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

Abstract

A compound represented by the following formula (1) or (2), a material for an organic electroluminescent element containing the compound, an organic electroluminescent element using the compound, and an electronic device containing the organic electroluminescent element. Each symbol in formula (1) or (2) is as defined in the specification.

Description

Technical Field

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

[0002] Generally, organic electroluminescent devices (hereinafter sometimes referred to as "organic EL devices") consist of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected into the luminescent region from the cathode side, and holes are injected into the luminescent region from the anode side. The injected electrons and holes recombine in the luminescent region to generate an excited state, which emits light when it returns to the ground state. Therefore, developing materials that efficiently transport electrons or holes to the luminescent region and facilitate electron-hole recombination is important for obtaining high-performance organic EL devices.

[0003] Patent documents 1-4 disclose compounds used as materials for organic electroluminescent elements.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Description of Chinese Patent Application Publication No. 116143765

[0007] Patent Document 2: U.S. Patent Application Publication No. 20180083197

[0008] Patent Document 3: International Publication No. 2023 / 287228

[0009] Patent Document 4: International Publication No. 2023 / 068794 Summary of the Invention

[0010] The problem the invention aims to solve

[0011] In the past, a large number of compounds for organic EL devices have been reported, but we are still looking for compounds that can further improve the performance of organic EL devices.

[0012] The present invention was made to solve the above-mentioned problems, and aims to provide compounds and materials for organic electroluminescent devices that further improve the performance of organic EL devices, especially compounds that further improve external quantum efficiency and lifetime, organic EL devices that further improve device performance, and electronic devices comprising such organic EL devices.

[0013] means for solving problems

[0014] The inventors have repeatedly conducted in-depth studies on the performance of organic EL elements containing novel compounds not disclosed in Patent Documents 1 to 4, and found that the performance of organic EL elements containing compounds represented by formula (1) or (2) below is further improved.

[0015] In one aspect of the invention, the invention provides a compound represented by the following formula (1) (hereinafter sometimes referred to as compound (1)).

[0016] [Chemical Formula 1]

[0017]

[0018] In equation (1),

[0019] • Selected from R 1 ~R 9 Two adjacent elements in the loop may bond together to form a ring or not bond together to form a ring.

[0020] • Selected from R 11 ~R 14 Two adjacent elements in the loop may bond together to form a ring or not bond together to form a ring.

[0021] • Selected from R 21 ~R 27 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0022] • The above-mentioned non-bonded R-terms that do not form a ring 1 ~R 9 Each is an independent hydrogen atom.

[0023] • The above R 11 ~R 14 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms.

[0024] • The above R 21 ~R 27 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0025] ·X 1 and X 2 Each can be an oxygen atom or a sulfur atom.

[0026] ·L 1 It is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group with 5 to 30 carbon atoms.

[0027] ·Ar 1 [A substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.]

[0028] In another aspect of the invention, the invention provides a compound represented by the following formula (2) (hereinafter sometimes referred to as compound (2)).

[0029] [Chemical Formula 2]

[0030]

[0031] In equation (2),

[0032] • Selected from R 31 ~R 33 One of them is a single bond that bonds with *1.

[0033] • Selected from R 51 ~R 55 One of them is a single bond that bonds with *a.

[0034] • Selected from R that is not one of the above single bonds 31 ~R 33 and R 34 ~R 40 Two adjacent elements in the loop may bond together to form a ring or not bond together to form a ring.

[0035] • Selected from R 41 ~R 44 Two adjacent elements in the loop may bond together to form a ring or not bond together to form a ring.

[0036] • Selected from R that is not one of the above single bonds 51 ~R 55 Two adjacent elements in the loop may bond together to form a ring or not bond together to form a ring.

[0037] • Selected from R 61 ~R 68 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0038] The above-mentioned Rs that are not mutually bonded and do not form a ring and are not single bonds 31 ~R 33 R and non-bonded to form a ring 34 ~R 40 Each is an independent hydrogen atom.

