Compounds and organic electroluminescent elements

Abstract

The compounds represented by formulas (1-1) and (1-3) below, or the compounds represented by formulas (1-2) and (1-3) below. R1~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. In the compounds shown in formulas (1-1) and (1-3), R5 to R7 and R 14 ~R 16 At least one of them is -N(R) 36 (R) 37 In the compounds shown in formulas (1-2) and (1-3), R2~R 16 At least one of them is -N(R) 36 (R) 37 ).

Description

Technical Field

[0001] This invention relates to novel compounds and organic electroluminescent elements. 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 into the light-emitting layer from the anode, and electrons are injected from the cathode. Furthermore, in the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] In the past, the performance of organic EL devices has been insufficient. While improvements in materials used in organic EL devices have been made to enhance performance, further high-performance applications are still required. In particular, improving the lifespan of organic EL devices is a crucial issue related to the lifespan of practically applicable products, thus demanding materials capable of achieving long lifespans for organic EL devices.

[0004] Patent document 1 discloses the use of compounds with specific structures in the light-emitting layer of organic EL elements.

[0005] Existing technical documents

[0006] Patent documents

[0007] Patent Document 1: International Publication No. 2019 / 111971. Summary of the Invention

[0008] The object of this invention is to provide a compound capable of manufacturing long-life organic EL elements.

[0009] Through repeated and in-depth research in order to achieve the above-mentioned objectives, the inventors discovered that if a compound with a specific structure is used, an organic EL element with excellent lifetime can be obtained, thus completing the present invention.

[0010] According to the present invention, the following compounds are provided.

[0011] The compounds shown in formulas (1-1) and (1-3) below, or the compounds shown in formulas (1-2) and (1-3) below,

[0012] [Chemistry 1]

[0013]

[0014] (In the aforementioned equations (1-1), (1-2), and (1-3),)

[0015] Ring A is an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, or a heterocycle with 5 to 50 substituted or unsubstituted carbon atoms;

[0016] The two bonding sites* in the aforementioned formula (1-1) are each bonded to the cyclic carbon atom of the aforementioned aromatic hydrocarbon ring of the aforementioned ring A, or the cyclic atom of the aforementioned heterocycle;

[0017] The three bonding sites* in the aforementioned formula (1-2) are each bonded to the cyclic carbon atom of the aforementioned aromatic hydrocarbon ring of the aforementioned ring A, or the cyclic atom of the aforementioned heterocycle;

[0018] R1~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0019] R1~R1 do not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 16 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0020] In the compounds shown in formulas (1-1) and (1-3) above, R5~R7 and R 14 ~R 16 At least one of them is -N(R) 36 (R) 37 In the compounds shown in formulas (1-2) and (1-3) above, R2~R 16 At least one of them is -N(R) 36 (R) 37 );

[0021] R1~R 16 Two or more adjacent groups form substituted or unsubstituted saturated or unsaturated rings, or R1~R 16At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0022] R 31 ~R 37 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted cyclic carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[0023] R 31 ~R 37 When each has multiple instances, there are multiple R's. 31 ~R 37 They can be the same or different.

[0024] According to the present invention, compounds capable of manufacturing long-life organic EL elements can be provided. Attached Figure Description

[0025] Figure 1 This is a diagram illustrating the schematic configuration of an organic EL element according to one aspect of the present invention. Detailed Implementation

[0026] [definition]

[0027] In this specification, hydrogen atoms include isotopes with different numbers of neutrons, namely, protium, deuterium, and tritium.

[0028] In this specification, in the chemical structural formula, hydrogen atoms, i.e. protium atoms, deuterium atoms, or tritium atoms, are bonded at positions not explicitly indicated by symbols such as "R" or "D" representing deuterium atoms.

[0029] In this specification, the number of cyclic carbon atoms refers to the number of carbon atoms in the atoms constituting the ring itself in a compound whose atoms are bonded into a cyclic structure (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 cyclic carbon atoms. The term "number of cyclic carbon atoms" as used below is the same unless otherwise specified. For example, the number of cyclic carbon atoms in a benzene ring is 6, in a naphthalene ring it is 10, in a pyridine ring it is 5, and in a furan ring it is 4. Additionally, for example, the number of cyclic carbon atoms in 9,9-diphenylfluorene is 13, and in 9,9'-spirodifluorene is 25.

[0030] Furthermore, when a benzene ring is substituent for, for example, an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the ring-forming process of a benzene ring with a substituent alkyl group is 6. Similarly, when a naphthalene ring is substituent for, for example, an alkyl group, the number of carbon atoms in that alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the ring-forming process of a naphthalene ring with a substituent alkyl group is 10.

[0031] 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) whose atoms are bonded into a cyclic structure (e.g., monocyclic, fused-ring, and ring aggregates). Atoms that do not constitute a ring (e.g., hydrogen atoms that end the bonds of the atoms constituting the ring) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same 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 atoms forming 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 with hydrogen atoms or substituents is 10.

[0032] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon atoms numbering XX~YY" refers to the number of carbon atoms when the ZZ group is unsubstituted, excluding the number of carbon atoms in the substituents. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0033] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms XX~YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substituted. Here, "YY" is greater than "XX", where "XX" represents an integer greater than 1 and "YY" represents an integer greater than 2.

[0034] In this specification, "unsubstituted ZZ group" means "unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0035] In this specification, "unsubstituted or unsubstituted ZZ group" means that the hydrogen atom of the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0036] Furthermore, in this specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms of the ZZ group are replaced by a substituent. Similarly, "substitution" in the case of "BB group substituted by AA group" also means that one or more hydrogen atoms of the BB group are replaced by an AA group.

[0037] Substituents described in this specification

[0038] The substituents described in this specification will be explained below.

[0039] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" as described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0040] Unless otherwise specified in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" specified in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0041] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkyl" as specified in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0042] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" specified in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0043] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" described in this specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0044] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted cycloalkyl" as described in this specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0045] Unless otherwise specified in this specification, the number of cyclic carbon atoms in the "unsubstituted aryl group" described in this specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0046] 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.

[0047] Unless otherwise specified in this specification, the number of carbon atoms in the "unsubstituted alkylene group" as described in this specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0048] • "Substituted or unsubstituted aryl groups"

[0049] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (In this document, 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, when "aryl" is mentioned alone, it includes both "unsubstituted aryl" and "substituted aryl".

[0050] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group are replaced by substituents. Examples of "substituted aryl" include, for instance, the group in Specific Example Group G1A below where one or more hydrogen atoms of an "unsubstituted aryl" group are replaced by substituents, and the substituted aryl group in Specific Example Group G1B below. Furthermore, the examples of "unsubstituted aryl" and "substituted aryl" listed here are merely examples; the "substituted aryl" as described in this specification also includes groups in Specific Example Group G1B below where the hydrogen atoms bonded to the carbon atoms of the aryl group itself are further replaced by substituents, and groups in Specific Example Group G1B below where the hydrogen atoms of the substituents are further replaced by substituents.

[0051] • Unsubstituted aryl groups (specific example group G1A):

[0052] Phenyl,

[0053] p-phenyl,

[0054] metaphenyl,

[0055] o-phenyl,

[0056] p - terphenyl - 4 - yl,

[0057] p - terphenyl - 3 - yl,

[0058] p - terphenyl - 2 - yl,

[0059] m - terphenyl - 4 - yl,

[0060] m - terphenyl - 3 - yl,

[0061] m - terphenyl - 2 - yl,

[0062] o - terphenyl - 4 - yl,

[0063] o - terphenyl - 3 - yl,

[0064] o - terphenyl - 2 - yl,

[0065] 1 - naphthyl,

[0066] 2 - naphthyl,

[0067] anthryl,

[0068] benzoanthryl,

[0069] [[ID=四十一]]phenanthryl,

[0070] benzophenanthryl,

[0071] phenalenyl,

[0072] pyrenyl,

[0073] chrysenyl,

[0074] benzochrysenyl,

[0075] triphenylenyl, <>

[0076] benzotriphenylenyl,

[0077] tetracenyl, <00>

[0078] pentacenyl,

[0079] fluorenyl,

[0080] 9,9'-spirobifluorenyl,

[0081] benzofluorenyl,

[0082] dibenzofluorenyl, <>

[0083] fluoranthenyl,

[0084] benzofluoranthenyl,

[0085] perylenyl, and

[0086] A monovalent aryl group derived by removing one hydrogen atom from the ring structure shown by the following general formulas (TEMP-1) to (TEMP-15).

[0087] [Chemistry 2]

[0088]

[0089] [Chemistry 3]

[0090] .

[0091] • Substituted aryl groups (specific example group G1B):

[0092] o-Tolyl,

[0093] m-Tolyl,

[0094] p-Tolyl,

[0095] p-Xylyl,

[0096] m-Xylyl,

[0097] o-xylyl,

[0098] p-isopropylphenyl,

[0099] m-Isopropylphenyl,

[0100] o-isopropylphenyl,

[0101] p-tert-butylphenyl,

[0102] m-tert-butylphenyl,

[0103] o-tert-butylphenyl,

[0104] 3,4,5-Trimethylphenyl

[0105] 9,9-Dimethylfluorenyl,

[0106] 9,9-Diphenylfluorenyl

[0107] 9,9-Bis(4-methylphenyl)fluorenyl,

[0108] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0109] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0110] cyanophenyl,

[0111] Triphenylsilylphenyl

[0112] Trimethylsilylphenyl

[0113] Phenylacetyl,

[0114] Naphthylphenyl, and

[0115] The aforementioned groups derived from the ring structures shown in general formulas (TEMP-1) to (TEMP-15) are groups in which one or more hydrogen atoms of a monovalent group are replaced by substituents.

[0116] • "Substituted or unsubstituted heterocyclic groups"

[0117] 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.

[0118] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0119] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0120] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (In this document, 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, when "heterocyclic group" is mentioned alone, it includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0121] "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 where the hydrogen atoms of the "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in Example Group G2B below. Furthermore, the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include groups in Example Group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself are further replaced by substituents, and groups in Example Group G2B where the hydrogen atoms of the substituents are further replaced by substituents.

[0122] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0123] Specific example group G2B includes, for example, the following: a substituted heterocyclic group containing a nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), a substituted heterocyclic group containing a sulfur atom (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4).

[0124] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0125] pyrrole,

[0126] Imidazole group,

[0127] pyrazolyl,

[0128] Triazole group,

[0129] Tetrazolyl,

[0130] Oxazolyl,

[0131] Isoxazolyl,

[0132] Oxadiazole group,

[0133] Thiazole group,

[0134] Isothiazolyl,

[0135] Thiadiazole group,

[0136] pyridyl,

[0137] pyridazinyl,

[0138] Pyrimidine group,

[0139] Pyrazinyl,

[0140] Triazine group

[0141] Indole,

[0142] Isoindolyl,

[0143] Indoleazine,

[0144] Quinazine-based

[0145] Quinoline,

[0146] Isoquinoline,

[0147] Crenoline group

[0148] Phthaloazine

[0149] Quinazolinyl,

[0150] Quinoxaloyl,

[0151] Benzimidazole group,

[0152] Indazole group,

[0153] phenanthroline,

[0154] phenanthridine,

[0155] acridine group,

[0156] Phenolicazine

[0157] Carbazole group,

[0158] Benzocarbazolyl,

[0159] Morpholinyl group

[0160] phenoxazine group,

[0161] phenothiazine group,

[0162] Azacarbazolyl and diazacarbazolyl.

[0163] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0164] furanyl,

[0165] Oxazolyl,

[0166] Isoxazolyl,

[0167] Oxadiazole group,

[0168] Xuton base,

[0169] Benzofuranyl,

[0170] Isobenzofuranyl,

[0171] Dibenzofuranyl,

[0172] Naphthobenzofuranyl,

[0173] Benzoxazolyl,

[0174] Benzisoxazole group,

[0175] phenoxazine group,

[0176] Morpholinyl group

[0177] Dinaphthylfuranyl,

[0178] Azadibenzofuranyl,

[0179] diazadibenzofuranyl,

[0180] Azanaphthalenebenzofuranyl, and

[0181] Diazanaphthenebenzofuranyl.

[0182] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0183] Thiophene group

[0184] Thiazole group,

[0185] Isothiazolyl,

[0186] Thiadiazole group,

[0187] benzothienyl group

[0188] isobenzothienyl group

[0189] dibenzothienyl group

[0190] Naphthobenzothienyl group

[0191] Benzothiazolyl,

[0192] Benzisothiazolyl,

[0193] phenothiazine group,

[0194] dinaphthothienyl group

[0195] azadibenzothienyl group

[0196] diazadibenzothienyl group

[0197] azanaphthobenzothienyl group, and

[0198] diazanaphthobenzothienyl group.

[0199] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0200] [Chemistry 4]

[0201]

[0202] [Chemistry 5]

[0203] .

[0204] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0205] In the aforementioned general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0206] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0207] (9-phenyl)carbazole group,

[0208] (9-Biphenyl)carbazolyl,

[0209] (9-Phenyl)phenylcarbazolyl,

[0210] (9-Naphthyl)carbazole,

[0211] Diphenylcarbazole-9-yl,

[0212] Phenylexacarbazole-9-yl,

[0213] Methylbenzimidazole,

[0214] Ethylbenzimidazole,

[0215] Phenylacetyl,

[0216] Biphenyltriazine,

[0217] diphenyltriazine group,

[0218] phenylquinazolinyl, and

[0219] Biphenylquinazolinyl.

[0220] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0221] Phenyl dibenzofuranyl,

[0222] Methyldibenzofuranyl,

[0223] tert-butyldibenzofuranyl, and

[0224] The monovalent residues of [9H-xanton-9,9'-[9H]fluorene].

[0225] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0226] Phenyl dibenzothiophene,

[0227] Methyldibenzothiophene,

[0228] tert-butyldibenzothiophene, and

[0229] The monovalent residue of [9H-thioxanth-9,9'-[9H]fluorene].

