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

Abstract

This invention relates to a compound represented by the following general formula (1). In general formula (1), X1 is CR1 or a nitrogen atom, X2 is CR2 or a nitrogen atom, X3 is CR3 or a nitrogen atom, X4 is CR4 or a nitrogen atom, X5 is CR5 or a nitrogen atom, X6 is CR6 or a nitrogen atom, X7 is CR7 or a nitrogen atom, or a carbon atom bonded to X8 by a single bond, X8 is CR8 or a nitrogen atom, or a carbon atom bonded to X7 by a single bond, X9 is CR9 or a nitrogen atom, X... 10 For CR 10 Or nitrogen atom, X 11 For CR 11 Or nitrogen atom, X 12 For CR 12 Or nitrogen atom, Q is CR Q Or nitrogen atoms, Y is NR Y1 oxygen atom, sulfur atom, C(R) Y2 (R) Y3 ) or Si(R Y4 (R) Y5 ), where each R is a hydrogen atom or a substituent.

Description

Technical Field

[0001] This invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices. Background Technology

[0002] When a 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, while electrons are injected from the cathode. Then, in the light-emitting layer, the injected holes recombine with the electrons to form excitons. At this point, according to the statistical theorem of electron spin, singlet excitons are generated at a ratio of 25% and triplet excitons at a ratio of 75%.

[0003] Fluorescent organic EL devices, which emit light from singlet excitons, are being used in full-color displays for mobile phones and televisions, but the internal quantum efficiency of 25% is considered the limit. Therefore, research is underway to improve the performance of organic EL devices. Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, half-width, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0004] For example, it is hoped that triplet excitons, in addition to singlet excitons, can be utilized to make organic EL devices emit light more efficiently. Against this background, a highly efficient fluorescent organic EL device utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") has been proposed and investigated.

[0005] The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon of reverse intersystem crossing from triplet excitons to singlet excitons under thermal influence when using materials with a small energy difference (ΔST) between singlet and triplet energy levels. For example, information on TADF is described in "Chiba Adachi, 'Device Properties of Organic Semiconductors,' Kodansha, April 1, 2012, pp. 261-268."

[0006] Compounds exhibiting thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF-type compounds) are known, for example, compounds in which the donor site and acceptor site are bonded within the molecule.

[0007] For example, Patent Document 1 can be cited as a reference for organic EL elements and compounds used in organic EL elements.

[0008] Existing technical documents

[0009] Patent documents

[0010] Patent Document 1: International Publication No. 2015 / 102118 Summary of the Invention

[0011] The technical problem that the invention aims to solve

[0012] The object of the present invention is to provide a compound capable of improving the performance of an organic EL element, a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element.

[0013] Solution to the above technical problems

[0014] According to one aspect of the present invention, a compound represented by the following general formula (1) can be provided.

[0015]

Chemistry 1

[0016]

[0017] (in the general formula (1),

[0018] X1 is either CR1 or a nitrogen atom.

[0019] X2 is either CR2 or a nitrogen atom.

[0020] X3 is either CR3 or a nitrogen atom.

[0021] X4 is either CR4 or a nitrogen atom.

[0022] X5 is either CR5 or a nitrogen atom.

[0023] X6 is either CR6 or a nitrogen atom.

[0024] X7 is either CR7 or a nitrogen atom, or a carbon atom bonded to X8 via a single bond.

[0025] X8 is either a CR8 or a nitrogen atom, or a carbon atom bonded to X7 via a single bond.

[0026] X9 is either CR9 or a nitrogen atom.

[0027] X 10 For CR 10 Or nitrogen atoms,

[0028] X 11 For CR 11 Or nitrogen atoms,

[0029] X 12 For CR 12 Or nitrogen atoms,

[0030] Q is CR Q Or nitrogen atoms,

[0031] Y is NR Y1oxygen atom, sulfur atom, C(R) Y2 (R) Y3 ) or Si(R Y4 (R) Y5 ),

[0032] R1~R6 and R9~R 11 One or more groups consisting of two or more adjacent elements.

[0033] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0034] They bond to each other to form substituted or unsubstituted fused rings, or

[0035] They do not bond with each other.

[0036] R3, R4 and R Y1 One or more groups consisting of two or more adjacent elements.

[0037] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0038] They bond to each other to form substituted or unsubstituted fused rings, or

[0039] They do not bond with each other.

[0040] R3, R4 and R Y1 At least one hydrogen atom in a monocyclic or fused ring formed by the mutual bonding of two or more adjacent groups is removed from...

[0041] Alkyl groups with 1 to 50 carbon atoms

[0042] Aryl groups with 6 to 50 carbon atoms in the ring,

[0043] Heterocyclic groups with 5 to 50 cyclic atoms

[0044] With -O-(R 920 The group represented by ) and

[0045] With -N(R 921 (R) 922 The group represented by ) consists of at least one substituent selected from the group that is substituted or not substituted.

[0046] At least one hydrogen atom in the substituent is substituted by an aryl group having 6 to 50 carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted.

[0047] R1 to R2 do not form the substituted or unsubstituted monocyclic rings and do not form the substituted or unsubstituted fused rings. 11 And R 12 ~R 13 and R QEach independently,

[0048] hydrogen atom,

[0049] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0050] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0051] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0052] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0053] With -Si(R 911 (R) 912 (R) 913 () represents a group,

[0054] With -O-(R 914 () represents a group,

[0055] With -S-(R 915 () represents a group,

[0056] With -N(R 916 (R) 917 () represents a group,

[0057] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[0058] -C(=O)R 918 The group represented

[0059] With -COOR 919 The group represented

[0060] Halogen atoms,

[0061] cyano,

[0062] Nitro,

[0063] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0064] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0065] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Y1 for

[0066] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0067] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0068] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0069] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0070] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0071] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0072] By R Y2 and R Y3 The group

[0073] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0074] They bond to each other to form substituted or unsubstituted fused rings, or

[0075] They do not bond with each other.

[0076] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Y2 and R Y3 And R Y4 and R Y5 Each independently,

[0077] hydrogen atom,

[0078] Halogen atoms,

[0079] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0080] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0081] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0082] R 911 ~R 922 Each independently,

[0083] hydrogen atom,

[0084] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0085] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0086] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0087] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0088] In the existence of multiple R 911 In the case of multiple R911 They are the same or different.

[0089] In the existence of multiple R 912 In the case of multiple R 912 They are the same or different.

[0090] In the existence of multiple R 913 In the case of multiple R 913 They are the same or different.

[0091] In the existence of multiple R 914 In the case of multiple R 914 They are the same or different.

[0092] In the existence of multiple R 915 In the case of multiple R 915 They are the same or different.

[0093] In the existence of multiple R 916 In the case of multiple R 916 They are the same or different.

[0094] In the existence of multiple R 917 In the case of multiple R 917 They are the same or different.

[0095] In the existence of multiple R 918 In the case of multiple R 918 They are the same or different.

[0096] In the existence of multiple R 919 In the case of multiple R 919 They are the same or different.

[0097] In the existence of multiple R 920 In the case of multiple R 920 They are the same or different.

[0098] In the existence of multiple R 921 In the case of multiple R 921 They are the same or different.

[0099] In the existence of multiple R 922 In the case of multiple R 922 They may be the same as or different from each other.

[0100] According to one aspect of the present invention, a material for an organic electroluminescent element comprising a compound of one aspect of the present invention can be provided.

[0101] According to one aspect of the present invention, an organic electroluminescent element is provided, having a cathode, an anode, and an organic layer contained between the cathode and the anode, the organic layer comprising a light-emitting layer, and at least one layer of the organic layer comprising a compound of one aspect of the present invention.

[0102] According to one aspect of the present invention, an electronic device may be provided, which is equipped with an organic electroluminescent element according to one aspect of the present invention.

[0103] According to one aspect of the present invention, a compound capable of improving the performance of organic electroluminescent devices can be provided. Furthermore, according to one aspect of the present invention, a material comprising the compound for an organic electroluminescent device can be provided. Furthermore, according to one aspect of the present invention, an organic electroluminescent device comprising the compound can be provided. Furthermore, according to one aspect of the present invention, an electronic device equipped with the organic electroluminescent device can be provided. Attached Figure Description

[0104] Figure 1 This is a diagram illustrating a schematic configuration of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0105] Figure 2 This is a schematic diagram of a device for measuring transient pulse (PL).

[0106] Figure 3 This is a graph showing an example of the decay curve of the transition PL.

[0107] Figure 4 This is a diagram showing the energy levels and energy transfer relationships of the first and second compounds in the light-emitting layer of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0108] Figure 5 This is a diagram showing the energy levels and energy transfer relationships of the first, second, and third compounds in the light-emitting layer of an example of an organic electroluminescent element according to a fourth embodiment of the present invention. Detailed Implementation

[0109] [definition]

[0110] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0111] In this specification, hydrogen atoms are assumed to be bonded at the bonding positions of symbols such as "R" or "D" representing deuterium atoms in the chemical structural formula, that is, protium atoms, deuterium atoms, or tritium atoms are bonded.

[0112] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the atoms constituting the ring itself in a compound with a cyclic structure formed by atomic bonds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. This also applies to the "number of carbon atoms forming a ring" described below unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Furthermore, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluoreneyl and 25 for 9,9'-spirodifluoreneyl.

[0113] Furthermore, when the benzene ring is substituted with an alkyl group, the number of carbon atoms in that alkyl group is not included in the total number of carbon atoms in the cyclic ring of the benzene ring. Therefore, the benzene ring substituted with an alkyl group has a total of 6 carbon atoms. Similarly, when the naphthalene ring is substituted with an alkyl group, the number of carbon atoms in that alkyl group is not included in the total number of carbon atoms in the cyclic ring of the naphthalene ring. Therefore, the naphthalene ring substituted with an alkyl group has a total of 10 carbon atoms.

[0114] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds (e.g., monocyclic compounds, fused-ring compounds, cross-linked compounds, carbocyclic compounds, and heterocyclic compounds) that form a cyclic structure (e.g., monocyclic, fused-ring, and aggregated rings) by atomic bonds. Atoms that do not constitute a ring (e.g., hydrogen atoms terminating the bonds between the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. This also applies to the "number of cyclic atoms" described below unless otherwise specified. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting substituents are not included in the number of cyclic atoms in the pyridine ring. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring bonded to hydrogen atoms or substituents is 10.

[0115] In this specification, the phrase "a ZZ group with XX to YY carbons, whether substituted or unsubstituted" refers to the number of carbons in the case where the ZZ group is unsubstituted, and the number of carbons in the case where there is no substitution. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1, and "YY" represents an integer greater than 2.

[0116] In this specification, the phrase "ZZ group with XX to YY atoms of substituted or unsubstituted atoms" refers to the number of atoms in the ZZ group when it is unsubstituted, and the number of atoms in the substituent group when it is unsubstituted. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0117] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0118] In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not substituted as a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0119] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by substituents. Similarly, "substitution" 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 AA group.

[0120] Substituents described in this specification

[0121] The substituents described in this specification are explained below.

[0122] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted aryl" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0123] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0124] Unless otherwise specified in this specification, the number of carbon atoms in "unsubstituted alkyl" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0125] Unless otherwise specified in this specification, the number of carbons in the "unsubstituted alkenyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0126] Unless otherwise specified in this specification, the number of carbons in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0127] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic structure of "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0128] Unless otherwise specified in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0129] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0130] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene" described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0131] • "Substituted or unsubstituted aryl groups"

[0132] As specific examples (specific example group G1) of "substituted or unsubstituted aryl" described in this specification, the following examples include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B). (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, the term "aryl" includes both "unsubstituted aryl" and "substituted aryl".

[0133] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents. Examples of "substituted aryl" include the group in Specific Example Group G1A below, in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by substituents, and the substituted aryl group in Specific Example Group G1B below. Furthermore, the examples of "unsubstituted aryl" and "substituted aryl" given here are only examples; the "substituted aryl" described in this specification also includes: groups in which hydrogen atoms bonded to the carbon atoms of the aryl group itself in the "substituted aryl" of Specific Example Group G1B below are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted aryl" of Specific Example Group G1B below are further replaced by substituents.

[0134] • Unsubstituted aryl groups (specific example group G1A):

[0135] phenyl,

[0136] p-phenyl,

[0137] metaphenyl,

[0138] o-phenyl,

[0139] p-Triphenyl-4-yl,

[0140] p-Triphenyl-3-yl,

[0141] p-Triphenyl-2-yl,

[0142] Meta-triphenyl-4-yl,

[0143] Meta-triphenyl-3-yl,

[0144] Meta-triphenyl-2-yl,

[0145] o-Triphenyl-4-yl,

[0146] o-Triphenyl-3-yl,

[0147] o-Triphenyl-2-yl,

[0148] 1-Naphthyl,

[0149] 2-Naphthyl,

[0150] anthracene,

[0151] Benzanthracene,

[0152] Fiki,

[0153] Benzphenanthrene,

[0154] Finadenyl,

[0155] Pyrene

[0156] base,

[0157] benzo[a] base,

[0158] Tri-phenylene,

[0159] Benzotrimethylene

[0160] Tetracenyl

[0161] Pentaphenyl

[0162] Fluorine

[0163] 9,9'-spirodifluorene,

[0164] benzo[f]fluorenyl,

[0165] Dibenzofluorene,

[0166] Fluoranthene base,

[0167] Benzofluoranthyl,

[0168] Perylene, and

[0169] A monovalent aryl group is derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0170]

Chemistry 2

[0171]

[0172]

Transformation 3

[0173]

[0174] • Substituted aryl groups (specific example group G1B):

[0175] o-Tolyl,

[0176] m-Tolyl,

[0177] p-Tolyl,

[0178] p-Xylyl,

[0179] m-Xylyl,

[0180] o-xylyl,

[0181] p-isopropylphenyl,

[0182] m-Isopropylphenyl,

[0183] o-isopropylphenyl,

[0184] p-tert-butylphenyl,

[0185] m-tert-butylphenyl,

[0186] o-tert-butylphenyl,

[0187] 3,4,5-Trimethylphenyl,

[0188] 9,9-Dimethylfluorenyl,

[0189] 9,9-Diphenylfluorenyl,

[0190] 9,9-bis(4-methylphenyl)fluorenyl,

[0191] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0192] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0193] Cyanophenyl,

[0194] Triphenylsilylphenyl

[0195] Trimethylsilylphenyl

[0196] Benzonaphthyl,

[0197] Naphthalenephenyl, and

[0198] A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) with substituents.

[0199] • "Substituted or unsubstituted heterocyclic groups"

[0200] The term "heterocyclic group" as used in this specification refers to a cyclic group containing at least one heteroatom in its cyclic atom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0201] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0202] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0203] As specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) are examples. (Here, an unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group."