[0039] • The above R 41 ~R 44 And R that is not a single bond as described above 51 ~R 55Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms.

[0040] • The above R 61 ~R 68 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

[0041] ·X 3 It consists of oxygen or sulfur atoms.

[0042] ·L 2 It is a single bond, a substituted or unsubstituted cyclic aryl group with 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic heteroaryl group with 5 to 30 carbon atoms.

[0043] ·Ar 2 [A substituted or unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic structure.]

[0044] In another embodiment, the present invention provides a material for an organic electroluminescent element comprising compound (1) or compound (2).

[0045] In another embodiment, the present invention provides an organic electroluminescent element having a cathode, an anode, and an organic layer located between the cathode and the anode, the organic layer being formed of a single layer or multiple layers including the light-emitting layer, wherein at least one layer selected from the group consisting of single layers and multiple layers constituting the organic layer comprises compound (1) or compound (2).

[0046] In another embodiment, the present invention provides an electronic device comprising the above-described organic electroluminescent element.

[0047] The effects of the invention

[0048] Organic EL elements containing the compound shown in formula (1) above exhibit improved element performance. Similarly, organic EL elements containing the compound shown in formula (2) above also exhibit improved element performance. Attached Figure Description

[0049] Figure 1 This is a schematic diagram illustrating the structure of an organic EL element according to one aspect of the present invention.

[0050] Figure 2 This is a schematic diagram illustrating the structure of an organic EL element according to another aspect of the present invention.

[0051] Figure 3This is a schematic diagram illustrating the structure of an organic EL element according to another aspect of the present invention. Detailed Implementation

[0052] [definition]

[0053] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0054] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0055] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as such unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluorene and 25 for 9,9'-spirobifluorene.

[0056] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the 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 cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the 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 cyclic naphthalene ring substituted with an alkyl group is 10.

[0057] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) 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 stated. 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 atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, 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 with bonded hydrogen atoms or substituents is 10.

[0058] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0059] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0060] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0061] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0062] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0063] Substituents described in this specification

[0064] The substituents described in this specification are explained below.

[0065] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0066] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0067] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0068] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0069] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0070] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0071] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0072] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0073] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0074] • "Substituted or unsubstituted aryl groups"

[0075] 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. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0076] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0077] • Unsubstituted aryl groups (specific example group G1A):

[0078] phenyl,

[0079] p-phenyl,

[0080] metaphenyl,

[0081] o-phenyl,

[0082] p-terphenyl-4-yl,

[0083] p-terphenyl-3-yl,

[0084] p-terphenyl-2-yl,

[0085] m-terphenyl-4-yl,

[0086] m-terphenyl-3-yl,

[0087] m-terphenyl-2-yl,

[0088] o-terphenyl-4-yl

[0089] o-terphenyl-3-yl

[0090] o-terphenyl-2-yl,

[0091] 1-Naphthyl,

[0092] 2-Naphthyl,

[0093] Anthryl,

[0094] Benzoanthryl,

[0095] Phenanthryl,

[0096] Benzophenanthryl,

[0097] Phenalenyl,

[0098] Pyrenyl,

[0099] Chrysenyl,

[0100] Benzochrysenyl,

[0101] Triphenylenyl,

[0102] Benzo[ghi]triphenylenyl,

[0103] Tetracenyl,

[0104] Pentacenyl,

[0105] Fluorenyl,

[0106] 9,9'-Spirobi[fluorenyl],

[0107] Benzo[h]fluorenyl,

[0108] Dibenzo[def,p]fluorenyl,

[0109] Fluorenyl,

[0110] Benzo[j]fluoranthenyl,

[0111] Perylenyl, and

[0112] monovalent aryl groups derived by removing one hydrogen atom from the ring structures represented by the following general formulas (TEMP-1) to (TEMP-15).