[0230] • Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structures shown in general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific example group G2B4):

[0231] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to one or more hydrogen atoms selected from the following: hydrogen atoms bonded to the cyclic carbon atom of the monovalent heterocyclic group, hydrogen atoms bonded to the nitrogen atom when at least one of XA and YA is NH, and hydrogen atoms of the methylene group when one of XA and YA is CH2.

[0232] • "Substituted or unsubstituted alkyl groups"

[0233] 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. (In this document, unsubstituted alkyl means the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl means the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when "alkyl" is mentioned alone, it includes both "unsubstituted alkyl" and "substituted alkyl".

[0234] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by substituents. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkyl" (specific example group G3A) are replaced by substituents, and examples of substituted alkyl (specific example group G3B), etc. In this specification, "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes straight-chain "unsubstituted alkyl" and branched-chain "unsubstituted alkyl". Furthermore, the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group itself in a "substituted alkyl" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in a "substituted alkyl" of specific example group G3B are further replaced by substituents.

[0235] • Unsubstituted alkyl groups (specific example group G3A):

[0236] methyl,

[0237] Ethyl,

[0238] n-propyl,

[0239] Isopropyl,

[0240] n-Butyl,

[0241] Isobutyl,

[0242] sec-butyl, and

[0243] tert-butyl.

[0244] • Substituted alkyl groups (specific example group G3B):

[0245] Heptafluoropropyl (including isomers),

[0246] Pentafluoroethyl,

[0247] 2,2,2-Trifluoroethyl, and

[0248] Trifluoromethyl

[0249] • "Substituted or unsubstituted alkenyl groups"

[0250] Specific examples of "substituted or unsubstituted alkenyl groups" described in this specification (specific example group G4) include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (In this document, "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 "alkenyl group" is mentioned alone, it includes both "unsubstituted alkenyl group" and "substituted alkenyl group".

[0251] "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 substituents in the "unsubstituted alkenyl" group (specific example group G4A) and examples of substituted alkenyl groups (specific example group G4B). Furthermore, the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl group itself are further replaced by substituents, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituents are further replaced by substituents.

[0252] • Unsubstituted alkenyl groups (specific example group G4A):

[0253] vinyl,

[0254] Allyl

[0255] 1-Butenyl,

[0256] 2-Butenyl, and

[0257] 3-Butenyl.

[0258] • Substituted alkenyl groups (specific example group G4B):

[0259] 1,3-Butadienyl,

[0260] 1-Methylvinyl

[0261] 1-Methylallyl,

[0262] 1,1-Dimethylallyl,

[0263] 2-Methylallyl, and

[0264] 1,2-Dimethylallyl.

[0265] • "Substituted or unsubstituted alkynyl groups"

[0266] 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. (In this text, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) Hereinafter, when "alkynyl group" is mentioned alone, it includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0267] "Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

[0268] • Unsubstituted alkynyl group (specific example group G5A):

[0269] Acetylene group.

[0270] • "Substituted or unsubstituted cycloalkyl groups"

[0271] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (In this document, 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, when "cycloalkyl" is mentioned alone, it includes both "unsubstituted cycloalkyl" and "substituted cycloalkyl".

[0272] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group are replaced by substituents. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) are replaced by substituents, and examples of substituted cycloalkyl groups (specific example group G6B). Furthermore, the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples; the "substituted cycloalkyl" as described in this specification also includes groups in which 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 are replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" group of specific example group G6B are further replaced by substituents.

[0273] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0274] Cyclopropyl

[0275] Cyclobutyl,

[0276] Cyclopentyl,

[0277] Cyclohexyl,

[0278] 1-Adamantyl,

[0279] 2-Adamantyl,

[0280] 1-Norbornel alkyl, and

[0281] 2-Norbornel alkyl.

[0282] • Substituted cycloalkyl groups (specific example group G6B):

[0283] 4-Methylcyclohexyl.

[0284] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0285] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the groups shown (specific example group G7) can be listed.

[0286] -Si(G1)(G1)(G1),

[0287] -Si(G1)(G2)(G2)

[0288] -Si(G1)(G1)(G2),

[0289] -Si(G2)(G2)(G2),

[0290] -Si(G3)(G3)(G3), and

[0291] -Si(G6)(G6)(G6). Here.

[0292] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0293] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0294] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0295] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0296] In -Si(G1)(G1)(G1), multiple G1s can be the same or different from each other.

[0297] In -Si(G1)(G2)(G2), multiple G2s can be the same or different from each other.

[0298] In -Si(G1)(G1)(G2), multiple G1s can be the same or different from each other.

[0299] In -Si(G2)(G2)(G2), multiple G2s can be the same or different from each other.

[0300] In -Si(G3)(G3)(G3), multiple G3s can be the same or different from each other.

[0301] In -Si(G6)(G6)(G6), multiple G6s can be the same or different from each other.

[0302] ·“-O-(R 904 The group shown in the figure”

[0303] As described in this specification, -O-(R) 904 Specific examples of the groups shown (specific example group G8) can be listed.

[0304] -O(G1)

[0305] -O(G2),

[0306] -O(G3), and

[0307] -O(G6).

[0308] Here,

[0309] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0310] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0311] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0312] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0313] ·“-S-(R 905 The group shown in the figure”

[0314] As described in this specification, -S-(R) 905 Specific examples of the groups shown (specific example group G9) can be listed.

[0315] -S(G1)

[0316] -S(G2),

[0317] -S(G3), and

[0318] -S(G6).

[0319] Here,

[0320] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0321] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0322] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0323] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0324] ·"-N(R 906 (R) 907 The group shown in the figure”

[0325] As described in this specification, -N(R) 906 (R) 907 Specific examples of the groups shown (specific example group G10) can be listed.

[0326] -N(G1)(G1),

[0327] -N(G2)(G2),

[0328] -N(G1)(G2),

[0329] -N(G3)(G3), and

[0330] -N(G6)(G6).

[0331] Here,

[0332] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0333] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0334] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0335] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0336] In -N(G1)(G1), multiple G1s can be the same or different from each other.

[0337] In -N(G2)(G2), multiple G2s can be the same or different from each other.

[0338] In -N(G3)(G3), multiple G3s can be the same or different from each other.

[0339] The multiple G6s in -N(G6)(G6) can be the same or different from each other.

[0340] • "Halogen atom"

[0341] Specific examples of "halogen atoms" as described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0342] • "Substituted or unsubstituted fluoroalkyl groups"

[0343] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group are replaced by a substituent. Furthermore, the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl" include groups in which one or more hydrogen atoms of the aforementioned "alkyl" group (specific example group G3) are replaced by fluorine atoms, etc.

[0344] • "Substituted or unsubstituted haloalkyl groups"

[0345] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group is replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group are replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group are replaced by a substituent. Furthermore, the term "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group are further replaced by substituents. As specific examples of "unsubstituted haloalkyl", examples can be given of groups in the aforementioned "alkyl" (specific example group G3) in which one or more hydrogen atoms are replaced by halogen atoms. Sometimes haloalkyl is referred to as alkyl halide.

[0346] • "Substituted or unsubstituted alkoxy groups"

[0347] As a specific example of the "substituted or unsubstituted alkoxy group" described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. Unless otherwise stated in this specification, the "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0348] • "Substituted or unsubstituted alkylthio groups"

[0349] As a specific example of the "substituted or unsubstituted alkylthio group" described in this specification, it is the group indicated by -S(G3), where G3 refers to the "substituted or unsubstituted alkyl group" described in specific example group G3. Unless otherwise stated in this specification, the "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18.

[0350] • "Substituted or unsubstituted aryloxy groups"

[0351] As a specific example of the "substituted or unsubstituted aryloxy group" described in this specification, it is the group represented by -O (G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise stated in this specification, the number of cyclic carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0352] • "Substituted or unsubstituted arylthio groups"

[0353] As a specific example of the "substituted or unsubstituted arylthio group" described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. Unless otherwise stated in this specification, the number of cyclic carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0354] • "Substituted or unsubstituted trialkylsilyl groups"

[0355] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "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 stated in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0356] • "Substituted or unsubstituted aralkyl groups"

[0357] As a specific example of the "substituted or unsubstituted aralkyl" described in this specification, it is the group shown as -(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 in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" replaced by "unsubstituted aryl", and unless otherwise described 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.

[0358] 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.

[0359] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirodifluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.

[0360] 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, and naphtho-benzofuranyl. 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.

[0361] In this specification, unless otherwise stated herein, the carbazoyl group specifically refers to any of the following groups.

[0362] [Chemistry 6]

[0363]

[0364] In this specification, unless otherwise stated herein, (9-phenyl)carbazolyl specifically refers to any of the following groups.

[0365] [Chemistry 7]

[0366]

[0367] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0368] In this specification, unless otherwise stated herein, dibenzofuranyl and dibenzothiopheneyl are specifically any of the following groups.

[0369] [Chemistry 8]

[0370]

[0371] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0372] 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.

[0373] • "Substituted or unsubstituted aryl groups"

[0374] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring of the aforementioned "substituted or unsubstituted aryl group". Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in specific example group G1.

[0375] • "Substituted or unsubstituted divalent heterocyclic group"

[0376] Unless otherwise stated, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived by removing one hydrogen atom from the heterocyclic group described above. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom from the heterocyclic group described in specific example group G2.

[0377] • "Substituted or unsubstituted alkylene compounds"

[0378] Unless otherwise stated, the "substituted or unsubstituted alkylene group" as described in this specification is a divalent group derived by removing one hydrogen atom from the alkyl chain of the aforementioned "substituted or unsubstituted alkylene group". Specific examples of "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkylene group" described in specific example group G3.

[0379] Unless otherwise stated in this specification, the substituted or unsubstituted aryl group described herein is preferably any group of the following general formulas (TEMP-42) to (TEMP-68).

[0380] [Chemistry 9]

[0381]

[0382] [Chemistry 10]

[0383]

[0384] In the aforementioned general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0385] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0386] [Chemistry 11]

[0387]

[0388] In the aforementioned general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0389] Formulas Q9 and Q 10 They can bond together to form a ring through single bonds.

[0390] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0391] [Chemistry 12]

[0392]

[0393] In the aforementioned general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0394] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0395] Unless otherwise stated in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0396] [Chemistry 13]

[0397]

[0398] [Chemistry 14]

[0399]

[0400] [Chemistry 15]

[0401]

[0402] In the aforementioned general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent;

[0403] [Chemistry 16]

[0404]

[0405] [Chemistry 17]

[0406]

[0407] [Chemistry 18]

[0408]

[0409] [Chemistry 19]

[0410]

[0411] In the aforementioned general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent;

[0412] The above is an explanation of the substituents described in this specification.

[0413] • "Cases where bonds form rings"

[0414] In this specification, the phrase "one or more groups of two or more adjacent elements 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 following: "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring," "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring," and "one or more groups of two or more adjacent elements not bonded together."

[0415] The following explanation addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter sometimes collectively referred to as "forming a ring by bonding"). An example is an anthracene compound represented by the following general formula (TEMP-103) with an anthracene ring as its parent skeleton.

[0416] [Chemistry 20]

[0417]

[0418] For example, R 921 ~R930 In the case of "one or more groups consisting of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements that forms a single group is R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0419] The phrase "one or more groups" refers to the fact that two or more groups consisting of two or more adjacent elements can simultaneously form a loop. For example, R 921 With R 922 They bond together to form a ring Q A Meanwhile, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0420] [Chemistry 21]

[0421]

[0422] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the bonded group of "two" adjacent elements as in the previous example, but also the bonded group of "three or more" adjacent elements. For example, it refers to: 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 , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse with the anthracene matrix, the anthracene compound represented by the aforementioned 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 There are a total of R 922 .

[0423] [Chemistry 22]

[0424]

[0425] The formed "monocyclic ring" or "fused ring" is only a structural feature of the formed ring and can be either a saturated or unsaturated ring. Even when forming a "monocyclic ring" or "fused ring," the "monocyclic ring" or "fused ring" can still form either a saturated or unsaturated ring. For example, the ring Q formed in the aforementioned general formula (TEMP-104) A and ring Q B These are respectively "monocyclic" or "fused-ring". Furthermore, the ring Q formed in the aforementioned general formula (TEMP-105) A and ring Q C It is a "fused ring". The ring Q of the aforementioned general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C They fuse to form fused rings. If the ring Q of the aforementioned 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 aforementioned general formula (TMEP-104) is... A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0426] "Unsaturated rings" include, in addition to aromatic hydrocarbon rings and aromatic heterocycles, aliphatic hydrocarbon rings (e.g., cyclohexene, cyclohexadiene, etc.) with unsaturated bonds, i.e., double and / or triple bonds, and non-aromatic heterocycles with unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinazonium, indoline, isoindoline, etc.). "Saturated rings" include aliphatic hydrocarbon rings without unsaturated bonds, or non-aromatic heterocycles without unsaturated bonds.

[0427] As a specific example of an aromatic hydrocarbon ring, the structure in specific example group G1, where the group is end-capped with a hydrogen atom, can be cited.

[0428] As a specific example of an aromatic heterocycle, the structure in example group G2 where the aromatic heterocycle group is end-capped with hydrogen atoms can be cited.

[0429] As a specific example of an aliphatic hydrocarbon ring, the structure in example group G6, where the group is end-capped with a hydrogen atom, can be cited.

[0430] "Ring formation" refers to the formation of a ring by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton further forming a ring with one or more arbitrary atoms. For example, R shown in the aforementioned general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The bonded anthracene skeleton consists of a ring formed by carbon atoms and one or more arbitrary atoms. As a specific example, R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and four carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0431] Unless otherwise stated in this specification, "any atom" is preferably selected from at least one atom chosen from carbon, nitrogen, oxygen, and sulfur. In any atom (e.g., in the case of carbon or nitrogen), bonds that do not form a ring can be capped by hydrogen atoms or substituted by "any substituents" described later. When any atom other than carbon is included, the resulting ring is a heterocycle.

