 968 The groups represented

[1220] -COOR 969 The groups represented

[1221] Halogen atoms,

[1222] Cyano,

[1223] Nitro,

[1224] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1225] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1226] R 961 ~R 969 Independently,

[1227] Hydrogen atoms,

[1228] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1229] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1230] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1231] In the presence of multiple R 961 In the case of multiple R 961 Same or different from each other,

[1232] In the presence of multiple R 962 In the case of multiple R 962 Same or different from each other,

[1233] In the presence of multiple R 963 In the case of multiple R 963 Same or different from each other,

[1234] In the presence of multiple R 964 In the case of multiple R 964 Same or different from each other,

[1235] In the presence of multiple R 965 In the case of multiple R 965 Same or different from each other,

[1236] In the presence of multiple R 966 In the case of multiple R966 Same or different from each other,

[1237] In the presence of multiple R 967 In the case of multiple R 967 Same or different from each other,

[1238] In the presence of multiple R 968 In the case of multiple R 968 Same or different from each other,

[1239] In the presence of multiple R 969 In the case of multiple R 969 The same or different from each other.)

[1240] (Compound represented by general formula (D10))

[1241] In the organic EL device of this embodiment, the compound M1 is preferably a compound represented by the following general formula (D10). The compound represented by the general formula (D1) is preferably a compound represented by the following general formula (D10).

[1242] [Chemistry 145]

[1243]

[1244] (In the general formula (D10),

[1245] X 1 CR 1 or nitrogen atoms,

[1246] X 2 CR 2 or nitrogen atoms,

[1247] X 3 CR 3 or nitrogen atoms,

[1248] X 4 CR 4 or nitrogen atoms,

[1249] X 5 CR 5 or nitrogen atoms,

[1250] X 6 CR 6 or nitrogen atoms,

[1251] X 7 CR 7 or nitrogen atom, or a single bond to X 8 Bonded carbon atoms,

[1252] X 8CR 8 or nitrogen atom, or a single bond to X 7 Bonded carbon atoms,

[1253] X 9 CR 9 or nitrogen atoms,

[1254] X 10 CR 10 or nitrogen atoms,

[1255] X 11 CR 11 or nitrogen atoms,

[1256] X 12 CR 12 or nitrogen atoms,

[1257] Q is CR Q or nitrogen atoms,

[1258] Y is NR Y1 , oxygen atom, sulfur atom, C(R Y2 )(R Y3 ) or Si(R Y4 )(R Y5 ), by R 1 ~R 6 and R 9 ~R 11 One or more of the adjacent two or more groups in are bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1259] bonded to each other to form a substituted or unsubstituted fused ring, or

[1260] Not bonded to each other,

[1261] By R 3 , R 4 and R Y1 One or more of the adjacent two or more groups in are bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1262] bonded to each other to form a substituted or unsubstituted fused ring, or

[1263] Not bonded to each other,

[1264] By R 3 , R 4 and R Y1 At least one hydrogen atom in one or more of the two or more adjacent groups of the monocyclic or condensed rings formed by mutual bonding is removed from

[1265] An alkyl group having 1 to 50 carbon atoms,

[1266] An aryl group having 6 to 50 ring carbon atoms,

[1267] a heterocyclic group having 5 to 50 ring atoms,

[1268] -O-(R 920 ) represented by, and

[1269] -N(R 921 )(R 922 ) is substituted or unsubstituted with at least one substituent selected from the group consisting of the groups represented by

[1270] 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,

[1271] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 1 ~R 11 and R 12 ~R 13 and R Q Independently,

[1272] Hydrogen atoms,

[1273] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1274] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1275] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1276] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1277] -Si(R 911 )(R 912 )(R 913 ) represents a group,

[1278] -O-(R 914 ) represents a group,

[1279] -S-(R 915 ) represents a group,

[1280] -N(R 916 )(R 917 ) represents a group,

[1281] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1282] -C(=O)R 918 The groups represented

[1283] -COOR 919 The groups represented

[1284] Halogen atoms,

[1285] Cyano,

[1286] Nitro,

[1287] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1288] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1289] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring Y1 for

[1290] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1291] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1292] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1293] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1294] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1295] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1296] By R Y2 and R Y3 The group composed

[1297] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1298] bonded to each other to form a substituted or unsubstituted fused ring, or

[1299] Not bonded to each other,

[1300] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring Y2 and R Y3 and R Y4 and R Y5 Independently,

[1301] Hydrogen atoms,

[1302] Halogen atoms,

[1303] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1304] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1305] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1306] R 911 ~R 922 Independently,

[1307] Hydrogen atoms,

[1308] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1309] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1310] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1311] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1312] In the presence of multiple R 911 In the case of multiple R 911 Same or different from each other,

[1313] In the presence of multiple R 912 In the case of multiple R 912 Same or different from each other,

[1314] In the presence of multiple R 913 In the case of multiple R 913 Same or different from each other,

[1315] In the presence of multiple R 914 In the case of multiple R 914 Same or different from each other,

[1316] In the presence of multiple R 915 In the case of multiple R 915 Same or different from each other,

[1317] In the presence of multiple R 916 In the case of multiple R 916 Same or different from each other,

[1318] In the presence of multiple R 917 In the case of multiple R 917 Same or different from each other,

[1319] In the presence of multiple R 918 In the case of multiple R 918 Same or different from each other,

[1320] In the presence of multiple R919 In the case of multiple R 919 Same or different from each other,

[1321] In the presence of multiple R 920 In the case of multiple R 920 Same or different from each other,

[1322] In the presence of multiple R 921 In the case of multiple R 921 Same or different from each other,

[1323] In the presence of multiple R 922 In the case of multiple R 922 The same or different from each other.)

[1324] In the compound represented by the general formula (D10), in X 7 To pass a single key with X 8 Bonded carbon atoms, X 8 To pass a single key with X 7 In the case of a bonded carbon atom, for example, the general formula (D10) is represented by the following general formula (D10A).

[1325] [Chemistry 146]

[1326]

[1327] (In the general formula (D10A), X 1 ~X 6 , X 9 ~X 12 , Y, Q and R 13 are independently the same as those defined in the general formula (D10).

[1328] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D12).

[1329] [Chemistry 147]

[1330]

[1331] (In the general formula (D12), R 1 ~R 13 , R Y1 , R Q are independently the same as those defined in the general formula (D10).

[1332] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D12A).

[1333] [Chemistry 148]

[1334]

[1335] (In the general formula (D12A), R 1 ~R 6 , R 9 ~R 13 , R Y1 , R Q are independently the same as those defined in the general formula (D10).

[1336] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D13).

[1337] [Chemistry 149]

[1338]

[1339] (In the general formula (D13),

[1340] R 1 ~R 3 , R 5 ~R 13 and R Q are independently the same as those defined in the general formula (D10),

[1341] By R x1 ~R x4 One or more of the groups of two or more adjacent

[1342] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1343] bonded to each other to form a substituted or unsubstituted fused ring, or

[1344] Not bonded to each other,

[1345] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring X1 ~R x4 Independently,

[1346] Hydrogen atoms,

[1347] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1348] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1349] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1350] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1351] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1352] -Si(R 931 )(R 932 )(R 933 ) represents a group,

[1353] -O-(R 934 ) represents a group,

[1354] -S-(R 935 ) represents a group,

[1355] -N(R 936 )(R 937 ) represents a group,

[1356] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1357] -C(=O)R 938 The groups represented

[1358] -COOR 939 The groups represented

[1359] Halogen atoms,

[1360] Cyano,

[1361] Nitro,

[1362] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1363] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1364] R 931 ~R 939 Independently,

[1365] Hydrogen atoms,

[1366] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1367] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1368] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1369] In the presence of multiple R 931 In the case of multiple R 931 Same or different from each other,

[1370] In the presence of multiple R 932 In the case of multiple R 932 Same or different from each other,

[1371] In the presence of multiple R 933 In the case of multiple R 933 Same or different from each other,

[1372] In the presence of multiple R 934 In the case of multiple R 934 Same or different from each other,

[1373] In the presence of multiple R 935 In the case of multiple R 935 Same or different from each other,

[1374] In the presence of multiple R 936 In the case of multiple R 936 Same or different from each other,

[1375] In the presence of multiple R 937 In the case of multiple R 937 Same or different from each other,

[1376] In the presence of multiple R 938 In the case of multiple R 938 Same or different from each other,

[1377] In the presence of multiple R 939 In the case of multiple R 939 The same or different from each other.)

[1378] In the general formula (D13), for example, R 5 and R 6 The constituent groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1379] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D13A).

[1380] [Chemistry 150]

[1381]

[1382] (In the general formula (D13A), R 1 ~R 3 , R 5 ~R 6 , R 9 ~R 13 and R Q are independently the same as those defined in the general formula (D10), R x1 ~R x4 are independently the same as those defined in the general formula (D13).

[1383] Among the compounds represented by the general formula (D10), R 1 ~R 13 and R Q Independently,

[1384] Hydrogen atoms,

[1385] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1386] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1387] A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[1388] Among the compounds represented by the general formula (D10), R 1 ~R 13 and R Q Independently,

[1389] Hydrogen atoms,

[1390] a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

[1391] a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1392] A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[1393] Among the compounds represented by the general formula (D10), R 1 ~R 3 , R 5 ~R 13 , R Q and R x1 ~R x4 Independently,

[1394] Hydrogen atoms,

[1395] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1396] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1397] A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[1398] Among the compounds represented by the general formula (D10), R 1 ~R 3 , R 5 ~R 13 , R Q and R x1 ~Rx4 Independently,

[1399] Hydrogen atoms,

[1400] a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

[1401] a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1402] A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[1403] Among the compounds represented by the general formula (D10), R 1 ~R 13 , R Q and R x1 ~R x4 Independently,

[1404] Hydrogen atoms,

[1405] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1406] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1407] A substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.

[1408] Among the compounds represented by the general formula (D10), R 1 ~R 13 , R Q and R x1 ~R x4 Independently,

[1409] Hydrogen atoms,

[1410] a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms,

[1411] a substituted or unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1412] A substituted or unsubstituted heteroaryl group having 5 to 25 ring atoms.

[1413] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D14).

[1414] [Chemistry 151]

[1415]

[1416] (In the general formula (D14), R 2 , R 6 , R 13 , RQ and R x2 Independently,

[1417] Hydrogen atoms,

[1418] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[1419] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or

[1420] A substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[1421] It is also preferred that the compound represented by the general formula (D10) is represented by the following general formula (D15).

[1422] [Chemistry 152]

[1423]

[1424] (In the general formula (D15), R 2 , R 6 , R 13 , R Q and R x2 Independently,

[1425] Hydrogen atoms,

[1426] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[1427] a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or

[1428] A substituted or unsubstituted heteroaryl group having 5 to 18 ring atoms.

[1429] Among the compounds represented by the general formula (D10), R 13 and R Q Independently,

[1430] a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,

[1431] Substituted or unsubstituted phenyl,

[1432] Substituted or unsubstituted naphthyl, or

[1433] A substituted or unsubstituted dibenzofuranyl group.

[1434] In the compound represented by the general formula (D10), preferably, R 6 and R x2 Each independently represents a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[1435] (Compound represented by general formula (20))

[1436] In the present embodiment, it is also preferred that the compound M1 is a compound represented by the following general formula (20).

[1437] [Chemistry 153]

[1438]

[1439] In the general formula (20),

[1440] X is a nitrogen atom or a carbon atom bonded to Y,

[1441] Y is a hydrogen atom or a substituent,

[1442] R 21 ~R 26 are independently a hydrogen atom or a substituent, or R 21 and R 22 Group, R 22 and R 23 Group, R 24 and R 25 The group, and R 25 and R 26 Any one or more of the groups are bonded to each other to form a ring,

[1443] Y and R as substituents 21 ~R 26 Independently from

[1444] A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1445] a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,

[1446] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[1447] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1448] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1449] a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms,

[1450] a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,

[1451] a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,

[1452] a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,

[1453] a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,

[1454] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[1455] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,

[1456] Halogen atoms,

[1457] carboxyl,

[1458] Substituted or unsubstituted ester group,

[1459] a substituted or unsubstituted carbamoyl group,

[1460] A substituted or unsubstituted amino group,

[1461] Nitro,

[1462] Cyano,

[1463] a substituted or unsubstituted silyl group, and

[1464] is selected from the group consisting of substituted or unsubstituted siloxane groups,

[1465] Z 21 and Z 22 are independently a substituent, or Z 21 and Z 22 Bonded to each other to form a ring,

[1466] Z as a substituent 21 and Z 22 Independently from

[1467] Halogen atoms,

[1468] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1469] a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,

[1470] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1471] a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,

[1472] a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and

[1473] The present invention is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

[1474] (Method for producing compound M1)

[1475] The compound M1 of this embodiment can be produced according to a known synthesis method, or can be produced by imitating the synthesis method using a known substitution reaction and raw materials that match the target compound.

[1476] (Specific example of compound M1)

[1477] As specific examples of compound M1 of the present embodiment, for example, the following compounds can be cited. However, the present invention is not limited to the specific examples of these compounds. In addition, the coordination bond between the boron atom and the nitrogen atom in the pyrromethene skeleton is represented by various marking methods such as solid lines, dotted lines, arrows or omissions. In this specification, it is represented by solid lines, or represented by dotted lines, or omitted.

[1478] [Chemistry 154]

[1479]

[1480] [Chemistry 155]

[1481]

[1482] [Chemistry 156]

[1483]

[1484] [Chemistry 157]

[1485]

[1486] [Chemistry 158]

[1487]

[1488] [Chemistry 159]

[1489]

[1490] [Chemistry 160]

[1491]

[1492] [Chemistry 161]

[1493]

[1494] [Chemistry 162]

[1495]

[1496] [Chemistry 163]

[1497]

[1498] <Relationship between Compound M1 and Compound M2 in the Emitting Layer>

[1499] In the organic EL device of this embodiment, it is preferred that the lowest excited singlet energy S of the compound M2 is 1 (M2) and the lowest excited singlet energy S of compound M1 1 (M1) satisfies the following mathematical formula…(number 1).