[0204] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the group in Example Group G2A below, in which hydrogen atoms of the "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in Example Group G2B below. In addition, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" given here are only examples. The "substituted heterocyclic groups" described in this specification also include: groups in which hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself in the "substituted heterocyclic group" of Example Group G2B are further replaced by substituents, and groups in which hydrogen atoms of the substituents in the "substituted heterocyclic group" of Example Group G2B are further replaced by substituents.

[0205] Specific example group G2A includes, for example, the following: 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 formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0206] Specific example group G2B includes, for example, the following: a heterocyclic group containing a nitrogen atom (specific example group G2B1), a heterocyclic group containing an oxygen atom (specific example group G2B2), a heterocyclic group containing a sulfur atom (specific example group G2B3), and a group obtained by substituting one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) as a substituent (specific example group G2B4).

[0207] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0208] pyrrole,

[0209] Imidazole group,

[0210] pyrazolyl,

[0211] Triazole group,

[0212] Tetrazolyl,

[0213] Oxazolyl,

[0214] Isoxazolyl,

[0215] Oxadiazole group,

[0216] Thiazole group,

[0217] Isothiazolyl,

[0218] Thiadiazole group,

[0219] pyridyl

[0220] pyridazinyl,

[0221] Pyrimidine group,

[0222] Pyrazinyl,

[0223] Triazine group

[0224] Indole,

[0225] Isoindolyl,

[0226] Indoleazine,

[0227] Quinazine-based

[0228] Quinoline,

[0229] Isoquinoline,

[0230] cinnolyl group

[0231] Phthaloazine

[0232] Quinazolinyl,

[0233] Quinoxaloyl,

[0234] Benzimidazole group,

[0235] Indazole group,

[0236] phenanthroline,

[0237] phenanthridine,

[0238] acridine group,

[0239] Phenazine group,

[0240] Carbazolyl,

[0241] Benzocarbazolyl,

[0242] Morpholinyl

[0243] phenoxazine group,

[0244] phenothiazine group,

[0245] Azacarbazolyl and diazacarbazolyl.

[0246] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0247] furanyl,

[0248] Oxazolyl,

[0249] Isoxazolyl,

[0250] Oxadiazole group,

[0251] Xuton base,

[0252] Benzofuranyl,

[0253] Isobenzofuranyl,

[0254] Dibenzofuranyl,

[0255] Naphthofuranyl,

[0256] Benzoxazolyl,

[0257] Benzisoxazole group,

[0258] phenoxazine group,

[0259] Morpholinyl

[0260] dinaphthylfuranyl,

[0261] Azadibenzofuranyl,

[0262] diazadibenzofuranyl,

[0263] Azanaphthalenebenzofuranyl, and

[0264] diazanaphthalenebenzofuranyl.

[0265] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0266] Thiophene group

[0267] Thiazole group,

[0268] Isothiazolyl,

[0269] Thiadiazole group,

[0270] benzothienyl group

[0271] isobenzothienyl group

[0272] dibenzothienyl group

[0273] Naphthobenzothienyl group

[0274] Benzothiazolyl,

[0275] Benzisothiazolyl,

[0276] phenothiazine group,

[0277] Dinaphthothienyl group

[0278] Azadibenzothienyl group

[0279] diazadibenzothienyl group

[0280] Azanaphthobenzothienyl group, and

[0281] diazanaphthobenzothienyl group.

[0282] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0283]

Chemistry 4

[0284]

[0285]

Transformation 5

[0286]

[0287] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently represented by an oxygen atom, a sulfur atom, NH, or CH2. Where X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0288] In the general formulas (TEMP-16) to (TEMP-33), X A and Y A In the case where at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0289] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0290] (9-phenyl)carbazole group,

[0291] (9-Biphenyl)carbazolyl,

[0292] (9-Phenyl)phenylcarbazolyl,

[0293] (9-Naphthyl)carbazole,

[0294] Diphenylcarbazole-9-yl,

[0295] Phenylexacarbazole-9-yl,

[0296] Methylbenzimidazole,

[0297] Ethylbenzimidazole,

[0298] Phenylacetyl,

[0299] Biphenyltriazine,

[0300] diphenyltriazine group,

[0301] Phenylacetyl and biphenylquinazolinyl.

[0302] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0303] Phenyl dibenzofuranyl,

[0304] Methyldibenzofuranyl,

[0305] tert-butyldibenzofuranyl, and

[0306] The monovalent residues of [9H-xanton-9,9'-[9H]fluorene].

[0307] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0308] Phenyl dibenzothiophene,

[0309] Methyldibenzothiophene,

[0310] tert-butyldibenzothiophene, and

[0311] The monovalent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0312] • Groups obtained by substituting one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) as substituents (specific example group G2B4):

[0313] The phrase "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, and hydrogen atoms bonded to X. A and Y A The nitrogen atom bonded to the hydrogen atom when at least one of them is NH, and X A and Y A In the case where one of the hydrogen atoms is CH2, one or more hydrogen atoms are selected from the hydrogen atoms of the methylene group.

[0314] • "Substituted or unsubstituted alkyl groups"

[0315] 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.

[0316] "Substituted alkyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group with substituents. Specific examples of "substituted alkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted alkyl" group (specific example group G3A) with substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain "unsubstituted alkyl". Furthermore, the examples of "unsubstituted alkyl" and "substituted alkyl" given here are only examples; the "substituted alkyl" described in this specification also includes groups obtained by further replacing the hydrogen atoms of the alkyl group itself in a "substituted alkyl" group (specific example group G3B) with substituents, and groups obtained by further replacing the hydrogen atoms of the substituents in a "substituted aryl" group (specific example group G3B) with substituents.

[0317] • Unsubstituted alkyl groups (specific example group G3A):

[0318] methyl,

[0319] Ethyl,

[0320] n-propyl,

[0321] Isopropyl,

[0322] n-Butyl,

[0323] Isobutyl,

[0324] sec-butyl, and

[0325] tert-butyl.

[0326] • Substituted alkyl groups (specific example group G3B):

[0327] Heptafluoropropyl (including isomers),

[0328] Pentafluoroethyl,

[0329] 2,2,2-Trifluoroethyl, and

[0330] Trifluoromethyl

[0331] • "Substituted or unsubstituted alkenyl groups"

[0332] As specific examples of "substituted or unsubstituted alkenyl groups" described in this specification (specific example group G4), the following examples include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0333] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by substituents. Specific examples of "substituted alkenyl" include the substituent group of the "unsubstituted alkenyl" (specific example group G4A) and examples of substituted alkenyl (specific example group G4B). Furthermore, the examples of "unsubstituted alkenyl" and "substituted alkenyl" given here are only examples; the "substituted alkenyl" described in this specification also includes: groups in the "substituted alkenyl" of specific example group G4B in which hydrogen atoms of the alkenyl itself are further replaced by substituents, and groups in the "substituted alkenyl" of specific example group G4B in which hydrogen atoms of the substituents are further replaced by substituents.

[0334] • Unsubstituted alkenyl groups (specific example group G4A):

[0335] vinyl,

[0336] Allyl

[0337] 1-Butenyl,

[0338] 2-Butenyl, and

[0339] 3-Butenyl.

[0340] • Substituted alkenyl groups (specific example group G4B):

[0341] 1,3-Butadienyl,

[0342] 1-Methylvinyl

[0343] 1-Methylallyl,

[0344] 1,1-Dimethylallyl,

[0345] 2-Methylallyl, and

[0346] 1,2-Dimethylallyl.

[0347] • "Substituted or unsubstituted alkynyl groups"

[0348] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) are examples. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, when simply referred to as "alkynyl group", it includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0349] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by substituents. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by substituents.

[0350] • Unsubstituted alkynyl group (specific example group G5A):

[0351] Acetylene group.

[0352] • "Substituted or unsubstituted cycloalkyl groups"

[0353] As specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6), the following examples include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B). (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 this specification, the term "cycloalkyl" includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0354] "Substituted cycloalkyl" refers to a group obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group with substituents. Specific examples of "substituted cycloalkyl" include groups obtained by replacing one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) with substituents, and examples of substituted cycloalkyl groups (specific example group G6B). Furthermore, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" given here are only examples; the "substituted cycloalkyl" described in this specification also includes groups obtained by replacing one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B with substituents, and groups obtained by further replacing the hydrogen atoms of the substituents in the "substituted cycloalkyl" group of specific example group G6B with substituents.

[0355] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0356] Cyclopropyl

[0357] Cyclobutyl,

[0358] Cyclopentyl,

[0359] Cyclohexyl,

[0360] 1-Adamantyl,

[0361] 2-Adamantyl,

[0362] 1-norborneol, and

[0363] 2-norborneol.

[0364] • Substituted cycloalkyl groups (specific example group G6B):

[0365] 4-Methylcyclohexyl.

[0366] • "with-Si(R 901 (R) 902 (R) 903 () represents the group

[0367] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group represented by ) (specific example group G7) can be given as follows:

[0368] -Si(G1)(G1)(G1),

[0369] -Si(G1)(G2)(G2),

[0370] -Si(G1)(G1)(G2),

[0371] -Si(G2)(G2)(G2),

[0372] -Si(G3)(G3)(G3), and

[0373] -Si(G6)(G6)(G6).

[0374] Here,

[0375] G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0376] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0377] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0378] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0379] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0380] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0381] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0382] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0383] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0384] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0385] ·“with-O-(R 904 () represents the group

[0386] As described in this specification, -O-(R) 904 Specific examples of the group represented by ) (specific example group G8) can be given as follows:

[0387] -O(G1)

[0388] -O(G2),

[0389] -O(G3), and

[0390] -O(G6).

[0391] Here,

[0392] G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0393] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0394] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0395] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0396] ·“with-S-(R 905 () represents the group

[0397] As described in this specification, -S-(R) 905 Specific examples of the group represented by ) (specific example group G9) can be given as follows:

[0398] -S(G1)

[0399] -S(G2),

[0400] -S(G3), and

[0401] -S(G6).

[0402] Here,

[0403] G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0404] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0405] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0406] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0407] • "with -N(R 906 (R) 907 () represents the group

[0408] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group represented by ) (specific example group G10) can be given as follows:

[0409] -N(G1)(G1),

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

[0411] -N(G1)(G2),

[0412] -N(G3)(G3), and

[0413] -N(G6)(G6).

[0414] Here,

[0415] G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0416] G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0417] G3 is the “substituted or unsubstituted alkyl group” described in the specific example group G3.

[0418] G6 is "substituted or unsubstituted cycloalkyl" as described in specific example group G6.

[0419] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0420] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0421] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0422] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0423] • "Halogen atom"

[0424] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0425] • "Substituted or unsubstituted fluoroalkyl groups"

[0426] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with a fluorine atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with fluorine atoms (perfluoroalkyl). Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group obtained by replacing one or more hydrogen atoms of the "fluoroalkyl" with a substituent. In addition, the term "substituted fluoroalkyl" as used in this specification also includes: a group obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl" with a substituent, and a group obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl" with a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the "alkyl" (specific example group G3) are replaced with fluorine atoms.

[0427] • "Substituted or unsubstituted haloalkyl groups"

[0428] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group obtained by replacing at least one hydrogen atom bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with a halogen atom, and also includes a group obtained by replacing all hydrogen atoms bonded to the carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl" with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group obtained by replacing one or more hydrogen atoms in the "haloalkyl" with a substituent. In addition, the term "substituted haloalkyl" as used in this specification also includes: a group obtained by further replacing one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl" with a substituent, and a group obtained by further replacing one or more hydrogen atoms of the substituent in the "substituted haloalkyl". As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms in the "alkyl" (specific example group G3) are replaced with halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0429] • "Substituted or unsubstituted alkoxy groups"

[0430] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is a group represented by -O (G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in this specification, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0431] • "Substituted or unsubstituted alkylthio groups"

[0432] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is a group represented by -S(G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise specified in this specification, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0433] • "Substituted or unsubstituted aryloxy groups"

[0434] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is a group represented by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0435] • "Substituted or unsubstituted arylthio groups"

[0436] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is a group represented by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise specified in this specification, the number of carbon atoms in the cyclic group of "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0437] • "Substituted or unsubstituted trialkylsilyl groups"

[0438] As a specific example of "trialkylsilyl" as described in this specification, it is a group represented by -Si(G3)(G3)(G3), where G3 refers to "substituted or unsubstituted alkyl" as described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be the same or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0439] • "Substituted or unsubstituted aralkyl groups"

[0440] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is a group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group obtained by replacing the hydrogen atom of "alkyl" with "aryl" as a substituent, and is a form of "substituted alkyl". "Unsubstituted aralkyl" is "unsubstituted alkyl" after "unsubstituted aryl" is substituted. Unless otherwise specified in this specification, the number of carbon atoms in "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18.

[0441] Specific examples of "substituted or unsubstituted aralkyl groups" 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.

[0442] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-phenyl, meta-phenyl, o-phenyl, p-triphenyl-4-yl, p-triphenyl-3-yl, p-triphenyl-2-yl, meta-triphenyl-4-yl, meta-triphenyl-3-yl, meta-triphenyl-2-yl, o-triphenyl-4-yl, o-triphenyl-3-yl, o-triphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyreneyl, etc. It includes methyl, triphenyl, fluorenyl, 9,9'-spirodifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0443] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, naphthalene Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0444] Unless otherwise specified in this specification, the carbazoyl group specifically refers to any of the following groups.

[0445]

Transformation 6

[0446]

[0447] Unless otherwise specified in this specification, (9-phenyl)carbazolyl specifically refers to any of the following groups.

[0448]

Transformation 7

[0449]

[0450] In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0451] Unless otherwise specified in this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups.

[0452]

Transformation 8

[0453]

[0454] In the general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0455] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl, etc.

[0456] • "Substituted or unsubstituted aryl groups"

[0457] Unless otherwise specified, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aromatic ring. Specific examples of "substituted or unsubstituted aryl 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 from the aromatic ring.

[0458] • "Substituted or unsubstituted divalent heterocyclic group"

[0459] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. As a specific example of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13), examples include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0460] • "Substituted or unsubstituted alkylene compounds"

[0461] Unless otherwise specified, the term "substituted or unsubstituted alkylene" as used in this specification refers to a divalent group derived from the "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0462] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0463]

Chemistry 9

[0464]

[0465]

Chemistry 10

[0466]

[0467] In the general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent, independently.

[0468] In the general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0469]

Chemistry 11

[0470]

[0471] In the general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent, independently.

[0472] Formula Q9 and Q 10 They can form rings by bonding with each other through single bonds.

[0473] In the general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0474]

Chemistry 12

[0475]

[0476] In the general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0477] In the general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0478] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any one of the following general formulas (TEMP-69) to (TEMP-102).