[0432] Unless otherwise specified in this specification, "one or more arbitrary atoms" constituting a monocyclic or fused ring are preferably two or more and less than 15, more preferably three or more and less than 12, and even more preferably three or more and less than 5.

[0433] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0434] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0435] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0436] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0437] "One or more groups consisting of two or more adjacent atoms" refers to either "a monocyclic ring formed by bonding with each other to form a substituted or unsubstituted ring" or "a fused ring formed by bonding with each other to form a substituted or unsubstituted ring". Unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms are bonded with each other to form an "unsaturated ring" containing a parent skeleton and at least one to 15 substituted or unsubstituted atoms selected from carbon, nitrogen, oxygen and sulfur atoms.

[0438] When a "monocyclic" or "fused-ring" structure has a substituent, the substituent is, for example, "any substituent" as described below. Specific examples of substituents in the above-mentioned "monocyclic" or "fused-ring" structures are the substituents described in the "Substituents Described in this Specification" section above.

[0439] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, "any substituent" as described later. Specific examples of substituents when the aforementioned "monocyclic ring" or "fused ring" has a substituent are the substituents described in the "Substituents Described in this Specification" section above.

[0440] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together with each other, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together with each other, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0441] Substituents referred to as "substituted or unsubstituted"

[0442] In one embodiment of this specification, the substituents referred to as "substituted or unsubstituted" (in this specification, sometimes referred to as "arbitrary substituents") are selected from, for example...

[0443] Unsubstituted alkyl groups with 1 to 50 carbon atoms

[0444] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0445] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0446] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0447] -Si(R 901 (R) 902 (R) 903 ),

[0448] -O-(R 904 ),

[0449] -S-(R 905 ),

[0450] -N(R 906 (R) 907 ),

[0451] Halogen atom, cyano group, nitro group,

[0452] Unsubstituted aryl groups with 6-50 cyclic carbon atoms, and

[0453] Unsubstituted heterocyclic groups with 5-50 cyclic atoms, etc.

[0454] Here, R 901 ~R 907 Each independently

[0455] hydrogen atom,

[0456] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0457] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0458] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0459] A heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0460] R 901 When there are more than two, more than two R 901 Whether they are the same or different,

[0461] R 902 When there are more than two, more than two R 902 Whether they are the same or different,

[0462] R 903 When there are more than two, more than two R 903 Whether they are the same or different,

[0463] R 904 When there are more than two, more than two R 904 Whether they are the same or different,

[0464] R 905 When there are more than two, more than two R 905 Whether they are the same or different,

[0465] R 906 When there are more than two, more than two R 906 Whether they are the same or different,

[0466] R 907 When there are more than two, more than two R 907 They are the same or different from each other.

[0467] In one embodiment, the substituent referred to as "substituted or unsubstituted" is selected from...

[0468] Alkyl groups with 1 to 50 carbon atoms

[0469] aryl groups with 6-50 carbon atoms in the ring, and

[0470] Groups in heterocyclic groups with 5 to 50 cyclic atoms.

[0471] In one embodiment, the substituent referred to as "substituted or unsubstituted" is selected from...

[0472] Alkyl groups with 1 to 18 carbon atoms

[0473] aryl groups with 6-18 carbon atoms in the ring, and

[0474] Groups in heterocyclic groups with 5 to 18 cyclic atoms.

[0475] Specific examples of each group of any of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described in this specification" above.

[0476] Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring.

[0477] Unless otherwise specified in this specification, any substituent may further have substituents. Substituents further having by any substituent are the same as those described above.

[0478] In this specification, the numerical range represented by "AA~BB" refers to 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.

[0479] [Novel Compounds]

[0480] One aspect of the present invention relates to compounds represented by formulas (1-1) and (1-3) below, or compounds represented by formulas (1-2) and (1-3) below.

[0481] [Chemistry 23]

[0482]

[0483] (In the aforementioned equations (1-1), (1-2), and (1-3),)

[0484] Ring A is an aromatic hydrocarbon ring with 6 to 50 substituted or unsubstituted carbon atoms, or a heterocycle with 5 to 50 substituted or unsubstituted carbon atoms;

[0485] The two bonding sites* in the aforementioned formula (1-1) are each bonded to the cyclic carbon atom of the aforementioned aromatic hydrocarbon ring of the aforementioned ring A, or the cyclic atom of the aforementioned heterocycle;

[0486] The three bonding sites* in the aforementioned formula (1-2) are each bonded to the cyclic carbon atom of the aforementioned aromatic hydrocarbon ring of the aforementioned ring A, or the cyclic atom of the aforementioned heterocycle;

[0487] R1~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0488] The aforementioned substituted or unsubstituted saturated or unsaturated rings R1~R did not form. 16 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0489] In the compounds shown in formulas (1-1) and (1-3) above, R5~R7 and R 14 ~R 16 At least one of them is -N(R) 36 (R) 37 In the compounds shown in formulas (1-2) and (1-3) above, R2~R 16 At least one of them is -N(R) 36 (R) 37 );

[0490] R1~R16 Two or more adjacent groups form substituted or unsubstituted saturated or unsaturated rings, or R1~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms (hereinafter sometimes referred to as substituent A);

[0491] R 31 ~R 37 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted cyclic carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[0492] R 31 ~R 37 When each has multiple instances, there are multiple R's. 31 ~R 37 They can be the same or different.

[0493] If the compounds involved in one aspect of the present invention are used, long-life organic EL elements can be manufactured.

[0494] Regarding "R1~R 16 The description states that "two or more adjacent rings can be selected to form substituted or unsubstituted saturated or unsaturated rings".

[0495] R1~R 16 "A group of two or more adjacent pairs" includes combinations such as R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, R1 and R2 and R3, etc.

[0496] When the "substituent" in the "substituted or unsubstituted" case of the above-mentioned saturated or unsaturated ring is the same as the substituent in the case of "substituted or unsubstituted" described below.

[0497] It should be noted that generally, in the compounds represented by the above formulas (1-2) and (1-3), R8 and R9 do not bond to each other to form a single bond.

[0498] The "saturated or unsaturated ring" means, for example, in the case where a ring is formed by R1 and R2, a ring formed by the carbon atom bonded to R1, the carbon atom bonded to R2, and one or more arbitrary atoms. Specifically, in the case where a ring is formed by R1 and R2, when the carbon atom bonded to R1, the carbon atom bonded to R2, and 4 carbon atoms form an unsaturated ring, the ring formed by R1 and R2 forms a benzene ring.

[0499] The "arbitrary atom" is preferably a C atom, N atom, O atom, or S atom. In the case of an arbitrary atom (such as a C atom or N atom), the bonding site that does not form a ring can be capped with a hydrogen atom or the like.

[0500] The "one or more arbitrary atoms" is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less arbitrary atoms.

[0501] Hereinafter, the expression "one or more groups of two or more adjacent ones among X to Y optionally form a substituted or unsubstituted saturated or unsaturated ring" has the same meaning as when X is replaced with the above R1 and Y is replaced with the above R 16 at that time.

[0502] The "*" (asterisk) in formula (1-1) is the bonding site bonded to ring A of formula (1-3). In formula (1-1), there are two "*", and each of the two "*" is bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring of ring A or a ring-forming atom of the heterocycle, constituting the compound.

[0503] The "*" (asterisk) in formula (1-2) is also the bonding site bonded to ring A of formula (1-3). In formula (1-2), there are three "*", and each of the three "*" is bonded to a ring-forming carbon atom of the aromatic hydrocarbon ring of ring A or a ring-forming atom of the heterocycle, constituting the compound.

[0504] In one embodiment, the aforementioned ring A is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring-forming carbon atoms, a substituted or unsubstituted heterocycle having 5 to 50 ring-forming atoms, or a benzene ring represented by the following formula (2).

[0505] [Chemical formula 24]

[0506]

[0507] (in the aforementioned formula (2),)

[0508] One of the two cyclic carbon atoms is bonded at a bonding site extending from the benzene ring B of the aforementioned formula (1-1) or formula (1-2), and the other is bonded at a bonding site extending from the benzene ring C of the aforementioned formula (1-3).

[0509] R 17 It is a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkylthio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0510] R 31 ~R 37 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted cyclic carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[0511] R 31 ~R 37 When each has multiple instances, there are multiple R's. 31 ~R 37 They can be the same or different;

[0512] n is an integer of 1 or 2; when n is 2, there are 2 R 17 They can be the same or different.

[0513] In the above embodiments, the two bonding sites* of the aforementioned formula (1-1) are each bonded to the cyclic carbon atom of the aforementioned fused aromatic hydrocarbon ring of the aforementioned ring A, the cyclic atom of the aforementioned heterocycle, or the cyclic carbon atom of the benzene ring shown in the aforementioned formula (2).

[0514] In the above embodiments, the three bonding sites* of the aforementioned formula (1-2) are each bonded to the cyclic carbon atom of the aforementioned fused aromatic hydrocarbon ring of the aforementioned ring A, the cyclic atom of the aforementioned heterocycle, or the cyclic carbon atom of the benzene ring shown in the aforementioned formula (2).

[0515] Fused aromatic rings refer to rings formed by the fusion of multiple aromatic rings. Therefore, biphenyl, for example, formed by the single bond of two aromatic rings, is not included in fused aromatic rings.

[0516] In the compounds shown in formulas (1-1) and (1-3), and in the compounds shown in formulas (1-2) and (1-3) below, R1~R 16 Two or more adjacent groups form substituted or unsubstituted saturated or unsaturated rings, or R1~R 16 At least one of them is a specific group (substituent A).

[0517] R1~R1 are saturated or unsaturated rings that do not form substituted or unsubstituted rings and are not substituent A. 16 It is a hydrogen atom or a substituent, and in one embodiment, each is independently selected from a hydrogen atom, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, and a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0518] In one embodiment, R1~R1 are saturated or unsaturated rings that are not substituted or unsubstituted and are not substituent A. 16 Each is independently selected from hydrogen atoms, aryl groups with 6 to 18 substituted or unsubstituted cyclic carbon atoms, and heterocyclic groups with 5 to 18 substituted or unsubstituted cyclic atoms.

[0519] In one embodiment, in the compounds shown in formulas (1-1) and (1-3), R1~R4, R 10 ~R 13 At least one of them is a substituent A, preferably R1, R3, or R4. 10 and R 12 At least one of them is a substituent A. Additionally, for example, R3 and R 12 They can be substituents A, R1, and R independently. 10 Each can be a substituent A independently.

[0520] In one embodiment, in the compounds shown in formulas (1-2) and (1-3), R2~R4, R9~R 13 At least one of them is a substituent A.

[0521] In one embodiment, substituent A is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, or a -Si(R) group.31 (R) 32 (R) 33 The alkyl group may contain halogen atoms, cyano groups, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or substituted or unsubstituted heterocyclic groups with 5 to 50 carbon atoms, preferably substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms. The alkyl group may have 1 to 30, 1 to 18, or 1 to 5 carbon atoms.

[0522] In one embodiment, in the compounds represented by formulas (1-1) and (1-3) above, R5 and R 14 At least one of them (e.g., R5 and R) 14 Both) are -N(R 36 (R) 37 ).

[0523] In one embodiment, in the compounds shown in formulas (1-2) and (1-3) above, R5~R8 and R 14 ~R 16 At least one of them is -N(R) 36 (R) 37 Preferably, R5 and R 14 At least one of them is -N(R) 36 (R) 37 ).

[0524] In one implementation, R 36 and R 37 Each is independently an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms. In this case, R 36 and R 37 All or some of the hydrogen atoms contained therein can be deuterium atoms.

[0525] In one implementation, R 36 and R 37 Each phenyl group can be substituted or unsubstituted. All or some of the hydrogen atoms in the phenyl group may be deuterium atoms.

[0526] In one embodiment, examples of substituents for the aforementioned aryl group (e.g., phenyl) with 6 to 50 carbon atoms or a monovalent heterocyclic group with 5 to 50 carbon atoms include alkyl groups with 1 to 5 carbon atoms and aryl groups (e.g., phenyl or naphthyl) with 6 to 12 carbon atoms. For example, both the alkyl group with 1 to 5 carbon atoms and the aryl group with 6 to 12 carbon atoms can be substituted for the phenyl group. Furthermore, all or part of the hydrogen atoms contained in the aforementioned aryl group with 6 to 12 carbon atoms can be deuterium atoms.

[0527] It should be noted that, generally, in the compounds shown in formulas (1-1) and (1-3) above, or in the compounds shown in formulas (1-2) and (1-3) above, R 36 and R 37 It will not be related to R1~R 16 They bond together to form a ring.

[0528] In one embodiment, the compound represented by formulas (1-1) and (1-3) above, or the compound represented by formulas (1-2) and (1-3) above, is a compound represented by formula (3), formula (4), formula (5) or formula (7) below.

[0529] [Chemistry 25]

[0530]

[0531] (In the aforementioned equations (3), (4), (5), and (7),)

[0532] Ring A' is a fused aromatic ring with 10 to 50 cyclic carbon atoms, either substituted or unsubstituted, or a heterocycle with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0533] R1~R 17 As defined in equations (1-1), (1-2), (1-3), and (2) above.

[0534] In one embodiment, the aforementioned substituted or unsubstituted fused aromatic hydrocarbon ring with 10 to 50 carbon atoms is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring.

[0535] In one embodiment, the aforementioned substituted or unsubstituted heterocycle with 5 to 50 cyclic atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.

[0536] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are selected from the compounds represented by formulas (6-1) to (6-31).