[1500] S 1 (M2)>S 1 (M1)…(Number 1)

[1501] The energy gap T of the preferred compound M2 at 77[K] 77K (M2) is larger than the energy gap T of compound M1 at 77[K] 77K (M1) That is, it is preferable to satisfy the relationship of the following mathematical formula (Equation 5).

[1502] T 77K (M2)>T 77K (M1)…(Number 5)

[1503] When the organic EL device of this embodiment is made to emit light, it is preferred that the compound M1 mainly emits light in the light-emitting layer.

[1504] TADF mechanism

[1505] Figure 4 : is a diagram showing an example of the relationship between the energy levels of the compound M2 and the compound M1 in the light-emitting layer. Figure 4 In the formula (A), S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1. T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2. T1(M2) represents the lowest excited triplet state of compound M2.

[1506] Figure 4 The dashed arrow from S1(M2) to S1(M1) in represents the Forster type energy transfer from the lowest excited singlet state of compound M2 to compound M1.

[1507] like Figure 4As 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%.

[1508] The organic EL element of this embodiment preferably emits red light or green light.

[1509] When the organic EL element of the present embodiment emits green light, the main peak wavelength of light emitted from the organic EL element is preferably not less than 500 nm and not more than 560 nm.

[1510] When the organic EL element of the present embodiment emits red light, the main peak wavelength of light emitted from the organic EL element is preferably not less than 600 nm and not more than 660 nm.

[1511] When the organic EL element of the present embodiment emits blue light, the main peak wavelength of light emitted from the organic EL element is preferably not less than 430 nm and not more than 480 nm.

[1512] The measurement of the main peak wavelength of light emitted from the organic EL element is performed as follows.

[1513] 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 .

[1514] 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 main peak wavelength (unit: nm).

[1515] Thickness of the light-emitting layer

[1516] The 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 further preferably 10 nm to 50 nm. If the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity, and if the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the increase of the driving voltage.

[1517] ·Content ratio of the compound in the light-emitting layer

[1518] The content of the compound M2 and the compound M1 contained in the light-emitting layer is preferably within the following ranges, for example.

[1519] The content of the compound M2 may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or 99% by mass or more and 99.9% by mass or less.

[1520] 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 %.

[1521] In addition, this embodiment does not exclude the inclusion of materials other than the compound M2 and the compound M1 in the light-emitting layer.

[1522] The light-emitting layer may contain only one compound M2, or may contain two or more compounds M2. The light-emitting layer may contain only one compound M1, or may contain two or more compounds M1.

[1523] (Substrate)

[1524] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, etc. 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 composed of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, etc. can be cited. In addition, an inorganic vapor-deposited film can also be used.

[1525] (anode)

[1526] 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).

[1527] 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.

[1528] 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.

[1529] It is also possible to use alkali metals such as lithium (Li) or cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing them, etc., which are elements belonging to Group 1 or Group 2 of the periodic table as materials 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.

[1530] (cathode)

[1531] 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 alkali metals such as lithium (Li) or cesium (Cs), and 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, which are elements belonging to Group 1 or Group 2 of the periodic table.

[1532] 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.

[1533] 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.

[1534] (Hole Injection Layer)

[1535] 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.

[1536] In addition, as the 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]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 other aromatic amine compounds.

[1537] 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.

[1538] (Hole Transport Layer)

[1539] 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 / Vs or higher hole mobility.

[1540] In the hole transport layer, carbazole derivatives such as CBP, CzPA, and 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.

[1541] 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 a single layer or a layer in which two or more layers formed of the above substances are stacked.

[1542] (Electron Transport Layer)

[1543] 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 weight organic compounds, Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as: Almq 3 ), bis(10-hydroxybenzo[h]quinolinolato)beryllium (abbreviated as: BeBq 2), BAlq, Znq, ZnPBO, ZnBTZ and other metal complexes, etc. In addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances mentioned here are mainly heteroaromatic compounds having 10 -6 cm 2 / Vs or more of the electron mobility. In addition, as long as the electron transport property is higher than the hole transport property of the material, it is also possible to use a material other than the above as the electron transport layer. In addition, the electron transport layer can be a single layer, or it can be a layer formed by stacking two or more layers of the above-mentioned materials.

[1544] 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.

[1545] (Electron Injection Layer)

[1546] The electron injection layer is a layer containing a substance with high electron injection properties. Lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), alkali metals, alkaline earth metals or their compounds such as lithium oxide (LiOx). In addition, substances obtained by making substances with electron transport properties contain alkali metals, alkaline earth metals or their compounds, specifically substances obtained by making Alq contain magnesium (Mg), etc. In addition, in this case, electron injection from the cathode can be performed more efficiently.

[1547] 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.

[1548] (Layer Formation Method)

[1549] 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.

[1550] (film thickness)

[1551] 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.

[1552] The organic EL element of the third embodiment contains the compound of the first embodiment as compound M2 and compound M1 having a minimum excited singlet energy smaller than compound M2 in the light-emitting layer. The organic EL element of the third embodiment contains the compound of the first embodiment (compound M2) having a high PLQY, and therefore, according to the third embodiment, a high-performance organic EL element capable of achieving at least one of high efficiency and long life can be provided.

[1553] [Fourth embodiment]

[1554] The structure of the organic EL element of the fourth embodiment is described. In the description of the fourth embodiment, the same components as those of the third embodiment are marked with the same reference numerals and names, and the description is omitted or simplified. In addition, in the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[1555] The organic EL device of the fourth embodiment is different from the organic EL device of the third embodiment in that the light-emitting layer further contains a compound M3. The other aspects are the same as those of the third embodiment.

[1556] That is, in the fourth embodiment, the light-emitting layer includes compound M3, compound M2 and compound M1. In this embodiment, compound M2 is preferably a host material, and compound M1 is preferably a dopant material.

[1557] (Compound M3)

[1558] The compound M3 of the present 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.

[1559] Although not particularly limited, the compound M3 is preferably a compound other than an amine compound. In addition, for example, a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative can be used as the compound M3, but the compound is not limited to these derivatives.

[1560] In this embodiment, the compound M3 is preferably a compound represented by the following general formula (3X) or (3Y).

[1561] (Compound represented by general formula (3X))

[1562] It is also preferred that the compound M3 is a compound represented by the following general formula (3X).

[1563] [Chemistry 164]

[1564]

[1565] (In the general formula (3X),

[1566] A 3 for

[1567] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1568] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1569] L 3 for

[1570] single bond,

[1571] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[1572] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1573] A divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or

[1574] a divalent group formed by bonding three groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

[1575] By R 31 ~R 38 One or more of the groups of two or more adjacent

[1576] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1577] bonded to each other to form a substituted or unsubstituted fused ring, or

[1578] Not bonded to each other,

[1579] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Independently,

[1580] Hydrogen atoms,

[1581] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1582] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[1583] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1584] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1585] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1586] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[1587] -O-(R 904 ) represents a group,

[1588] -S-(R 905 ) represents a group,

[1589] -N(R 906 )(R 907 ) represents a group,

[1590] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1591] -C(=O)R 908 The groups represented

[1592] -COOR 909 The groups represented

[1593] Halogen atoms,

[1594] Cyano,

[1595] Nitro,

[1596] -P(=O)(R 931 )(R 932 ) represents a group,

[1597] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[1598] -B(R 936 )(R 937 ) represents a group,

[1599] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1600] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1601] A group represented by the following general formula (3A).

[1602] [Chemistry 165]

[1603]

[1604] (In the general formula (3A),

[1605] R B for

[1606] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1607] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[1608] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1609] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1610] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1611] -Si(R 901 )(R902 )(R 903 ) represents a group,

[1612] -O-(R 904 ) represents a group,

[1613] -S-(R 905 ) represents a group,

[1614] -N(R 906 )(R 907 ) represents a group,

[1615] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1616] -C(=O)R 908 The groups represented

[1617] -COOR 909 The groups represented

[1618] Halogen atoms,

[1619] Cyano,

[1620] Nitro,

[1621] -P(=O)(R 931 )(R 932 ) represents a group,

[1622] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[1623] -B(R 936 )(R 937 ) represents a group,

[1624] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1625] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1626] In the presence of multiple R B When multiple R B Same or different from each other,

[1627] L 31 for

[1628] single bond,

[1629] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group,

[1630] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the heterocyclic group, or

[1631] a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group,

[1632] L 32 for

[1633] single bond,

[1634] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[1635] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1636] n 3 is 1, 2, 3, 4 or 5,

[1637] In L 31 In the case of a single bond, n 3 =1, L 32 is bonded to a carbon atom of the six-membered ring in the general formula (3X),

[1638] In the presence of multiple L 32 When multiple L 32 Same or different from each other,

[1639] * is a site bonded to a carbon atom of the six-membered ring in the general formula (3X).

[1640] (In compound M3, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 Independently,

[1641] Hydrogen atoms,

[1642] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1643] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1644] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1645] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1646] In the presence of multiple R 901 In the case of multiple R 901 Same or different from each other,

[1647] In the presence of multiple R 902 In the case of multiple R 902 Same or different from each other,

[1648] In the presence of multiple R 903 In the case of multiple R 903 Same or different from each other,

[1649] In the presence of multiple R 904 In the case of multiple R 904 Same or different from each other,

[1650] In the presence of multiple R 905 In the case of multiple R 905 Same or different from each other,

[1651] In the presence of multiple R 906 In the case of multiple R 906 Same or different from each other,

[1652] In the presence of multiple R 907 In the case of multiple R 907 Same or different from each other,

[1653] In the presence of multiple R 908 In the case of multiple R 908 Same or different from each other,

[1654] In the presence of multiple R 909 In the case of multiple R 909 Same or different from each other,

[1655] In the presence of multiple R 931 In the case of multiple R 931 Same or different from each other,

[1656] In the presence of multiple R 932 In the case of multiple R 932 Same or different from each other,

[1657] In the presence of multiple R 933In the case of multiple R 933 Same or different from each other,

[1658] In the presence of multiple R 934 In the case of multiple R 934 Same or different from each other,

[1659] In the presence of multiple R 935 In the case of multiple R 935 Same or different from each other,

[1660] In the presence of multiple R 936 In the case of multiple R 936 Same or different from each other,

[1661] In the presence of multiple R 937 In the case of multiple R 937 The same or different from each other.)

[1662] It is also preferred that the compound M3 is a compound represented by any one of the following general formulas (31) to (36).

[1663] [Chemistry 166]

[1664]

[1665] [Chemistry 167]

[1666]

[1667] [Chemistry 168]

[1668]

[1669] (In the general formulas (31) to (36),

[1670] A 3 and L 3 Respectively with A in the general formula (3X) 3 and L 3 Synonymous,

[1671] By R 341 ~R 350 One or more of the groups of two or more adjacent

[1672] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1673] bonded to each other to form a substituted or unsubstituted fused ring, or

[1674] Not bonded to each other,

[1675] X 31 is a sulfur atom, an oxygen atom, NR352 or CR 353 R 354 ,

[1676] By R 353 and R 354 The group composed

[1677] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1678] bonded to each other to form a substituted or unsubstituted fused ring, or

[1679] Not bonded to each other,

[1680] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 341 ~R 350 , R 352 , R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 353 and R 354 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous.)

[1681] In compound M3, preferably R 352 for

[1682] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1683] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1684] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1685] In compound M3, preferably R 353 and R 354 The group composed

[1686] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1687] bonded to each other to form a substituted or unsubstituted fused ring, or

[1688] Not bonded to each other,

[1689] R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 353 and R 354 Independently,

[1690] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1691] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1692] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1693] Preferably, in compound M3, X 31 is a sulfur atom or an oxygen atom.

[1694] Preferably, in compound M3, A 3 It is a group represented by any one of the following general formulae (A31) to (A37).

[1695] [Chemistry 169]

[1696]

[1697] [Chemistry 170]

[1698]

[1699] (In the general formulae (A31) to (A37),

[1700] By multiple R 300 One or more of the groups of two or more adjacent

[1701] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1702] bonded to each other to form a substituted or unsubstituted fused ring, or

[1703] Not bonded to each other,

[1704] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 300 , and R 333 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous,

[1705] The * in the general formulae (A31) to (A37) represent the L of the compound M3. 3 Bonding location.)

[1706] It is also preferred that in compound M3, A 3 It is a group represented by the general formula (A34), (A35) or (A37).

[1707] It is also preferred that the compound M3 is a compound represented by any one of the following general formulas (311) to (316).

[1708] [Chemistry 171]

[1709]

[1710] [Chemistry 172]

[1711]

[1712] [Chemistry 173]

[1713]

[1714] [Chemistry 174]

[1715]

[1716] [Chemistry 175]

[1717]

[1718] [Chemistry 176]

[1719]

[1720] (In the general formulas (311) to (316),

[1721] L 3 and L in the general formula (3X) 3 Synonymous,

[1722] By multiple R 300 One or more of the groups of two or more adjacent

[1723] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1724] bonded to each other to form a substituted or unsubstituted fused ring, or

[1725] Not bonded to each other,

[1726] By R 341 ~R 350 One or more of the groups of two or more adjacent

[1727] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1728] bonded to each other to form a substituted or unsubstituted fused ring, or

[1729] Not bonded to each other,

[1730] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 300 , and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 341 ~R350 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous.)

[1731] It is also preferred that the compound M3 is a compound represented by the following general formula (321).

[1732] [Chemistry 177]

[1733]

[1734] (In the general formula (321),

[1735] L 3 and L in the general formula (3X) 3 Synonymous,

[1736] R 31 ~R 38 , and R 301 ~R 308 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous.)

[1737] Preferably, in compound M3, L 3 It is a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[1738] Preferably, in compound M3, L 3 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

[1739] Preferably, in compound M3, L 3 It is a group represented by the following general formula (317).