[0479]

Chemistry 13

[0480]

[0481]

Chemistry 14

[0482]

[0483]

Chemistry 15

[0484]

[0485] In the general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0486]

Chemistry 16

[0487]

[0488]

Chemistry 17

[0489] [Chemistry 18]

[0490]

[0491]

Chemistry 19

[0492]

[0493] In the general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0494] The above is an explanation of the substituents described in this specification.

[0495] • "Cases where bonds form rings"

[0496] In this specification, the phrase "two or more adjacent groups forming one or more groups bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "two or more adjacent groups forming one or more groups bonded together to form a substituted or unsubstituted monocyclic ring," "two or more adjacent groups forming one or more groups bonded together to form a substituted or unsubstituted fused ring," and "two or more adjacent groups forming one or more groups not bonded together."

[0497] The following description addresses the cases of "two or more adjacent groups forming one or more groups bonding together to form a substituted or unsubstituted monocyclic ring" and "two or more adjacent groups forming one or more adjacent groups bonding together to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "the case of bonding to form a ring"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring parent skeleton will be used as an example.

[0498]

Chemistry 20

[0499]

[0500] For example, in R 921 ~R 930In the context of "one or more adjacent groups forming a ring by mutual bonding", the group consisting of two adjacent elements that form a 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 also includes R 929 With R 921 The group.

[0501] The phrase "one or more groups" refers to the fact that two or more adjacent groups can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A At the same time R 925 With R 926 They bond together to form a ring Q B In the case of anthracene compounds represented by the general formula (TEMP-103), the anthracene compounds are represented by the following general formula (TEMP-104).

[0502]

Chemistry 21

[0503]

[0504] The case of "a group of two or more adjacent bonds forming a ring" refers not only to the bonded group of "two" adjacent bonds as in the example above, but also to the bonded group of "three or more" adjacent bonds. For example, representing R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C 3 adjacent (R) 921 R 922 and R 923When the groups formed by the rings Q bond together to form a ring, thereby fused to the anthracene matrix, 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 .

[0505]

Chemistry 22

[0506]

[0507] The formed "single ring" or "fused ring" can be either a saturated or unsaturated ring, depending solely on the structure of the ring. Even when a "single ring" or "fused ring" is formed from "two adjacent rings forming a group," it can still be either a saturated or unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B These are referred to as "single ring" or "fused ring," respectively. Furthermore, the ring Q formed in the general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C They fuse to form a fused ring. If the ring Q of the general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. If the ring Q of the general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0508] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0509] As a specific example of an aromatic hydrocarbon ring, a structure in which the group exemplified in specific example group G1 is terminated by a hydrogen atom can be given.

[0510] As a specific example of an aromatic heterocycle, the structure in which the aromatic heterocycle group is terminated by a hydrogen atom can be cited as a specific example in specific example group G2.

[0511] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group exemplified in specific example group G6 is terminated by a hydrogen atom can be cited.

[0512] "Ring formation" refers to the formation of a ring by multiple atoms of the parent skeleton alone, or by multiple atoms of the parent skeleton and one or more arbitrary elements. For example, the ring shown in the general formula (TEMP-104), R 921 With R 922 The ring Q formed by mutual bonding A Indicated by R 921 The carbon atoms of the bonded anthracene skeleton, and R 922 A ring formed by carbon atoms in a bonded anthracene framework and one or more arbitrary elements. As a specific example, in anthracene... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms of the bonded anthracene skeleton, and R 922 When the carbon atoms of the bonded anthracene skeleton, or four carbon atoms, form a monocyclic unsaturated ring, it is due to R 921 With R 922 The resulting ring is a benzene ring.

[0513] Unless otherwise specified in this specification, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the case of any element (e.g., in the case of carbon or nitrogen), bonds that do not form a ring may be terminated by hydrogen atoms or substituted by "any substituents" described later. In the case of any element other than carbon, the resulting ring is a heterocycle.

[0514] Unless otherwise specified in this specification, the number of "one or more arbitrary elements" constituting a monocyclic or fused ring is preferably two or more but less than 15, more preferably three or more but less than 12, and even more preferably three or more but less than 5.

[0515] Unless otherwise specified in this specification, "monocyclic" is preferred over "fused ring".

[0516] Unless otherwise specified in this specification, "unsaturated ring" is preferred over "saturated ring".

[0517] Unless otherwise specified in this specification, "monocyclic" is preferably a benzene ring.

[0518] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0519] Unless otherwise specified in this specification, when "one or more of the groups consisting of two or more adjacent atoms" is "mutually bonded to form a substituted or unsubstituted monocyclic ring" or "mutually bonded to form a substituted or unsubstituted fused ring", it is preferable that one or more of the groups consisting of two or more adjacent atoms are mutually bonded to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and one or more but no more than 15 elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0520] In the case of substituents in the aforementioned “monocyclic” or “fused-ring” structures, the substituents are, for example, the “arbitrary substituents” described later. Specific examples of substituents in the case of substituents in the aforementioned “monocyclic” or “fused-ring” structures are the substituents described in the “Substituents Described in this Specification” section above.

[0521] When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, the "arbitrary substituents" described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents described in this specification" above.

[0522] The above explains the cases of "two or more adjacent groups forming a single ring or a substituted or unsubstituted ring by bonding with each other" and "two or more adjacent groups forming a fused ring or a substituted or unsubstituted ring by bonding with each other" ("the case of forming a ring by bonding").

[0523] Substituents in cases of "substituted or unsubstituted"

[0524] In one embodiment of this specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "arbitrary substituent" in this specification) is, for example, from...

[0525] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[0526] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0527] Unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0528] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0529] -Si(R 901 (R) 902 (R) 903 ),

[0530] -O-(R 904 ),

[0531] -S-(R905 ),

[0532] -N(R 906 (R) 907 ),

[0533] Halogen atom, cyano group, nitro group,

[0534] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0535] Selected groups from the group consisting of unsubstituted heterocyclic groups having 5 to 50 cyclic atoms, etc.

[0536] Here, R 901 ~R 907 Each independently,

[0537] hydrogen atom,

[0538] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0539] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0540] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0541] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0542] When there are more than 2 R 901 In the case of 2 or more R 901 They are the same or different.

[0543] When there are more than 2 R 902 In the case of 2 or more R 902 They are the same or different.

[0544] When there are more than 2 R 903 In the case of 2 or more R 903 They are the same or different.

[0545] When there are more than 2 R 904 In the case of 2 or more R 904 They are the same or different.

[0546] When there are more than 2 R 905 In the case of 2 or more R 905 They are the same or different.

[0547] When there are more than 2 R 906 In the case of 2 or more R 906 They are the same or different.

[0548] When there are more than 2 R 907 In the case of 2 or more R 907 They are the same or different from each other.

[0549] In one embodiment, the substituent in the case of "substituted or unsubstituted" is from...

[0550] Alkyl groups with 1 to 50 carbon atoms

[0551] Aryl groups with 6 to 50 carbon atoms in the ring, and

[0552] The selected group is composed of heterocyclic groups with 5 to 50 cyclic atoms.

[0553] In one embodiment, the substituent in the case of "substituted or unsubstituted" is from...

[0554] Alkyl groups with 1 to 18 carbon atoms

[0555] aryl groups with 6 to 18 carbon atoms, and

[0556] The selected group is composed of heterocyclic groups with 5 to 18 cyclic atoms.

[0557] Specific examples of each group of any of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents described in this specification" above.

[0558] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming 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 forming a benzene ring.

[0559] Unless otherwise specified in this specification, any substituent may further have substituents. Any further substituents of any substituent are the same as those described above.

[0560] In this specification, the numerical range referred to as "AA~BB" means the range included by taking the value AA before "AA~BB" as the lower limit and the value BB after "AA~BB" as the upper limit.

[0561] [First Implementation]

[0562] (compound)

[0563] The compounds of this embodiment are represented by the following general formula (1). Sometimes the compounds of this embodiment are referred to as compounds represented by general formula (1).

[0564]

Chemistry 23

[0565]

[0566] (in the general formula (1),

[0567] X1 is either CR1 or a nitrogen atom.

[0568] X2 is either CR2 or a nitrogen atom.

[0569] X3 is either CR3 or a nitrogen atom.

[0570] X4 is either CR4 or a nitrogen atom.

[0571] X5 is either CR5 or a nitrogen atom.

[0572] X6 is either CR6 or a nitrogen atom.

[0573] X7 is either CR7 or a nitrogen atom, or a carbon atom bonded to X8 via a single bond.

[0574] X8 is either a CR8 or a nitrogen atom, or a carbon atom bonded to X7 via a single bond.

[0575] X9 is either CR9 or a nitrogen atom.

[0576] X 10 For CR 10 Or nitrogen atoms,

[0577] X 11 For CR 11 Or nitrogen atoms,

[0578] X 12 For CR 12 Or nitrogen atoms,

[0579] Q is CR Q Or nitrogen atoms,

[0580] Y is NR Y1 oxygen atom, sulfur atom, C(R) Y2 (R) Y3 ) or Si(R Y4 (R) Y5 ),

[0581] R1~R6 and R9~R 11 One or more groups consisting of two or more adjacent elements.

[0582] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0583] They bond to each other to form substituted or unsubstituted fused rings, or

[0584] They do not bond with each other.

[0585] R3, R4 and R Y1 One or more groups consisting of two or more adjacent elements.

[0586] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0587] They bond to each other to form substituted or unsubstituted fused rings, or

[0588] They do not bond with each other.

[0589] R3, R4 and R Y1 At least one hydrogen atom in a monocyclic or fused ring formed by the mutual bonding of two or more adjacent groups is removed from...

[0590] Alkyl groups with 1 to 50 carbon atoms

[0591] Aryl groups with 6 to 50 carbon atoms in the ring,

[0592] Heterocyclic groups with 5 to 50 cyclic atoms

[0593] With -O-(R 920 The group represented by ) and

[0594] With -N(R 921 (R) 922 The group represented by ) consists of at least one substituent selected from the group that is substituted or not substituted.

[0595] At least one hydrogen atom in the substituent is substituted by an aryl group having 6 to 50 carbon atoms or an alkyl group having 1 to 50 carbon atoms, or is not substituted.

[0596] R1 to R2 do not form the substituted or unsubstituted monocyclic rings and do not form the substituted or unsubstituted fused rings. 11 And R 12 ~R 13 and R Q Each independently,

[0597] hydrogen atom,

[0598] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0599] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0600] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0601] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0602] With -Si(R 911 (R)912 (R) 913 () represents a group,

[0603] With -O-(R 914 () represents a group,

[0604] With -S-(R 915 () represents a group,

[0605] With -N(R 916 (R) 917 () represents a group,

[0606] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[0607] -C(=O)R 918 The group represented

[0608] With -COOR 919 The group represented

[0609] Halogen atoms,

[0610] cyano,

[0611] Nitro,

[0612] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0613] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0614] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Y1 for

[0615] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0616] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0617] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0618] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0619] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0620] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0621] By R Y2 and R Y3 The group

[0622] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0623] They bond to each other to form substituted or unsubstituted fused rings, or

[0624] They do not bond with each other.

[0625] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. Y2 and R Y3 And R Y4 and R Y5 Each independently,

[0626] hydrogen atom,

[0627] Halogen atoms,

[0628] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0629] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0630] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0631] R 911 ~R 922 Each independently,

[0632] hydrogen atom,

[0633] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0634] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0635] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0636] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0637] In the existence of multiple R 911 In the case of multiple R 911 They are the same or different.

[0638] In the existence of multiple R 912 In the case of multiple R 912 They are the same or different.

[0639] In the existence of multiple R 913 In the case of multiple R 913 They are the same or different.

[0640] In the existence of multiple R 914 In the case of multiple R 914 They are the same or different.

[0641] In the existence of multiple R 915 In the case of multiple R 915 They are the same or different.

[0642] In the existence of multiple R 916 In the case of multiple R 916 They are the same or different.

[0643] In the existence of multiple R 917 In the case of multiple R 917 They are the same or different.

[0644] In the existence of multiple R 918 In the case of multiple R 918 They are the same or different.

[0645] In the existence of multiple R 919 In the case of multiple R 919 They are the same or different.

[0646] In the existence of multiple R 920 In the case of multiple R 920 They are the same or different.

[0647] In the existence of multiple R 921 In the case of multiple R 921 They are the same or different.

[0648] In the existence of multiple R 922 In the case of multiple R 922 They may be the same as or different from each other.

[0649] In the compounds of this embodiment, when X7 is a carbon atom bonded to X8 by a single bond and X8 is a carbon atom bonded to X7 by a single bond, for example, the general formula (1) is represented by the following general formula (1A).

[0650]

Chemistry 24

[0651]

[0652] (In the general formula (1A), X1~X6, X9~X 12 Y, Q and R 13 Each is independently consistent with the one defined in the general formula (1).

[0653] The compound in this embodiment is preferably represented by the following general formula (2).

[0654]

Chemistry 25

[0655]

[0656] (In the general formula (2), R1~R 13 R Y1 R Q Each is independently consistent with the one defined in the general formula (1).

[0657] The compound in this embodiment is preferably represented by the following general formula (2A).

[0658]

Chemistry 26

[0659]

[0660] (In the general formula (2A), R1~R6, R9~R 13 R Y1 R Q Each is independently consistent with the one defined in the general formula (1).

[0661] The compound in this embodiment is preferably represented by the following general formula (3).

[0662]

Chemistry 27

[0663]

[0664] (in the general formula (3),

[0665] R1~R3, R5~R 13 and R Q Each independently corresponds to the one defined in the general formula (1), R x1 ~R x4 One or more groups consisting of two or more adjacent elements.

[0666] They bond to each other to form substituted or unsubstituted monocyclic rings, or

[0667] They bond to each other to form substituted or unsubstituted fused rings, or

[0668] They do not bond with each other.

[0669] R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. X1 ~R x4 Each independently,

[0670] hydrogen atom,

[0671] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0672] Alkenes with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0673] Alkyne groups with 2 to 50 carbon atoms, whether substituted or unsubstituted.

[0674] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0675] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[0676] With -Si(R 931 (R) 932 (R) 933 () represents a group,

[0677] With -O-(R 934 () represents a group,

[0678] With -S-(R 935 () represents a group,

[0679] With -N(R 936 (R) 937 () represents a group,

[0680] Aryl groups, substituted or unsubstituted, having 7 to 50 carbon atoms

[0681] -C(=O)R 938 The group represented

[0682] With -COOR 939 The group represented

[0683] Halogen atoms,

[0684] cyano,

[0685] Nitro,

[0686] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0687] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0688] R 931 ~R 939 Each independently,

[0689] hydrogen atom,

[0690] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0691] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0692] Heterocyclic groups with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0693] In the existence of multiple R 931 In the case of multiple R 931 They are the same or different.