[0537] [Chemistry 26]

[0538]

[0539] [Chemistry 27]

[0540]

[0541] [Chemistry 28]

[0542]

[0543] [Chemistry 29]

[0544]

[0545] (In the aforementioned equations (6-1) to (6-31),

[0546] R1~R7 and R 10 ~R 17 As defined in equations (1-1), (1-2), (1-3), and (2) above;

[0547] X represents O, S, and NR. 25 or C(R) 26 (R) 27 );

[0548] R 21 ~R 27 Two or more adjacent rings may be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0549] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 21 ~R 27 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0550] R 31 ~R 37 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted cyclic carbon atoms, an aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or a monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic carbon atoms.

[0551] R 31 ~R 37 When each has multiple instances, there are multiple R's. 31 ~R 37 They can be the same or different.

[0552] In one embodiment, the compounds represented by formulas (1-2) and (1-3) are compounds represented by formula (7-1).

[0553] [Chemistry 30]

[0554]

[0555] (In the aforementioned equation (7-1),

[0556] R2~R 13 and R 15 ~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0557] R2~R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 13 and R 15 ~R 16 , and R 17 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0558] R2~R 13 and R 15 ~R 16Two or more adjacent groups form substituted or unsubstituted saturated or unsaturated rings, or R2~R 13 and R 15 ~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0559] R A and R B Each of the following is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 50 monovalent heterocyclic atoms.

[0560] In one embodiment, the compounds represented by the aforementioned formulas (1-2) and (1-3) are compounds represented by the following formula (7-2).

[0561] [Chemistry 31]

[0562]

[0563] (In the aforementioned equation (7-2),

[0564] R2~R4 and R6~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0565] R2~R4 and R6~R6 do not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 16 , and R 17Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0566] R2~R4 and R6~R 16 Two or more adjacent groups of 1 or more form substituted or unsubstituted saturated or unsaturated rings, or R2~R4 and R6~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0567] R C and R D Each of the following is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 50 monovalent heterocyclic atoms.

[0568] In one embodiment, the compounds represented by the aforementioned formulas (1-2) and (1-3) are compounds represented by the following formula (7-3).

[0569] [Chemistry 32]

[0570]

[0571] (In the aforementioned equation (7-3),

[0572] R2~R4、R6~R 13 and R 15 ~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0573] R2~R4, R6~R6 do not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 13 and R 15 ~R 16 , and R 17 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0574] R2~R4、R6~R 13 and R 15 ~R 16 Two or more adjacent groups of 1 or more form substituted or unsubstituted saturated or unsaturated rings, or R2~R4, R6~R 13 and R 15 ~R 16At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0575] R A R B R C and R D Each of the following is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 50 monovalent heterocyclic atoms.

[0576] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are compounds represented by formula (8) below.

[0577] [Chemistry 33]

[0578]

[0579] (in the aforementioned formula (8),)

[0580] R1~R4, R6~R7 and R 10 ~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0581] R1~R4, R6~R7 and R1 do not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 10 ~R 16 , and R 17Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, substituted or unsubstituted aryl group with 6-50 cyclic carbon atoms, or substituted or unsubstituted heterocyclic group with 5-50 monovalent cyclic atoms; 2 R 17 They can be the same as each other, or they can be different;

[0582] R1~R4, R6~R7 and R 10 ~R 16 Two or more adjacent groups of 1 or more form substituted or unsubstituted saturated or unsaturated rings, or R1~R4, R6~R7 and R 10 ~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0583] R A and R BEach of the following is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 50 monovalent heterocyclic atoms.

[0584] In one embodiment, the compounds represented by formulas (1-1) and (1-3) are compounds represented by formula (9).

[0585] [Chemistry 34]

[0586]

[0587] (in the aforementioned equation (9),)

[0588] R1~R4, R6~R7, R 10 ~R 13 and R 15 ~R 16 Two or more adjacent elements can be selected to form substituted or unsubstituted saturated or unsaturated rings.

[0589] R1~R4, R6~R7, R... do not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 10 ~R 13 and R 15 ~R 16 , and R 17 Each of the following is independently a hydrogen atom, an alkyl group with 1 to 50 substituted or unsubstituted carbon atoms, a haloalkyl group with 1 to 50 substituted or unsubstituted carbon atoms, an alkenyl group with 2 to 50 substituted or unsubstituted carbon atoms, an alkynyl group with 2 to 50 substituted or unsubstituted carbon atoms, a cycloalkyl group with 3 to 50 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 50 substituted or unsubstituted carbon atoms, an alkathio group with 1 to 50 substituted or unsubstituted carbon atoms, an aryloxy group with 6 to 50 substituted or unsubstituted carbon atoms, an arylthio group with 6 to 50 substituted or unsubstituted carbon atoms, an aralkyl group with 7 to 50 substituted or unsubstituted carbon atoms, or -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 -N(R) 36 (R) 37 ), halogen atom, cyano, nitro, substituted or unsubstituted aryl group with 6-50 cyclic carbon atoms, or substituted or unsubstituted heterocyclic group with 5-50 monovalent cyclic atoms; 2 R 17 They can be the same as each other, or they can be different;

[0590] R1~R4, R6~R7, R 10 ~R13 and R 15 ~R 16 Two or more adjacent groups of 1 or more form substituted or unsubstituted saturated or unsaturated rings, or R1~R4R6~R7, R 10 ~R 13 and R 15 ~R 16 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted alkyl group having 7 to 50 carbon atoms, or a -Si(R 31 (R) 32 (R) 33 -C(=O)R 34 -COOR 35 Halogen atom, cyano, nitro, aryl group with 6 to 50 substituted or unsubstituted cyclic carbon atoms, or monovalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms;

[0591] R A R B R C and R D Each of the following is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 50 monovalent heterocyclic atoms.

[0592] In one embodiment, the compound represented by the aforementioned formula (9) is the compound represented by the following formula (9-1).

[0593] [Chemistry 35]

[0594]

[0595] (In the aforementioned equation (9-1),

[0596] R1~R4, R 10 ~R 13 R 17 R A R B R C and R D As defined in equation (9) above).

[0597] In one embodiment, the compound represented by the aforementioned formula (9) is the compound represented by the following formula (9-2).

[0598] [Chemistry 36]

[0599]

[0600] (In the aforementioned equation (9-2),

[0601] R3, R 12 R 17 R A R B R C and R D As defined in equation (9) above).

[0602] In one embodiment, the compound represented by the aforementioned formula (9) is the compound represented by the following formula (9-3).

[0603] [Chemistry 37]

[0604]

[0605] (In the aforementioned equation (9-3),

[0606] R1, R 10 R 17 R A R B R C and R D As defined in equation (9) above).

[0607] It should be noted that, generally, in the compounds shown by the aforementioned formulas (7-1), (7-2), (7-3), (8), (9), (9-1), (9-2), and (9-3), R A and R B and R C and R D It will not be related to R1~R 17 and R 31 ~R 37 They bond together to form a ring.

[0608] In one implementation, R A R B R C and R D Each is independently an aryl group with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms (substituted or unsubstituted).

[0609] In one implementation, R A R BR C and R D When each is independently an aryl group with 6 to 50 cyclic carbon atoms (substituted or unsubstituted) or a monovalent heterocyclic group with 5 to 50 cyclic carbon atoms (substituted or unsubstituted), R A R B R C and R D All or some of the hydrogen atoms contained therein are deuterium atoms.

[0610] In one implementation, R A R B R C and R D Each phenyl group can be substituted or unsubstituted. All or some of the hydrogen atoms in the phenyl group may be deuterium atoms.

[0611] In one embodiment, examples of substituents for the aforementioned aryl group (e.g., phenyl) with 6 to 50 carbon atoms or a monovalent heterocyclic group with 5 to 50 carbon atoms include alkyl groups with 1 to 5 carbon atoms and aryl groups (e.g., phenyl or naphthyl) with 6 to 12 carbon atoms. For example, both the alkyl group with 1 to 5 carbon atoms and the aryl group with 6 to 12 carbon atoms can be substituted for the phenyl group. Furthermore, all or part of the hydrogen atoms contained in the aforementioned aryl group with 6 to 12 carbon atoms can be deuterium atoms.

[0612] In one implementation, R A R B R C and R D Each is independently a phenyl substituted with an alkyl group having 1 to 5 carbon atoms, a phenyl substituted with an aryl group having 6 to 12 carbon atoms, a phenyl substituted with an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 12 carbon atoms, or an unsubstituted phenyl.

[0613] In one implementation, as R A and R B Combination (R) A R B Examples of such phenyl groups include (unsubstituted phenyl, unsubstituted phenyl), (unsubstituted phenyl, phenyl substituted with alkyl groups having 1 to 5 carbon atoms), (phenyl substituted with alkyl groups having 1 to 5 carbon atoms, phenyl substituted with alkyl groups having 1 to 5 carbon atoms), (unsubstituted phenyl, phenyl substituted with aryl groups having 6 to 12 carbon atoms), (phenyl substituted with alkyl groups having 1 to 5 carbon atoms, phenyl substituted with aryl groups having 6 to 12 carbon atoms), (phenyl substituted with aryl groups having 6 to 12 carbon atoms, phenyl substituted with aryl groups having 6 to 12 carbon atoms), (unsubstituted phenyl, phenyl substituted with alkyl groups having 1 to 5 carbon atoms and phenyl substituted with aryl groups having 6 to 12 carbon atoms), etc.

[0614] As R C and R D Combination (R) C R D Examples of R mentioned above can be cited. A and R B Combination (R) A R B The same combination.

[0615] In one implementation, R 17 Each is a hydrogen atom.

[0616] In the compounds shown in formulas (1-1) and (1-3), and in the compounds shown in formulas (1-2) and (1-3), the substituents in the "substituted or unsubstituted" case are selected from alkyl groups having 1 to 50 carbon atoms, haloalkyl groups having 1 to 50 carbon atoms, alkenyl groups having 2 to 50 carbon atoms, alkynyl groups having 2 to 50 carbon atoms, cycloalkyl groups having 3 to 50 carbon atoms, alkoxy groups having 1 to 50 carbon atoms, alkylthio groups having 1 to 50 carbon atoms, aryloxy groups having 6 to 50 carbon atoms, arylthio groups having 6 to 50 carbon atoms, arylalkyl groups having 7 to 50 carbon atoms, -Si(R 41 (R) 42 (R) 43 -C(=O)R 44 -COOR 45 -S(=O)2R 46 -P(=O)(R 47 (R) 48 ), -Ge(R 49 (R) 50 (R) 51 ), -N(R 52 (R) 53 (Here, R) 41 ~R 53 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 cyclic carbon atoms, or a monovalent heterocyclic group having 5 to 50 cyclic atoms; R 41 ~R 53 When there are more than two, R is more than two. 41 ~R 53 (The elements can be the same or different), hydroxyl, halogen atom, cyano, nitro, aryl with 6 to 50 cyclic carbon atoms, and monovalent heterocyclic group with 5 to 50 cyclic atoms.

[0617] In one embodiment, the substituents in the "substituted or unsubstituted" cases of the compounds shown in formulas (1-1) and (1-3), and the compounds shown in formulas (1-2) and (1-3) are alkyl groups with 1 to 50 carbon atoms, aryl groups with 6 to 50 cyclic carbon atoms, and monovalent heterocyclic groups with 5 to 50 cyclic atoms.

[0618] In one embodiment, the substituents in the "substituted or unsubstituted" cases of the compounds shown in formulas (1-1) and (1-3), and the compounds shown in formulas (1-2) and (1-3) are selected from alkyl groups having 1 to 30 carbon atoms, aryl groups having 6 to 30 cyclic carbon atoms, and monovalent heterocyclic groups having 5 to 30 cyclic atoms.

[0619] In one embodiment, the substituents in the compounds shown in formulas (1-1) and (1-3), and in the compounds shown in formulas (1-2) and (1-3) where the substituent is “substituted or unsubstituted”, are selected from alkyl groups having 1 to 18 carbon atoms, aryl groups having 6 to 18 cyclic carbon atoms, and monovalent heterocyclic groups having 5 to 18 cyclic atoms.

[0620] The specific examples of substituents, substituents, and halogen atoms in the compounds shown in formulas (1-1) and (1-3), and in the case of "substituted or unsubstituted", are the same as those described above.

[0621] The compounds shown in formulas (1-1) and (1-3), or the compounds shown in formulas (1-2) and (1-3), can be synthesized according to the examples by using known alternative reactions and starting materials that are consistent with the target.

[0622] The following describes specific examples of compounds represented by formulas (1-1) and (1-3), or formulas (1-2) and (1-3), but these are merely illustrative examples, and the compounds represented by formulas (1-1) and (1-3), or formulas (1-2) and (1-3), are not limited to the specific examples described below. In the specific examples described below, Me represents methyl and Ph represents phenyl.

[0623] [Chemistry 38]

[0624]

[0625] [Chemistry 39]

[0626]

[0627] [Chemistry 40]

[0628]

[0629] [Chemistry 41]

[0630]

[0631] [Chemistry 42]

[0632]

[0633] [Chemistry 43]

[0634]

[0635] [Chemistry 44]

[0636]

[0637] [Chemistry 45]

[0638]

[0639] [Chemistry 46]

[0640]

[0641] [Chemistry 47]

[0642]

[0643] [Chemistry 48]

[0644]

[0645] [Chemistry 49]

[0646]

[0647] [Transformation 50]

[0648]

[0649] [Chemistry 51]

[0650]

[0651] [Chemistry 52]

[0652]

[0653] [Chemistry 53]

[0654]

[0655] [Chemistry 54]

[0656]

[0657] [Chemistry 55]

[0658]

[0659] [Chemistry 56]

[0660]

[0661] [Chemistry 57]

[0662]

[0663] [Chem.58]

[0664]

[0665] [Chemistry 59]

[0666]

[0667] [Transformation 60]

[0668]

[0669] [Chemistry 61]

[0670]

[0671] [Chemistry 62]

[0672]

[0673] [Chemistry 63]

[0674]

[0675] [Chemistry 64]

[0676]

[0677] [Chemistry 65]

[0678]

[0679] [Chemistry 66]

[0680]

[0681] [Chemistry 67]

[0682]

[0683] [Chemistry 68]

[0684]

[0685] [Chemistry 69]

[0686]

[0687] [Chemistry 70]

[0688]

[0689] [Chemistry 71]

[0690]

[0691] [Chemistry 72]

[0692]

[0693] [Chemistry 73]

[0694]

[0695] [Chemistry 74]

[0696]

[0697] [Chemistry 75]

[0698]

[0699] [Chemistry 76]

[0700]

[0701] [Chemistry 77]

[0702]

[0703] [Chemistry 78]

[0704]

[0705] [Chemistry 79]

[0706]

[0707] [Chemistry 80]

[0708]

[0709] [Chemistry 81]

[0710]

[0711] [Chemistry 82]

[0712]

[0713] Materials for Organic Electroluminescent Devices

[0714] The compounds involved in one aspect of the present invention are useful as materials for organic EL elements, as materials for the light-emitting layer of organic EL elements, and particularly as dopant materials for the light-emitting layer.