[0113] [Chemical formula 3]

[0114]

[0115] [Chemical formula 4]

[0116]

[0117] · Substituted aryl groups (specific example group G1B):

[0118] o-Tolyl,

[0119] m-Tolyl,

[0120] p-Tolyl,

[0121] p-Xylyl,

[0122] m-Xylyl,

[0123] o-xylyl,

[0124] p-isopropylphenyl,

[0125] m-Isopropylphenyl,

[0126] o-isopropylphenyl,

[0127] p-tert-butylphenyl,

[0128] m-tert-butylphenyl,

[0129] o-tert-butylphenyl,

[0130] 3,4,5-Trimethylphenyl

[0131] 9,9-Dimethylfluorenyl,

[0132] 9,9-Diphenylfluorenyl

[0133] 9,9-Bis(4-methylphenyl)fluorenyl,

[0134] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0135] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0136] cyanophenyl,

[0137] Triphenylsilylphenyl

[0138] Trimethylsilylphenyl

[0139] Phenynaphthyl,

[0140] Naphthylphenyl, and

[0141] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) by substitution of one or more hydrogen atoms of a monovalent group with a substituent.

[0142] • "Substituted or unsubstituted heterocyclic groups"

[0143] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0144] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0145] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0146] 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. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0147] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that 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 the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0148] 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 from the ring structures shown in the following general formulas (TEMP-16) to (TEMP-33) by removing one hydrogen atom (specific example group G2A4).

[0149] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (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) have been substituted with a substituent (specific example group G2B4).

[0150] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0151] pyrrole,

[0152] Imidazole group,

[0153] pyrazolyl,

[0154] Triazole group,

[0155] Tetrazolyl,

[0156] Oxazolyl,

[0157] Isoxazolyl,

[0158] Oxadiazole group,

[0159] Thiazole group,

[0160] Isothiazolyl,

[0161] Thiadiazole group,

[0162] pyridyl,

[0163] pyridazinyl,

[0164] Pyrimidine group,

[0165] Pyrazinyl,

[0166] Triazine group

[0167] Indole,

[0168] Isoindolyl,

[0169] Indazine-based

[0170] Quinazine-based

[0171] Quinoline,

[0172] Isoquinoline,

[0173] Crenoline group

[0174] Phthaloazine

[0175] Quinazolinyl,

[0176] Quinoxaloyl,

[0177] Benzimidazole group,

[0178] Indazole group,

[0179] phenanthroline,

[0180] phenanthridine,

[0181] acridine group,

[0182] Phenazine group,

[0183] Carbazolyl,

[0184] Benzocarbazolyl,

[0185] Morpholinyl,

[0186] phenoxazine group,

[0187] phenothiazine group,

[0188] Azacarbazolyl and diazacarbazolyl.

[0189] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0190] furanyl,

[0191] Oxazolyl,

[0192] Isoxazolyl,

[0193] Oxadiazole group,

[0194] Xuton base,

[0195] Benzofuranyl,

[0196] Isobenzofuranyl,

[0197] Dibenzofuranyl,

[0198] Naphthobenzofuranyl,

[0199] Benzoxazolyl,

[0200] Benzisoxazole group,

[0201] phenoxazine group,

[0202] Morpholinyl,

[0203] Dinaphthylfuranyl,

[0204] Azadibenzofuranyl,

[0205] diazadibenzofuranyl,

[0206] Azanaphthalenebenzofuranyl, and

[0207] Diazanaphthenebenzofuranyl.

[0208] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0209] Thiophene group

[0210] Thiazole group,

[0211] Isothiazolyl,

[0212] Thiadiazole group,

[0213] benzothienyl

[0214] isobenzothienyl

[0215] dibenzothienyl

[0216] Naphthobenzothienyl

[0217] Benzothiazolyl,

[0218] Benzisothiazolyl,

[0219] phenothiazine group,

[0220] dinaphthothienyl

[0221] azadibenzothienyl

[0222] diazadibenzothienyl

[0223] azanaphthobenzothienyl and

[0224] diazanaphthobenzothienyl.