[1740] [Chemistry 178]

[1741]

[1742] (In the general formula (317), R 310 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous, * each independently represents a bonding position. )

[1743] It is also preferred that in compound M3, L 3 It contains a divalent group represented by the following general formula (318) or general formula (319).

[1744] It is also preferred that in compound M3, L 3 It is a divalent group represented by the following general formula (318) or general formula (319).

[1745] It is also preferred that the compound M3 is a compound represented by the following general formula (322) or general formula (323).

[1746] [Chemistry 179]

[1747]

[1748] [Chemistry 180]

[1749]

[1750] (In the general formula (322) and the general formula (323),

[1751] L 31 for

[1752] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[1753] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms, or

[1754] a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[1755] Among them, L 31 Contains a divalent group represented by the following general formula (318) or general formula (319),

[1756] R 31 ~R 38 , R 300 , and R 321 ~R 328 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous.)

[1757] [Chemistry 181]

[1758]

[1759] (In the general formula (319),

[1760] By multiple R 304 Two adjacent groups of the compounds in the formula (320) are bonded to each other to form a ring represented by the general formula (320).

[1761] In the general formula (320), 1* and 2* each independently represent 304 the bonding position of the bonded ring,

[1762] In the general formula (318), R 302 , R in the general formula (319) 303 , R which does not form a ring represented by the general formula (320) 304 , and R in the general formula (320) 305 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous,

[1763] In the general formulae (318) to (320), * represents a bonding position.

[1764] In compound M3, as L 3 or L 31 The group represented by the general formula (319) is, for example, a group represented by the following general formula (319A).

[1765] [Chemistry 182]

[1766]

[1767] (In the general formula (319A), R 303 , R 304 and R 305 R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 In the same way, * in the general formula (319A) represents a bonding position.

[1768] It is also preferred that compound M3 is a compound represented by the general formula (322), wherein L 31 It is a group represented by the general formula (318).

[1769] It is also preferred that the compound M3 is a compound represented by the following general formula (324).

[1770] [Chemistry 183]

[1771]

[1772] (In the general formula (324), R 31 ~R 38 , R 300 , and R 302R that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 31 ~R 38 Synonymous.)

[1773] Preferably, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 Independently,

[1774] Hydrogen atoms,

[1775] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1776] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1777] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1778] The group represented by the general formula (3A) is

[1779] In the general formula (3A), R B for

[1780] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1781] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1782] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1783] Preferably, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 Independently,

[1784] Hydrogen atoms,

[1785] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1786] The group represented by the general formula (3A) is

[1787] In the general formula (3A), R B It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1788] Preferably, R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring. 31 ~R 38 Independently,

[1789] Hydrogen atoms,

[1790] Substituted or unsubstituted phenyl, or

[1791] The group represented by the general formula (3A) is

[1792] In the general formula (3A), R B is substituted or unsubstituted phenyl.

[1793] It is also preferred that the compound M3 is a compound having no pyridine ring, pyrimidine ring or triazine ring.

[1794] (Compound represented by general formula (3Y))

[1795] It is also preferred that the compound M3 is a compound represented by the following general formula (3Y).

[1796] [Chemistry 184]

[1797]

[1798] (In the general formula (3Y),

[1799] Y 31 ~Y 36 CR 3 or nitrogen atoms,

[1800] Among them, Y 31 ~Y 36 At least two of them are nitrogen atoms,

[1801] In the presence of multiple R 3 In the case of multiple R 3 One or more of the groups of two or more adjacent

[1802] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1803] bonded to each other to form a substituted or unsubstituted fused ring, or

[1804] Not bonded to each other,

[1805] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 3 Independently,

[1806] Hydrogen atoms,

[1807] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1808] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[1809] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1810] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1811] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1812] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[1813] -O-(R 904 ) represents a group,

[1814] -S-(R 905 ) represents a group,

[1815] -N(R 906 )(R 907 ) represents a group,

[1816] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1817] -C(=O)R 908 The groups represented

[1818] -COOR 909 The groups represented

[1819] Halogen atoms,

[1820] Cyano,

[1821] Nitro,

[1822] -P(=O)(R 931 )(R 932 ) represents a group,

[1823] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[1824] -B(R 936 )(R 937 ) represents a group,

[1825] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1826] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1827] A group represented by the following general formula (3B).

[1828] [Chemistry 185]

[1829]

[1830] (In the general formula (3B), R B , L 31 , L 32 and n 3 are independently B , L 31 , L 32 and n 3 Synonymous,

[1831] In the presence of multiple R B When multiple R B Same or different from each other,

[1832] In L 31 In the case of a single bond, n 3 =1, L 32 is bonded to a carbon atom of the six-membered ring in the general formula (3Y),

[1833] In the presence of multiple L 32 When multiple L 32 Same or different from each other,

[1834] * is a site bonded to a carbon atom of the six-membered ring in the general formula (3Y).

[1835] Preferably, compound M3 does not contain a pyridine ring in the molecule.

[1836] It is also preferred that the compound M3 is a compound represented by the following general formula (31a) or general formula (32a).

[1837] [Chemistry 186]

[1838]

[1839] (In the general formula (32a),

[1840] By R 35 ~R 37 One or more of the groups of two or more adjacent

[1841] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1842] bonded to each other to form a substituted or unsubstituted fused ring, or

[1843] Not bonded to each other,

[1844] In the general formula (31a), R 31 ~R 33 , and R in the general formula (32a) 34and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 35 ~R 37 are independently connected to R in the general formula (3Y) 3 Synonymous.)

[1845] It is also preferred that the compound M3 is a compound represented by the general formula (31a).

[1846] Preferably, R in the general formula (3Y) 3 Independently,

[1847] Hydrogen atoms,

[1848] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1849] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1850] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

[1851] A group represented by the general formula (3B).

[1852] Preferably, R in the general formula (3Y) 3 Independently,

[1853] Hydrogen atoms,

[1854] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1855] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1856] A group represented by the general formula (3B).

[1857] It is preferred that the compound M3 represented by the general formula (3Y) has at least one group selected from the group consisting of groups represented by the following general formulae (B31) to (B44) in the molecule.

[1858] [Chemistry 187]

[1859]

[1860] [Chemistry 188]

[1861]

[1862] (In the general formulae (B31) to (B38),

[1863] By multiple R 300 One or more of the groups of two or more adjacent

[1864] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1865] bonded to each other to form a substituted or unsubstituted fused ring, or

[1866] Not bonded to each other,

[1867] By R 331 and R 332 The group composed

[1868] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1869] bonded to each other to form a substituted or unsubstituted fused ring, or

[1870] Not bonded to each other,

[1871] R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 300 , R 331 and R 332 , and R 333 Independently,

[1872] Hydrogen atoms,

[1873] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1874] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[1875] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1876] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1877] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1878] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[1879] -O-(R 904 ) represents a group,

[1880] -S-(R 905 ) represents a group,

[1881] -N(R 906 )(R 907 ) represents a group,

[1882] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1883] -C(=O)R908 The groups represented

[1884] -COOR 909 The groups represented

[1885] Halogen atoms,

[1886] Cyano,

[1887] Nitro,

[1888] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1889] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1890] The * in the general formulae (B31) to (B38) respectively represent the positions of bonding to other atoms in the molecule of the compound M3.

[1891] [Chemistry 189]

[1892]

[1893] [Chemistry 190]

[1894]

[1895] [Chemistry 191]

[1896]

[1897] (In the general formulae (B39) to (B44),

[1898] By R 341 ~R 350 One or more of the groups of two or more adjacent

[1899] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1900] bonded to each other to form a substituted or unsubstituted fused ring, or

[1901] Not bonded to each other,

[1902] Among them, R 341 ~R 351 At least one of represents a position bonded to other atoms in the molecule of the compound M3,

[1903] X 31 is a sulfur atom, an oxygen atom, NR 352 or CR 353 R 354 ,

[1904] By R353 and R 354 The group composed

[1905] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1906] bonded to each other to form a substituted or unsubstituted fused ring, or

[1907] Not bonded to each other,

[1908] R is not bonded to other atoms in the molecule of the compound M3, and does not form the substituted or unsubstituted monocyclic ring or the substituted or unsubstituted condensed ring. 341 ~R 351 , R 352 and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 353 and R 354 Independently,

[1909] Hydrogen atoms,

[1910] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1911] a substituted or unsubstituted halogenated alkyl group having 1 to 50 carbon atoms,

[1912] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1913] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1914] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1915] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[1916] -O-(R 904 ) represents a group,

[1917] -S-(R 905 ) represents a group,

[1918] -N(R 906 )(R 907 ) represents a group,

[1919] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1920] -C(=O)R 908 The groups represented

[1921] -COOR 909The groups represented

[1922] Halogen atoms,

[1923] Cyano,

[1924] Nitro,

[1925] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1926] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1927] It is preferred that the compound M3 represented by the general formula (3Y) has at least one group selected from the group consisting of groups represented by the general formulae (B38) to (B44) in the molecule.

[1928] Preferably, in the general formula (3Y), Y 31 ~Y 36 At least one of them is CR 3 ,

[1929] At least 1 R 3 is a group represented by the general formula (3B), R B It is any one of the groups represented by the general formulae (B31) to (B44).

[1930] Preferably, in the general formula (3Y), Y 31 ~Y 36 At least one of them is CR 3 ,

[1931] At least 1 R 3 is a group represented by the general formula (3B), R B It is any one of the groups represented by the general formulae (B38) to (B44).

[1932] Preferably, in the general formulae (3A) and (3B), L 31 for

[1933] single bond,

[1934] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, or

[1935] a divalent group formed by bonding two groups selected from the group consisting of substituted or unsubstituted arylene groups having 6 to 50 ring carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group,

[1936] L 32 Independently,

[1937] Single key, or

[1938] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[1939] Preferably, in the general formulae (3A) and (3B), L 31 for

[1940] Single key, or

[1941] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[1942] n 3 is 1,

[1943] L 32 for

[1944] Single key, or

[1945] A substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.

[1946] Preferably, in the general formulae (3A) and (3B), L 31 for

[1947] single bond,

[1948] Substituted or unsubstituted phenylene,

[1949] Substituted or unsubstituted biphenylene, or

[1950] a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, or a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the divalent group,

[1951] n 3 is 1,

[1952] L 32 for

[1953] single bond,

[1954] Substituted or unsubstituted phenylene, or

[1955] Substituted or unsubstituted biphenylene.

[1956] Among the compounds represented by the general formulae (3X) and (3Y), R 352 for

[1957] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1958] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1959] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1960] Among the compounds represented by the general formulae (3X) and (3Y), preferably 353 and R 354 The group composed

[1961] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1962] bonded to each other to form a substituted or unsubstituted fused ring, or

[1963] Not bonded to each other,

[1964] R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 353 and R 354 Independently,

[1965] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1966] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1967] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1968] In the compounds represented by the general formula (3X) and (3Y), the substituent in the case of "substituted or unsubstituted" is preferably

[1969] unsubstituted alkyl having 1 to 25 carbon atoms,

[1970] unsubstituted alkenyl having 2 to 25 carbon atoms,

[1971] unsubstituted alkynyl having 2 to 25 carbon atoms,

[1972] unsubstituted cycloalkyl having 3 to 25 ring carbon atoms,

[1973] -Si(R 901 )(R 902 )(R 903 ) represents a group,

[1974] -O-(R 904 ) represents a group,

[1975] -S-(R 905 ) represents a group,

[1976] -N(R 906 )(R 907 ) represents a group,

[1977] unsubstituted aralkyl having 7 to 50 carbon atoms,

[1978] -C(=O)R 908 The groups represented

[1979] -COOR 909 The groups represented

[1980] -P(=O)(R 931 )(R 932 ) represents a group,

[1981] Take -Ge(R 933 )(R 934 )(R 935 ) represents a group,

[1982] -B(R 936 )(R 937 ) represents a group,

[1983] -S(=O) 2 R 938 The groups represented

[1984] Halogen atoms,

[1985] Cyano,

[1986] Nitro,

[1987] unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1988] an unsubstituted heterocyclic group having 5 to 25 ring atoms,

[1989] R 901 ~R 909 and R 931 ~R 938 Independently,

[1990] Hydrogen atoms,

[1991] unsubstituted alkyl having 1 to 25 carbon atoms,

[1992] unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1993] An unsubstituted heterocyclic group having 5 to 25 ring atoms.

[1994] In the compounds represented by the general formula (3X) and (3Y), the substituent in the case of "substituted or unsubstituted" is preferably

[1995] Halogen atoms,

[1996] an unsubstituted alkyl group having 1 to 25 carbon atoms,

[1997] unsubstituted aryl group having 6 to 25 ring carbon atoms, or

[1998] An unsubstituted heterocyclic group having 5 to 25 ring atoms.

[1999] In the compounds represented by the general formula (3X) and (3Y), the substituent in the case of "substituted or unsubstituted" is preferably

[2000] an unsubstituted alkyl group having 1 to 10 carbon atoms,

[2001] unsubstituted aryl group having 6 to 12 ring carbon atoms, or

[2002] An unsubstituted heterocyclic group having 5 to 12 ring atoms.

[2003] In the compounds represented by the general formulae (3X) and (3Y), it is also preferred that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[2004] (Method for producing compound M3)

[2005] The compound M3 of this embodiment can be produced by a known method.

[2006] (Specific example of compound M3)

[2007] 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.