[0715] By using the compound involved in one aspect of the present invention in the light-emitting layer of an organic EL element, a long-life organic EL element can be obtained.

[0716] [Organic EL Components]

[0717] An organic EL element according to one aspect of the present invention has a cathode, an anode, and at least one organic layer disposed between the cathode and the anode, wherein at least one of the at least one organic layers contains a compound represented by formulas (1-1) and (1-3) or a compound represented by formulas (1-2) and (1-3).

[0718] Reference Figure 1 This describes the general configuration of an organic EL element according to one aspect of the present invention.

[0719] An organic EL element 1 according to one aspect of the present invention has a substrate 2, an anode 3, a light-emitting layer 5 as an organic layer, a cathode 10, an organic layer 4 between the anode 3 and the light-emitting layer 5, and an organic layer 6 between the light-emitting layer 5 and the cathode 10.

[0720] Organic layer 4 and organic layer 6 can each be a single layer or contain multiple layers.

[0721] Furthermore, organic layer 4 may also contain a hole transport domain. The hole transport domain may include a hole injection layer, a hole transport layer, an electron blocking layer, etc. Organic layer 6 may contain an electron transport domain. The electron transport domain may include an electron injection layer, an electron transport layer, a hole blocking layer, etc.

[0722] The compounds represented by formulas (1-1) and (1-3) or formulas (1-2) and (1-3) are contained in the organic layer 4, the light-emitting layer 5, or the organic layer 6. In one embodiment, the compounds represented by formulas (1-1) and (1-3) or formulas (1-2) and (1-3) are contained in the light-emitting layer 5. The compounds represented by formulas (1-1) and (1-3) or formulas (1-2) and (1-3) can function as dopant materials in the light-emitting layer 5.

[0723] In an organic EL element according to one aspect of the present invention, at least one of the aforementioned at least one organic layer comprises a first compound and a different second compound, wherein the first compound is a compound represented by formulas (1-1) and (1-3) or a compound represented by formulas (1-2) and (1-3).

[0724] In one embodiment of the present invention, the aforementioned second compound is a heterocyclic compound or a fused aromatic compound in the organic EL element.

[0725] In one embodiment of the present invention, the aforementioned second compound is an anthracene derivative in the organic EL element.

[0726] In one aspect of the present invention, the aforementioned second compound in the organic EL element is a compound represented by the following formula (10).

[0727] <The compound shown in formula (10)>

[0728] The compound shown in formula (10) will be described.

[0729] [Chemistry 83]

[0730]

[0731] In formula (10),

[0732] R 101 ~R 110 Two or more adjacent rings form a substituted or unsubstituted saturated or unsaturated ring, or do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring.

[0733] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 101 ~R 110 Each independently is

[0734] hydrogen atom,

[0735] Substituent R, or

[0736] The group shown in the following formula (11).

[0737] -L 101 -Ar 101 (11)

[0738] (In formula (11),

[0739] L 101 yes

[0740] single bond,

[0741] Substituted or unsubstituted arylene groups with 6 to 50 cyclic carbon atoms, or

[0742] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms;

[0743] Ar 101 yes

[0744] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0745] (Substituted or unsubstituted heterocyclic groups with 5 to 50 monovalent cyclic atoms).

[0746] The aforementioned substituent R is

[0747] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0748] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0749] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0750] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0751] -Si(R 901 (R) 902 (R) 903 ),

[0752] -O-(R 904 ),

[0753] -S-(R 905 ),

[0754] -N(R 906 (R) 907 ),

[0755] Halogen atom, cyano group, nitro group,

[0756] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0757] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted;

[0758] When there are two or more substituents R mentioned above, the two or more substituents R can be the same or different;

[0759] R 901 ~R 907 Each independently is

[0760] hydrogen atom,

[0761] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0762] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0763] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0764] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted;

[0765] R 901 ~R 907 In the case of two or more R, two or more R 901 ~R 907 Each can be the same or different;

[0766] However, R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 101 ~R 110 At least one of them is a group represented by the aforementioned formula (11); if there are more than two of the aforementioned formula (11), the groups represented by the more than two of the aforementioned formula (11) may be the same or different.

[0767] The compound shown in formula (10) above can have deuterium atoms as hydrogen atoms.

[0768] In one implementation, Ar in the aforementioned formula (10) 101 At least one of them is a substituted or unsubstituted aryl group with 6 to 50 cyclic carbon atoms.

[0769] In one implementation, Ar in the aforementioned formula (10) 101 At least one of them is a monovalent heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0770] In one implementation, all Ar in the aforementioned formula (10) 101 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted. Multiple Ar... 101 They can be the same as each other, or they can be different.

[0771] In one implementation, Ar in the aforementioned formula (10) 101 One of them is a monovalent heterocyclic group with 5-50 cyclic atoms, either substituted or unsubstituted; the rest are Ar... 101 It is an aryl group with 6 to 50 cyclic carbon atoms, either substituted or unsubstituted. Multiple Ar... 101 They can be the same as each other, or they can be different.

[0772] In one embodiment, L in the aforementioned formula (10) 101 At least one of them is a single bond.

[0773] In one embodiment, L in the aforementioned formula (10) 101 All are single keys.

[0774] In one embodiment, L in the aforementioned formula (10) 101 At least one of them is a substituted or unsubstituted cyclic aryl group with 6 to 50 carbon atoms.

[0775] In one embodiment, L in the aforementioned formula (10) 101 At least one of them is a substituted or unsubstituted phenylene or a substituted or unsubstituted naphthylene.

[0776] In one implementation, -L in the aforementioned formula (10) 101 -Ar 101 The groups shown are selected from

[0777] Substituted or unsubstituted phenyl

[0778] Substituted or unsubstituted naphthyl groups

[0779] Substituted or unsubstituted biphenyl,

[0780] Replaced or unreplaced foetida

[0781] Substituted or unsubstituted benzo[phenanthrene]

[0782] Substituted or unsubstituted fluorene

[0783] Substituted or unsubstituted benzofluorene,

[0784] Substituted or unsubstituted dibenzofuranyl,

[0785] Substituted or unsubstituted naphthobenzofuranyl,

[0786] Substituted or unsubstituted dibenzothiophene group, and

[0787] Substituted or unsubstituted carbazolyl group.

[0788] In one embodiment, the substituent R in the aforementioned formula (10) is each independently...

[0789] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0790] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0791] -Si(R 901 (R) 902 (R) 903 ),

[0792] -O-(R 904 ),

[0793] -S-(R 905 ),

[0794] -N(R 906 (R) 907 ),

[0795] Halogen atom, cyano group, nitro group, or

[0796] Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0797] R 901 ~R 907 As defined in equation (10) above.

[0798] In one embodiment, the "substituted or unsubstituted" substituents in the aforementioned formula (10) are each independently...

[0799] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0800] Alkenes with 2 to 50 carbon atoms, substituted or unsubstituted

[0801] Alkyne groups with 2 to 50 carbon atoms, substituted or unsubstituted.

[0802] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0803] -Si(R 901 (R) 902 (R) 903 ),

[0804] -O-(R 904 ),

[0805] -S-(R 905 ),

[0806] -N(R 906 (R) 907 ),

[0807] Halogen atom, cyano group, nitro group,

[0808] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0809] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0810] R 901 ~R 907 As defined in equation (10) above.

[0811] In one embodiment, the "substituted or unsubstituted" substituents in the aforementioned formula (10) are each independently...

[0812] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0813] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0814] -Si(R 901 (R)902 (R) 903 ),

[0815] -O-(R 904 ),

[0816] -S-(R 905 ),

[0817] -N(R 906 (R) 907 ),

[0818] Halogen atom, cyano group, nitro group, or

[0819] Aryl groups with 6 to 50 cyclic carbon atoms, substituted or unsubstituted.

[0820] R 901 ~R 907 As defined in equation (10) above.

[0821] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the aforementioned formula (10) is selected from...

[0822] Alkyl groups with 1 to 18 carbon atoms

[0823] aryl groups with 6-18 carbon atoms in the ring, and

[0824] A monovalent heterocyclic group with 5 to 18 cyclic atoms.

[0825] In one embodiment, the substituent in the case of “substituted or unsubstituted” in the aforementioned formula (10) is an alkyl group having 1 to 5 carbon atoms.

[0826] In one embodiment, the compound represented by the aforementioned formula (10) is the compound represented by the following formula (20).

[0827] [Chemistry 84]

[0828]

[0829] (In equation (20), R) 101 ~R 108 L 101 and Ar 101 As defined in equation (10) above).

[0830] The compound shown in formula (20) above can have deuterium atoms as hydrogen atoms.

[0831] That is, in one embodiment, the compound represented by formula (10) or formula (20) has at least two groups represented by formula (11).

[0832] In one embodiment, the compound represented by formula (10) or formula (20) has two or three groups represented by formula (11).

[0833] In one embodiment, R in the aforementioned formulas (10) and (20) 101 ~R 110 The aforementioned substituted or unsubstituted saturated or unsaturated rings have not been formed.

[0834] In one embodiment, R in the aforementioned formulas (10) and (20) 101 ~R 110 It is a hydrogen atom.

[0835] In one embodiment, in the compound represented by the aforementioned formula (20), Ar 101 At least one of them is a monovalent group having the structure shown in the following formula (50).

[0836] [Chemistry 85]

[0837]

[0838] (in formula (50),)

[0839] X 151 Is it O, S, or C(R)? 161 (R) 162 );

[0840] R 151 ~R 160 One of them is related to L 101 Bonded single bonds.

[0841] Not with L 101 bonded single bond R 151 ~R 154 Two or more adjacent ones, and R 155 ~R 160 Two or more adjacent rings are bonded to each other to form substituted or unsubstituted saturated or unsaturated rings, or no substituted or unsubstituted saturated or unsaturated rings are formed.

[0842] R 161 and R 162 They bond with each other to form substituted or unsubstituted saturated or unsaturated rings, or they do not form substituted or unsubstituted saturated or unsaturated rings.

[0843] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 161 and R 162 and not related to L 101 R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 151~R 160 Each is independently a hydrogen atom or a substituent R.

[0844] The aforementioned substituent R is as defined in equation (10) above.

[0845] Ar groups that are not monovalent groups having the structure shown in formula (50) above 101 yes

[0846] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0847] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms in a divalent ring).

[0848] In the aforementioned formula (50), L 101 There are no particular restrictions on the location where a single bond is formed.

[0849] In one implementation, R in the aforementioned formula (50) 151 ~R 154 One of them, or R 155 ~R 160 One of them is related to L 101 Bonded single bonds.

[0850] In one implementation, Ar 101 It is the following formula (50-R) 152 (50-R) 153 (50-R) 154 (50-R) 157 ) or (50-R 158 The group with a 1-valent charge is shown in the figure.

[0851] [Chemistry 86]

[0852]

[0853] (Formula (50-R) 152 (50-R) 153 (50-R) 154 (50-R) 157 ) and (50-R 158 In ), X 151 R 151 ~R 160 As defined in the aforementioned equation (50);

[0854] *and L 101 (bonding).

[0855] In one embodiment, the compound represented by the aforementioned formula (20) is the compound represented by the following formula (30).

[0856] [Chemistry 87]

[0857]

[0858] (In equation (30), L) 101 and Ar 101 As defined in equation (10) above;

[0859] R 101A ~R 108A Two adjacent rings that do not form substituted or unsubstituted saturated or unsaturated rings;

[0860] R 101A ~R 108A Each independently is

[0861] hydrogen atom, or

[0862] Substituent R;

[0863] The aforementioned substituent R is as defined in equation (10) above.

[0864] That is, the compound shown in formula (30) above is a compound having two groups shown in the aforementioned formula (11).

[0865] The compound shown in formula (30) above essentially only has protium atoms as hydrogen atoms.

[0866] It should be noted that "substantially having only protium atoms" means that, relative to the total number of compounds (protium bodies) that have the same structure and have only protium atoms as hydrogen atoms and compounds (deuterium bodies) that have deuterium atoms as hydrogen atoms, the proportion of protium bodies is 90 mol% or more, 95 mol% or more, or 99 mol% or more.

[0867] In one embodiment, the compound represented by the aforementioned formula (30) is the compound represented by the following formula (31).

[0868] [Chemistry 88]

[0869]

[0870] (In equation (31), L) 101 and Ar 101 As defined in equation (10) above;

[0871] R 101A ~R 108A As defined in equation (30) above;

[0872] X b For O, S, N(R) 131 ) or C(R 132 (R) 133 );

[0873] R 121 ~R 128 and R 131 ~R 133 One of them is related to L 101 Bonded single bonds;

[0874] Not with L 101 bonded single bond R 121 ~R 128 Two or more adjacent rings in one group form a substituted or unsubstituted saturated or unsaturated ring, or do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring;

[0875] Not with L 101 R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 121 ~R 128 Each independently is

[0876] hydrogen atom, or

[0877] Substituent R;

[0878] The aforementioned substituent R is as defined in equation (10) above;

[0879] Not with L 101 bonded single bond R 131 ~R 133 Each independently is

[0880] hydrogen atom,

[0881] Alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted

[0882] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0883] Substituted or unsubstituted aryl groups with 6 to 50 cyclic carbon atoms, or

[0884] A monovalent heterocyclic group with 5 to 50 cyclic atoms, substituted or unsubstituted;

[0885] R 131 ~R 133 In the case of two or more R, two or more R 131 ~R 133 (The elements can be the same or different).