[0225] • The monovalent heterocyclic group 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):

[0226] [Chemical Formula 5]

[0227]

[0228] [Chemical Formula 6]

[0229]

[0230] In the above 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.

[0231] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen 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.

[0232] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0233] (9-phenyl)carbazole group,

[0234] (9-Biphenyl)carbazole,

[0235] (9-Phenyl)phenylcarbazoyl,

[0236] (9-Naphthyl)carbazole,

[0237] Diphenylcarbazole-9-yl,

[0238] Phenylexacarbazole-9-yl,

[0239] Methylbenzimidazole,

[0240] Ethylbenzimidazole,

[0241] Phenylacetyl,

[0242] Biphenyltriazine

[0243] diphenyltriazine group,

[0244] phenylquinazolinyl, and

[0245] Biphenylquinazolinyl.

[0246] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0247] Phenyl dibenzofuranyl,

[0248] Methyldibenzofuranyl,

[0249] tert-butyldibenzofuranyl, and

[0250] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0251] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0252] Phenyl dibenzothiophene,

[0253] Methyldibenzothiophene,

[0254] tert-butyldibenzothiophene, and

[0255] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0256] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0257] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0258] • "Substituted or unsubstituted alkyl groups"

[0259] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0260] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that 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 in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0261] • Unsubstituted alkyl groups (specific example group G3A):

[0262] methyl,

[0263] Ethyl,

[0264] n-propyl,

[0265] Isopropyl,

[0266] n-Butyl,

[0267] Isobutyl,

[0268] sec-butyl, and

[0269] tert-butyl.

[0270] • Substituted alkyl groups (specific example group G3B):

[0271] Heptafluoropropyl (including isomers),

[0272] Pentafluoroethyl,

[0273] 2,2,2-Trifluoroethyl, and

[0274] Trifluoromethyl

[0275] • "Substituted or unsubstituted alkenyl groups"

[0276] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0277] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that 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 itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0278] • Unsubstituted alkenyl groups (specific example group G4A):

[0279] vinyl,

[0280] Allyl

[0281] 1-Butenyl,

[0282] 2-Butenyl, and

[0283] 3-Butenyl.

[0284] • Substituted alkenyl groups (specific example group G4B):

[0285] 1,3-Butadienyl,

[0286] 1-Methylvinyl

[0287] 1-Methylallyl,

[0288] 1,1-Dimethylallyl,

[0289] 2-Methylallyl, and

[0290] 1,2-Dimethylallyl.

[0291] • "Substituted or unsubstituted alkynyl groups"

[0292] 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) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0293] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0294] • Unsubstituted alkynyl group (specific example group G5A):

[0295] Acetylene

[0296] • "Substituted or unsubstituted cycloalkyl groups"

[0297] 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. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0298] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" 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 have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0299] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0300] Cyclopropyl

[0301] Cyclobutyl,

[0302] Cyclopentyl,

[0303] Cyclohexyl,

[0304] 1-Adamantyl,

[0305] 2-Adamantyl,

[0306] 1-norborneol, and

[0307] 2-norborneol.

[0308] • Substituted cycloalkyl groups (specific example group G6B):

[0309] 4-Methylcyclohexyl.

[0310] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0311] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0312] -Si(G1)(G1)(G1),

[0313] -Si(G1)(G2)(G2)

[0314] -Si(G1)(G1)(G2),

[0315] -Si(G2)(G2)(G2),

[0316] -Si(G3)(G3)(G3) and

[0317] -Si(G6)(G6)(G6). Here,

[0318] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0319] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0320] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0321] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0322] In -Si(G1)(G1)(G1), multiple G1s may be the same or different from each other.

[0323] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0324] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0325] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0326] In -Si(G3)(G3)(G3), multiple G3s may be the same or different from each other.

[0327] In -Si(G6)(G6)(G6), multiple G6s may be the same or different from each other.

[0328] ·“-O-(R 904 The group shown in the figure”

[0329] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0330] -O(G1)

[0331] -O(G2),

[0332] -O(G3) and

[0333] -O(G6).