[0694] In the existence of multiple R 932 In the case of multiple R 932 They are the same or different.

[0695] In the existence of multiple R 933 In the case of multiple R 933 They are the same or different.

[0696] In the existence of multiple R 934 In the case of multiple R 934 They are the same or different.

[0697] In the existence of multiple R 935 In the case of multiple R 935 They are the same or different.

[0698] In the existence of multiple R 936 In the case of multiple R 936 They are the same or different.

[0699] In the existence of multiple R 937 In the case of multiple R 937 They are the same or different.

[0700] In the existence of multiple R 938 In the case of multiple R 938 They are the same or different.

[0701] In the existence of multiple R 939 In the case of multiple R 939 They may be the same as or different from each other.

[0702] In addition, in the general formula (3), for example, the group consisting of R5 and R6 is bonded to each other to form a substituted or unsubstituted monocyclic ring, or is bonded to each other to form a substituted or unsubstituted fused ring, or is not bonded to each other.

[0703] The compound in this embodiment is preferably represented by the following general formula (3A).

[0704]

Chemistry 28

[0705]

[0706] (In the general formula (3A), R1~R3, R5~R6, R9~R 13 and R Q Each independently corresponds to the one defined in the general formula (1), R x1 ~R x4 Each is independently consistent with the one defined in general formula (3).

[0707] In the compounds of this embodiment, R1 to R2 are also preferred.13 and R Q Each independently,

[0708] hydrogen atom,

[0709] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0710] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0711] A heteroaryl group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0712] In the compounds of this embodiment, R1 to R2 are also preferred. 13 and R Q Each independently,

[0713] hydrogen atom,

[0714] Substituted or unsubstituted alkyl groups having 1 to 25 carbon atoms

[0715] Substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0716] A heteroaryl group with 5 to 25 cyclic atoms, either substituted or unsubstituted.

[0717] In the compounds of this embodiment, R1 to R3 and R5 to R6 are also preferred. 13 R Q and R x1 ~R x4 Each independently,

[0718] hydrogen atom,

[0719] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0720] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0721] A heteroaryl group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0722] In the compounds of this embodiment, R1 to R3 and R5 to R6 are also preferred. 13 R Q and R x1 ~R x4 Each independently,

[0723] hydrogen atom,

[0724] Substituted or unsubstituted alkyl groups having 1 to 25 carbon atoms

[0725] Substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0726] A heteroaryl group with 5 to 25 cyclic atoms, either substituted or unsubstituted.

[0727] In the compounds of this embodiment, R1 to R2 are preferred. 13 R Q and R x1 ~R x4 Each independently,

[0728] hydrogen atom,

[0729] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0730] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0731] A heteroaryl group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0732] In the compounds of this embodiment, R1 to R2 are preferred. 13 R Q and R x1 ~R x4 Each independently,

[0733] hydrogen atom,

[0734] Substituted or unsubstituted alkyl groups having 1 to 25 carbon atoms

[0735] Substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0736] A heteroaryl group with 5 to 25 cyclic atoms, either substituted or unsubstituted.

[0737] The compound in this embodiment is preferably represented by the following general formula (4).

[0738]

Chemistry 29

[0739]

[0740] (In the general formula (4), R2, R6, R 13 R Q and R x2 Each independently,

[0741] hydrogen atom,

[0742] Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms

[0743] Substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or

[0744] (Substituted or unsubstituted heteroaryl groups with 5 to 18 cyclic atoms)

[0745] The compound in this embodiment is preferably represented by the following general formula (5).

[0746]

Transformation 30

[0747]

[0748] (In the general formula (5), R2, R6, R 13 R Q and R x2 Each independently,

[0749] hydrogen atom,

[0750] Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms

[0751] Substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, or

[0752] (Substituted or unsubstituted heteroaryl groups with 5 to 18 cyclic atoms)

[0753] In the compounds of this embodiment, R is preferred. 13 and R Q Each independently,

[0754] Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms

[0755] Substituted or unsubstituted phenyl

[0756] Substituted or unsubstituted naphthyl, or

[0757] Substituted or unsubstituted dibenzofuranyl groups.

[0758] R6 and R are preferred x2 Alkyl groups having hydrogen atoms, or substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, each independently.

[0759] In the compounds of this embodiment, the substituents are preferably in the case of "substituted or unsubstituted".

[0760] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[0761] Unsubstituted alkenyl groups with 2 to 25 carbon atoms

[0762] Unsubstituted alkynyl groups with 2 to 25 carbon atoms

[0763] Unsubstituted cycloalkyl groups with 3 to 25 carbon atoms

[0764] With -Si(R 901 (R) 902 (R) 903 () represents a group,

[0765] With -O-(R 904 () represents a group,

[0766] With -S-(R 905 () represents a group,

[0767] With -N(R 906 (R) 907 () represents a group,

[0768] Unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0769] -C(=O)R 908 The group represented

[0770] With -COOR 909 The group represented

[0771] Take -S(=O)2R 941 The group represented

[0772] -P(=O)(R) 942 (R) 943 () represents a group,

[0773] Take -Ge(R 944 (R) 945 (R) 946 () represents a group,

[0774] Halogen atoms,

[0775] cyano,

[0776] Nitro,

[0777] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0778] Unsubstituted heterocyclic groups with 5 to 25 cyclic atoms

[0779] R 901 ~R 909 And R 941 ~R 946 Each independently,

[0780] hydrogen atom,

[0781] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[0782] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0783] Unsubstituted heterocyclic groups with 5 to 25 cyclic atoms.

[0784] In the compounds of this embodiment, the substituents are preferably in the case of "substituted or unsubstituted".

[0785] Halogen atoms,

[0786] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[0787] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0788] Unsubstituted heterocyclic groups with 5 to 25 cyclic atoms.

[0789] In the compounds of this embodiment, the substituents are preferably in the case of "substituted or unsubstituted".

[0790] Unsubstituted alkyl groups having 1 to 10 carbon atoms

[0791] Unsubstituted aryl groups with 6 to 12 carbon atoms, or

[0792] Unsubstituted heterocyclic groups with 5 to 12 cyclic atoms.

[0793] In the compounds of this embodiment, it is also preferable that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[0794] • The main peak wavelength of the compound

[0795] The main peak wavelength of the compound in this embodiment is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 530 nm or less.

[0796] In this specification, the dominant peak wavelength of a compound refers to the wavelength at which the measured compound reaches its peak at 10 nm. -6 10 moles per liter or more -5 A toluene solution dissolved at a concentration below mol / L is used to measure the fluorescence spectrum at the wavelength of the peak of the fluorescence spectrum where the luminescence intensity reaches its maximum. A spectrophotometer (Hitachi F-7000) can be used as the measuring device.

[0797] • Method for manufacturing the compound of this embodiment

[0798] The compounds of this embodiment can be manufactured by the synthesis method described in the examples below, or by using known alternative reactions and starting materials that match the target compound, in accordance with the synthesis method described in the examples below.

[0799] Specific examples of compounds in this embodiment

[0800] Specific examples of compounds used in this embodiment include the following compounds. However, the present invention is not limited to these specific examples.

[0801]

Chemistry 31

[0802]

[0803]

Chemistry 32

[0804]

[0805]

Transformation 33

[0806]

[0807]

Transformation 34

[0808]

[0809]

Chemistry 35

[0810]

[0811]

Transformation 36

[0812]

[0813]

Chemistry 37

[0814]

[0815]

Transformation 38

[0816]

[0817]

Chemistry 39

[0818]

[0819]

Chemistry 40

[0820]

[0821]

Chemistry 41

[0822]

[0823]

Chemistry 42

[0824]

[0825]

Chemistry 43

[0826]

[0827] The compound according to this embodiment can improve the performance of organic EL devices. According to one embodiment, it is possible to reduce the driving voltage, increase the EQE, and emit light with a narrower main peak half-width from the device.

[0828] [Second Implementation]

[0829] (Materials used in organic electroluminescent devices)

[0830] The material for the organic electroluminescent element in this embodiment contains the compound of the first embodiment. As one example, a material for the organic electroluminescent element containing only the compound of the first embodiment can be cited; as another example, a material for the organic electroluminescent element containing the compound of the first embodiment and other compounds different from those in the first embodiment can be cited.

[0831] In the materials for organic electroluminescent elements according to this embodiment, the compound of the first embodiment is preferably a dopant material. In this case, the material for organic electroluminescent elements may also include the compound of the first embodiment as a dopant material and other compounds such as the host material.

[0832] [Third Implementation Method]

[0833] (Organic electroluminescent device)

[0834] The organic EL element of this embodiment will be described.

[0835] The organic EL element of this embodiment has a cathode, an anode, and an organic layer contained between the cathode and the anode. The organic layer comprises at least one layer composed of an organic compound. Alternatively, the organic layer is formed by stacking multiple layers composed of organic compounds. The organic layer may also contain inorganic compounds. At least one layer of the organic layer contains a compound of the first embodiment (a compound represented by the general formula (1)).

[0836] The organic layer may be composed of a single light-emitting layer, or it may contain layers that can be used in organic EL devices. There is no particular limitation on the layers that can be used in organic EL devices, and examples include at least one layer selected from the group consisting of hole injection layers, hole transport layers, electron injection layers, electron transport layers, and blocking layers.

[0837] Figure 1 The diagram shows a schematic configuration of an example of an organic EL element according to this embodiment.

[0838] 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 constructed by sequentially stacking 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 from the anode 3 side. This invention is not limited to... Figure 1 The structure of the organic EL element shown.

[0839] (Emitting layer)

[0840] The organic layer of the organic EL element in this embodiment includes a light-emitting layer.

[0841] The light-emitting layer preferably contains the compound of the first embodiment (a compound represented by the general formula (1)).

[0842] The luminescent layer preferably further comprises a delayed-fluorescence luminescent material.

[0843] When the luminescent layer comprises the compound of the first embodiment and the delayed fluorescence luminescent material, the lowest excitation singlet energy S1(H) of the delayed fluorescence luminescent material and the lowest excitation singlet energy S1(D) of the compound of the first embodiment (represented by the general formula (1)) preferably satisfy the following mathematical formula (number 1).

[0844] S1(H)>S1(D)…(Number 1)

[0845] In the organic EL element of this embodiment, the light-emitting layer preferably comprises a first compound and a second compound. The first compound in the light-emitting layer is preferably the compound of the first embodiment.

[0846] In this scheme, the second compound is preferably a host material (sometimes also called a matrix material), and the first compound is preferably a dopant material (sometimes also called a guest material, emitter, or luminescent material).

[0847] In this specification, "body material" refers to a material contained, for example, at "50% by mass or more of the layer". Therefore, for example, the light-emitting layer contains the second compound at 50% by mass or more of the total mass of the light-emitting layer. Furthermore, for example, the "body material" may also be contained at 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more of the layer.

[0848] In the organic EL element of this embodiment, the lowest excitation singlet energy S1(M1) of the first compound and the lowest excitation singlet energy S1(M2) of the second compound preferably satisfy the following mathematical expression (Equation 3).

[0849] S1(M2)>S1(M1)…(Number 3)

[0850] The preferred bandgap T is at 77 [K] for the first compound. 77K The band gap T when (M1) is less than 77 [K] of the second compound. 77K (M2). That is, preferably, the relationship satisfies the following mathematical expression (number 5).

[0851] T 77K (M2)>T77K (M1)…(Number 5)

[0852] Preferably, when the organic EL element of this embodiment emits light, the compound of the first embodiment, which is the first compound, mainly emits light in the light-emitting layer.

[0853] In one embodiment, the light-emitting layer may also contain a metal complex.

[0854] Furthermore, in one embodiment, the light-emitting layer preferably does not contain metal complexes.

[0855] Furthermore, in one embodiment, the light-emitting layer preferably does not contain phosphorescent materials (dopant materials).

[0856] Furthermore, in one embodiment, the light-emitting layer is preferably free of heavy metal complexes and phosphorescent rare-earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0857] In this embodiment, when the light-emitting layer contains the compound of the first embodiment, it is preferable that the light-emitting layer does not contain phosphorescent metal complexes, and preferably also does not contain metal complexes other than phosphorescent metal complexes.

[0858] (First compound)

[0859] The first compound is preferably the compound of the first embodiment.

[0860] In one embodiment, the first compound is a fluorescent compound that does not exhibit delayed fluorescence.

[0861] (Second compound)

[0862] The second compound is not particularly limited, but in the organic EL element of this embodiment, the second compound is preferably a delayed fluorescence luminescent material.

[0863] In the organic EL element of this embodiment, the delayed fluorescence luminescent material, which is the second compound, is preferably used as the main material.

[0864] In the organic EL element of this embodiment, the delayed fluorescence luminescent material, which is the second compound, is preferably used as the main material, and the compound of the first embodiment, which is the first compound, is used as the dopant material.

[0865] (Delayed fluorescence)

[0866] Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). This literature states that if the energy difference ΔE between the excited singlet and excited triplet states of a fluorescent material can be reduced... 13 In this case, the reverse energy transfer from the excited triplet state to the excited singlet state, which typically has a low migration probability, occurs efficiently, producing thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is illustrated in Figure 10.38 of this document. The delayed-fluorescent material in this embodiment is preferably a compound that demonstrates thermally activated delayed fluorescence generated by such a mechanism.

[0867] Typically, delayed fluorescence can be confirmed by transition PL (Photo Luminescence) measurements.

[0868] Furthermore, the behavior of delayed fluorescence can be analyzed based on the decay curve obtained from transition PL measurements. Transition PL measurement refers to the method of exciting a sample by irradiating it with a pulsed laser and measuring the decay behavior (transition characteristics) of PL emission after irradiation stops. PL emission in TADF materials consists of two components: the emission component from singlet excitons generated by the initial PL excitation and the emission component from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after irradiation with a pulsed laser.

[0869] On the other hand, delayed fluorescence originates from the emission of singlet excitons generated via long-lived triplet excitons, and therefore decays slowly. Consequently, there is a significant time difference between the emission of singlet excitons generated from the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[0870] Figure 2 The diagram shows a schematic of an example apparatus for measuring transient PL. Figure 2 The method for measuring transition PL and an example of analyzing the behavior of delayed fluorescence are explained.

[0871] Figure 2 The transition PL measurement device 100 includes: a pulsed laser unit 101 for irradiating light of a specified wavelength; a sample chamber 102 for housing the measurement sample; a beam splitter 103 for splitting the light emitted from the measurement sample; a streak camera 104 for imaging a two-dimensional image; and a personal computer 105 for reading and analyzing the two-dimensional image. Furthermore, the measurement of transition PL is not limited to... Figure 2 The device described.