[0886] In one embodiment, the compound represented by the aforementioned formula (31) is the compound represented by the following formula (32).

[0887] [Chemistry 89]

[0888]

[0889] (In equation (32), R) 101A ~R 108A L 101 Ar 101 R 121 ~R 128 R 132 and R 133 As defined in equation (31) above).

[0890] In one embodiment, the compound represented by the aforementioned formula (31) is the compound represented by the following formula (33).

[0891] [Chemistry 90]

[0892]

[0893] (In equation (33), R) 101A ~R 108A L 101 Ar 101 and R 121 ~R 128 As defined in equation (31) above;

[0894] X c Is it O, S, or NR? 131 ;

[0895] R 131 As defined in equation (31) above).

[0896] In one embodiment, the compound represented by the aforementioned formula (31) is the compound represented by the following formula (34).

[0897] [Chemistry 91]

[0898]

[0899] (In equation (34), R) 101A ~R 108A L 101 and Ar 101 As defined in equation (31) above;

[0900] X c Is it O, S, or NR? 131 ;

[0901] R 131 As defined in equation (31) above;

[0902] R 121A ~R 128A One of them is related to L 101Bonded single bonds;

[0903] Not with L 101 bonded single bond R 121A ~R 128A Two or more adjacent rings that do not form substituted or unsubstituted saturated or unsaturated rings;

[0904] Not with L 101 bonded single bond R 121A ~R 128A Each independently is

[0905] hydrogen atom, or

[0906] Substituent R;

[0907] The aforementioned substituent R is as defined in equation (10) above.

[0908] In one embodiment, the compound represented by the aforementioned formula (31) is the compound represented by the following formula (35).

[0909] [Chemistry 92]

[0910]

[0911] In equation (35), R 101A ~R 108A L 101 Ar 101 and X b As defined in equation (31) above;

[0912] R 121A ~R 124A Two or more adjacent rings in a group are not bonded to each other to form substituted or unsubstituted saturated or unsaturated rings.

[0913] R 125B and R 126B R 126B and R 127B and R 127B and R 128B Any one of them is bonded to each other to form a ring as shown in formula (35a) or (35b);

[0914] [Chemistry 93]

[0915]

[0916] In equations (35a) and (35b),

[0917] Each of the two asterisks is associated with R. 125B and R R126B R 126B and R127B and R 127B and R 128B Any one of the bonds;

[0918] R 141 ~R 144 Each independently is

[0919] hydrogen atom, or

[0920] Substituent R;

[0921] The aforementioned substituent R is as defined in equation (10) above;

[0922] X d (Is it O or S).

[0923] R 121A ~R 124A R that does not form the ring shown in formula (35a) or (35b) above 125B ~R 128B and R 141 ~R 144 One of them is related to L 101 Bonded single bonds.

[0924] Not with L 101 bonded single bond R 121A ~R 124A And not related to L 101 R consisting of bonded single bonds and not forming a ring as shown in formula (35a) or (35b) above. 125B ~R 128B Each independently is

[0925] hydrogen atom, or

[0926] Substituent R;

[0927] The aforementioned substituent R is as defined in the aforementioned equation (10).

[0928] In one embodiment, the compound represented by the aforementioned formula (35) is the compound represented by the following formula (36).

[0929] [Chemistry 94]

[0930]

[0931] (In equation (36), R) 101A ~R 108A L 101 Ar 101 and R 125B ~R 128B As defined in equation (35) above).

[0932] In one embodiment, the compound represented by the aforementioned formula (34) is the compound represented by the following formula (37).

[0933] [Chem. 95]

[0934]

[0935] (In equation (37), R) 101A ~R 108A R 125A ~R 128A L 101 and Ar 101 As defined in equation (34) above).

[0936] In one embodiment, R in the aforementioned equations (30) to (37) 101A ~R 108A It is a hydrogen atom.

[0937] In one embodiment, the compound represented by the aforementioned formula (10) is the compound represented by the following formula (40).

[0938] [Chemistry 96]

[0939]

[0940] (In equation (40), L) 101 and Ar 101 As defined in equation (10) above;

[0941] R 101A and R 103A ~R 108A Two or more adjacent rings form a substituted or unsubstituted saturated or unsaturated ring, or do not form the aforementioned substituted or unsubstituted saturated or unsaturated ring;

[0942] R does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 101A and R 103A ~R 108A Each independently is

[0943] hydrogen atom, or

[0944] Substituent R;

[0945] The aforementioned substituent R is as defined in equation (10) above.

[0946] That is, the compound shown in formula (40) is a compound having three groups shown in formula (11). Furthermore, the compound shown in formula (40) essentially only has protium atoms as hydrogen atoms.

[0947] In one embodiment, the compound represented by the aforementioned formula (40) is represented by the following formula (41).

[0948] [Chemistry 97]

[0949]

[0950] (In equation (41), L) 101 and Ar 101 As defined in equation (40) above).

[0951] In one embodiment, the compound represented by the aforementioned formula (40) is a compound represented by any one of the following formulas (42-1) to (42-3).

[0952] [Chem. 98]

[0953]

[0954] (In equations (42-1)~(42-3), R) 101A ~R 108A L 101 and Ar 101 As defined in equation (40) above).

[0955] In one embodiment, the compound represented by the aforementioned formulas (42-1) to (42-3) is a compound represented by any one of the following formulas (43-1) to (43-3).

[0956] [Chemistry 99]

[0957]

[0958] (In equations (43-1)~(43-3), L) 101 and Ar 101 As defined in equation (40) above).

[0959] In one embodiment, -L in the aforementioned formulas (40), (41), (42-1)~(42-3), and (43-1)~(43-3) 101 -Ar 101 The group shown is

[0960] Substituted or unsubstituted phenyl

[0961] Substituted or unsubstituted naphthyl groups

[0962] Substituted or unsubstituted biphenyl,

[0963] Replaced or unreplaced foetida

[0964] Substituted or unsubstituted benzo[phenanthrene]

[0965] Substituted or unsubstituted fluorene

[0966] Substituted or unsubstituted benzofluorene,

[0967] Substituted or unsubstituted dibenzofuranyl,

[0968] Substituted or unsubstituted naphthobenzofuranyl,

[0969] Substituted or unsubstituted dibenzothiophene group, and

[0970] Substituted or unsubstituted carbazolyl group.

[0971] In one embodiment, the compounds represented by formula (10) or formula (20) above comprise compounds in which at least one of the hydrogen atoms is a deuterium atom.

[0972] In one implementation, the aforementioned formula (20)

[0973] R as a hydrogen atom 101 ~R 108 ,

[0974] R as the aforementioned substituent R 101 ~R 108 The hydrogen atoms it possesses

[0975] L 101 The hydrogen atoms it possesses

[0976] L 101 The substituents possess hydrogen atoms,

[0977] Ar 101 The hydrogen atoms it possesses, and

[0978] Ar 101 The hydrogen atoms present in the substituents

[0979] At least one of them is a deuterium atom.

[0980] The compounds shown in formulas (30) to (37) above contain compounds in which at least one of the hydrogen atoms is a deuterium atom.

[0981] In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by formulas (30) to (37) is a deuterium atom.

[0982] In one embodiment, the compound represented by the aforementioned formula (30) is the compound represented by the following formula (30D).

[0983] [Chemistry 100]

[0984]

[0985] (In formula (30D), R) 101A ~R 108A L 101 and Ar 101 As defined in equation (30) above;

[0986] However, R as a hydrogen atom 101A ~R 110A ,

[0987] R as the aforementioned substituent R 101A ~R 110A The hydrogen atoms it possesses

[0988] L 101 The hydrogen atoms it possesses

[0989] L 101 The substituents possess hydrogen atoms,

[0990] Ar 101 The hydrogen atoms it possesses, and

[0991] Ar 101 The hydrogen atoms present in the substituents

[0992] At least one of them is a deuterium atom.

[0993] That is, the compound represented by formula (30D) is a compound in which at least one of the hydrogen atoms of the compound represented by formula (30) is a deuterium atom.

[0994] In one embodiment, R in the aforementioned formula (30D) is a hydrogen atom. 101A ~R 108A At least one of them is a deuterium atom.

[0995] In one embodiment, the compound represented by the aforementioned formula (30D) is the compound represented by the following formula (31D).

[0996] [Chemistry 101]

[0997]

[0998] (In equation (31D), R) 101A ~R 108A L 101 and Ar 101 As defined in the aforementioned formula (30D);

[0999] X d Is it O or S?

[1000] R 121 ~R128 One of them is related to L 101 Bonded single bonds.

[1001] Not with L 101 bonded single bond R 121 ~R 128 Two or more adjacent rings form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.

[1002] Not with L 101 R consists of bonded single bonds and does not form the aforementioned substituted or unsubstituted saturated or unsaturated rings. 121 ~R 128 Each independently is

[1003] hydrogen atom, or

[1004] Substituent R;

[1005] The aforementioned substituent R is as defined in equation (10) above;

[1006] However, R as a hydrogen atom 101A ~R 110A ,

[1007] R as the aforementioned substituent R 101A ~R 110A The hydrogen atoms it possesses

[1008] L 101 The hydrogen atoms it possesses

[1009] L 101 The substituents possess hydrogen atoms,

[1010] Ar 101 The hydrogen atoms it possesses

[1011] Ar 101 The hydrogen atoms present in the substituents

[1012] R as a hydrogen atom 121 ~R 128 ,and

[1013] R as the aforementioned substituent R 121 ~R 128 The hydrogen atoms it possesses

[1014] At least one of them is a deuterium atom.

[1015] In one embodiment, the compound represented by the aforementioned formula (31D) is the compound represented by the following formula (32D).

[1016] [Chemistry 102]

[1017]

[1018] (In equation (32D), R) 101A ~R 108A R 125A ~R 128A L 101 and Ar 101 As defined in the aforementioned equation (31D);

[1019] but,

[1020] R as a hydrogen atom 101A ~R 108A ,

[1021] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms it possesses

[1022] R as a hydrogen atom 125A ~R 128A ,

[1023] R as the aforementioned substituent R 125A ~R 128A The hydrogen atoms it possesses

[1024] In formula (32D), the hydrogen atoms bonded to the carbon atoms of the dibenzofuran skeleton,

[1025] L 101 The hydrogen atoms it possesses

[1026] L 101 The substituents possess hydrogen atoms,

[1027] Ar 101 The hydrogen atoms it possesses, and

[1028] Ar 101 The hydrogen atoms present in the substituents

[1029] At least one of them is a deuterium atom.

[1030] In one embodiment, the compound represented by the aforementioned formula (32D) is a compound represented by the following formula (32D-1) or (32D-2).

[1031] [Chemistry 103]

[1032]

[1033] In equations (32D-1) and (32D-2), R 101A ~R 108A R 125A ~R128A L 101 and Ar 101 As defined in the aforementioned equation (32D);

[1034] but,

[1035] R as a hydrogen atom 101A ~R 108A ,

[1036] R as the aforementioned substituent R 101A ~R 108A The hydrogen atoms it possesses

[1037] R as a hydrogen atom 125A ~R 128A ,

[1038] R as the aforementioned substituent R 125A ~R 128A The hydrogen atoms it possesses

[1039] The hydrogen atoms bonded to the carbon atoms of the dibenzofuran skeleton in formulas (32D-1) and (32D-2)

[1040] L 101 The hydrogen atoms it possesses

[1041] L 101 The substituents possess hydrogen atoms,

[1042] Ar 101 The hydrogen atoms it possesses, and

[1043] Ar 101 The hydrogen atoms present in the substituents

[1044] At least one of them is a deuterium atom.

[1045] In one embodiment, at least one of the hydrogen atoms in the compounds represented by the aforementioned formulas (40), (41), (42-1) to (42-3) or (43-1) to (43-3) is a deuterium atom.

[1046] In one embodiment, the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compound represented by formula (41) (R as hydrogen atoms) 101A ~R 108A At least one of them is a deuterium atom.

[1047] In one embodiment, the compound represented by the aforementioned formula (40) is the compound represented by the following formula (40D).

[1048] [Chemistry 104]

[1049]

[1050] (In formula (40D), L) 101 and Ar 101 As defined in equation (10) above;

[1051] R 101A and R 103A ~R 108A Two or more adjacent rings that do not form substituted or unsubstituted saturated or unsaturated rings;

[1052] R 101A and R 103A ~R 108A Each independently is

[1053] hydrogen atom, or

[1054] Substituent R;

[1055] The aforementioned substituent R is as defined in equation (10) above;

[1056] However, R as a hydrogen atom 101A and R 103A ~R 108A ,

[1057] R as the aforementioned substituent R 101A and R 103A ~R 108A The hydrogen atoms it possesses

[1058] L 101 The hydrogen atoms it possesses

[1059] L 101 The substituents possess hydrogen atoms,

[1060] Ar 101 The hydrogen atoms it possesses, and

[1061] Ar 101 The substituents possess hydrogen atoms,

[1062] At least one of them is a deuterium atom.

[1063] In one embodiment, R in the aforementioned formula (40D) 101A and R 103A ~R 108A At least one of them is a deuterium atom.

[1064] In one embodiment, the compound represented by the aforementioned formula (40D) is the compound represented by the following formula (41D).