[0334] Here,

[0335] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0336] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0337] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0338] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0339] ·“-S-(R 905 The group shown in the figure”

[0340] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0341] -S(G1)

[0342] -S(G2),

[0343] -S(G3) and

[0344] -S(G6).

[0345] Here,

[0346] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0347] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0348] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0349] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0350] ·"-N(R 906 (R) 907 The group shown in the figure”

[0351] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0352] -N(G1)(G1),

[0353] -N(G2)(G2),

[0354] -N(G1)(G2),

[0355] -N(G3)(G3) and

[0356] -N(G6)(G6).

[0357] Here,

[0358] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0359] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0360] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0361] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0362] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0363] In -N(G2)(G2), multiple G2 values ​​may be the same or different from each other.

[0364] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0365] In -N(G6)(G6), multiple G6 values ​​may be the same or different from each other.

[0366] • "Halogen atom"

[0367] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0368] • "Substituted or unsubstituted fluoroalkyl groups"

[0369] 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 has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been 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 have been replaced by a substituent. It should be noted that 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 have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0370] • "Substituted or unsubstituted haloalkyl groups"

[0371] 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 has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been 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 have been replaced by a substituent. It should be noted that "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 have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0372] • "Substituted or unsubstituted alkoxy groups"

[0373] As a specific example of "substituted or unsubstituted alkoxy group" as 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. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0374] • "Substituted or unsubstituted alkylthio groups"

[0375] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0376] • "Substituted or unsubstituted aryloxy groups"

[0377] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0378] • "Substituted or unsubstituted arylthio groups"

[0379] As a specific example of "substituted or unsubstituted arylthio group" as 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. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0380] • "Substituted or unsubstituted trialkylsilyl groups"

[0381] 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" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified 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.

[0382] • "Substituted or unsubstituted aralkyl groups"

[0383] As a specific example of "substituted or unsubstituted aralkyl" as 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" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0384] 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.

[0385] 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'-spirobisfluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.

[0386] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, 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.

[0387] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0388] [Chemical Formula 7]

[0389]

[0390] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0391] [Chemical Formula 8]

[0392]

[0393] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0394] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0395] [Chemical Formula 9]

[0396]

[0397] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0398] 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.

[0399] • "Substituted or unsubstituted aryl groups"

[0400] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification refers to a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.

[0401] • "Substituted or unsubstituted divalent heterocyclic groups"

[0402] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0403] • "Substituted or unsubstituted alkylene compounds"

[0404] Unless otherwise stated, "substituted or unsubstituted alkylene" as described in this specification refers to a divalent group derived from the aforementioned "substituted or unsubstituted alkyl" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0405] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).

[0406] [Chemical Formula 10]

[0407]

[0408] [Chemical Formula 11]

[0409]

[0410] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0411] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0412] [Chemical Formula 12]

[0413]

[0414] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0415] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0416] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0417] [Chemical Formula 13]

[0418]

[0419] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0420] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0421] Unless otherwise specified 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).

[0422] [Chemical Formula 14]

[0423]

[0424] [Chemical Formula 15]

[0425]

[0426] [Chemical Formula 16]

[0427]

[0428] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0429] [Chemical Formula 17]

[0430]

[0431] [Chemical Formula 18]

[0432]

[0433] [Chemical Formula 19]

[0434]

[0435] [Chemical Formula 20]

[0436]

[0437] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0438] The above is an explanation of "substituents described in this specification".

[0439] • "Cases where bonds form rings"

[0440] In this specification, the description of "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 cases of "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".

[0441] The following description 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, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0442] [Chemical Formula 21]

[0443]

[0444] For example, in the case of R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", the group consisting of two adjacent elements that form a group refers to R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0445] 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, in R... 921 With R 922 They bond together to form a ring QA Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0446] [Chemical Formula 22]

[0447]

[0448] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, this 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 923 When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above 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 .