[2008] [Chemistry 192]

[2009]

[2010] [Chemistry 193]

[2011]

[2012] [Chemistry 194]

[2013]

[2014] [Chemistry 195]

[2015]

[2016] [Chemistry 196]

[2017]

[2018] [Chemistry 197]

[2019]

[2020] [Chemistry 198]

[2021]

[2022] [Chemistry 199]

[2023]

[2024] [Chemistry 200]

[2025]

[2026] [Chemistry 201]

[2027]

[2028] [Chemistry 202]

[2029]

[2030] [Chemistry 203]

[2031]

[2032] [Chemistry 204]

[2033]

[2034] [Chemistry 205]

[2035]

[2036] [Chemistry 206]

[2037]

[2038] [Chemistry 207]

[2039]

[2040] [Chemistry 208]

[2041]

[2042] [Chemistry 209]

[2043]

[2044] [Chemistry 210]

[2045]

[2046] [Chemistry 211]

[2047]

[2048] [Chemistry 212]

[2049]

[2050] [Chemistry 213]

[2051]

[2052] [Chemistry 214]

[2053]

[2054] [Chemistry 215]

[2055]

[2056] [Chemistry 216]

[2057]

[2058] [Chemistry 217]

[2059]

[2060] [Chemistry 218]

[2061]

[2062] [Chemistry 219]

[2063]

[2064] [Chemistry 220]

[2065]

[2066] [Chemistry 221]

[2067]

[2068] [Chemistry 222]

[2069]

[2070] [Chemistry 223]

[2071]

[2072] [Chemistry 224]

[2073]

[2074] [Chemistry 225]

[2075]

[2076] [Chemistry 226]

[2077]

[2078] [Chemistry 227]

[2079]

[2080] [Chemistry 228]

[2081]

[2082] [Chemistry 229]

[2083]

[2084] [Chemistry 230]

[2085]

[2086] [Chemistry 231]

[2087]

[2088] <Relationship among Compound M3, Compound M2, and Compound M1 in the Emitting Layer>

[2089] In the organic EL device of this embodiment, it is preferred that the lowest excited singlet energy S of the compound M2 is 1 (M2) and the lowest excited singlet energy S of compound M1 1 (M1) satisfies the relationship of the following mathematical formula (1).

[2090] S 1 (M2)>S 1 (M1)…(Number 1)

[2091] In the organic EL device of this embodiment, it is preferred that the lowest excited singlet energy S of the compound M2 is 1 (M2) and the lowest excited singlet energy S of compound M3 1 (M3) satisfies the relationship of the following mathematical formula (2).

[2092] S 1 (M3)>S 1 (M2)…(number 2)

[2093] In addition, it is preferred that the lowest excited singlet energy S of compound M3 is 1 (M3) is greater than the lowest excited singlet energy S of compound M1 1 (M1).

[2094] S 1 (M3)>S 1 (M1)…(number 2A)

[2095] The lowest excited singlet energy S of the preferred compound M3 is 1 (M3) and the lowest excited singlet energy S of compound M2 1 (M2) and the lowest excited singlet energy S of compound M1 1 (M1) satisfies the relationship of the following mathematical formula (numeral 2B).

[2096] S 1 (M3)>S 1 (M2)>S 1 (M1)…(Number 2B)

[2097] In the organic EL device of this embodiment, it is preferred that the energy gap T of the compound M3 at 77 [K] is 77K (M3) is larger than the energy gap T of compound M2 at 77[K] 77K (M2).

[2098] In the organic EL device of this embodiment, it is preferred that the energy gap T of the compound M2 at 77 [K] is 77K (M2) is larger than the energy gap T of compound M1 at 77[K] 77K (M1).

[2099] In the organic EL device of this embodiment, it is preferred that the compound M3, the compound M2, and the compound M1 satisfy the relationship of the following mathematical formula (Formula 5A).

[2100] T 77K (M3)>T 77K (M2)>T 77K (M1)…(number 5A)

[2101] 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.

[2102] The organic EL element of this embodiment preferably emits red light or green light.

[2103] ·Content ratio of the compound in the light-emitting layer

[2104] 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.

[2105] The content of the compound M3 is preferably 10% by mass or more and 80% by mass or less.

[2106] 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.

[2107] 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 %.

[2108] 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.

[2109] 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.

[2110] 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 5 In 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.

[2111] 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%.

[2112] The organic EL element of the fourth embodiment contains the compound of the first embodiment as compound M2, compound M1 having a lower minimum excited singlet energy than compound M2, and compound M3 having a higher minimum excited singlet energy than compound M2 in the light-emitting layer. The organic EL element of the fourth embodiment contains the compound of the first embodiment (compound M2) having a high PLQY, and therefore, according to the fourth embodiment, a high-performance organic EL element capable of achieving at least one of high efficiency and long life can be provided.

[2113] [Fifth embodiment]

[2114] The structure of the organic EL element of the fifth embodiment is described. In the description of the fifth embodiment, the same components as those of the third embodiment or the fourth embodiment are marked with the same reference numerals and names, etc., and the description is omitted or simplified. In addition, in the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment or the fourth embodiment can be used.

[2115] The organic EL device of the fifth embodiment is different from the organic EL device of the third embodiment or the fourth embodiment in that the light-emitting layer contains the compound M2 and the compound M3 but does not contain the compound M1. The other aspects are the same as those of the third embodiment or the fourth embodiment.

[2116] That is, in the fifth embodiment, the light-emitting layer includes the compound M2 and the compound M3.

[2117] In the case of this embodiment, the compound M3 is preferably a host material, and the compound M2 is preferably a dopant material.

[2118] In this embodiment, when the light-emitting layer contains the compound of the first embodiment, the light-emitting layer preferably does not contain a phosphorescent metal complex, and preferably does not contain a metal complex other than the phosphorescent metal complex.

[2119] <Compound M2>

[2120] Compound M2 is the compound of the first embodiment.

[2121] It is preferred that the compound M2 is a delayed fluorescence compound.

[2122] <Compound M3>

[2123] The compound M3 is the same as the compound M3 described in the fourth embodiment.

[2124] <Relationship between Compound M2 and Compound M3 in the Emitting Layer>

[2125] In the organic EL device of this embodiment, it is preferred that the lowest excited singlet energy S of the compound M2 is 1 (M2) and the lowest excited singlet energy S of compound M3 1 (M3) satisfies the relationship of the following mathematical formula (2).

[2126] S 1 (M3)>S 1 (M2)…(number 2)

[2127] 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).

[2128] Figure 6 It is a diagram for explaining the principle of light emission according to the embodiment of the present invention.

[2129] exist Figure 6 In the formula, 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.

[2130] like Figure 6 As shown, if a compound having a small ΔST(M2) is used as compound M2, the lowest excited triplet state T1(M2) of compound M2 can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) by thermal energy.

[2131] By utilizing the reverse intersystem crossing caused by the compound M2, for example, light emission as shown in the following (i) or the following (ii) can be observed.

[2132] (i) When the light-emitting layer does not contain a fluorescent dopant whose lowest excited singlet state S1 is lower 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.

[2133] (ii) When the light-emitting layer contains a fluorescent dopant (fluorescent compound M1 in the third embodiment or the fourth embodiment) whose lowest excited singlet state S1 is lower than the lowest excited singlet state S1(M2) of compound M2, light emission from the fluorescent dopant can be observed.

[2134] In the organic EL device of this embodiment, the light emission shown in (i) can be observed. In the organic EL device of the third embodiment or the fourth embodiment, the light emission shown in (ii) can be observed.

[2135] ·Content ratio of the compound in the light-emitting layer

[2136] The content of the compound M2 and the compound M3 contained in the light-emitting layer is preferably within the following ranges, for example.

[2137] The content of the compound M2 is preferably 10 mass % to 90 mass %, more preferably 10 mass % to 80 mass %, further preferably 10 mass % to 60 mass %, and even more preferably 20 mass % to 60 mass %.

[2138] The content of the compound M3 is preferably 10% by mass or more and 90% by mass or less.

[2139] The upper limit of the total content of the compound M2 and the compound M3 in the light-emitting layer is 100 mass %.

[2140] The light-emitting layer may contain only one compound M2, or may contain two or more compounds M2. The light-emitting layer may contain only one compound M3, or may contain two or more compounds M3.

[2141] The organic EL element of the fifth embodiment contains the compound of the first embodiment as compound M2 and compound M3 having a lower minimum excited singlet energy than compound M2 in the light-emitting layer. The organic EL element of the fifth embodiment contains the compound of the first embodiment (compound M2) having a high PLQY, and therefore, according to the fifth embodiment, a high-performance organic EL element capable of achieving at least one of high efficiency and long life can be provided.

[2142] [Sixth embodiment]

[2143] [Electronic equipment]

[2144] The electronic device of this embodiment is equipped with any of the organic EL elements of the above embodiments. As electronic devices, for example, display devices and light-emitting devices can be cited. As display devices, for example, display components (such as organic EL panel modules, etc.), televisions, mobile phones, tablet computers, and personal computers can be cited. As light-emitting devices, for example, lighting and vehicle lamps can be cited.

[2145] [Variations of Embodiments]

[2146] 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.

[2147] 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.

[2148] 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.

[2149] 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.

[2150] 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.

[2151] 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.

[2152] 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.

[2153] It is preferred that the light-emitting layer is in contact with the blocking layer.

[2154] 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.

[2155] Example

[2156] The present invention is further described in detail with reference to the following examples, but the present invention is not limited to these examples.

[2157] <Compound>

[2158] The structures of the compounds represented by the general formula (1) used for producing the organic EL devices of Examples 1-1 to 1-5, Examples 2-1 to 2-11, Examples 3-1 to 3-24, and Examples 4-1 to 4-25 are shown below.

[2159] [Chemistry 232]

[2160]

[2161] [Chemistry 233]

[2162]

[2163] [Chemistry 234]

[2164]

[2165] [Chemistry 235]

[2166]

[2167] [Chemistry 236]

[2168]

[2169] [Chemistry 237]

[2170]

[2171] [Chemistry 238]

[2172]

[2173] [Chemistry 239]

[2174]

[2175] The structures of the compounds used for producing the organic EL devices of Comparative Examples 1-1, 2-1, 3-1, and 4-1 are shown below.

[2176] [Chemistry 240]

[2177]

[2178] The structures of other compounds used for producing the organic EL devices of Examples 1-1 to 1-5, Examples 2-1 to 2-11, Examples 3-1 to 3-24, Examples 4-1 to 4-25, Comparative Examples 1-1, 2-1, 3-1, and 4-1 are shown below.

[2179] [Chemistry 241]

[2180]

[2181] [Chemistry 242]

[2182]

[2183] [Chemistry 243]

[2184]

[2185] <Production of organic EL elements (1)>

[2186] An organic EL device was produced and evaluated as follows.

[2187] (Example 1-1)

[2188] 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.

[2189] 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.

[2190] Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 110 nm.

[2191] Next, compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[2192] Next, the compound CBP was vapor-deposited on the second hole transport layer to form an electron blocking layer with a film thickness of 5 nm.

[2193] Next, compound M3-1 as compound M3 and compound A-1 as compound M2 were co-evaporated on the electron blocking layer to form a 25 nm thick light-emitting layer. The concentration of compound M3-1 in the light-emitting layer was set to 75% by mass, and the concentration of compound A-1 was set to 25% by mass.

[2194] Next, compound ET-1 was vapor-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 5 nm.

[2195] Next, compound ET-2 was deposited on the hole blocking layer to form an electron transporting layer with a thickness of 50 nm.

[2196] Next, LiF was vapor-deposited on the electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[2197] Then, metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode with a film thickness of 80 nm.

[2198] The device configuration of the organic EL device of Example 1-1 is schematically shown as follows.

[2199] ITO(130) / HT-1: HA(10, 97%: 3%) / HT-1(110) / HT-2(5) / CBP(5) / M3-1: A-1(25, 75%: 25%) / ET-1(5) / ET-2(50) / LiF(1) / Al(80)

[2200] In addition, the numbers in parentheses indicate the film thickness (unit: nm).

[2201] In the same bracket, the percentage numbers (97%:3%) show the ratio (mass %) of compound HT-1 and compound HA in the hole injection layer, and the percentage numbers (75%:25%) show the ratio (mass %) of compound M3-1 and compound A-1 in the light-emitting layer. The same notation is used below.

[2202] (Example 1-2 to Example 1-5)

[2203] Organic EL devices of Examples 1-2 to 1-5 were prepared in the same manner as in Example 1-1 except that Compound A-1 used as Compound M2 in the light-emitting layer of Example 1-1 was changed to Compound M2 described in Table 1, respectively.

[2204] (Comparative Example 1-1)

[2205] An organic EL device of Comparative Example 1-1 was prepared in the same manner as in Example 1-1, except that Compound A-1 as Compound M2 used in the light-emitting layer of Example 1-1 was changed to Compound M2 described in Table 1.

[2206] (Example 2-1)

[2207] The organic EL element of Example 2-1 was prepared in the same manner as in Example 1-1, except that compound M3-1 as compound M3, compound A-1 as compound M2, and compound GD as compound M1 were co-evaporated to form a light-emitting layer with a thickness of 25 nm to replace the light-emitting layer of Example 1-1, and the concentration of compound M3-1 in the light-emitting layer was set to 74 mass %, the concentration of compound A-1 was set to 25 mass %, and the concentration of compound GD was set to 1 mass %.

[2208] The device configuration of the organic EL device of Example 2-1 is schematically shown as follows.

[2209] ITO(130) / HT-1: HA(10, 97%: 3%) / HT-1(110) / HT-2(5) / CBP(5) / M3-1: A-1: ​​GD(25, 74%: 25%: 1%) / ET-1(5) / ET-2(50) / LiF(1) / Al(80)

[2210] (Example 2-2 to Example 2-11)

[2211] Organic EL devices of Examples 2-2 to 2-11 were prepared in the same manner as in Example 2-1 except that Compound A-1 used as Compound M2 in the light-emitting layer of Example 2-1 was changed to Compound M2 described in Table 2, respectively.

[2212] (Comparative Example 2-1)

[2213] An organic EL device of Comparative Example 2-1 was prepared in the same manner as in Example 2-1, except that Compound A-1 as Compound M2 used in the light-emitting layer of Example 2-1 was changed to Compound M2 described in Table 2.

[2214] <Evaluation of Organic EL Devices (1)>

[2215] The following evaluations were performed on the produced organic EL elements. The evaluation results are shown in Tables 1 and 2. In addition, although the comparative compound Ref-1 used in Comparative Examples 1-1 and 2-1 does not belong to Compound M2, it is marked in the same column as Compound M2 for convenience. In addition, the evaluation results of the compounds used in the light-emitting layers of each example are also shown in Tables 1 and 2.