[1065] [Chemistry 105]

[1066]

[1067] (In formula (41D), L) 101 and Ar 101 As defined in the aforementioned formula (40D);

[1068] However, in equation (41D)

[1069] Hydrogen atoms bonded to the carbon atoms that make up the anthracene skeleton

[1070] L 101 The hydrogen atoms it possesses

[1071] L 101 The substituents possess hydrogen atoms,

[1072] Ar 101 The hydrogen atoms it possesses, and

[1073] Ar 101 The substituents possess hydrogen atoms,

[1074] At least one of them is a deuterium atom.

[1075] In one embodiment, the compound represented by the aforementioned formula (40D) is a compound represented by any one of the following formulas (42D-1) to (42D-3).

[1076] [Chemistry 106]

[1077]

[1078] (In equations (42D-1)~(42D-3), R) 101A ~R 108A L 101 and Ar 101 As defined in the aforementioned formula (40D);

[1079] However, in the aforementioned equation (42D-1)

[1080] R as a hydrogen atom 101A and R 103A ~R 108A ,

[1081] R as the aforementioned substituent R 101A and R 103A ~R 108A The hydrogen atoms it possesses

[1082] L 101 The hydrogen atoms it possesses

[1083] L 101The substituents possess hydrogen atoms,

[1084] Ar 101 The hydrogen atoms it possesses

[1085] Ar 101 The hydrogen atoms present in the substituents, and

[1086] At least one of the hydrogen atoms bonded to the carbon atom constituting the phenyl group in the aforementioned formula (42D-1) is a deuterium atom;

[1087] In the aforementioned formula (42D-2), R is the hydrogen atom. 101A and R 103A ~R 108A ,

[1088] R as the aforementioned substituent R 101A and R 103A ~R 108A The hydrogen atoms it possesses

[1089] L 101 The hydrogen atoms it possesses

[1090] L 101 The substituents possess hydrogen atoms,

[1091] Ar 101 The hydrogen atoms it possesses

[1092] Ar 101 The hydrogen atoms present in the substituents, and

[1093] At least one of the hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (42D-2) is a deuterium atom.

[1094] In the aforementioned formula (42D-3), R is the hydrogen atom. 101A and R 103A ~R 108A ,

[1095] R as the aforementioned substituent R 101A and R 103A ~R 108A The hydrogen atoms it possesses

[1096] L 101 The hydrogen atoms it possesses

[1097] L 101 The substituents possess hydrogen atoms,

[1098] Ar 101 The hydrogen atoms it possesses

[1099] Ar 101The hydrogen atoms present in the substituents, and

[1100] The hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (42D-3)

[1101] At least one of them is a deuterium atom.

[1102] In one embodiment, the compound represented by the aforementioned formulas (42D-1) to (42D-3) is a compound represented by any one of the following formulas (43D-1) to (43D-3).

[1103] [Chemistry 107]

[1104]

[1105] (In equations (43D-1)~(43D-3), L) 101 and Ar 101 As defined in the aforementioned formula (40D);

[1106] However, the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the aforementioned formula (43D-1),

[1107] L 101 The hydrogen atoms it possesses

[1108] L 101 The substituents possess hydrogen atoms,

[1109] Ar 101 The hydrogen atoms it possesses

[1110] Ar 101 The substituents possess hydrogen atoms, and

[1111] At least one of the hydrogen atoms bonded to the carbon atom constituting the phenyl group in the aforementioned formula (43D-1) is a deuterium atom;

[1112] The hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the aforementioned formula (43D-2),

[1113] L 101 The hydrogen atoms it possesses

[1114] L 101 The substituents possess hydrogen atoms,

[1115] Ar 101 The hydrogen atoms it possesses

[1116] Ar 101 The substituents possess hydrogen atoms, and

[1117] At least one of the hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (43D-2) is a deuterium atom.

[1118] The hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the aforementioned formula (43D-3),

[1119] L 101 The hydrogen atoms it possesses

[1120] L 101 The substituents possess hydrogen atoms,

[1121] Ar 101 The hydrogen atoms it possesses

[1122] Ar 101 The substituents possess hydrogen atoms, and

[1123] The hydrogen atoms bonded to the carbon atom constituting the naphthyl group in the aforementioned formula (43D-3)

[1124] At least one of them is a deuterium atom.

[1125] Examples of compounds represented by formula (10) include those shown below. The compounds represented by formula (10) are not limited to these specific examples. In the following examples, Me represents a methyl group and D represents a deuterium atom.

[1126] [Chemistry 108]

[1127]

[1128] [Chemistry 109]

[1129]

[1130] [Chemical 110]

[1131]

[1132] [Chemistry 111]

[1133]

[1134] [Chemistry 112]

[1135]

[1136] [Chemistry 113]

[1137]

[1138] [Chemistry 114]

[1139]

[1140] [Chemistry 115]

[1141]

[1142] [Chemistry 116]

[1143]

[1144] [Chemistry 117]

[1145]

[1146] [Chemistry 118]

[1147]

[1148] [Chemistry 119]

[1149]

[1150] [Chemistry 120]

[1151]

[1152] As described above, the organic EL element involved in one aspect of the present invention has a cathode and an anode, and a light-emitting layer between the cathode and the anode. The light-emitting layer comprises the compounds shown in formulas (1-1) and (1-3), or the compounds shown in formulas (1-2) and (1-3). Apart from this, conventionally known materials and elements can be used as long as the effect of the present invention is not impaired.

[1153] The content of the compounds represented by formulas (1-1) and (1-3) or formulas (1-2) and (1-3) in the luminescent layer is preferably 1% by mass or more and 20% by mass or less relative to the total luminescent layer.

[1154] As a representative element structure of the organic EL element of the present invention, examples can be given.

[1155] (1) Anode / Light-emitting layer / Cathode

[1156] (2) Anode / hole injection layer / light-emitting layer / cathode

[1157] (3) Anode / Light-emitting layer / Electron injection and transport layer / Cathode

[1158] (4) Anode / hole injection layer / light-emitting layer / electron injection and transport layer / cathode

[1159] (5) Anode / Organic Semiconductor Layer / Light Emitting Layer / Cathode

[1160] (6) Anode / Organic Semiconductor Layer / Electron Barrier Layer / Light Emitting Layer / Cathode

[1161] (7) Anode / Organic Semiconductor Layer / Light Emitting Layer / Adhesion Improvement Layer / Cathode

[1162] (8) Anode / Hole injection·Transport layer / Light-emitting layer / Electron injection·Transport layer / Cathode

[1163] (9) Anode / Insulating layer / Light-emitting layer / Insulating layer / Cathode

[1164] (10) Anode / Inorganic semiconductor layer / Insulating layer / Light-emitting layer / Insulating layer / Cathode

[1165] (11) Anode / Organic Semiconductor Layer / Insulating Layer / Light Emitting Layer / Insulating Layer / Cathode

[1166] (12) Anode / Insulating layer / Hole injection·Transport layer / Light-emitting layer / Insulating layer / Cathode

[1167] (13) Anode / Insulating layer / Hole injection·Transport layer / Light-emitting layer / Electron injection·Transport layer / Cathode

[1168] Structures such as...

[1169] Of the above, the configuration of (8) is preferred, but it is not limited thereto.

[1170] In this specification, "hole injection and transport layer" refers to "at least one of hole injection layer and hole transport layer", and "electron injection and transport layer" refers to "at least one of electron injection layer and electron transport layer".

[1171] Hereinafter, components that can be used in an organic EL element according to one aspect of the present invention, and materials other than the compounds described above that constitute each layer, will be described.

[1172] (Substrate)

[1173] The substrate serves as a support for the light-emitting element. Materials such as glass, quartz, and plastic can be used as substrates. Additionally, flexible substrates can be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate or polyvinyl chloride.

[1174] (anode)

[1175] In the anode formed on the substrate, metals, alloys, conductive compounds, and mixtures thereof with a high work function (specifically 4.0 eV or higher) are preferably used. Examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride).

[1176] (hole injection layer)

[1177] The hole injection layer is a layer containing a substance with high hole injection capability. Substances with high hole injection capability may include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymers (oligomers, dendritic polymers, polymers, etc.).

[1178] (Hole transport layer)

[1179] A hole transport layer is a layer containing a substance with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used. However, any other substance can be used as long as it has high hole transport capacity compared to electrons. It should be noted that the layer containing the substance with high hole transport capacity can be a single layer, or two or more layers formed from the above substances can be stacked.

[1180] (Guest (dopant) material of the light-emitting layer)

[1181] The luminescent layer is a layer containing a highly luminescent material. Besides the materials used in this invention as described above (the compounds shown in formulas (1-1) and (1-3), or the compounds shown in formulas (1-2) and (1-3), various other materials can be used. For example, as a highly luminescent material, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound capable of emitting light from a singlet excited state, and a phosphorescent compound is a compound capable of emitting light from a triplet excited state.

[1182] Blue-based fluorescent materials suitable for use in the luminescent layer include pyrene derivatives, styrylamine derivatives, phenylene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, and triarylamine derivatives. Green-based fluorescent materials suitable for use in the luminescent layer include aromatic amine derivatives. Red-based fluorescent materials suitable for use in the luminescent layer include tetraphenylene derivatives and diamine derivatives.

[1183] Blue phosphorescent materials suitable for use in the luminescent layer utilize metal complexes such as iridium, osmium, and platinum complexes. Green phosphorescent materials suitable for use in the luminescent layer utilize iridium complexes. Red phosphorescent materials suitable for use in the luminescent layer utilize metal complexes such as iridium, platinum, terbium, and europium complexes.

[1184] (Main material of the light-emitting layer)

[1185] As the luminescent layer, it can be configured to disperse the aforementioned highly luminescent substance (guest material) in other substances (host material). As the substance used to disperse the highly luminescent substance, in addition to the material used in the present invention described above (the compound shown in formula (10)), various substances can be used, and it is preferable to use a substance with a higher minimum empty orbital level (LUMO level) and a lower maximum occupied orbital level (HOMO level) compared to the highly luminescent substance.

[1186] As the main material for dispersing substances with high luminescence, the following are used: 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes; 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthrene derivatives; 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, tetraphenyl derivatives, fluoranthene derivatives, benzo[a]phenanthrene derivatives, fluorene derivatives, or β-derived derivatives; and 4) aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[1187] Furthermore, delayed fluorescence (thermally activated delayed fluorescence) compounds can also be used as the host material. The luminescent layer preferably comprises the materials used in the present invention as described above, and the delayed fluorescence host compound.

[1188] (Electron transport layer)

[1189] The electron transport layer is a layer containing substances with high electron transport properties. The electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymeric compounds.

[1190] (Electron injection layer)

[1191] The electron-injection layer is a layer containing materials with high electron-injection potential. Metal complexes such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and 8-hydroxyquinazoline-lithium (Liq), as well as lithium oxides (LiO), can be used in the electron-injection layer. x Alkali metals, alkaline earth metals, or their compounds, etc.

[1192] (cathode)

[1193] In the cathode, metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV) are preferred. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[1194] In the organic EL element according to one aspect of the present invention, the method of forming each layer is not particularly limited. Conventionally known formation methods based on vacuum evaporation, spin coating, etc., can be used. Each layer, such as the light-emitting layer, can be formed by known coating methods such as vacuum evaporation, molecular beam evaporation (MBE), or impregnation with a solution obtained in a solvent, spin coating, casting, rod coating, roll coating, etc.

[1195] In one aspect of the organic EL element, the film thickness of each layer is not particularly limited. Generally, in order to suppress defects such as pinholes, suppress the applied voltage to a low level, and improve luminous efficiency, the thickness is usually preferred to be in the range of several nm to 1 μm.

[1196] [Electronic Devices]

[1197] An electronic device according to one aspect of the present invention is characterized by having an organic EL element according to one aspect of the present invention.

[1198] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones or personal computers, and light-emitting devices such as lighting or vehicle lamps. Example

[1199] The following describes embodiments of the present invention. The present invention is not limited by these embodiments.

[1200] <Compound>

[1201] The compounds represented by formulas (1-1) and (1-3), or the compounds represented by formulas (1-2) and (1-3) used in the examples are shown below.

[1202] [Chemistry 121]

[1203]

[1204] [Chemistry 122]

[1205]

[1206] [Chemistry 123]

[1207]

[1208] The compounds used in the comparative examples are shown below.

[1209] [Chemistry 124]

[1210]

[1211] Other compounds used in the examples and comparative examples are shown below.

[1212] [Chemistry 125]

[1213]

[1214] Example 1

[1215] <Fabrication of Organic EL Components>

[1216] A glass substrate (manufactured by Geomatics Co., Ltd.) with an ITO transparent electrode (anode) and a thickness of 25mm×75mm×1.1mm was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1217] A washed glass substrate with a transparent electrode is mounted on a substrate support of a vacuum evaporation apparatus. First, HI compound is deposited on the surface where the transparent electrode is formed, covering the transparent electrode, to form a 5 nm thick HI film. This HI film functions as a hole injection layer.

[1218] Following the deposition of the HI film, compound HT1 is then deposited to form an HT1 film with a thickness of 80 nm on the HI film. This HT1 film functions as the first hole transport layer.

[1219] After the HT1 film is formed, compound HT2 is deposited by vapor deposition to form an HT2 film with a thickness of 10 nm on the HT1 film. This HT2 film functions as a second hole transport layer.

[1220] BH-1 (host material) and BD-1 (dopant material) were co-deposited on the HT2 film in such a way that the weight ratio of compound BD-1 reached 2% to form a light-emitting layer with a film thickness of 25 nm.

[1221] Compound HBL was deposited on the emitting layer to form an electron transport layer with a thickness of 10 nm. Compound ET, used as an electron injection material, was then deposited on the electron transport layer to form an electron injection layer with a thickness of 15 nm. LiF was then deposited on the electron injection layer to form a LiF film with a thickness of 1 nm. Metallic Al was then deposited on the LiF film to form a metal cathode with a thickness of 80 nm.

[1222] If the component configuration of the organic EL element of Example 1 is briefly shown, it will be described as follows.