[0872] The sample housed in the sample chamber 102 can be obtained by forming a thin film on a quartz substrate by doping the matrix material with a dopant material at a concentration of 12% by mass.

[0873] For the thin film sample housed in the sample chamber 102, a pulsed laser is irradiated from the pulsed laser unit 101 to excite the doped material. The emitted light is extracted in a direction 90 degrees relative to the irradiation direction of the excitation light, and the extracted light is split by the beam splitter 103 to form a two-dimensional image in the streak camera 104. The result is a two-dimensional image with the vertical axis corresponding to time, the horizontal axis corresponding to wavelength, and the bright spots corresponding to emission intensity. If this two-dimensional image is cut along a specified time axis, an emission spectrum with emission intensity as the vertical axis and wavelength as the horizontal axis can be obtained. Furthermore, if this two-dimensional image is cut along the wavelength axis, a decay curve (transition pulse) with the logarithm of emission intensity as the vertical axis and time as the horizontal axis can be obtained.

[0874] For example, using the following reference compound H1 as the matrix material and the following reference compound D1 as the dopant material, thin film sample A was prepared as described above, and transition PL measurements were performed.

[0875]

Chemistry 44

[0876]

[0877] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. Thin film sample B was prepared using the reference compound H2 as the matrix material and the reference compound D1 as the dopant material, as described above.

[0878] Figure 3 The attenuation curves obtained from the transition PL measured on thin film sample A and thin film sample B are shown in the figure.

[0879]

Chemistry 45

[0880]

[0881] As described above, by measuring the transition PL (luminescence intensity), a luminescence decay curve can be obtained with luminescence intensity as the vertical axis and time as the horizontal axis. Based on this luminescence decay curve, the fluorescence intensity ratio of fluorescence emitted from a singlet excited state generated by photoexcitation to delayed fluorescence emitted from a singlet excited state generated via reverse energy transfer from a triplet excited state can be calculated. In materials with delayed fluorescence, the proportion of slowly decaying delayed fluorescence intensity is relatively large compared to the intensity of rapidly decaying fluorescence.

[0882] Specifically, luminescence from materials with delayed fluorescence can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence that is immediately observed from the excited state after being excited by a pulse of light (light from a pulsed laser) of a wavelength absorbed by the material with delayed fluorescence. Delay luminescence refers to luminescence that is not immediately observed after being excited by the pulse of light but is observed later.

[0883] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[0884] Furthermore, in this specification, a sample prepared by the method described below is used in the measurement of the delayed fluorescence of the delayed fluorescence luminescent material. For example, the delayed fluorescence luminescent material is dissolved in toluene, and a dilute solution with an absorbance of less than 0.05 at the excitation wavelength is prepared to eliminate the effect of self-absorption. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an oxygen-free sample solution saturated with argon.

[0885] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. Using the fluorescence area intensities of the two spectra, the total fluorescence quantum yield was calculated according to equation (1) in Morris et al., J. Phys. Chem., 80(1976)969.

[0886] In this embodiment, the amount of Prompt emission (instantaneous emission) of the target compound (delayed fluorescence luminescent material) is set as X. P Set the amount of delayed emission to X. D At that time, X D / X P The value is preferably 0.05 or higher.

[0887] The measurement of the amount and ratio of Prompt luminescence and Delay luminescence for compounds other than delayed fluorescent luminescent materials in this specification is the same as the measurement of the amount and ratio of Prompt luminescence and Delay luminescence for delayed fluorescent luminescent materials.

[0888] ·△ST

[0889] In this embodiment, the minimum excited singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as △ST.

[0890] The lowest excitation singlet energy S1(H) of the delayed fluorescence luminescent material and the band gap T at 77[K] of the delayed fluorescence luminescent material 77K The difference ΔST(H) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, ΔST(H) preferably satisfies the following mathematical expressions (number 10), (number 11), (number 12), or (number 13).

[0891] △ST(H)=S1(H)-T 77K (H) < 0.3 eV… (Number 10)

[0892] △ST(H)=S1(H)-T 77K (H) < 0.2 eV… (Mathematics 11)

[0893] △ST(H)=S1(H)-T 77K (H) < 0.1 eV… (Number 12)

[0894] △ST(H)=S1(H)-T 77K (H) < 0.01 eV… (Number 13)

[0895] • Relationship between triplet energy and band gap at 77 K

[0896] Here, the relationship between the triplet energy and the band gap at 77 [K] is explained. In this embodiment, the band gap at 77 [K] differs from the normally defined triplet energy.

[0897] The triplet energy was measured as follows. First, the compound to be measured was dissolved in a suitable solvent, and the resulting solution was sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the triplet energy was calculated based on the wavelength value of the intersection of the tangent and the horizontal axis according to the prescribed conversion formula.

[0898] In this embodiment, the compound with thermally activated delayed fluorescence (ΔST) is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are more likely to occur even at low temperatures (77 K), resulting in the coexistence of excited singlet and excited triplet states. As a result, the spectrum measured in the same manner as described above can be considered to contain emission from both the excited singlet and excited triplet states, making it difficult to distinguish which state the emission originates from, but the triplet energy value is essentially dominant.

[0899] Therefore, in this embodiment, the measurement method is the same as that for the usual triplet energy T, but in order to distinguish it strictly, the measured value is referred to as the bandgap T. 77K The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) at a concentration of 10 μmol / L, and the solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength) was measured at a low temperature (77 K). A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge [nm], the energy calculated according to the following conversion formula (F1) is taken as the band gap T at 77[K]. 77K .

[0900] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[0901] The tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum is drawn as shown below. Consider this tangent as it moves along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the point on the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis value increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent to the rising edge of the short-wavelength side of the phosphorescence spectrum.

[0902] Furthermore, the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point closest to the maximum value on the shortest wavelength side and where the slope value is the maximum value is taken as the tangent line for the rising edge of the short wavelength side of the phosphorescence spectrum.

[0903] Phosphorescence can be measured using the main body of the Hitachi High Technology Co., Ltd. F-4500 spectrophotometer. However, the measuring device is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.

[0904] • Lowest excited singlet energy S1

[0905] The following methods can be cited as examples of methods for measuring the lowest excited singlet energy S1 using a solution (sometimes called the solution method).

[0906] A 10 μmol / L toluene solution of the compound to be measured was placed in a quartz cell, and the absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis: absorption intensity, horizontal axis: wavelength). A tangent was drawn to the falling edge of the long wavelength side of the absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy.

[0907] Conversion formula (F2): S1[eV]=1239.85 / λedge

[0908] As an absorption spectroscopy measuring device, an example of such a device is the Hitachi spectrophotometer (device name: U3310), but it is not limited to this.

[0909] The tangent to the falling edge of the absorption spectrum on the longer wavelength side is plotted as shown below. Consider this tangent at various points on the spectral curve as the maximum value on the longest wavelength side of the absorption spectrum is moved along the longer wavelength direction. This tangent repeatedly shows a decreasing and then increasing slope as the curve descends (i.e., as the vertical axis value decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent to the falling edge of the longer wavelength side of the absorption spectrum.

[0910] In addition, the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[0911] Compounds represented by general formula (2)

[0912] In this embodiment, the delayed fluorescence luminescent material is not particularly limited to any compound that has delayed fluorescence properties. In one embodiment, the delayed fluorescence luminescent material is a compound represented by the following general formula (2).

[0913]

Chemistry 46

[0914]

[0915] In the general formula (2),

[0916] A is an acceptor (electron-accepting) site, a group having a local structure selected from the following general formulas (a-1) to (a-7). In the presence of multiple A groups, the A groups may be identical or different from each other, and the A groups may bond together to form saturated or unsaturated rings.

[0917] B is a donor (electron-donating) site, possessing a local structure selected from the following general formulas (b-1) to (b-6). In the presence of multiple Bs, the multiple Bs may be identical or different from each other, and the Bs can bond together to form saturated or unsaturated rings.

[0918] a, b, and d can be 1, 2, 3, 4, or 5 independently.

[0919] c can be 0, 1, 2, 3, 4, or 5.

[0920] When c is 0, A and B are bonded by single bonds or spiral bonds.

[0921] When c is 1, 2, 3, 4, or 5, L is from

[0922] Substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, and

[0923] The linking group selected from the group consisting of substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms, where multiple Ls are present, the multiple Ls may be the same or different from each other, and the Ls may bond together to form saturated or unsaturated rings.

[0924]

Chemistry 47

[0925]

[0926]

Chemistry 48

[0927]

[0928] In the general formulas (b-1) to (b-6),

[0929] Two or more adjacent Rs in a plurality of Rs form a group of substituted or unsubstituted monocyclic rings, or are bonded to each other to form substituted or unsubstituted fused rings, or are not bonded to each other. The Rs that do not form either the substituted or unsubstituted monocyclic rings or the substituted or unsubstituted fused rings are each independently […].

[0930] hydrogen atom,

[0931] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[0932] Substituted or unsubstituted heterocyclic groups with 5 to 30 cyclic atoms

[0933] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or

[0934] Substituted or unsubstituted cycloalkyl groups with a cyclic carbon number of 3 to 30.

[0935] In the case of multiple Rs, the multiple Rs may be the same as each other or different from each other.

[0936] As an example of the bonding states of a compound represented by the general formula (2), the bonding states shown in Table 1 below can be cited as an example.

[0937] Table 1

[0938]

[0939] Method for manufacturing delayed fluorescence luminescent materials

[0940] Delayed fluorescence luminescent materials can be manufactured using known methods. Furthermore, delayed fluorescence luminescent materials can also be manufactured by mimicking known methods, using known alternative reactions and raw materials that match the target material.

[0941] Specific examples of delayed fluorescence luminescent materials

[0942] Specific examples of delayed-fluorescence luminescent materials include the following compounds. However, the present invention is not limited to these specific examples of delayed-fluorescence luminescent materials.

[0943]

Chemistry 49

[0944]

[0945] • (TADF mechanism)

[0946] Figure 4 This is a diagram illustrating an example of the relationship between the energy levels of the second compound M2 when the luminescent layer is a delayed-fluorescence luminescent material and the first compound M1 when it is a compound of the first embodiment. Figure 4 In this diagram, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound M1. T1(M1) represents the lowest excited triplet state of the first compound M1. S1(M2) represents the lowest excited singlet state of the second compound M2. T1(M2) represents the lowest excited triplet state of the second compound M2.

[0947] Figure 4 The dashed arrow from S1(M2) to S1(M1) in the diagram represents the energy transfer from the lowest excited singlet state of the second compound M2 to the Forster-type state of the first compound M1.

[0948] like Figure 4As shown, if a compound with a smaller ΔST(M2) (a delayed-fluorescent material) is used as the second compound M2, the lowest excited triplet state T1(M2) can undergo a reverse intersystem crossing to the lowest excited singlet state S1(M2) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound M2 to the first compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound 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%.

[0949] The second compound serving as the host material can also be a compound with a higher lowest unoccupied orbital level (LUMO) and a lower highest occupied orbital level (HOMO) compared to the dopant material. Examples of host materials include: (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives; (3) anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or... (3) Fused aromatic compounds such as carbazole derivatives; (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[0950] The organic EL element of this embodiment preferably emits green light.

[0951] In the case where the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[0952] The main peak wavelength of light emitted from the organic EL element is measured as described below.

[0953] The measurement was performed using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage was applied to an organic EL element to achieve a current density of 10 mA / cm². 2 The spectrophotometric emission brightness spectrum at that time.

[0954] In the obtained spectrophotometric emission brightness spectrum, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum is measured and taken as the main peak wavelength (unit: nm).

[0955] • Film thickness of the light-emitting layer

[0956] In this embodiment, the thickness of the light-emitting layer in the organic EL element is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. If the thickness of the light-emitting layer is 5 nm or more, the formation of the light-emitting layer and the adjustment of its color become easier; if the thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise of the driving voltage.

[0957] • The content of compounds in the luminescent layer

[0958] The content of the first compound and the second compound in the light-emitting layer is preferably within, for example, the following range.

[0959] The content of the first compound is preferably 0.01% by mass or more and 10% by mass, more preferably 0.01% by mass or more and 5% by mass, and even more preferably 0.01% by mass or more and 2% by mass.

[0960] The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[0961] Furthermore, this embodiment does not exclude the inclusion of materials other than the first compound and the second compound in the light-emitting layer.

[0962] The luminescent layer may contain only one first compound or two or more first compounds. The luminescent layer may contain only one second compound or two or more second compounds.

[0963] (Substrate)

[0964] The substrate is used as a support for organic EL elements. Materials such as glass, quartz, and plastic can be used as substrates. Flexible substrates can also be used. Flexible substrates are (flexible) substrates that can be bent; examples include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, inorganic vapor-deposited films can also be used.

[0965] (anode)

[0966] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), silicon- or silicon-oxide-containing indium tin oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[0967] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Furthermore, for indium oxide containing tungsten oxide and zinc oxide, it can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. In addition, it can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other methods.

[0968] 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 is easy to inject holes (cavities). Therefore, materials that can be used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0969] It is also possible to use elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) or cesium (Cs), and alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing them, which are materials with low work functions. Furthermore, when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Moreover, when using silver paste, coating or inkjet methods can be used.

[0970] (cathode)

[0971] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof with a low work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, such as alkali metals like lithium (Li) or cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and their alloys (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and their alloys.

[0972] Furthermore, when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[0973] Furthermore, by incorporating an electron injection layer, cathodes can be formed using various conductive materials such as Al, Ag, ITO, graphene, and silicon- or silicon-oxide-containing indium tin oxide, regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[0974] (hole injection layer)

[0975] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[0976] In addition, examples of substances with high hole injection potential include 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (TDATA). Aromatic amine compounds such as 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), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) are also mentioned.

[0977] Furthermore, as substances with high hole injection capability, polymeric compounds (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymeric compounds with added acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0978] (Hole transport layer)

[0979] The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N Aromatic amine compounds such as [-phenylamino]biphenyl (abbreviated: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: MTDATA), and 4,4'-bis[N-(spiro-9,9'-difluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: BSPB) are mentioned here. The substances discussed here mainly possess 10... -6 cm 2 Substances with a hole mobility of / Vs or higher.

[0980] 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) (PVK) or poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[0981] However, any other material may be used as long as it has a higher hole transport capacity than electrons. Furthermore, the layer containing the material with high hole transport capacity can be not only a single layer, but also a layer obtained by stacking two or more layers of the aforementioned material.

[0982] (Electron transport layer)

[0983] The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (p-EtTAZ), phenanthroline (BPhen), copper hydroxide (BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (BzOs) can also be used. The substances mentioned here mainly possess 10... -6 cm 2 Materials with an electron mobility of / Vs or higher. Furthermore, any material whose electron transport is higher than its hole transport can be used as the electron transport layer, except for those mentioned above. Moreover, the electron transport layer can be not only a single layer, but also a layer formed by stacking two or more layers of the aforementioned materials.