[2216] (Lifespan LT95)

[2217] 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: time)) 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.

[2218] "LT95 (relative value)" shown in Table 1 was calculated based on the measured value of LT95 of each example (Example 1-1 to Example 1-5 and Comparative Example 1-1) and the following mathematical formula (numeral 1X).

[2219] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1-1) × 100 ... (number 1X)

[2220] (External quantum efficiency EQE)

[2221] The organic EL element was measured by applying a voltage to a current density of 10.00 mA / cm using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.). 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 2 shows "EQE (relative value)" (unit: %).

[2222] The "EQE (relative value)" shown in Table 2 was calculated based on the measured value of EQE of each example (Example 2-1 to Example 2-11 and Comparative Example 2-1) and the following mathematical formula (numeral 2X).

[2223] EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) × 100 ... (number 2X)

[2224] (Maximum peak wavelength λ p and luminous half width (FWHM)

[2225] The organic EL element was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.) by applying a voltage to the element so that the current density of the element reached 10.00 mA / cm 2 The maximum peak wavelength λ was calculated from the obtained spectral emission brightness spectrum. p (Unit: nm) and the half-width value FWHM (Unit: nm). FWHM is the abbreviation of Full Width that Half Maximum.

[2226] (CIE1931 chromaticity)

[2227] The organic EL element was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta, Inc.) by applying a voltage to the element so that the current density reached 10.00 mA / cm 2 CIE1931 chromaticity coordinates (x, y) at .

[2228] [Table 1]

[2229]

[2230] [Table 2]

[2231]

[2232] <Production of organic EL elements (2)>

[2233] (Example 3-1)

[2234] 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.

[2235] The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum evaporation device, and compound HT-3 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-3 in the hole injection layer was set to 97% by mass, and the concentration of compound HA was set to 3% by mass.

[2236] Next, compound HT-3 was vapor-deposited on the hole injection layer to form a first hole transport layer with a film thickness of 90 nm.

[2237] Next, compound HT-4 was vapor-deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 30 nm.

[2238] Next, compound M3-2 as compound M3 and compound A-1 as compound M2 were co-evaporated on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The concentration of compound M3-2 in the light-emitting layer was set to 75% by mass, and the concentration of compound A-1 was set to 25% by mass.

[2239] Next, compound ET-3 was vapor-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 5 nm.

[2240] Next, compound ET-4 and compound Liq were co-evaporated on the hole blocking layer to form an electron transport layer with a thickness of 50 nm. The concentration of compound ET-4 in the electron transport layer was 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.

[2241] Next, ytterbium (Yb) was vapor-deposited on the electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[2242] Then, metal aluminum (Al) was vapor-deposited on the electron injection layer to form a metal Al cathode with a film thickness of 80 nm.

[2243] The device configuration of the organic EL device of Example 3-1 is schematically shown as follows.

[2244] ITO (130) / HT-3: HA (10, 97%: 3%) / HT-3 (90) / HT-4 (30) / M3-2: A-1 (25, 75%: 25%) / ET-3 (5) / ET-4: Liq (50, 50%: 50%) / Yb (1) / Al (80)

[2245] (Example 3-2 to Example 3-20)

[2246] Organic EL devices of Examples 3-2 to 3-20 were prepared in the same manner as in Example 3-1 except that Compound A-1 used as Compound M2 in the light-emitting layer of Example 3-1 was changed to Compound M2 described in Table 3, respectively.

[2247] (Example 3-21 to Example 3-24)

[2248] Organic EL devices of Examples 3-21 to 3-24 were prepared in the same manner as in Example 3-1 except that Compound A-1 used as Compound M2 in the light-emitting layer of Example 3-1 was changed to Compound M2 described in Table 4, respectively.

[2249] (Comparative Example 3-1)

[2250] An organic EL device of Comparative Example 3-1 was prepared in the same manner as in Example 3-1, except that Compound A-1 used as Compound M2 in the light-emitting layer of Example 3-1 was changed to Compound M2 described in Table 3.

[2251] (Example 4-1)

[2252] The organic EL element of Example 4-1 was prepared in the same manner as in Example 3-1, except that compound M3-2 as compound M3, compound A-40 as compound M2, and compound GD2 as compound M1 were co-evaporated to form a light-emitting layer with a thickness of 25 nm to replace the light-emitting layer of Example 3-1, and the concentration of compound M3-2 in the light-emitting layer was set to 74.4 mass %, the concentration of compound A-40 was set to 25 mass %, and the concentration of compound GD2 was set to 0.6 mass %.

[2253] The device configuration of the organic EL device of Example 4-1 is schematically shown as follows.

[2254] ITO (130) / HT-3: HA (10, 97%: 3%) / HT-3 (90) / HT-4 (30) / M3-2: A-40: GD2 (25, 74.4%: 25%: 0.6%) / ET-3 (5) / ET-4: Liq (50, 50%: 50%) / Yb (1) / Al (80)

[2255] (Example 4-2)

[2256] An organic EL device of Example 4-2 was prepared in the same manner as in Example 4-1, except that the compound A-40 used as the compound M2 in the light-emitting layer of Example 4-1 was changed to the compound M2 described in Table 5.

[2257] (Example 4-3 to Example 4-25)

[2258] Organic EL devices of Examples 4-3 to 4-25 were prepared in the same manner as in Example 4-1 except that the compound A-40 used as the compound M2 in the light-emitting layer of Example 4-1 was changed to the compound M2 described in Tables 6 and 7, respectively.

[2259] (Comparative Example 4-1)

[2260] An organic EL device of Comparative Example 4-1 was prepared in the same manner as in Example 4-1, except that the compound A-40 used as the compound M2 in the light-emitting layer of Example 4-1 was changed to the compound M2 described in Table 5.

[2261] <Evaluation of Organic EL Devices (2)>

[2262] The organic EL elements produced in Examples 3-1 to 3-24, Examples 4-1 to 4-25, Comparative Examples 3-1 and 4-1 were evaluated for the items shown in Tables 3, 4, 5, 6 and 7 by the method described in <Evaluation of Organic EL Elements (1)>. The evaluation results are shown in Tables 3, 4, 5, 6 and 7.

[2263] The "EQE (relative value)" shown in Tables 3 and 4 was calculated based on the measured value of EQE of each example (Example 3-1 to Example 3-24 and Comparative Example 3-1) and the following mathematical formula (Equation 3X).

[2264] EQE (relative value) = (EQE of each example / EQE of Comparative Example 3-1) × 100 ... (number 3X)

[2265] The "EQE (relative value)" shown in Tables 5, 6, and 7 was calculated based on the measured value of EQE of each example (Example 4-1 to Example 4-25 and Comparative Example 4-1) and the following mathematical formula (Equation 4X).

[2266] EQE (relative value) = (EQE of each example / EQE of Comparative Example 4-1) × 100 ... (number 4 ×)

[2267] [Table 3]

[2268]

[2269] [Table 4]

[2270]

[2271] [Table 5]

[2272]

[2273] [Table 6]

[2274]

[2275] [Table 7]

[2276]

[2277] The organic EL device of the example using the compound represented by the general formula (1) has improved device performance compared with the organic EL device of the comparative example.

[2278] <Evaluation of Compounds>

[2279] The compounds used in the production of Examples and the following compounds were evaluated.

[2280] [Chemistry 244]

[2281]

[2282] [Chemistry 245]

[2283]

[2284] (Measurement of fluorescence quantum yield (PLQY))

[2285] The compound to be measured was dissolved in toluene so as to have a concentration of 5 μmol / L to prepare a toluene solution, and then the solution was nitrogen bubbled for 5 minutes and sealed to prevent the outside air from entering.

[2286] The PLQY of the prepared toluene solution of the compound to be measured was measured using an absolute PL (photoluminescence) quantum yield measuring apparatus Quantaurus-QY (manufactured by Hamamatsu Photonics Co., Ltd.).

[2287] (Maximum peak wavelength of the compound)

[2288] The maximum peak wavelength λ of the compound was measured by the following method.

[2289] 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 spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Technologies Co., Ltd. In addition, the luminescence spectrum measuring device is not limited to the device used here. In the luminescence spectrum, the peak wavelength of the fluorescence spectrum with the maximum luminescence intensity is taken as the maximum peak wavelength λ.

[2290] (Delayed fluorescence of the compound)

[2291] Delayed fluorescence is achieved by utilizing Figure 1 The transition PL was measured by the device shown in the figure. The compound A-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.

[2292] 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.

[2293] After being excited by pulsed light (light irradiated by pulsed laser) of a wavelength absorbed by the compound A-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.

[2294] 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 for calculating the amount of prompt luminescence and delay luminescence is not limited to the device described in reference 1 or Figure 1 The device described in .

[2295] Compounds A-2 to A-42 and comparative compound Ref-1 were measured in the same manner as compound A-1.

[2296] For compounds A-1 to A-42 and comparative compound Ref-1, it was confirmed that the amount of Delay luminescence was 5% or more relative to the amount of Prompt luminescence. Specifically, for compounds A-1 to A-42 and comparative compound Ref-1, X D / X P The value of is 0.05 or more.

[2297] (The lowest excited singlet energy S 1 )

[2298] The lowest excited singlet energy S of the compound to be measured is measured by the solution method. 1 .

[2299] (Energy gap T 77K and △ST)

[2300] Using the energy gap T described in the above “Relationship between triplet energy and energy gap at 77 [K]” 77K The measurement method has an effect on the ability of the measured compound to wash 77K Take measurements.

[2301] For compounds A-1 to A-42 and comparative compound Ref-1, according to the energy gap T 77K The value of the lowest excited singlet energy S 1 The value of confirms △ST. "<0.01" in the table means that △ST is less than 0.01eV.

[2302] [Table 8]

[2303]

[2304] <Synthesis example>

[2305] (Synthesis of Compound A-1)

[2306] The synthesis method of compound A-1 is described below.

[2307] [Chemistry 246]

[2308]

[2309] Under nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (165g, 607mmol), cuprous cyanide (120g, 1335mmol) and NMP (800ml) were added to a 2L three-necked flask and stirred at 150°C for 5 hours. 1L of dichloromethane was added to the reaction mixture, filtered using diatomaceous earth, and the filtrate was concentrated using an evaporator. The solid obtained after concentration was purified by silica gel chromatography to obtain 58g of a white solid. The obtained white solid was identified as intermediate Ma (yield 58%) by analysis of GS-MS (Gas Chromatograph Mass Spectrometer). NMP is the abbreviation of N-methyl-2-pyrrolidone.

[2310] Under nitrogen atmosphere, intermediate Ma (20g, 122mmol), potassium carbonate (33.7g, 244mmol), diacetoxypalladium (1.368g, 6.09mmol), tricyclohexylphosphine (5.13g, 18.28mmol), bromobenzene (31.9ml, 305mmol), 2-ethylhexanoic acid (7.81ml, 48.7mmol) and xylene (250ml) were added to a 500mL three-necked flask and stirred at 100°C for 5 hours. 200ml of dichloromethane was added to the reaction solution and passed through diatomaceous earth. The dichloromethane of the obtained solution was removed and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 12g of white solid. The obtained white solid was identified as intermediate Mb (yield 31%) by GC-MS analysis.

[2311] [Chemistry 247]

[2312]

[2313] Under nitrogen atmosphere, 3-bromodibenzothiophene (26.3 g, 100 mmol), trimethylsilyl chloride (33 g, 300 mmol) and THF (150 mL) were added to a 500 ml three-necked flask. After the materials in the three-necked flask were cooled to -78°C by a dry ice / acetone bath, 125 ml of lithium diisopropylamide (2M, THF solution) was added dropwise. Stir at -78°C for 2 hours, then return to room temperature and stir for further 2 hours. After stirring, water (100 mL) was added to the three-necked flask and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine and dried with magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. 200 ml of dichloromethane was added to the obtained liquid, followed by iodine monochloride (49 g, 300 mmol) being added dropwise at 0°C, and then stirred at 40°C for 6 hours. The mixture was returned to room temperature, saturated sodium bisulfite aqueous solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain the intermediate Mc (28 g, 72 mmol, yield 72%).

[2314] Under nitrogen atmosphere, intermediate Mc (24.5 g, 63.0 mmol), dibenzo[b, d]thiophene-4-amine (12.55 g, 63.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.865 g, 0.945 mmol), Xantphos (4,5-bis(diphenylphosphine-9,9-dimethylxanthene) (1.385 g, 1.889 mmol), sodium tert-butoxide (9.08 g, 94 mmol) and 210 mL of toluene were added to a 500 ml three-necked flask, heated and stirred at 60°C for 8 hours, and then cooled to room temperature (25°C). The precipitated solid was filtered and washed with 200 ml of toluene to obtain 25 g of a white solid. The obtained white solid was identified as intermediate Md (yield 86%) by GC-MS analysis.

[2315] Under nitrogen atmosphere, intermediate Md (9.5 g, 20.7 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.36 g, 0.82 mmol), palladium (II) acetate (0.093 g, 0.41 mmol), potassium carbonate (5.8 g, 42 mmol) and 60 mL of N, N-dimethylacetamide (DMAc) were added to a 200 ml three-necked flask, and stirred at 160 ° C for 10 hours and then cooled to room temperature (25 ° C). The precipitated solid was filtered and washed with acetone to obtain 6.9 g of white solid. The obtained white solid was identified as intermediate Me (yield 86%) by ASAP-MS analysis. ASAP-MS is the abbreviation of Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[2316] [Chemistry 248]

[2317]

[2318] Under nitrogen atmosphere, intermediate Mb (3.0 g, 9.48 mmol), intermediate Me (3.6 g, 9.5 mmol), potassium carbonate (2.6 g, 19 mmol) and 50 mL of DMF were added to a 200 mL three-necked flask and stirred at 100 ° C for 4 hours. 100 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 4.1 g of yellow solid. The obtained yellow solid was identified as intermediate Mf (yield 64%) by ASAP-MS analysis. DMF is the abbreviation of N, N-dimethylformamide.