[0449] [Chemical Formula 23]

[0450]

[0451] In the formed "single ring" or "fused ring", the ring itself can be either a saturated or unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one of two adjacent groups", it can still be either a saturated or unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q CFusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0452] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0453] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0454] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0455] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0456] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above 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 carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of 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 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0457] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0458] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0459] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0460] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0461] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0462] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0463] In the case of "one or more groups consisting of two or more adjacent atoms" or "forming a substituted or unsubstituted monocyclic ring by mutual bonding" or "forming a substituted or unsubstituted fused ring by mutual bonding", unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms form an "unsaturated ring" formed by mutual bonding of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0464] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0465] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0466] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together, whether substituted or unsubstituted" ("the case of forming a ring by bonding").

[0467] Substituents when described as "substituted or unsubstituted"

[0468] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...

[0469] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0470] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0471] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0472] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0473] -Si(R 901 (R) 902 (R) 903 ),

[0474] -O-(R 904 ),

[0475] -S-(R 905 ),

[0476] -N(R 906 (R) 907 ),

[0477] Halogen atom, cyano group, nitro group,

[0478] Unsubstituted aryl groups with 6 to 50 carbon atoms, and

[0479] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0480] Groups, etc., in the composition group

[0481] Here, R 901 ~R 907 Each independently

[0482] hydrogen atom,

[0483] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0484] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0485] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0486] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0487] In R 901 In the case of two or more R, two or more R 901 They are the same or different.

[0488] In R902 In the case of two or more R, two or more R 902 They are the same or different.

[0489] In R 903 In the case of two or more R, two or more R 903 They are the same or different.

[0490] In R 904 In the case of two or more R, two or more R 904 They are the same or different.

[0491] In R 905 In the case of two or more R, two or more R 905 They are the same or different.

[0492] In R 906 In the case of two or more R, two or more R 906 They are the same or different.

[0493] In R 907 In the case of two or more R, two or more R 907 They are the same or different.

[0494] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0495] Alkyl groups with 1 to 50 carbon atoms

[0496] aryl groups with 6 to 50 carbon atoms, and

[0497] Heterocyclic groups with 5 to 50 cyclic atoms

[0498] The groups in the group.

[0499] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0500] Alkyl groups having 1 to 18 carbon atoms

[0501] aryl groups with 6 to 18 carbon atoms, and

[0502] Heterocyclic groups with 5 to 18 cyclic atoms

[0503] The groups in the group.

[0504] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0505] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0506] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0507] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0508] The compounds of the present invention will be described below.

[0509] One aspect of the present invention relates to a compound as shown above, represented by the following formula (1) or (2).

[0510] Hereinafter, the compounds of the present invention represented by formula (1) and the various formulas included in formula (1) described below will sometimes be referred to simply as "compound (1)" or "inventive compound (1)". In addition, the compounds of the present invention represented by formula (2) and the various formulas included in formula (2) described below will sometimes also be referred to in the same way as above.

[0511] It should be noted that in this specification, sometimes in order to indicate the meaning of "invented compound (1) alone, invented compound (2) alone, or both of invented compounds (1) and (2)," it is also referred to simply as "invented compound" or "compound."

[0512] One aspect of the present invention relates to an inventive compound (1) represented by the following formula (1).

[0513] [Chemical Formula 24]

[0514]

[0515] The symbols in equation (1) and those included in equation (1) in subsequent descriptions will be explained below. Unless otherwise stated, the same symbols have the same meaning.

[0516] In equation (1), R is selected from 1 ~R 9 Two adjacent elements in the mixture may bond together to form a ring, or they may not bond together to form a ring. Preferably, the element is selected from R... 1 ~R 9Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0517] In equation (1), R is selected from 11 ~R 14 Two adjacent elements in the mixture may bond together to form a ring, or they may not bond together to form a ring. Preferably, the element is selected from R... 11 ~R 14 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0518] In equation (1), R is selected from 21 ~R 27 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0519] The above-mentioned R that do not bond with each other and do not form a ring 1 ~R 9 Each is an independent hydrogen atom.