[0984] Furthermore, polymeric compounds can also be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[0985] (Electron injection layer)

[0986] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. In addition, materials obtained by containing alkali metals, alkaline earth metals, or their compounds in a substance with electron transport properties can be used, specifically materials obtained by containing magnesium (Mg) in Alq. Furthermore, in this case, electron injection from the cathode can be performed more efficiently.

[0987] Alternatively, the electron injection layer can also be a composite material formed by mixing an organic compound with an electron donor. Such a composite material generates electrons in the organic compound through the electron donor, thus exhibiting excellent electron injection and electron transport properties. In this case, the organic compound is preferably a material with excellent electron transport properties, specifically, substances constituting the aforementioned electron transport layer (metal complexes or heteroaromatic compounds, etc.) can be used. The electron donor is any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. Furthermore, alkali metal oxides or alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, barium oxides, etc. In addition, Lewis bases such as magnesium oxide can also be used. Furthermore, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[0988] (Layer Formation Method)

[0989] The method for forming each layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. Known methods such as dry film formation methods such as vacuum evaporation, sputtering, plasma, and ion plating, or wet film formation methods such as spin coating, dip coating, flow coating, and inkjet coating can be used.

[0990] (film thickness)

[0991] The thickness of each organic layer of the organic EL element in this embodiment is not limited except as specifically mentioned above. However, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a higher applied voltage is required and the efficiency will be reduced. Therefore, the preferred thickness is usually in the range of several nm to 1 μm.

[0992] The organic EL element of this embodiment contains the compound of the first embodiment, thus improving performance. According to one embodiment, an organic EL element with lower driving voltage, higher EQE, and narrower half-width at half-maximum of the light emitted from the element can be provided.

[0993] [Fourth Implementation Method]

[0994] (Organic electroluminescent device)

[0995] The structure of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same reference numerals and names as in the third embodiment are given, and descriptions are omitted or simplified. Furthermore, in the fourth embodiment, the same materials and compounds as those described in the third embodiment can be used for materials and compounds not specifically mentioned.

[0996] The organic EL element of the fourth embodiment differs from the organic EL element of the third embodiment in that the light-emitting layer further comprises a third compound. Otherwise, it is the same as the third embodiment.

[0997] In the fourth embodiment, it is preferable that the light-emitting layer comprises a first compound, a second compound, and a third compound. In this embodiment, it is more preferable that the first compound is the compound of the first embodiment, and even more preferable that the second compound is a delayed fluorescence luminescent material. Furthermore, in this embodiment, it is preferable that the first compound is a dopant material, and preferably that the second compound is the host material. Furthermore, it is preferable that the third compound is not a dopant material. For example, the light-emitting layer of the fourth embodiment may contain the second and third compounds at a rate of 50% or more by mass of the total mass of the light-emitting layer, or at a rate of 60% or more by mass of the layer, 70% or more by mass of the layer, 80% or more by mass of the layer, 90% or more by mass of the layer, or 95% or more by mass of the layer.

[0998] (Third compound)

[0999] The third compound can be a compound with delayed fluorescence or a compound without delayed fluorescence.

[1000] While not particularly limited, the third compound is preferably a compound other than an amine compound. That is, the third compound is preferably unsubstituted or unsubstituted amino groups. Furthermore, carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives can be used as the third compound, for example, but are not limited to these derivatives.

[1001] The third compound is also preferably a compound in which at least one of the following general formula (31), general formula (32), general formula (33A), and general formula (34A) is contained in a molecule.

[1002] [Transformation 50]

[1003]

[1004]

Chemistry 51

[1005]

[1006] In the general formula (31),

[1007] Y 31 ~Y 36 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound.

[1008] Among them, Y 31 ~Y 36 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound.

[1009] In the general formula (32),

[1010] Y 41 ~Y 48 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound.

[1011] Among them, Y 41 ~Y 48 At least one of them is a carbon atom bonded to other atoms in the molecule of the third compound.

[1012] X 30 Nitrogen, oxygen, or sulfur atoms that are bonded to other atoms in the molecule of the third compound.

[1013] In the general formulas (33A) and (34A), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[1014] The third compound preferably has a total of 2 to 10 local structures represented by the general formula (31) and local structures represented by the general formula (32) in a molecule, and more preferably has a total of 4 to 8 local structures represented by the general formula (31) and local structures represented by the general formula (32) in a molecule.

[1015] In the general formula (32), Y is also preferred. 41 ~Y 48 At least two of them are carbon atoms bonded to other atoms in the molecule of the third compound, forming a ring structure containing the carbon atoms.

[1016] For example, the preferred local structure represented by the general formula (32) is any one of the local structures selected from the group consisting of the local structures represented by the following general formulas (321), (322), (323), (324), (325) and (326).

[1017]

Chemistry 52

[1018]

[1019]

Chemistry 53

[1020]

[1021]

Chemistry 54

[1022]

[1023] In the general formulas (321) to (326),

[1024] X 30 Each of the nitrogen, oxygen, or sulfur atoms is independently bonded to other atoms in the molecule of the third compound.

[1025] Y 41 ~Y 48 Each carbon atom is either an independent nitrogen atom or bonded to other atoms in the molecule of the third compound.

[1026] X 31 Each of the following is an independent nitrogen atom, oxygen atom, sulfur atom, or carbon atom bonded to other atoms in the molecule of the third compound.

[1027] Y 61 ~Y 64 Carbon atoms that are either nitrogen atoms or carbon atoms bonded independently to other atoms in the molecule of a third compound.

[1028] In this embodiment, the third compound preferably has a local structure represented by general formula (323) in general formulas (321) to (326).

[1029] The local structure represented by the general formula (31) is preferably included in the third compound as at least any one of the groups selected from the group represented by the general formula (33) and the group represented by the general formula (34).

[1030] The third compound is also preferably having at least one of the local structures represented by the following general formulas (33) and (34). As shown in the local structures represented by the following general formulas (33) and (34), the bonding sites are located at meta positions, thus enabling the third compound to achieve a band gap T at 77 [K]. 77K (M3) remains at a high level.

[1031]

Transformation 55

[1032]

[1033] In the general formula (33), Y 31 Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[1034] In the general formula (34), Y 32 Y 34 and Y 36 Each independently consists of a nitrogen atom or CR 31 .

[1035] In the general formulas (33) and (34),

[1036] R 31 Each can be an independent hydrogen atom or a substituent.

[1037] R as a substituent 31 Independently from

[1038] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[1039] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1040] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1041] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[1042] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[1043] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[1044] Substituted or unsubstituted silyl groups

[1045] Replacement of germanium-based

[1046] Substituted phosphine oxide group,

[1047] Halogen atoms,

[1048] cyano,

[1049] Nitro, and

[1050] Choose from the group consisting of substituted or unsubstituted carboxyl groups.

[1051] Wherein, the R 31 The aryl group, whether substituted or unsubstituted, with a cyclic carbon number of 6 to 30, is preferably a non-fused ring.

[1052] In the general formulas (33) and (34), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[1053] In the general formula (33), Y is preferred. 31 Y 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[1054] Furthermore, in the general formula (34), Y is preferred. 32 Y 34 and Y 36 CR independently 31 Multiple R 31 They are the same or different from each other.

[1055] The preferred substituted germanium-based form is -Ge(R) 301 )3 indicates. R 301 Each is an independent substituent. Substituent R 301 Preferably, it is an alkyl group with 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted. Multiple R 301 They are the same or different from each other.

[1056] The local structure represented by the general formula (32) is preferably included in the third compound as at least one group selected from the group composed of the groups represented by the following general formulas (35) to (39) and the following general formula (30a).

[1057]

Transformation 56

[1058]

[1059]

Chemistry 57

[1060]

[1061]

Transformation 58

[1062]

[1063] In the general formula (35), Y 41 ~Y 48 Each independently consists of a nitrogen atom or CR 32 .

[1064] In the general formulas (36) and (37), Y 41 ~Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[1065] In the general formula (38), Y 41 Y 42 Y 44 Y 45 Y 47 and Y 48 Each independently consists of a nitrogen atom or CR 32 .

[1066] In the general formula (39), Y 42 ~Y 48 Each independently consists of a nitrogen atom or CR 32 .

[1067] In the general formula (30a), Y 42 ~Y 47 Each independently consists of a nitrogen atom or CR 32 .

[1068] In the general formulas (35) to (39) and (30a),

[1069] R 32 Each can be an independent hydrogen atom or a substituent.

[1070] R as a substituent 32 from

[1071] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[1072] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1073] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1074] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[1075] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[1076] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[1077] Substituted or unsubstituted silyl groups

[1078] Replacement of germanium-based

[1079] Substituted phosphine oxide group,

[1080] Halogen atoms,

[1081] cyano,

[1082] Nitro, and

[1083] Choose from the group consisting of substituted or unsubstituted carboxyl groups.

[1084] Multiple R 32 They are the same or different from each other.

[1085] In the general formulas (37) to (39) and (30a),

[1086] X 30 For NR 33 oxygen or sulfur atoms

[1087] R 33 from

[1088] substituted or unsubstituted aryl groups with 6 to 30 carbon atoms

[1089] Substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms

[1090] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1091] Substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms

[1092] Substituted or unsubstituted cycloalkyl groups with 3 to 30 carbon atoms

[1093] Aryl groups, substituted or unsubstituted, having 7 to 30 carbon atoms

[1094] Substituted or unsubstituted silyl groups

[1095] Replacement of germanium-based

[1096] Substituted phosphine oxide group,

[1097] Fluorine atom,

[1098] cyano,

[1099] Nitro, and

[1100] Choose from the group consisting of substituted or unsubstituted carboxyl groups.

[1101] Multiple R 33 They are the same or different from each other.

[1102] Wherein, the R 33 The aryl group, whether substituted or unsubstituted, with a cyclic carbon number of 6 to 30, is preferably a non-fused ring.

[1103] In general formulas (35) to (39) and general formula (30a), * independently represents the site where the compound is bonded to other atoms or other structures in the molecule of the third compound.

[1104] In the general formula (35), Y is preferred. 41 ~Y 48 CR independently 32 In the general formulas (36) and (37), Y is preferred. 41 ~Y 45 Y 47 and Y 48 CR independently 32 In the general formula (38), Y is preferred. 41 Y 42 Y 44 Y 45 Y 47 and Y 48 CR independently 32 In the general formula (39), Y is preferred. 42 ~Y 48 CR independently 32 In the general formula (30a), Y is preferred. 42 ~Y 47 CR independently 32 Multiple R 32 They are the same or different from each other.

[1105] In the third compound, X 30 Preferably, it contains oxygen atoms or sulfur atoms, and more preferably oxygen atoms.

[1106] In the third compound, R is preferred. 31 and R 32 Each is independently a hydrogen atom or a substituent, and R as a substituent 31 and R as a substituent 32 Each group is independently selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 cyclic atoms. More preferably, R. 31 and R 32 It consists of a hydrogen atom, a cyano group, an aryl group with 6 to 30 substituted or unsubstituted cyclic carbon atoms, or a heteroaryl group with 5 to 30 substituted or unsubstituted cyclic atoms. Specifically, R, as a substituent... 31 and R as a substituent32 When the aryl group is a substituted or unsubstituted cyclic carbon group with a carbon number of 6 to 30, the aryl group is preferably a non-fused ring.

[1107] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[1108] Examples of substituents in the third compound are shown below, but the invention is not limited to these examples.

[1109] Specific examples of aryl (sometimes called aromatic hydrocarbon groups) include phenyl, tolyl, xylyl, naphthyl, phenanthrene, pyrene, etc. Benzyl, benzo[c]phenanthrene, benzo[g] Examples of suitable compounds include phenyl, benzo[a]anthrayl, triphenylene, fluorenyl, 9,9-dimethylfluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, biphenyl, terphenyl, tetraphenyl, fluoranthyl, etc., with phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, triphenylene, and fluorenyl being preferred examples.

[1110] Examples of aryl groups with substituents include tolyl, xylyl, and 9,9-dimethylfluorenyl.

[1111] As illustrated in the specific example, aryl groups include both fused aryl groups and unfused aryl groups.

[1112] The preferred aryl group is phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, triphenylene, or fluorene.

[1113] Specific examples of heteroaryl groups (sometimes called heterocyclic groups, heteroaromatic cyclic groups, or aromatic heterocyclic groups) include pyrroloyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, triazinyl, indoleyl, isoindoleyl, imidazoyl, benzimidazolyl, indoleyl, imidazo[1,2-a]pyridinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, azadibenzothiophenyl, quinyl Phinyl, isoquinolinyl, quinoxolinyl, quinazolinyl, naphridinyl, carbazole, azacarbazole, phenanthridine, acridine, phenantholinyl, phenazinyl, phenothiazinyl, phenotoxazinyl, oxazolyl, oxadiazolyl, furo-coryl, benzoxazolyl, thiophene, thiazolyl, thiadiazolyl, benzothiazolyl, triazolyl, tetrazolyl, etc., preferably including dibenzofuranyl, dibenzothiophene, carbazole, pyridinyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothiophene.

[1114] As a heteroaryl group, it is preferably dibenzofuranyl, dibenzothiophene, carbazoyl, pyridyl, pyrimidinyl, triazine, azidodibenzofuranyl or azidodibenzothiophene, and more preferably dibenzofuranyl, dibenzothiophene, azidodibenzofuranyl or azidodibenzothiophene.

[1115] In the third compound, the substituted silyl group is preferably selected from the group consisting of substituted or unsubstituted trialkylsilyl groups, substituted or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups.

[1116] Specific examples of substituted or unsubstituted trialkylsilyl compounds include trimethylsilyl and triethylsilyl.

[1117] Specific examples of substituted or unsubstituted arylalkylsilyl compounds include diphenylmethylsilyl, xylylmethylsilyl, and phenyldimethylsilyl.

[1118] Specific examples of substituted or unsubstituted triarylsilyl compounds include triphenylsilyl and trimethylsilyl.

[1119] In the third compound, the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group.

[1120] Specific examples of substituted or unsubstituted diarylphosphine oxides include diphenylphosphine oxide and xylylphosphine oxide.

[1121] In the third compound, a substituted carboxyl group can be, for example, benzoyloxy.

[1122] Method for manufacturing the third compound

[1123] The third compound can be manufactured by methods described, for example, in International Publication Nos. 2012 / 153780 and 2013 / 038650. Furthermore, the third compound can be manufactured, for example, by using known alternative reactions and starting materials that are compatible with the target compound.

[1124] Specific examples of the third compound

[1125] Specific examples of the third compound in this embodiment are shown below. However, the third compound in this invention is not limited to these specific examples.