[2319] Under nitrogen atmosphere, 12H-[1]benzothieno[2,3-a]carbazole (0.809 g, 2.96 mmol), sodium hydride (containing 40% oil by mass) (0.14 g, 3.55 mmol) and 15 mL of DMF were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mf (2 g, 2.96 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.6 g of a yellow solid. The obtained yellow solid was identified as compound A-1 (yield 58%) by ASAP-MS analysis.

[2320] (Synthesis of Compound A-2)

[2321] The synthesis method of compound A-2 is described below.

[2322] [Chemistry 249]

[2323]

[2324] Under nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (0.971 g, 3.55 mmol), sodium hydride (containing 40% oil by mass) (0.14 g, 3.55 mmol) and 15 mL of DMF were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mf (2 g, 2.96 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.2 g of a yellow solid. The obtained yellow solid was identified as compound A-2 (yield 80%) by ASAP-MS analysis.

[2325] (Synthesis of Compound A-3)

[2326] The synthesis method of compound A-3 is described below.

[2327] [Chemistry 250]

[2328]

[2329] In a 500 ml three-necked flask under nitrogen atmosphere, intermediate Mc (20 g, 51.4 mmol), dibenzo[b,d]furan-4-amine (9.42 g, 51.4 mmol), Pd 2 dba 3 (0.706g, 0.771mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(triphenyl-14-phosphine) (1.130g, 1.542mmol), NaOt-Bu (7.41g, 77mmol) and toluene (171ml) were heated and stirred at 60°C for 8 hours and then cooled to room temperature (25°C). The precipitated solid was filtered and washed with 200mL of toluene to obtain 19g of white solid. The obtained white solid was identified as intermediate Mg by GC-MS analysis (yield 83%).

[2330] Under nitrogen atmosphere, intermediate Mg (15 g, 33.8 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.430 g, 1.013 mmol), palladium (II) acetate (0.114 g, 0.506 mmol), potassium carbonate (9.80 g, 70.9 mmol) and DMAc (169 ml) were added to a 300 ml three-necked flask, and stirred at 140° C. for 6 hours and then cooled to room temperature (25° C.). The precipitated solid was filtered and washed with acetone to obtain 8.4 g of a white solid. The obtained white solid was identified as intermediate Mh (yield 69%) by ASAP-MS analysis.

[2331] [Chemistry 251]

[2332]

[2333] Under nitrogen atmosphere, intermediate Mh (0.532 g, 1.465 mmol), sodium hydride (containing 40% oil by mass) (0.064 g, 1.598 mmol) and 15 mL of DMF were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mf (0.9 g, 1.332 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 0.7 g of a yellow solid. The obtained yellow solid was identified as compound A-3 (yield 52%) by ASAP-MS analysis.

[2334] (Synthesis of Compound A-4)

[2335] The synthesis method of compound A-4 is described below.

[2336] [Chemistry 252]

[2337]

[2338] Under nitrogen atmosphere, intermediate Mb (3 g, 9.48 mmol), tripotassium phosphate (4.03 g, 18.97 mmol), intermediate Mh (3.45 g, 9.48 mmol) and DMF (47.4 ml) were added to a 200 mL three-necked flask and stirred at 60°C for 4 hours. 100 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 4.9 g of a yellow solid. It was identified as intermediate Mi (yield 78%) by ASAP-MS analysis.

[2339] Under nitrogen atmosphere, 12H-[1]benzothieno[2,3-a]carbazole (0.912 g, 3.33 mmol), sodium hydride (containing 40% by mass oil) (0.133 g, 3.33 mmol) and DMF (15.16 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mi (2 g, 3.03 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.1 g of a yellow solid. The obtained yellow solid was identified as compound A-4 (yield 40%) by ASAP-MS analysis.

[2340] (Synthesis of Compound A-5)

[2341] The synthesis method of compound A-5 is described below.

[2342] [Chemistry 253]

[2343]

[2344] Under nitrogen atmosphere, 5H-benzo[4,5]thieno[3,2-c]carbazole (0.646 g, 2.365 mmol), sodium hydride (containing 40% by mass oil) (0.095 g, 2.365 mmol) and DMF (19.70 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mi (1.3 g, 1.970 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.4 g of a yellow solid. The obtained yellow solid was identified as compound A-5 (yield 78%) by ASAP-MS analysis.

[2345] (Synthesis of Compound A-6)

[2346] The synthesis method of compound A-6 is described below.

[2347] [Chemistry 254]

[2348]

[2349] Under nitrogen atmosphere, intermediate Mh (1 g, 3.16 mmol), sodium hydride (containing 40% by mass oil) (0.278 g, 6.96 mmol) and DMF (15.8 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mb (2.53 g, 6.96 mmol) was added to the reaction mixture and stirred at 100°C for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.1 g of a yellow solid. The obtained yellow solid was identified as compound A-6 (yield 66%) by ASAP-MS analysis.

[2350] (Synthesis of Compound A-7)

[2351] The synthesis method of compound A-7 is described below.

[2352] [Chemistry 255]

[2353]

[2354] Under nitrogen atmosphere, 1,3-dibromo-2,5-difluorobenzene (35 g, 129 mmol), cuprous cyanide (25.4 g, 283 mmol) and NMP (257 ml) were added to a 1L three-necked flask and stirred at 150°C for 5 hours. 500 mL of dichloromethane was added to the reaction mixture, filtered using diatomaceous earth, and the filtrate was concentrated using an evaporator. The solid obtained after concentration was purified by silica gel chromatography and recrystallized from ethanol to obtain 12 g of a white solid. The obtained white solid was identified as intermediate Mj (yield 57%) by GC-MS analysis.

[2355] Under nitrogen atmosphere, 2,5-difluoroisophthalonitrile (6.3 g, 38.4 mmol), potassium carbonate (11.67 g, 84 mmol), diacetoxypalladium (0.431 g, 1.919 mmol), tricyclohexylphosphonium tetrafluoroborate (2.120 g, 5.76 mmol), bromobenzene (12.05 ml, 115 mmol), 2-ethylhexanoic acid (2.460 ml, 15.36 mmol) and xylene (80 ml) were added to a 300 mL three-necked flask and stirred at 100 ° C for 5 hours. 100 ml of dichloromethane was added to the reaction solution and passed through diatomaceous earth. The dichloromethane of the obtained solution was concentrated and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 5.2 g of white solid. The obtained white solid was identified as intermediate Mk (yield 43%) by GC-MS analysis.

[2356] [Chemistry 256]

[2357]

[2358] Under nitrogen atmosphere, intermediate Mk (1.5 g, 4.74 mmol), intermediate Me (1.8 g, 4.74 mmol), tripotassium phosphate (3.02 g, 14.23 mmol) and DMF (23.71 ml) were added to a 200 mL three-necked flask and stirred at 60°C for 4 hours. 100 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 2 g of a yellow solid. The obtained yellow solid was identified as intermediate ML (yield 62%) by ASAP-MS analysis.

[2359] Under nitrogen atmosphere, 12H-[1]benzothieno[2,3-a]carbazole (0.922 g, 3.37 mmol), sodium hydride (containing 40% by mass oil) (0.124 g, 3.09 mmol) and DMF (14.06 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate ML (1.9 g, 2.81 mmol) was added to the reaction mixture and stirred at 70°C for 8 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.8 g of a yellow solid. The obtained yellow solid was identified as compound A-7 (yield 69%) by ASAP-MS analysis.

[2360] (Synthesis of Compound A-8)

[2361] The synthesis method of compound A-8 is described below.

[2362] [Chemistry 257]

[2363]

[2364] Under nitrogen atmosphere, intermediate Mk (2.4 g, 7.59 mmol), 12H-[1]benzothieno[2,3-a]carbazole (2.074 g, 7.59 mmol), tripotassium phosphate (4.83 g, 22.76 mmol) and DMF (37.9 ml) were added to a 200 mL three-necked flask and stirred at 50°C for 4 hours. 100 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 4 g of a yellow solid. The obtained yellow solid was identified as intermediate M-k2 (yield 93%) by ASAP-MS analysis.

[2365] Under nitrogen atmosphere, intermediate Me (1.332 g, 3.51 mmol), sodium hydride (containing 40% oil by mass) (0.154 g, 3.86 mmol) and DMF (14.06 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate M-k2 (2 g, 3.51 mmol) was added to the reaction mixture and stirred at 170°C for 14 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 0.98 g of a yellow solid. The obtained yellow solid was identified as compound A-8 (yield 30%) by ASAP-MS analysis.

[2366] (Synthesis of Compound A-9)

[2367] The synthesis method of compound A-9 is described below.

[2368] [Chemistry 258]

[2369]

[2370] Under nitrogen atmosphere, 9H-carbazole (2.313 g, 13.84 mmol), sodium hydride (containing 40% oil by mass) (0.488 g, 12.21 mmol) and DMF (40.7 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mf (5.5 g, 8.14 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 6.3 g of a yellow solid. The obtained yellow solid was identified as compound A-9 (yield 94%) by ASAP-MS analysis.

[2371] (Synthesis of Compound A-10)

[2372] The synthesis method of compound A-10 is described below.

[2373] [Chemistry 259]

[2374]

[2375] Under nitrogen atmosphere, 12H-benzofurano[2,3-a]carbazole (1.466 g, 5.70 mmol), sodium hydride (containing 40% oil by mass) (0.228 g, 5.70 mmol) and DMF (17.26 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Then, intermediate Mf (3.5 g, 5.18 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.7 g of a yellow solid. The obtained yellow solid was identified as compound A-10 (yield 78%) by ASAP-MS analysis.

[2376] (Synthesis of Compound A-11)

[2377] The synthesis method of compound A-11 is described below.

[2378] [Chemistry 260]

[2379]

[2380] Under nitrogen atmosphere, 5-bromo-1,3-difluoro-2-iodobenzene (4.00 g, 12.54 mmol), o-toluene boronic acid (3.75 g, 27.60 mmol), potassium carbonate (10.40 g, 75.00 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium (0.266 g, 0.376 mmol), DME (66.9 ml) and ion exchange water (16.7 ml) were added to a 200 mL three-necked flask, and stirred at 90° C. for 5 hours. 100 ml of ion exchange water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mm (3.50 g, 11.9 mmol, yield 95%).

[2381] [Chemistry 261]

[2382]

[2383] Under nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (2.428 ml, 14.27 mmol) and THF (20 ml) were added to a 200 ml three-necked flask. After the material in the three-necked flask was cooled to -78°C by a dry ice / acetone bath, 14.3 ml of n-butyl lithium (1.6 M, hexane solution) was added dropwise. Stir at 0°C for 20 minutes, cool to -78°C, then add a solution obtained by dissolving the intermediate Mm (3.5 g, 11.89 mmol) in 20 ml of THF, and stir for 15 minutes. After stirring, bromine (1.218 ml, 23.78 mmol) was added to the solution, and stirred for 20 minutes after returning to room temperature. After stirring, a saturated sodium bisulfite aqueous solution (100 mL) was added to the solution, and the organic layer was extracted with hexane, and the extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained liquid was dissolved in 20 ml of THF, and the prepared solution was added dropwise to the THF solution of LiTMP prepared again at -78 ° C and stirred for 15 minutes. Bromine (0.77 ml, 15.0 mmol) was added thereto, and stirred for 20 minutes after returning to room temperature. Saturated sodium bisulfite aqueous solution (100 mL) was added to the stirred solution, and the organic layer was extracted with hexane, and the extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mn (2.75 g, 6.07 mmol, yield 51%). LiTMP is the abbreviation of 2,2,6,6-tetramethylpiperidinium lithium.

[2384] Under nitrogen atmosphere, intermediate Mn (2.75 g, 6.07 mmol), cuprous cyanide (1.31 g, 14.6 mmol) and DMF (66 ml) were added to a 1L three-necked flask and stirred at 150°C for 5 hours. 500 mL of dichloromethane was added to the reaction mixture, filtered using diatomaceous earth, and the filtrate was concentrated using an evaporator. The solid obtained after concentration was purified by silica gel chromatography to obtain 1.0 g of a white solid. The obtained white solid was identified as intermediate Mo by GC-MS analysis (yield 44%).

[2385] [Chemistry 262]

[2386]

[2387] Under nitrogen atmosphere, intermediate Mo (1.0 g, 2.90 mmol), cesium fluoride (1.32 g, 8.71 mmol), intermediate Me (1.1 g, 2.90 mmol) and DMF (10.0 ml) were added to a 100 mL eggplant flask and stirred at room temperature for 20 hours. 50 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 1.5 g of a yellow solid. The obtained yellow solid was identified as intermediate Mp (yield 75%) by ASAP-MS analysis.

[2388] Under nitrogen atmosphere, intermediate Mp (1.54 g, 2.20 mmol), 12H-[1]benzothieno[2,3-a]carbazole (0.718 g, 2.63 mmol), cesium fluoride (1.00 g, 6.56 mmol) and DMF (11.0 ml) were added to a 100 mL eggplant flask and stirred at 50°C for 1 hour. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.62 g of a yellow solid. The obtained yellow solid was identified as compound A-11 (yield 77%) by ASAP-MS analysis.

[2389] (Synthesis of Compound A-12)

[2390] The synthesis method of compound A-12 is described below.

[2391] [Chemistry 263]

[2392]

[2393] Under nitrogen atmosphere, 5-bromo-1,3-difluoro-2-iodobenzene (5.00 g, 15.68 mmol), o-toluene boronic acid (2.13 g, 15.68 mmol), potassium phosphate (9.98 g, 47.00 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.128 g, 0.157 mmol), DME (84.1 ml) and ion exchange water (20.9 ml) were added to a 200 mL three-necked flask and stirred at room temperature for 1 hour. 100 ml of ion exchange water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and the washed organic layer was dried over magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mq (3.47 g, 12.3 mmol, yield 78%).