[0520] The above R 11 ~R 14 Each of the atoms is independently a hydrogen atom, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms.

[0521] In the above R 11 ~R 14 Examples of unsubstituted alkyl groups having 1 to 30 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0522] Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or pentyl are preferred; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl are preferred; and particularly preferably methyl or tert-butyl are preferred.

[0523] In the above R 11 ~R 14 Among the unsubstituted aryl groups with 6 to 30 carbon atoms mentioned above, examples of such aryl groups include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthryl, benzo[a]phenanthryl, phenatenyl, styryl, penfenyl, pyrene, styryl, benzo[a]styryl, fluorenyl, fluoranyl, perylene, triphenylene, benzo[a]triphenylene, etc.

[0524] Among them, phenyl, biphenyl, terphenyl or naphthyl are preferred; more preferably phenyl or naphthyl.

[0525] The above R 21~R 27 Each of the following is independently a hydrogen atom, a substituted or unsubstituted carbon atom having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic carbon atom having 3 to 10 carbon atoms, preferably a cycloalkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted cyclic carbon atom having 6 to 18 carbon atoms, preferably an aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic carbon atom having 5 to 18 carbon atoms, preferably a heteroaryl group having 5 to 13 carbon atoms.

[0526] In the above R 21 ~R 27 Among the unsubstituted alkyl groups having 1 to 10 carbon atoms mentioned above, examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc.

[0527] Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl are preferred; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl are preferred; methyl or tert-butyl are even more preferred; and tert-butyl is particularly preferred.

[0528] In the above R 21 ~R 27 Among the unsubstituted cycloalkyl groups with 3 to 10 carbon atoms mentioned above, examples of such cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl, and 2-adamantyl.

[0529] Among them, cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl or 2-adamantyl are preferred; more preferably cyclohexyl, 1-adamantyl or 2-adamantyl are preferred.

[0530] In the above R 21 ~R 27 Among the unsubstituted aryl groups with 6 to 18 carbon atoms mentioned above, examples of such aryl groups include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzo[anthracene], phenanthryl, benzo[phenanthryl], phenatenyl, pyrene, phenyl, fluorenyl, fluoranyl, and triphenylene.

[0531] Among them, phenyl, biphenyl, terphenyl or naphthyl are preferred; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl are preferred; even more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl are preferred; particularly preferably phenyl.

[0532] In the above R 21 ~R 27 Among the unsubstituted heteroaryl groups with 5 to 18 cyclic atoms mentioned above, examples of such heteroaryl groups include pyrroloyl, furanyl, thiopheneyl, pyridyl, imidazopyridyl, pyridinyl, pyrazinyl, triazinyl, imidazoyl, oxazolyl, thiazoyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazoyl, triazolyl, tetrazolyl, indoleyl, isoyndoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazoyl, indoleyl, benziisoxazolyl, benziisothiazoyl, phenanthidyl, acridineyl, phenanthrololinyl, phenazinyl, phenothiazinyl, phenothiazinyl, xanthonyl, benzofuranyl, iso... Benzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl (also known as "benzothienyl"), isobenzothienyl (also known as "isobenzothienyl"), naphthobenzothienyl (also known as "naphthobenzothienyl"), dibenzothienyl (also known as "dibenzothienyl"), carbazoyl (including 9-carbazoyl, or 1-carbazoyl, 2-carbazoyl, 3-carbazoyl, or 4-carbazoyl), dihydroacridyl, phenanthrynyl, acridineyl, phenanthrolynyl, phenazinyl, phenothiazinyl, phenotoxazinyl, acridineyl, xanthonyl, etc.

[0533] Among them, pyrroleyl, furanyl, thiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothiopheneyl, isobenzothiopheneyl, naphthobenzothiopheneyl, dibenzothiopheneyl, or carbazoleyl are preferred; more preferably dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl are preferred.

[0534] In another embodiment, it is preferred that the aforementioned R... 11 ~R 14 Each is an independent hydrogen atom.