[1126]

Chemistry 59

[1127]

[1128]

Transformation 60

[1129]

[1130]

Chemistry 61

[1131]

[1132]

Transformation 62

[1133]

[1134] (The relationship between the first, second, and third compounds in the luminescent layer)

[1135] In the organic EL element of this embodiment, when the light-emitting layer includes a second compound and a third compound, it is preferable that the lowest excitation singlet energy S1(M2) of the second compound and the lowest excitation singlet energy S1(M3) of the third compound satisfy the following mathematical formula (Equation 2).

[1136] S1(M3)>S1(M2) (Number 2)

[1137] The band gap T at 77 [K] is preferably that of the third compound. 77K The band gap T when (M3) is greater than 77 [K] of the first compound. 77K (M1).

[1138] The band gap T at 77 [K] is preferably that of the third compound. 77K The band gap T when (M3) is greater than 77 [K] of the second compound. 77K (M2).

[1139] Preferably, the lowest excited singlet state energy S1(M1) of the first compound, the lowest excited singlet state energy S1(M2) of the second compound, and the lowest excited singlet state energy S1(M3) of the third compound satisfy the following mathematical expression (Equation 2A).

[1140] S1(M3)>S1(M2)>S1(M1)…(Number 2A)

[1141] The preferred bandgap T is at 77 [K] for the first compound. 77K The band gap T at 77 [K] for (M1) and the second compound 77K The band gap T of (M2) and the third compound at 77 [K] 77K (M3) satisfies the following mathematical expression (number 2B).

[1142] T 77K (M3)>T 77K (M2)>T 77K (M1)…(Number 2B)

[1143] Preferably, when the organic EL element of this embodiment emits light, the compound of the first embodiment mainly emits light in the light-emitting layer.

[1144] Preferably, the organic EL element of this embodiment emits green light in the same way as the organic EL element of the third embodiment.

[1145] In the case where the organic EL element of this embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[1146] The peak wavelength of light emitted from the organic EL element can be measured using the same method as the organic EL element in the third embodiment.

[1147] • The content of compounds in the luminescent layer

[1148] When the light-emitting layer contains a first compound, a second compound, and a third compound, the content of the first compound, the second compound, and the third compound in the light-emitting layer is preferably within, for example, the following range.

[1149] The content of the first compound is preferably 0.01% by mass or more and 10% by mass, more preferably 0.01% by mass or more and 5% by mass, and even more preferably 0.01% by mass or more and 2% by mass.

[1150] The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less.

[1151] The content of the third compound is preferably 10% by mass or more and 80% by mass or less.

[1152] The total content of the first compound, the second compound, and the third compound in the light-emitting layer is capped at 100% by mass. Furthermore, it is not excluded that the light-emitting layer in this embodiment may contain materials other than the first compound, the second compound, and the third compound.

[1153] The luminescent layer may contain only one first compound or two or more first compounds. The luminescent layer may contain only one second compound or two or more second compounds. The luminescent layer may contain only one third compound or two or more third compounds.

[1154] Figure 5 This is a diagram illustrating an example of the relationship between the energy levels of the first, second, and third compounds in the luminescent layer. Figure 5In this diagram, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the first compound, and T1(M1) represents the lowest excited triplet state of the first compound. S1(M2) represents the lowest excited singlet state of the second compound, and T1(M2) represents the lowest excited triplet state of the second compound. S1(M3) represents the lowest excited singlet state of the third compound, and T1(M3) represents the lowest excited triplet state of the third compound. Figure 5 The dashed arrow from S1(M2) to S1(M1) in the diagram represents the energy transfer from the lowest excited singlet state of the second compound to the Forster-type state of the first compound.

[1155] like Figure 5 As shown, if a compound with a smaller ΔST(M2) is used as the second compound (a delayed-emission fluorescent material), the lowest excited triplet state T1(M2) can undergo a reverse intersystem crossing to the lowest excited singlet state S1(M2) via thermal energy. Furthermore, a Foster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the second compound to the first compound, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the first compound can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1156] The organic EL element of this embodiment contains the compound of the first embodiment, thus improving performance. According to one embodiment, it is possible to provide an organic EL element with a lower driving voltage, higher EQE, and narrower half-width at half-maximum of the light emitted from the element.

[1157] [Fifth Implementation Method]

[1158] (Electronic devices)

[1159] The electronic device of this embodiment is equipped with an organic EL element from any of the above embodiments. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablet computers, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

[1160] [Changes in implementation method]

[1161] Furthermore, the present invention is not limited to the above-described embodiments, and any modifications or improvements made within the scope of achieving the objectives of the present invention are included within the scope of the present invention.

[1162] For example, the light-emitting layer is not limited to a single layer; multiple light-emitting layers can be stacked. When an organic EL element has multiple light-emitting layers, it is sufficient for at least one organic layer to satisfy the conditions described in the above embodiments; preferably, at least one light-emitting layer contains the compound of the first embodiment. When one of the multiple light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layers can be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize electron migration from the triplet excited state to the ground state.

[1163] Furthermore, in the case of an organic EL element having multiple light-emitting layers, these light-emitting layers can be arranged adjacent to each other, or they can be a so-called tandem organic EL element consisting of multiple light-emitting units stacked with an intermediate layer in between.

[1164] Alternatively, a blocking layer may be disposed adjacent to at least one of the anode and cathode sides of the light-emitting layer. The blocking layer is preferably disposed grounded with the light-emitting layer to block at least one of holes, electrons, and excitons.

[1165] For example, when a barrier layer is grounded on the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the cathode side layer (e.g., an electron transport layer) of the barrier layer. In the case of an organic EL element that includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer.

[1166] Furthermore, when a blocking layer is grounded on the anode side of the light-emitting layer, the blocking layer transports holes and prevents electrons from reaching the anode side layer of the blocking layer (e.g., a hole transport layer). In the case of an organic EL element that includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer.

[1167] Alternatively, the blocking layer can be positioned adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to its surrounding layers. This prevents excitons generated in the light-emitting layer from moving to layers on the electrode side of the blocking layer (e.g., electron transport layers and hole transport layers).

[1168] Preferably, the light-emitting layer is bonded to the blocking layer.

[1169] In addition, the specific structure and shape in the implementation of the present invention may adopt other structures within the scope of achieving the purpose of the present invention.

[1170] Example

[1171] The following describes embodiments of the present invention. The present invention is not limited to these embodiments in any way.

[1172] <Compound>

[1173] The compound represented by the general formula (1) for the production of the organic EL element of Example 1 is as follows.

[1174] [Chemical Formula 63]

[1175]

[1176] The comparative compound for the production of the organic EL element of Comparative Example 1 is as follows.

[1177] [Chemical Formula 64]

[1178]

[1179] Other compounds for the production of the organic EL elements of the examples and comparative examples are as follows.

[1180] [Chemical Formula 65]

[1181]

[1182] [Chemical Formula 66]

[1183]

[1184] [Chemical Formula 67]

[1185]

[1186] [Fabrication of Organic EL Element]

[1187] The organic EL element was fabricated and evaluated as follows.

[1188] (Example 1)

[1189] A glass substrate (manufactured by Giohma Technology Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically washed in isopropyl alcohol for 5 minutes and then UV-ozone washed for 1 minute. The film thickness of ITO was set to 130 nm.

[1190] The washed glass substrate with the transparent electrode wire was mounted on the substrate holder of a vacuum evaporation apparatus, and the compounds HT-1 and HA were co-evaporated in such a manner as to cover the transparent electrode on the surface on the side where the transparent electrode wire was formed, thereby forming a hole injection layer with a film thickness of 10 nm. The concentration of the compound HT-1 in the hole injection layer was set to 97% by mass, and the concentration of the compound HA was set to 3% by mass.

[1191] Next, the compound HT-1 was evaporated on the hole injection layer to form a first hole transport layer with a film thickness of 110 nm.

[1192] Next, compound HT-2 is deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[1193] Next, compound GD-1 (as the first compound), compound TADF-1 (as the second compound), and compound D-1 (as the third compound) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The concentration of compound TADF-1 in the light-emitting layer was set to 25% by mass, the concentration of compound GD-1 was set to 1% by mass, and the concentration of compound D-1 was set to 74% by mass.

[1194] Next, compound ET-1 is deposited on the luminescent layer to form a first electron transport layer with a thickness of 5 nm.

[1195] Next, compound ET-2 is deposited on the first electron transport layer to form a second electron transport layer with a thickness of 50 nm.

[1196] Next, lithium fluoride (LiF) is deposited on the second electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1197] Then, metallic aluminum (Al) is deposited on the electron-injecting electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1198] If the component configuration of Embodiment 1 is shown in a simplified manner, it is as follows.

[1199] ITO (130) / HT-1: HA (10, 97%: 3%) / HT-1 (110) / HT-2 (10) / D-1: TADF-1: GD-1 (25, 74%: 25%: 1%) / ET-1 (5) / ET-2 (50) / LiF (1) / Al (80)

[1200] Additionally, the numbers in parentheses indicate the film thickness (unit: nm).

[1201] Within the same brackets, the percentages (97% : 3%) indicate the proportions (mass %) of compounds HT-1 and HA in the hole injection layer, and the percentages (74% : 25% : 1%) indicate the proportions (mass %) of the third, second, and first compounds in the luminescent layer. The same labeling applies below.

[1202] (Comparative Example 1)

[1203] Except that the compound GD-1 in Example 1 was replaced with the first compound listed in Table 2, the organic EL element of Comparative Example 1 was prepared in the same manner as in Example 1.

[1204] <Evaluation of Organic EL Components>

[1205] The organic EL elements fabricated were evaluated as follows. The evaluation results are shown in Table 2. In addition, the lowest excitation singlet state energy S1 and main peak wavelength of the compounds of general formula (1) used in the luminescent layers of each embodiment, the thermally activated delayed fluorescence (ΔST and Delay / Prompt ratio) and lowest excitation singlet state energy S1 of the second compound, and the lowest excitation singlet state energy S1 of the third compound are also shown in Table 2.

[1206] • Drive voltage (V)

[1207] The measurement involved applying current between the anode and cathode to achieve a current density of 10 mA / cm² in the organic EL element. 2 Voltage at that time (unit: V).

[1208] CIE 1931 colorimetry

[1209] The current density of the organic EL element was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Corporation) when a voltage was applied to the element to achieve a current density of 10 mA / cm². 2 The spectrophotometer of the time was obtained. CIEx and CIEy were calculated based on the obtained spectrophotometer.

[1210] External quantum efficiency (EQE)

[1211] The current density of the organic EL element was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Corporation) when a voltage was applied to the element to achieve a current density of 10 mA / cm². 2 The spectroscopic emission brightness spectrum at that time was obtained. Based on the obtained spectroscopic emission brightness spectrum, it was assumed that Lambertian emission occurred, and the external quantum efficiency EQE (in %) was calculated.

[1212] • Main peak wavelength (λp) and emission half-width (FWHM)

[1213] The current density of the organic EL element was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Corporation) when a voltage was applied to the element to achieve a current density of 10 mA / cm². 2 The spectroscopic emission intensity spectrum at time [time] was obtained. The wavelength λ of the main peak was calculated from the obtained spectroscopic emission intensity spectrum. p (Unit: nm). Furthermore, the emission half-width (FWHM) was measured based on the obtained spectrophotometric emission brightness spectrum (unit: nm).

[1214] Table 2

[1215]

[1216] If the organic EL element of Example 1 is compared with the organic EL element of Comparative Example 1, the main peak wavelength of the elements is the same, but the driving voltage of Example 1 is lower, the EQE is higher, and the half-width is narrower. It can be considered that by introducing benzoindole as a compound represented by general formula (1) to generate multiple resonance effects of boron and nitrogen, it is possible to simultaneously achieve luminescence in the green region and narrowing of the half-width of the spectrum.

[1217] <Compound Evaluation>

[1218] The physical properties of the compounds listed in Table 2 were measured using the following methods.

[1219] (Delayed fluorescence)

[1220] Delayed fluorescence of compound TADF-1

[1221] Delayed fluorescence by utilizing Figure 2 The apparatus shown is used to measure the transition PL for confirmation. The compound TADF-1 is dissolved in toluene, and to eliminate the effect of self-absorption, a dilute solution with an absorbance below 0.05 at the excitation wavelength is prepared. Furthermore, to prevent extinction caused by oxygen, the sample solution is frozen and degassed, then sealed in a covered cell under an argon atmosphere, thereby preparing an argon-saturated, oxygen-free sample solution.

[1222] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of the ethanol solution of 9,10-dibenzane was measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of the two spectra, according to equation (1) in Morris et al., J. Phys. Chem., 80(1976)969.

[1223] Upon excitation by pulsed light (light irradiated by a pulsed laser) at a wavelength absorbed by the compound TADF-1, there exists prompt emission (instantaneous emission) immediately observable from the excitation state and delayed emission (delayed emission) not immediately observable after excitation. In this embodiment, delayed fluorescence emission refers to the amount of delayed emission (delayed emission) being 5% or more relative to the amount of prompt emission (instantaneous emission). Specifically, this is expressed as X. P Set the amount of delayed emission (delayed emission) to X. D At that time, X D / X P The value is above 0.05.

[1224] The amounts of Prompt and Delay luminescence, and their ratio, can be determined using the same method as described in "Nature 492, 234-238, 2012" (Reference 1). Furthermore, the apparatus used to calculate the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1. Figure 2 The device described in the text.

[1225] For compound TADF-1, it was confirmed that the amount of delayed luminescence was more than 5% relative to the amount of prompt luminescence.

[1226] Specifically, for compound TADF-1, X D / X P The value is 0.05 or higher. In Table 2, "Delay / Prompt" indicates "X". D / X P The value of X D / X P The value ">0.05" indicates a value greater than 0.05.

[1227] ·△ST

[1228] The lowest excited singlet state energies S1 of compounds GD-1, Ref-1, TADF-1, and D-1 were measured using the solution method described above. The band gap T, as described in the section on "Relationship between triplet state energy and band gap at 77 [K]", was used. 77K The measurement method was used to measure the bandgap T of compound TADF-1 at 77 [K]. 77K .

[1229] Based on the measured minimum excited singlet energy S1 and the band gap T at 77 [K] 77K Calculate the ΔST of compound TADF-1.

[1230] • The main peak wavelength of the compound

[1231] A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The fluorescence spectrum of the sample was measured at room temperature (300 K) (vertical axis: fluorescence intensity, horizontal axis: wavelength). In this embodiment, the fluorescence spectrum was measured using a Hitachi spectrophotometer (device name: F-7000). However, the fluorescence spectroscopy measuring device is not limited to the one used herein. In the fluorescence spectrum, the wavelength of the peak with the highest fluorescence intensity was taken as the main peak wavelength of the compound.