[2394] Under nitrogen atmosphere, intermediate Mq (3.47 g, 12.3 mmol), phenylboric acid (2.26 g, 18.54 mmol), potassium phosphate (7.87 g, 37.1 mmol), bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium (0.101 g, 0.124 mmol), DME (65.9 ml) and ion exchange water (16.5 ml) were added to a 200 mL three-necked flask and stirred at 60°C for 2 hours. 100 ml of ion exchange water was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate Mr (3.15 g, 11.2 mmol, yield 90%).

[2395] [Chemistry 264]

[2396]

[2397] Under nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (3.19 ml, 18.73 mmol) and THF (40 ml) were added to a 200 ml three-necked flask. After the material in the three-necked flask was cooled to -78°C by a dry ice / acetone bath, 18.7 ml of n-butyl lithium (1.6 M, hexane solution) was added dropwise. Stir at 0°C for 20 minutes, and after cooling to -78°C, a solution obtained by dissolving the intermediate Mr (3.15 g, 11.2 mmol) in 20 ml of THF was added and stirred for 15 minutes. After stirring, bromine (1.28 ml, 25.0 mmol) was added to the solution, and the solution was returned to room temperature and stirred for 20 minutes. After stirring, a saturated sodium bisulfite aqueous solution (100 mL) was added to the solution, and the organic layer was extracted with hexane, and the extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained liquid was dissolved in 20 ml of THF, and the prepared solution was added dropwise to the THF solution of LiTMP prepared again at -78 ° C and stirred for 15 minutes. Bromine (1.28 ml, 25.0 mmol) was added thereto, and the mixture was stirred for 20 minutes after returning to room temperature. After stirring, saturated aqueous sodium bisulfite solution (100 mL) was added to the solution, and the organic layer was extracted with hexane, the extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain an intermediate Ms (4.16 g, 9.51 mmol, yield 85%).

[2398] Under nitrogen atmosphere, add intermediate Ms (4.16g, 9.51mmol), cuprous cyanide (2.20g, 24.6mmol) and DMF (112ml) to a 1L three-necked flask and stir at 160°C for 10 hours. Add 500mL of dichloromethane to the reaction mixture, filter with diatomaceous earth, and concentrate the filtrate with an evaporator. Purify the solid obtained after concentration by silica gel chromatography to obtain 1.57g of white solid. By GC-MS analysis, the obtained white solid was identified as intermediate Mt (yield 42%).

[2399] [Chemistry 265]

[2400]

[2401] Under nitrogen atmosphere, intermediate Mt (1.0 g, 3.03 mmol), cesium fluoride (1.38 g, 9.08 mmol), intermediate Me (1.15 g, 3.03 mmol) and DMF (15.0 ml) were added to a 100 mL eggplant flask and stirred at room temperature for 20 hours. 50 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 1.55 g of a yellow solid. The obtained yellow solid was identified as intermediate Mu (yield 74%) by ASAP-MS analysis.

[2402] Under nitrogen atmosphere, intermediate Mu (1.55 g, 2.25 mmol), 12H-[1]benzothieno[2,3-a]carbazole (0.737 g, 2.70 mmol), cesium fluoride (1.02 g, 6.74 mmol) and DMF (11.0 ml) were added to a 100 mL eggplant flask and stirred at 50°C for 1 hour. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 1.6 g of a yellow solid. The obtained yellow solid was identified as compound A-12 (yield 75%) by ASAP-MS analysis.

[2403] (Synthesis of Compound A-13)

[2404] The synthesis method of compound A-13 is described below.

[2405] [Chemistry 266]

[2406]

[2407] Under nitrogen atmosphere, intermediate Ma (20g, 122mmol), diacetoxypalladium (1.368g, 6.09mmol), tricyclohexylphosphine (5.13g, 18.28mmol), potassium carbonate (42.1g, 305mmol) and xylene (244ml) were added to a 500mL three-necked flask and stirred at room temperature for 30 minutes. Then, 2-ethylhexanoic acid (7.81ml, 48.7mmol) and 1-bromo-4-(tert-butyl)benzene (45.7ml, 268mmol) were added and stirred at 100°C for 5 hours. The reaction solution was returned to room temperature, 200ml of dichloromethane was added, and passed through diatomaceous earth. The dichloromethane of the obtained solution was removed, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 36g of white solid. The obtained white solid was identified as intermediate Mv (yield 69%) by GC-MS analysis.

[2408] [Chemistry 267]

[2409]

[2410] Under nitrogen atmosphere, intermediate Mv (7.2 g, 16.80 mmol), intermediate Me (6.38 g, 16.80 mmol), potassium carbonate (4.64 g, 33.6 mmol) and DMF (56.0 ml) were added to a 200 mL three-necked flask and stirred at 100 ° C for 4 hours. 100 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 12 g of a yellow solid. The obtained yellow solid was identified as intermediate Mw (yield 91%) by ASAP-MS analysis.

[2411] Under nitrogen atmosphere, intermediate Mw (3 g, 3.81 mmol), 12H-benzo[4,5]thieno[2,3-a]carbazole (1.249 g, 4.57 mmol), potassium carbonate (0.789 g, 5.71 mmol) and DMF (12.69 ml) were added to a 100 mL three-necked flask and stirred at 120°C for 4 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.5 g of a yellow solid. The obtained yellow solid was identified as compound A-13 (yield 88%) by ASAP-MS analysis.

[2412] (Synthesis of Compound A-14)

[2413] The synthesis method of compound A-14 is described below.

[2414] [Chemistry 268]

[2415]

[2416] Under nitrogen atmosphere, 5H-pyrido [3, 2-b] indole (0.684 g, 4.07 mmol), potassium carbonate (0.614 g, 4.44 mmol), intermediate Mf (2.5 g, 3.70 mmol) and DMF (12.33 ml) were added to a 100 mL three-necked flask and stirred at 140°C for 4 hours. 20 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.1 g of a yellow solid. The obtained yellow solid was identified as compound A-14 (yield 88%) by ASAP-MS analysis.

[2417] (Synthesis of Compound A-15)

[2418] The synthesis method of compound A-15 is described below.

[2419] [Chemistry 269]

[2420]

[2421] Under a nitrogen atmosphere, 4-phenyl-9H-carbazole (1.1 g, 4.44 mmol), sodium hydride (containing 40% by mass oil) (0.18 g, 4.44 mmol) and DMF (37 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 1 hour. Then, the intermediate Mf (2.5 g, 3.70 mmol) was added at 0°C, the temperature was slowly raised to room temperature, and then stirred at room temperature for 1 hour. After stirring, 30 ml of ion exchange water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain a yellow solid. By analysis of ASAP-MS, the obtained yellow solid was identified as compound A-15 (yield 72%).

[2422] (Synthesis of Compound A-16)

[2423] The synthesis method of compound A-16 is described below.

[2424] [Chemistry 270]

[2425]

[2426] Under a nitrogen atmosphere, 2-phenyl-9H-carbazole (1.1 g, 4.44 mmol), sodium hydride (containing 40% by mass oil) (0.18 g, 4.44 mmol) and DMF (37 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 1 hour. Then, the intermediate Mf (2.5 g, 3.70 mmol) was added at 0°C, the temperature was slowly raised to room temperature, and then stirred at room temperature for 1 hour. 30 ml of ion exchange water was added to the reaction mixture, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain a yellow solid. The obtained yellow solid was identified as compound A-16 (yield 63%) by ASAP-MS analysis.

[2427] (Synthesis of Compound A-17)

[2428] The synthesis method of compound A-17 is described below.

[2429] [Chemistry 271]

[2430]

[2431] Under nitrogen atmosphere, boric acid, B-(6-phenyl-4-dibenzothienyl)-(40g, 132mmol), aminosulfonic acid (29.7g, 263mmol), acetonitrile (658ml) and sodium hydroxide (1M) (881ml, 881mmol) were added to a 1000mL three-necked flask and stirred at room temperature for 24 hours. After stirring, toluene was used for extraction to recover the organic layer. The solvent was removed from the recovered organic layer using an evaporator the next day. The solid obtained was purified by silica gel column chromatography to obtain 17g of white solid. The obtained white solid was identified as intermediate M-1 (yield 48%) by GC-MS analysis.

[2432] Under nitrogen atmosphere, intermediate M-1 (10.6 g, 38.6 mmol), intermediate Mc (15 g, 38.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.353 g, 0.386 mmol), Xantphos (1.13 g, 1.54 mmol), sodium tert-butoxide (5.56 g, 57.8 mmol) and toluene (129 ml) were added to a 500 mL three-necked flask, heated and stirred at 100° C. for 8 hours, and then cooled to room temperature (25° C.). The solution obtained after cooling was purified by silica gel chromatography to obtain 25 g of a white solid. The obtained white solid was identified as intermediate M-2 (yield 77%) by ASAP-MS analysis.

[2433] Under nitrogen atmosphere, intermediate M-2 (8.5 g, 15.84 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.202 g, 0.475 mmol), palladium (II) acetate (0.053 g, 0.238 mmol), potassium carbonate (4.60 g, 33.3 mmol) and N,N-dimethylacetamide (DMAc) (52.8 ml) were added to a 200 mL three-necked flask, and stirred at 160° C. for 10 hours and then cooled to room temperature (25° C.). The precipitated solid was filtered and washed with methanol to obtain 7.2 g of a white solid. The obtained white solid was identified as intermediate M-3 (yield 73%) by ASAP-MS analysis.

[2434] [Chemistry 272]

[2435]

[2436] Under nitrogen atmosphere, intermediate M-3 (4.0 g, 8.8 mmol), cesium fluoride (2.7 g, 17.6 mmol), intermediate Mb (2.9 g, 9.22 mmol) and DMF (30 ml) were added to a 100 mL eggplant flask and stirred at room temperature for 12 hours. After stirring, 50 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 5.5 g of a yellow solid. The obtained yellow solid was identified as intermediate M-4 (yield 83%) by ASAP-MS analysis.

[2437] [Chemistry 273]

[2438]

[2439] Under a nitrogen atmosphere, 9H-carbazole (1.0 g, 45.98 mmol), sodium hydride (containing 40% by mass oil) (0.24 g, 5.98 mmol) and DMF (40 mL) were added to a 100 mL three-necked flask and stirred at 0°C for 1 hour. Then, intermediate M-4 (3.0 g, 3.99 mmol) was added at 0°C, the temperature was slowly raised to room temperature, and then stirred at room temperature for 1 hour. After stirring, 30 mL of ion exchange water was added to the reaction mixture, and the precipitated solid was filtered. The solid obtained was purified by silica gel column chromatography to obtain 2.9 g of a yellow solid. By analysis of ASAP-MS, the obtained yellow solid was identified as compound A-17 (yield 81%).

[2440] (Synthesis of Compound A-18)

[2441] The synthesis method of compound A-18 is described below.

[2442] [Chemistry 274]

[2443]

[2444] Under nitrogen atmosphere, boric acid, B-(6-phenyl-4-dibenzothienyl)-(50 g, 164 mmol), N-bromosuccinimide (NBS) (32.2 g, 181 mmol), potassium acetate (KOAc) (3.23 g, 32.9 mmol) and acetonitrile (470 ml) were added to a 1000 mL three-necked flask and stirred at 50° C. for 6 hours. After stirring, 400 mL of ion exchange water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 44 g of a white solid. The obtained white solid was identified as intermediate M-5 (yield 79%) by ASAP-MS analysis.

[2445] Under nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (26.1ml, 153mmol) and THF (236ml) were added to a 1000mL three-necked flask and ice-cooled to 0°C using an ice bath. n-Butyl lithium (1.6M hexane solution) (96ml, 153mmol) was added dropwise to the ice-cooled reaction solution. After the addition, the mixture was stirred at 0°C for 30 minutes. The mixture was then cooled to -78°C using a dry ice / methanol bath. After cooling, triisopropyl borate (33.3g, 177mmol) and intermediate M-5 (40g, 118mmol) were added in sequence, and the mixture was slowly heated from -78°C to room temperature while stirring. After the reaction was completed, 100ml of 10% hydrochloric acid was added dropwise. After the addition, the organic layer was recovered and the solid obtained was washed with toluene to obtain 40g of a white solid. The obtained white solid was identified as intermediate M-6 (yield 89%) by ASAP-MS analysis.

[2446] Under nitrogen atmosphere, intermediate M-6 (40 g, 104 mmol), N-chlorosuccinimide (NCS) (13.94 g, 104 mmol), cuprous chloride (I) (10.34 g, 104 mmol) and acetonitrile (348 ml) were added to a 1000 mL three-necked flask and stirred at 60 ° C for 6 hours. 300 mL of dichloromethane was added to the reaction mixture, and the obtained solution was concentrated by diatomaceous earth. The obtained solid was purified by silica gel column chromatography to obtain 28 g of white solid. The obtained white solid was identified as intermediate M-7 (yield 72%) by ASAP-MS analysis.

[2447] [Chemistry 275]

[2448]

[2449] Under nitrogen atmosphere, intermediate M-1 (3.5 g, 12.6 mmol), intermediate M-7 (4.7 g, 12.6 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.353 g, 0.386 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.17 g, 0.19 mmol), sodium tert-butoxide (1.8 g, 19.0 mmol) and toluene (42 ml) were added to a 100 mL three-necked flask, and heated and stirred at 60° C. for 8 hours and then cooled to room temperature (25° C.). The obtained solution was purified by silica gel chromatography to obtain 5 g of a white solid. The obtained white solid was identified as intermediate M-8 (yield 70%) by ASAP-MS analysis.

[2450] Under nitrogen atmosphere, intermediate M-8 (25 g, 44 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.202 g, 0.475 mmol), palladium (II) acetate (0.15 g, 0.66 mmol), potassium carbonate (13 g, 92 mmol) and N,N-dimethylacetamide (DMAc) (220 ml) were added to a 500 mL three-necked flask, and stirred at 160° C. for 10 hours and then cooled to room temperature (25° C.). The precipitated solid was filtered and washed with methanol to obtain 18 g of a white solid. The obtained white solid was identified as intermediate M-9 (yield 77%) by ASAP-MS analysis.