[1223] ITO(130) / HI1(5) / HT1(80) / HT2(10) / BH-1:BD-1(25:2%) / HBL(10) / ET(15) / LiF(1) / Al(80)

[1224] The numbers in parentheses represent the film thickness (unit: nm).

[1225] <Evaluation of Organic EL Components>

[1226] For the obtained organic EL device, a current density of 50 mA / cm² was applied. 2 A voltage was applied in a manner that measured the time (LT95) until the brightness reached 95% relative to the initial brightness. The results are shown in Table 1. It should be noted that the values ​​in the table are relative to the case where LT95 in Comparative Example 1 described later is 100%.

[1227] The evaluation results are shown in Table 1.

[1228] Examples 2-15 and Comparative Example 1

[1229] The compounds described in Table 1 were used as dopant materials for the light-emitting layer. Organic EL devices were fabricated using the same method as in Example 1, and their performance was evaluated. The results are shown in Table 1.

[1230]

[1231] <Compound Synthesis>

[1232] Compounds BD-1~16 and BD-Ref were synthesized via the general synthetic route described below.

[1233] [Chemistry 126]

[1234]

[1235] (1) Synthesis of BD-1

[1236] BD-1 was synthesized according to the following synthetic route.

[1237] [Chemistry 127]

[1238]

[1239] Intermediate A (9.00 g) and 4-tert-butylcyclohexane-1-one (5.38 g) were added to acetic acid (35 mL), and the mixture was heated at 100 °C for 6 hours under an argon atmosphere with stirring. Dichloromethane and water were added to the reaction solution, the organic phase was separated, and washed with an aqueous sodium bicarbonate solution. After concentration under reduced pressure, the mixture was purified by column chromatography to obtain intermediate B-1 (5.94 g, 50% yield).

[1240] [Chemistry 128]

[1241]

[1242] Intermediate B-1 (6.32 g) and 2,3-dichloro-5,6-dicyano-p-benzoquinone (8.42 g) were added to toluene (90 mL), and the mixture was heated at 100 °C for 3 hours under an argon atmosphere with stirring. The reaction solution was filtered through diatomaceous earth and purified by column chromatography to obtain intermediate C-1 (5.50 g, yield 88%).

[1243] [Chemistry 129]

[1244]

[1245] Intermediate C-1 (5.80 g), bis(pinacolyl)diboron (13.12 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.25 g), and potassium acetate (3.38 g) were added to 1,4-dioxane (120 mL), and heated at 100 °C for 4 hours under an argon atmosphere with stirring. The reaction solution was filtered through diatomaceous earth and purified by column chromatography and recrystallization to obtain intermediate D-1 (3.65 g, yield 55%).

[1246] [Chemistry 130]

[1247]

[1248] Intermediate D-1 (8.37 g), 1,4-dibromo-2,5-diiodobenzene (4.30 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II)dichloromethane complex (0.29 g), and potassium carbonate (3.66 g) were added to a mixed solvent of toluene (129 mL) and water (65 mL). The mixture was heated at 90 °C for 7 hours under an argon atmosphere with stirring. Toluene and water were then added to the reaction solution, and the mixture was stirred at room temperature. The organic phase was separated, subjected to column chromatography, and washed with toluene to give intermediate E-1 (4.42 g, yield 67%).

[1249] [Chemistry 131]

[1250]

[1251] Intermediate E-1 (5.04 g), cuprous iodide (I) (0.13 g), 1,10-phenanthroline monohydrate (0.24 g), and potassium carbonate (2.33 g) were added to dimethylformamide (135 mL), and the mixture was heated at 100 °C for 3 hours under an argon atmosphere with stirring. Water (150 mL) was added to the reaction solution, and the solid was filtered off and purified by column chromatography to obtain intermediate F-1 (3.54 g, 90% yield).

[1252] [Chemistry 132]

[1253]

[1254] In a toluene (60 mL) suspension of intermediate F-1 (0.71 g), diphenylamine (0.43 g), tris(diphenylmethyleneacetone)dipalladium (0) (0.06 g), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (0.23 g), a toluene solution (1 M, 2.8 mL) of hexamethyldisilamide lithium (LiHMDS) was added dropwise. The mixture was heated at 100 °C for 3 hours under an argon atmosphere with stirring. After cooling to room temperature, the reaction solution was subjected to column chromatography. The crude product was purified by column chromatography and recrystallization to obtain BD-1 (0.72 g, 70% yield). The molecular weight of BD-1 was 851.11, and the mass spectrometry analysis of the obtained compound showed m / z (mass to charge ratio) = 851, therefore it was identified as compound BD-1.

[1255] (2) Synthesis of compound BD-2

[1256] 4,4'-dimethyl-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-2 has a molecular weight of 907.22, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 907, thus identifying it as compound BD-2.

[1257] (3) Synthesis of compound BD-3

[1258] 4,4'-Diethyl-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-3 has a molecular weight of 963.33, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 963, thus identifying it as compound BD-3.

[1259] (4) Synthesis of compound BD-4

[1260] 4-Isopropyl-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-4 has a molecular weight of 935.27, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 935, thus identifying it as compound BD-4.

[1261] (5) Synthesis of compound BD-5

[1262] 3,3'-dimethyl-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-5 has a molecular weight of 907.22, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 907, thus identifying it as compound BD-5.

[1263] (6) Synthesis of compound BD-6

[1264] 3-tert-butyl-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-6 has a molecular weight of 963.33, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 963, thus identifying it as compound BD-6.

[1265] (7) Synthesis of compound BD-Ref

[1266] [Chemistry 133]

[1267]

[1268] Cyclohexanone was used as a reactant instead of 4-tert-butylcyclohexane-1-one. Otherwise, intermediate F-Ref was synthesized by the same method as intermediates B-1 to F-1.

[1269] Intermediate F-Ref was used instead of intermediate F-1 as a reactant, and the compound was otherwise synthesized using the same method as that used for compound BD-1. BD-Ref has a molecular weight of 738.89, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 738, thus identifying it as compound BD-Ref.

[1270] (8) Synthesis of compound BD-7

[1271] As a reactant, N-(4-tert-butylphenyl)-[1,1'-biphenyl]-2-amine was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as compound BD-1. BD-7 has a molecular weight of 1115.52, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1115, thus identifying it as compound BD-7.

[1272] (9) Synthesis of compound BD-8

[1273] N-phenyl-[1,1'-biphenyl]-2-amine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-8 has a molecular weight of 1003.31, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1003, thus identifying it as compound BD-8.

[1274] (10) Synthesis of compound BD-9

[1275] 2-(1-Naphthyl)-diphenylamine was used instead of diphenylamine as a reactant, and the compound was otherwise synthesized using the same method as compound BD-1. BD-9 has a molecular weight of 1103.43, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1103, thus identifying it as compound BD-9.

[1276] (11) Synthesis of compound BD-10

[1277] [Chemistry 134]

[1278]

[1279] [1,1'-biphenyl]-2-amine (21.4 g), 1-bromo-3-tert-butylbenzene (27.0 g), tris(diphenylmethyleneacetone)dipalladium(0) (1.74 g), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) (2.37 g), and sodium tert-butoxide (17.1 g) were added to toluene (253 mL), and the mixture was heated at 100 °C for 3 hours under an argon atmosphere with stirring. The reaction solution was filtered through diatomaceous earth and purified by column chromatography to obtain intermediate G-1 (28.6 g, yield 75%).

[1280] As a reactant, intermediate G-1 was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as that used for compound BD-1. BD-10 has a molecular weight of 1115.52, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1115, thus identifying it as compound BD-10.

[1281] (12) Synthesis of compound BD-11

[1282] [Chemistry 135]

[1283]

[1284] As reactants, 4-tert-butyl-[1,1'-biphenyl]-2-amine was used instead of [1,1'-biphenyl]-2-amine, and bromobenzene was used instead of 1-bromo-3-tert-butylbenzene. Otherwise, intermediate G-2 was synthesized by the same method as intermediate G-1.

[1285] As a reactant, intermediate G-2 was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as that used for compound BD-1. BD-11 has a molecular weight of 1115.52, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1115, thus identifying it as compound BD-11.

[1286] (13) Synthesis of compound BD-12

[1287] [Chemistry 136]

[1288]

[1289] As reactants, [1,1'-biphenyl-2',3',4',5',6'-d5]-2-amine was used instead of [1,1'-biphenyl]-2-amine, and bromobenzene-d5 was used instead of 1-bromo-3-tert-butylbenzene. Otherwise, intermediate G-3 was synthesized by the same method as intermediate G-1.

[1290] As a reactant, intermediate G-3 was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as compound BD-1. BD-12 has a molecular weight of 1023.43, and the mass spectrometry analysis of the obtained compound showed an m / z (mass to charge ratio) of 1023, thus identifying it as compound BD-12.

[1291] (14) Synthesis of compound BD-13

[1292] [Chemistry 137]

[1293]

[1294] As a reaction raw material, bromobenzene-d5 was used instead of 1-bromo-3-tert-butylbenzene. Otherwise, intermediate G-4 was synthesized by the same method as intermediate G-1.

[1295] As a reactant, intermediate G-4 was used instead of diphenylamine. Otherwise, the compound was synthesized using the same method as that used for compound BD-1. BD-13 has a molecular weight of 1013.37, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1013, thus identifying it as compound BD-13.

[1296] (15) Synthesis of compound BD-14

[1297] [Chemistry 138]

[1298]

[1299] As reactants, [1,1'-biphenyl-2',3',4',5',6'-d5]-2-amine was used instead of [1,1'-biphenyl]-2-amine, and bromobenzene was used instead of 1-bromo-3-tert-butylbenzene. Otherwise, intermediate G-5 was synthesized by the same method as intermediate G-1.

[1300] As a reactant, intermediate G-5 was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as that used for compound BD-1. BD-14 has a molecular weight of 1013.37, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1013, thus identifying it as compound BD-14.

[1301] (16) Synthesis of compound BD-15

[1302] [Chemistry 139]

[1303]

[1304] As reactants, [1,1'-biphenyl-2',3,3',4,4',5,5',6,6'-d9]-2-amine was used instead of [1,1'-biphenyl]-2-amine, and bromobenzene-d5 was used instead of 1-bromo-3-tert-butylbenzene. Otherwise, intermediate G-6 was synthesized by the same method as intermediate G-1.

[1305] As a reactant, intermediate G-6 was used instead of diphenylamine, and the compound was otherwise synthesized using the same method as compound BD-1. BD-15 has a molecular weight of 1031.48, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 1031, thus identifying it as compound BD-15.

[1306] (17) Synthesis of compound BD-16

[1307] [Chemistry 140]

[1308]

[1309] As a reaction raw material, 2-tert-butylcyclohexane-1-one was used instead of 4-tert-butylcyclohexane-1-one. Otherwise, intermediate F-2 was synthesized by the same method as intermediates B-1 to F-1.

[1310] Intermediate F-2 was used instead of intermediate F-1 as a reactant, and the compound was otherwise synthesized using the same method as that used for compound BD-1. BD-16 has a molecular weight of 851.11, and the mass spectrometry analysis of the resulting compound showed an m / z (mass to charge ratio) of 851, thus identifying it as compound BD-16.

[1311] Several embodiments and / or examples of the present invention have been described in detail above. However, those skilled in the art can readily make various modifications to these illustrated embodiments and / or examples without substantially departing from the new teachings and effects of the present invention. Therefore, these various modifications are included within the scope of the present invention.

[1312] The entire contents of this application, including the references contained herein and the application based on the priority of the Paris Convention, are hereby incorporated.

Claims

1. Selected from the following compounds:

2. A compound selected from (BD-1) to (BD-7) and (BD-16) below.

3. A material for organic electroluminescent devices, comprising the compound of claim 1 or 2.

4. An organic electroluminescent element having a cathode, an anode, and at least one organic layer disposed between the cathode and the anode. At least one of the aforementioned at least one organic layer comprises the compound of claim 1 or 2.

5. The organic electroluminescent element according to claim 4, wherein, At least one of the aforementioned at least one organic layer comprises a first compound and a second compound that is different from the first compound, wherein the first compound is the compound according to claim 1 or 2. The aforementioned second compound is the compound shown in formula (20). In equation (20), R 101 ~R 108 Two or more adjacent rings in one or more groups do not form unsubstituted saturated or unsaturated rings; R 101 ~R 108 Each independently is hydrogen atom, or Substituent R, L 101 yes single bond, Unsubstituted arylene groups with 6 to 18 cyclic carbon atoms, or Unsubstituted divalent heterocyclic groups with 5–18 cyclic atoms; Ar 101 yes Unsubstituted aryl groups with 6 to 18 cyclic carbon atoms, or Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms in a monovalent state; The aforementioned substituent R is Unsubstituted alkyl groups having 1 to 6 carbon atoms Unsubstituted aryl groups with 6 to 18 cyclic carbon atoms, or Unsubstituted heterocyclic groups with 5 to 18 cyclic atoms in a monovalent state; When there are two or more substituents R, the two or more substituents R can be the same or different.

6. The organic electroluminescent element according to claim 5, wherein, Ar 101 At least one of them is an unsubstituted aryl group with 6 to 18 cyclic carbon atoms.

7. The organic electroluminescent element according to claim 4 or 5, wherein, At least one of the aforementioned at least one organic layer is a light-emitting layer.

8. The organic electroluminescent element according to claim 7, wherein, A hole transport layer is present between the aforementioned anode and the aforementioned light-emitting layer.

9. The organic electroluminescent element according to claim 7, wherein, An electron transport layer is provided between the aforementioned cathode and the aforementioned light-emitting layer.

10. The organic electroluminescent element according to claim 7, wherein, The aforementioned luminescent layer comprises the compound shown in formula (20).

11. The organic electroluminescent element according to claim 7, wherein, The aforementioned luminescent layer further comprises a host compound with delayed fluorescence.

12. An electronic device having an organic electroluminescent element according to any one of claims 4 to 11.

Images