[1232] <Compound Synthesis>

[1233] (Synthetic Example 1) Synthesis of Compound GD-1

[1234] [Manufacturing of Intermediate 1-1]

[1235]

Transformation 68

[1236]

[1237] Under an argon atmosphere, a mixture of 4.28 g of 2-amino-3-iodonaphthalene, 3.40 g of 1,2-diphenylacetylene, 178 mg of palladium(II) acetate, 446 mg of tricyclohexylphosphine, 5.49 g of potassium carbonate, and 360 mL of N-methylpyrrolidone was stirred at 110 °C for 5 hours. The resulting mixture was cooled to room temperature, and a portion of the N-methylpyrrolidone was distilled off under reduced pressure. The mixture was then diluted with tert-butyl methyl ether and added to water. The aqueous layer was extracted with tert-butyl methyl ether, the organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give 2.78 g (55%) of intermediate 1-1. In the reaction scheme, Pd(OAc)₂ is palladium(II) acetate, Cy₃P is tricyclohexylphosphine, and NMP is N-methylpyrrolidone.

[1238] [Manufacturing of Intermediates 1-2]

[1239]

Transformation 69

[1240]

[1241] Under an argon atmosphere, a mixture of 2-bromo-1,3-difluoro-5-iodobenzene (47.8 g), phenylboronic acid (18.29 g), tripotassium phosphate (39.8 g), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.09 g), 1,4-dioxane (250 mL), and water (125 mL) was stirred at room temperature for 4 hours. Toluene (250 mL) and water (200 mL) were added to the resulting mixture. The aqueous layer was extracted with toluene, the organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The residue was purified by silica gel column chromatography to give 35.1 g (87%) of intermediate 1-2. In the reaction scheme, Pd(dppf)Cl2 is [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[1242] [Manufacturing of Intermediates 1-3]

[1243]

Transformation 70

[1244]

[1245] Under an argon atmosphere, a mixture of intermediate 1-1 (6.39 g), intermediate 1-2 (10.76 g), tripotassium phosphate (21.23 g), and dimethylformamide (140 mL) was stirred at 105 °C for 48 hours. After distilling off a portion of the dimethylformamide under reduced pressure, the mixture was added to water and extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine, dried with magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to give 6.2 g (55%) of intermediate 1-3. In the reaction protocol, DMF was used as dimethylformamide.

[1246] [Manufacturing of Intermediates 1-4]

[1247]

Chemistry 71

[1248]

[1249] Under an argon atmosphere, a mixture of intermediate 1-3 (6.14 g), 3,6-di-tert-butyl-9H-carbazole (3.32 g), tripotassium phosphate (6.88 g), and dimethylformamide (96 mL) was stirred at 105 °C for 20 hours. A portion of the dimethylformamide was distilled off under reduced pressure, and the resulting mixture was added to 150 mL of water and stirred. The precipitated solid was filtered off, washed with water, and dried under reduced pressure. The resulting solid was then suspended in 220 mL of ethanol and refluxed for 1 hour. The solid was then filtered off, yielding 7.31 g (82%) of intermediate 1-4.

[1250] [Preparation of compound GD-1]

[1251]

Chemistry 72

[1252]

[1253] Under an argon atmosphere, intermediate 1-4 (2.23 g) was added to tert-butylbenzene (33 mL). After cooling to -20 °C, a 1.9 M tert-butyllithium pentane solution (2.8 mL) was added dropwise. After the addition, the mixture was heated to 70 °C and stirred for 30 minutes. Components with boiling points lower than tert-butylbenzene were then distilled off under reduced pressure. The mixture was cooled to -55 °C, and boron tribromide (0.57 mL) was added. The mixture was then heated to room temperature and stirred for 1 hour. Next, the mixture was cooled to 0 °C, and N,N-diisopropylethylamine (1.19 mL) was added. The mixture was stirred at room temperature until heating and convergence occurred, then heated to 130 °C and stirred overnight. After distilling off tert-butylbenzene under reduced pressure, the residue was purified by rapid chromatography to obtain 350 mg of the orange compound. Mass spectrometry analysis showed that the orange compound was the target analyte, with a molecular weight of 757.4 [M+H] relative to a molecular weight of 756.8. + In the reaction scheme, t-BuLi is tert-butyllithium, and DIPEA is N,N-diisopropylethylamine.

[1254] Explanation of reference numerals in the attached figures

[1255] 1 Organic EL element

[1256] 2 substrate

[1257] 3 Anode

[1258] 4 Cathode

[1259] 5. Light-emitting layer

[1260] 6. Hole injection layer

[1261] 7. Hole transmission

[1262] 8. Electron transport layer

[1263] 9. Electron injection layer.

Claims

1. A compound, characterized in that, Represented by the following general formula (4), In the general formula (4), R Q R2 and R 13 Each independently, hydrogen atom, or Unsubstituted aryl groups with 6 to 12 carbon atoms in the cyclic group. R x2 R6 and R6 are independent of each other. hydrogen atom, or Unsubstituted alkyl groups having 1 to 10 carbon atoms.

2. The compound according to claim 1, characterized in that, R 13 and R Q Each independently, Unsubstituted phenyl, or Unsubstituted naphthyl group.

3. The compound according to claim 1 or 2, characterized in that, The main peak wavelength is between 500nm and 560nm.

4. The compound according to claim 1 or 2, characterized in that, The main peak wavelength is between 500nm and 540nm.

5. The compound according to claim 1 or 2, characterized in that, The main peak wavelength is between 510nm and 530nm.

6. The compound according to claim 3, characterized in that, The dominant wavelength of a compound refers to the wavelength at which the measured compound reaches its peak at 10 nm. -6 10 moles per liter or more -5 The fluorescence intensity of a toluene solution dissolved at a concentration below mol / L reaches the peak wavelength of the fluorescence spectrum.

7. The compound according to claim 1, characterized in that, Choose from the group consisting of the following compounds. 。 8. A material for use in organic electroluminescent devices, characterized in that, It comprises the compound as described in any one of claims 1 to 7.

9. An organic electroluminescent element comprising a cathode, an anode, and an organic layer contained between the cathode and the anode, characterized in that, The organic layer includes a light-emitting layer. At least one layer of the organic layer comprises a compound according to any one of claims 1 to 7.

10. The organic electroluminescent element as described in claim 9, characterized in that, The luminescent layer contains the compound.

11. The organic electroluminescent element as described in claim 9, characterized in that, The luminescent layer further comprises a delayed-fluorescence luminescent material.

12. The organic electroluminescent element as described in claim 11, characterized in that, The lowest excitation singlet energy S1(H) of the delayed fluorescence luminescent material and the lowest excitation singlet energy S1(D) of the compound satisfy the following mathematical formula (Form 1). S1(H)>S1(D)…(Number 1).

13. An organic electroluminescent element comprising a cathode, an anode, and an organic layer contained between the cathode and the anode, characterized in that, The organic layer includes a light-emitting layer. The light-emitting layer comprises a first compound and a second compound. The first compound is the compound according to any one of claims 1 to 7. The first compound is a dopant material. The second compound is the main material.

14. The organic electroluminescent element as described in claim 13, characterized in that, The lowest excited singlet state energy S1(M1) of the first compound and the lowest excited singlet state energy S1(M2) of the second compound satisfy the following mathematical expression (Equation 3): S1(M2)>S1(M1)…(number 3).

15. The organic electroluminescent element as described in claim 13 or 14, characterized in that, The band gap T of the first compound at 77 K 77K (M1) and the band gap T at 77 [K] of the second compound 77K (M2) satisfies the following mathematical expression (number 5) relationship, T 77K (M2)>T 77K (M1)…(Number 5).

16. The organic electroluminescent element as described in claim 13 or 14, characterized in that, The light-emitting layer also contains a third compound.

17. The organic electroluminescent element as described in claim 16, characterized in that, The lowest excited singlet state energy S1(M2) of the second compound and the lowest excited singlet state energy S1(M3) of the third compound satisfy the following mathematical expression (Equation 2): S1(M3)>S1(M2)…(number 2).

18. The organic electroluminescent element as described in claim 16, characterized in that, The lowest excited singlet state energy S1(M1) of the first compound, the lowest excited singlet state energy S1(M2) of the second compound, and the lowest excited singlet state energy S1(M3) of the third compound satisfy the following mathematical expression (Equation 2A). S1(M3)>S1(M2)>S1(M1)…(Number 2A).

19. The organic electroluminescent element as claimed in claim 16, characterized in that, The band gap T of the third compound at 77 [K] 77K (M3) is greater than the band gap T when it is greater than 77 [K] of the first compound. 77K (M1).

20. The organic electroluminescent element as claimed in claim 16, characterized in that, The band gap T of the third compound at 77 [K] 77K (M3) is greater than the band gap T when it is greater than 77 [K] of the second compound. 77K (M2).

21. The organic electroluminescent element as described in claim 16, characterized in that, The band gap T of the first compound at 77 K 77K (M1) and the band gap T at 77 [K] of the second compound 77K (M2) and the band gap T at 77 [K] of the third compound 77K (M3) satisfies the following mathematical expression (number 2B) relationship, T 77K (M3)>T 77K (M2)>T 77K (M1)…(Number 2B).

22. The organic electroluminescent element as described in claim 16, characterized in that, The third compound is a compound that does not exhibit delayed fluorescence.

23. The organic electroluminescent element as described in claim 16, characterized in that, The third compound does not contain substituted or unsubstituted amino groups.

24. The organic electroluminescent element as described in claim 13 or 14, characterized in that, The first compound is a fluorescent compound that does not exhibit delayed fluorescence.

25. The organic electroluminescent element as described in claim 13, characterized in that, The second compound is a delayed fluorescence luminescent material.

26. The organic electroluminescent element as described in claim 11 or 25, characterized in that, The lowest excitation singlet energy S1(H) of the delayed fluorescence luminescent material and the band gap T of the delayed fluorescence luminescent material at 77 [K] 77K The difference between (H) and ΔST(H) satisfies the following mathematical expression (Mathematics 10): △ST(H) = S1(H) - T 77K (H) < 0.3 eV… (number 10).

27. The organic electroluminescent element as described in claim 26, characterized in that, The △ST(H) satisfies the following mathematical expression (number 11), △ST(H) = S1(H) - T 77K (H) < 0.2 eV… (number 11).

28. The organic electroluminescent element as described in claim 26, characterized in that, The △ST(H) satisfies the following mathematical expression (number 12), △ST(H) = S1(H) - T 77K (H) < 0.1 eV… (number 12).

29. The organic electroluminescent element as described in claim 26, characterized in that, The △ST(H) satisfies the following mathematical expression (Mathematics 13), △ST(H) = S1(H) - T 77K (H) < 0.01 eV… (Number 13).

30. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The light-emitting layer does not contain metal complexes.

31. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The light-emitting layer does not contain phosphorescent materials.

32. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The light-emitting layer does not contain heavy metal complexes or phosphorescent rare earth metal complexes.

33. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The light-emitting layer does not contain iridium complexes, osmium complexes, or platinum complexes.

34. The organic electroluminescent element as described in claim 9 or 13, characterized in that, It emits a green light.

35. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The main peak wavelength of the light emitted from the organic electroluminescent element is above 500 nm and below 560 nm.

36. The organic electroluminescent element as described in claim 35, characterized in that, A voltage is applied to the organic electroluminescent element to achieve a current density of 10 mA / cm². 2 In the spectrophotometric emission brightness spectrum at a given time, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum is taken as the main peak wavelength, and the unit of the main peak wavelength is nm.

37. The organic electroluminescent element according to any one of claims 19 to 21, characterized in that, Will be used as band gap T 77K The compound to be measured was dissolved in EPA at a concentration of 10 μmol / L in a volume ratio of diethyl ether:isopentane:ethanol = 5:5:

2. This solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum was measured at 77 K. A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge The energy calculated according to the following conversion formula (F1) will be used as the band gap T at 77 [K]. 77K In this phosphorescence spectrum, the vertical axis represents the phosphorescence intensity, and the horizontal axis represents the wavelength, λ. edge The unit is nm, and the bandgap is T. 77K The unit is eV. Conversion formula (F1): T 77K =1239.85 / λ edge .

38. The organic electroluminescent element as described in claim 26, characterized in that, Will be used as band gap T 77K The compound to be measured was dissolved in EPA at a concentration of 10 μmol / L in a volume ratio of diethyl ether:isopentane:ethanol = 5:5:

2. This solution was placed in a quartz cell as the measurement sample. For this measurement sample, the phosphorescence spectrum was measured at 77 K. A tangent was drawn to the rising edge of the short wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent and the horizontal axis was determined. edge The energy calculated according to the following conversion formula (F1) will be used as the band gap T at 77 [K]. 77K In this phosphorescence spectrum, the vertical axis represents the phosphorescence intensity, and the horizontal axis represents the wavelength, λ. edge The unit is nm, and the bandgap is T. 77K The unit is eV. Conversion formula (F1): T 77K =1239.85 / λ edge .

39. The organic electroluminescent element according to any one of claims 12, 14, 17 and 18, characterized in that, A 10 μmol / L toluene solution of the compound used to measure the lowest excited singlet energy S1 was placed in a quartz cell, and the absorption spectrum of the sample was measured at 300 K. A tangent was drawn to the falling edge of the longer wavelength side of the absorption spectrum. The wavelength value λedge at the intersection of this tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy S1. Here, the vertical axis of the absorption spectrum represents the absorption intensity, the horizontal axis represents the wavelength, the unit of λedge is nm, and the unit of the lowest excited singlet energy S1 is eV. Conversion formula (F2): S1[eV]=1239.85 / λedge.

40. The organic electroluminescent element as claimed in claim 26, characterized in that, A 10 μmol / L toluene solution of the compound used to measure the lowest excited singlet energy S1 was placed in a quartz cell, and the absorption spectrum of the sample was measured at 300 K. A tangent was drawn to the falling edge of the longer wavelength side of the absorption spectrum. The wavelength value λedge at the intersection of this tangent and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy S1. Here, the vertical axis of the absorption spectrum represents the absorption intensity, the horizontal axis represents the wavelength, the unit of λedge is nm, and the unit of the lowest excited singlet energy S1 is eV. Conversion formula (F2): S1[eV]=1239.85 / λedge.

41. The organic electroluminescent element as described in claim 9 or 13, characterized in that, The light-emitting layer contains the following compound, GD-1. 。 42. The organic electroluminescent element as described in claim 41, characterized in that, The light-emitting layer contains the following compounds: D-1 and TADF-1. 。 43. An electronic device, characterized in that, It is equipped with an organic electroluminescent element as described in any one of claims 9 to 42.

Images