[2451] [Chemistry 276]

[2452]

[2453] Under nitrogen atmosphere, intermediate M-9 (18 g, 8.8 mmol), cesium fluoride (7.7 g, 51 mmol), intermediate Mb (11 g, 35.5 mmol) and DMF (230 ml) were added to a 500 mL eggplant flask and stirred at room temperature for 12 hours. 200 ml of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 20 g of a yellow solid. The obtained yellow solid was identified as intermediate M-10 (yield 71%) by ASAP-MS analysis.

[2454] [Chemistry 277]

[2455]

[2456] Under a nitrogen atmosphere, 2-phenyl-9h-carbazole (1.4 g, 5.80 mmol), sodium hydride (containing 40% by mass oil) (0.23 g, 5.80 mmol) and DMF (50 ml) were added to a 100 mL three-necked flask and stirred at 0°C for 1 hour. Then, intermediate M-10 (4.0 g, 4.83 mmol) was added at 0°C, the temperature was slowly raised to room temperature, and then stirred at room temperature for 1 hour. 30 ml of ion exchange water was added to the reaction mixture, and the precipitated solid was filtered out. The solid obtained was purified by silica gel column chromatography to obtain 2.9 g of a yellow solid. The obtained yellow solid was identified as compound A-18 (yield 89%) by ASAP-MS analysis.

[2457] (Synthesis of Compound A-19)

[2458] The synthesis method of compound A-19 is described below.

[2459] [Chemistry 278]

[2460]

[2461] Under nitrogen atmosphere, 4-bromo-9H-carbazole (66.6 g, 271 mmol), (2-chlorophenyl)boric acid (44.4 g, 284 mmol), potassium carbonate (56.1 g, 406 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.1 g, 1.35 mmol), THF (200 ml) and ion exchange water (65 ml) were added to a 500 mL three-necked flask and stirred at room temperature for 8 hours. After stirring, the reaction solution was concentrated. 100 ml of ion exchange water was added to the concentrated reaction solution, the organic layer was extracted with toluene, the extracted organic layer was washed with water and brine, dried with magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after the solvent was removed under reduced pressure was purified by silica gel column chromatography to obtain a white solid. The obtained white solid was identified as intermediate M-11 (yield 96%) using ASAP-MS.

[2462] Under nitrogen atmosphere, intermediate M-11 (6 g, 21.6 mmol), diazabicycloundecene (DBU) (9.67 ml, 64.8 mmol), bis(tri-tert-butylphosphine)palladium (0) (0.552 g, 1.080 mmol) and N, N-dimethylacetamide (DMAc) (22 ml) were added to a 100 ml three-necked flask, and heated, stirred and refluxed for 20 hours. After the reaction was completed, 100 ml of ion exchange water was added, and the organic layer was extracted with toluene. The extracted organic layer was washed with water and brine, dried with sodium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after the solvent was removed under reduced pressure was purified by silica gel column chromatography to obtain 2.8 g of a white solid. The obtained white solid was identified as intermediate M-12 (yield 54%) using ASAP-MS.

[2463] [Chemistry 279]

[2464]

[2465] Under nitrogen atmosphere, intermediate M-12 (1.29 g, 5.33 mmol), sodium hydride (containing 40% oil by mass) (0.21 g, 5.33 mmol) and DMF (45 ml) were added to a 200 mL three-necked flask and stirred at 0°C for 1 hour. Then, intermediate Mf (3.0 g, 4.44 mmol) was added at 0°C, the temperature was slowly raised to room temperature, and then stirred at room temperature for 1 hour. 50 ml of ethyl acetate was added to the reaction mixture and the solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain 3.4 g of a yellow solid. The obtained yellow solid was identified as compound A-19 (yield 85%) by ASAP-MS analysis.

[2466] (Synthesis of Compound A-20)

[2467] The synthesis method of compound A-20 is described below.

[2468] [Chemistry 280]

[2469]

[2470] Under nitrogen atmosphere, 2-bromo-1,3-difluoro-5-iodobenzene (7.00 g, 21.95 mmol), [1,1'-biphenyl]-2-ylboronic acid (4.78 g, 24.15 mmol), potassium phosphate (13.98 g, 65.90 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.359 g, 0.439 mmol), DME (117 ml) and ion exchange water (29 ml) were added to a 200 mL three-necked flask, and stirred at room temperature for 8 hours. After the reaction solution was concentrated, 20 ml of ion exchange water was added, the organic layer was extracted with dichloromethane, the extracted organic layer was washed with water and brine, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. The solvent was removed under reduced pressure and the resulting compound was purified by silica gel column chromatography to obtain Intermediate T-1 (6.97 g, 20.05 mmol, yield 91%).

[2471] Under nitrogen atmosphere, intermediate T-1 (6.97 g, 20.05 mmol), phenylboronic acid (2.95 g, 24.23 mmol), potassium carbonate (12.86 g, 60.6 mmol), 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.330 g, 0.404 mmol), DME (108 ml) and ion exchange water (26.9 ml) were added to a 200 mL three-necked flask and stirred at 60°C for 4 hours. After the reaction solution was concentrated, 20 ml of ion exchange water was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and brine, dried with magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after the solvent was removed under reduced pressure was purified by silica gel column chromatography to obtain intermediate T-2 (6.23 g, 18.1 mmol, yield 90%).

[2472] [Chemistry 281]

[2473]

[2474] Under nitrogen atmosphere, 2,2,6,6-tetramethylpiperidine (6.16 ml, 36.2 mmol) and THF (60 ml) were added to a 200 ml three-necked flask. After the material in the three-necked flask was cooled to -78°C by a dry ice / acetone bath, 22.6 ml of n-butyl lithium (1.6 M, hexane solution) was added dropwise. After stirring at 0°C for 20 minutes, the solution obtained by dissolving intermediate T-2 (6.2 g, 18.1 mmol) in 60 ml of THF was added to the three-necked flask and stirred for 20 minutes. Bromine (2.32 ml, 45.0 mmol) was added to the reaction solution, and the mixture was returned to room temperature and stirred for 20 minutes. Saturated aqueous sodium bisulfite solution (100 mL) was added to the reaction solution, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate. The dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was passed through silica gel column chromatography, and the solvent was removed under reduced pressure using a rotary evaporator. The obtained liquid was dissolved in 60 ml of THF, added dropwise to the THF solution of LiTMP prepared again at -78 ° C and stirred for 15 minutes. Bromine (2.32 ml, 45.0 mmol) was added to the reaction solution, and stirred for 20 minutes after returning to room temperature. Saturated aqueous sodium bisulfite solution (100 mL) was added to the reaction solution, and the organic layer was extracted with hexane. The extracted organic layer was washed with water and brine, and the washed organic layer was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate T-3 (8.1 g, 16.2 mmol, yield 89%).

[2475] Under nitrogen atmosphere, intermediate T-3 (8.1 g, 16.2 mmol), cuprous cyanide (3.19 g, 35.6 mmol) and NMP (162 ml) were added to a 1 L three-necked flask and stirred at 180 ° C for 10 hours. 500 mL of dichloromethane was added to the reaction mixture, filtered using diatomaceous earth, and the filtrate was concentrated using an evaporator. The solid obtained was purified by silica gel chromatography to obtain 1.74 g of a white solid. The obtained white solid was identified as intermediate T-4 (yield 27%) by GC-MS analysis.

[2476] [Chemistry 282]

[2477]

[2478] Under nitrogen atmosphere, intermediate T-4 (1.95 g, 4.97 mmol), cesium fluoride (2.27 g, 14.9 mmol), intermediate Me (1.89 g, 4.97 mmol) and DMF (49.7 ml) were added to a 100 mL eggplant flask and stirred at room temperature for 20 hours. 50 mL of ion exchange water was added to the reaction solution and the precipitated solid was filtered out. The filtered solid was purified by silica gel column chromatography to obtain 2.9 g of a yellow solid. The obtained yellow solid was identified as intermediate T-5 (yield 78%) by ASAP-MS analysis.

[2479] Under nitrogen atmosphere, intermediate T-5 (1.5 g, 2.00 mmol), 9H-carbazole (0.567 g, 3.39 mmol), cesium fluoride (0.909 g, 5.98 mmol) and DMF (20 ml) were added to a 100 mL eggplant flask and stirred at 80 ° C for 4 hours. 200 mL of methanol was added to the reaction mixture, and the precipitated solid was purified by column chromatography to obtain 0.9 g of a yellow solid. The obtained yellow solid was identified as compound A-20 (yield 50%) by ASAP-MS analysis.

[2480] (Synthesis of Compound A-21)

[2481] The synthesis method of compound A-21 is described below.

[2482] [Chemi...

Claims

1. A compound, It is characterized in that It is represented by the following general formula (126A), In the general formula (126A), CN is cyano, D 11 is a group represented by the following general formula (132), D 12 is a group represented by the following general formula (11), R 102 and R 104 is an unsubstituted phenyl group, In the general formula (132), R 111 ~R 118 The adjacent groups of two or more in R are not bonded to each other. 195 ~R 198 The adjacent groups of two or more are not bonded to each other. In the general formula (11), R 1 ~R 8 , and R in the general formula (132) 111 ~R 118 and R 195 ~R 198 Independently, a hydrogen atom, an unsubstituted phenyl group, an unsubstituted p-biphenyl group, an unsubstituted m-biphenyl group, or an unsubstituted o-biphenyl group, X 11 and X 12 Each independently represents a sulfur atom or an oxygen atom, and * represents a position bonded to a benzene ring.

2. The compound according to claim 1, It is characterized in that In the general formula (11), R 1 ~R 8 , and R in the general formula (132) 111 ~R 118 and R 195 ~R 198 Each independently represents a hydrogen atom or an unsubstituted phenyl group.

3. The compound according to claim 1 or 2, It is characterized in that X 11 A sulfur atom.

4. The compound according to claim 1 or 2, It is characterized in that X 11 and X 12 A sulfur atom.

5. The compound according to claim 1 or 2, It is characterized in that Contains deuterium atoms.

6. A material for an organic electroluminescent element, It is characterized in that Containing the compound according to claim 1 or 2.

7. An organic electroluminescent element, It is characterized in that It has a cathode, an anode, and an organic layer. The organic layer contains the compound according to claim 1 or 2 as compound M2.

8. The organic electroluminescent element according to claim 7, It is characterized in that The organic layer has at least one light-emitting layer, The light-emitting layer includes the compound M2.

9. The organic electroluminescent element according to claim 8, It is characterized in that The light-emitting layer comprises the compound M2 and further comprises a compound M1, The compound M1 is a fluorescent compound. The lowest excited singlet energy S of the compound M1 1 (M1) and the lowest excited singlet energy S of the compound M2 1 (M2) satisfies the following mathematical formula (1), S 1 (M2)>S 1 (M1)…(Number 1).

10. The organic electroluminescent element according to claim 9, It is characterized in that The compound M1 is a compound represented by the following general formula (D1): In the general formula (D1), Ring A, Ring B, Ring D, Ring E and Ring F are each independently A substituted or unsubstituted aromatic ring having 6 to 30 ring carbon atoms, and a ring structure selected from the group consisting of a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms, Only one of ring B and ring D exists, or both ring B and ring D exist. When both ring B and ring D are present, ring B and ring D share the bond connecting Zc and Zh. Only one of the ring E and the ring F is present, or both the ring E and the ring F are present, When both ring E and ring F are present, ring E and ring F share the bond connecting Zf and Zi. Za is a nitrogen atom or a carbon atom, When ring B is present, Zb is a nitrogen atom or a carbon atom, When ring B is absent, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb 1 )(Rb 2 ) or Si(Rb 3 )(Rb 4 ), Zc is a nitrogen atom or a carbon atom, When ring D is present, Zd is a nitrogen atom or a carbon atom, In the absence of ring D, Zd is an oxygen atom, a sulfur atom or NRd, When ring E is present, Ze is a nitrogen atom or a carbon atom, In the absence of ring E, Ze is an oxygen atom, a sulfur atom or NRe, Zf is a nitrogen atom or a carbon atom, When ring F is present, Zg is a nitrogen atom or a carbon atom, In the absence of ring F, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg 1 )(Rg 2 ) or Si(Rg 3 )(Rg 4 ), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb, Rb 1 , Rb 2 , Rb 3 , Rb 4 、Rd、Re、Rg、Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are each independently a hydrogen atom or a substituent, Rb, Rb as a substituent 1 , Rb 2 , Rb 3 , Rb 4 、Rd、Re、Rg、Rg 1 , Rg 2 , Rg 3 , Rg 4 and Rh are independently, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, The bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

11. The organic electroluminescent element according to claim 9, It is characterized in that The compound M1 is a compound represented by the following general formula (20): In the general formula (20), X is a nitrogen atom or a carbon atom bonded to Y, Y is a hydrogen atom or a substituent, R 21 ~R 26 are independently a hydrogen atom or a substituent, or R 21 and R 22 Group, R 22 and R 23 Group, R 24 and R 25 The group, and R 25 and R 26 Any one or more of the groups are bonded to each other to form a ring, Y and R as substituents 21 ~R 26 Independently from A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, Halogen atoms, carboxyl, Substituted or unsubstituted ester group, a substituted or unsubstituted carbamoyl group, A substituted or unsubstituted amino group, Nitro, Cyano, a substituted or unsubstituted silyl group, and is selected from the group consisting of substituted or unsubstituted siloxane groups, Z 21 and Z 22 are independently a substituent, or Z 21 and Z 22 Bonded to each other to form a ring, Z as a substituent 21 and Z 22 Independently from Halogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and The present invention is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

12. The organic electroluminescent element according to claim 8, It is characterized in that The light-emitting layer includes the compound M2 and further includes a compound M3, The lowest excited singlet state energy S of the compound M2 1 (M2) and the lowest excited singlet energy S of the compound M3 1 (M3) satisfies the following mathematical formula (2): S 1 (M3)>S 1 (M2)…(number 2).

13. An electronic device, It is characterized in that The organic electroluminescent element according to claim 7 is mounted.

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