[0535] In another embodiment, it is preferred that the aforementioned R...21 ~R 27 Each is an independent hydrogen atom.

[0536] In another embodiment, it is preferred that, for the aforementioned R... 1 ~R 9 R 11 ~R 14 and R 21 ~R 27 As far as R is concerned, 1 ~R 9 The hydrogen atoms and R contained therein 11 ~R 14 The hydrogen atoms and R contained therein 21 ~R 27 At least one of the hydrogen atoms contained therein is a protium atom.

[0537] In equation (1), X 1 and X 2 Each atom is an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0538] In equation (1), L 1 The cyclic group is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group with 5 to 30 carbon atoms, particularly preferably 5 to 18 carbon atoms.

[0539] In L 1 Among the substituted or unsubstituted aryl groups with 6 to 30 cyclic atoms mentioned above, examples of such aryl groups can be cited for the R group mentioned above. 11 ~R 14 And the above R 21 ~R 27 The divalent group obtained by removing one hydrogen atom from the substituted or unsubstituted aryl group described herein can preferably be substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene, etc.

[0540] Among them, substituted or unsubstituted phenylene oxides are preferred.

[0541] In L 1Among the substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms mentioned above, examples of such heteroaryl groups include pyridine, furyl, thiophene, pyridinyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyridazolyl, isoxazolyl, and isothiazolyl. Azolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl The following are compounds: phenanthroline, phenazinyl, phenanthiazinyl, phenoxazinyl, phenanthreneyl, benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl (also known as "benzothienylene"), isobenzothienyl (also known as "isobenzothienylene"), naphthobenzothienyl (also known as "naphthobenzothienylene"), dibenzothienyl (also known as "dibenzothienylene"), or carbazoyl (including 9-carbazoyl, or 1-carbazoyl, 2-carbazoyl, 3-carbazoyl, or 4-carbazoyl).

[0542] In another option, L is preferred. 1 It is a substituted or unsubstituted arylene group with 6 to 12 carbon atoms, more preferably a substituted or unsubstituted phenylene group.

[0543] In equation (1), Ar 1 The aryl group is a cyclic group with 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms, and may be substituted or unsubstituted.

[0544] In Ar 1 Among the unsubstituted aryl groups with 6 to 30 carbon atoms mentioned above, examples of such aryl groups include those related to the aforementioned R. 11 ~R 14 And the above R 21 ~R 27 The substituted or unsubstituted aryl groups with 6 to 30 carbon atoms are recorded.

[0545] Among them, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, or substituted or unsubstituted biphenyl are preferred, and substituted or unsubstituted biphenyl are even more preferred.

[0546] In another scenario, the aforementioned Ar1 Preferably, it is an aryl group with 6 to 12 carbon atoms that has been substituted or unsubstituted, and more preferably, it is a biphenyl group that has been substituted or unsubstituted.

[0547] In another embodiment, it is preferred that, as described above, Ar 1 It is represented by the following formulas (2A), (2B), (2C), (2D), or (2E).

[0548] [Chemical Formula 25]

[0549]

[0550] In equation (2A), *21 represents the relationship between L and L. 1 Bonded single bonds.

[0551] In equation (2A), the values ​​selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23.

[0552] R is not the single bond mentioned above. 101 ~R 105 And R which is not a single bond 106 ~R 110 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0553] Selected from R that is not one of the above single bonds 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0554] Selected from R that is not one of the above single bonds 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0555] In equation (2A), R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms.

[0556] In equation (2A), the values ​​selected from R 111 ~R 115 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0557] Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and for R 21 The records are the same.

[0558] Details and preferred examples of the above-mentioned substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, and for R 21 The records are the same.

[0559] Among the substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, examples of unsubstituted aryl groups include phenyl, biphenyl, and naphthyl.

[0560] Among them, phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl are preferred; more preferably phenyl, or 1-naphthyl or 2-naphthyl; particularly preferably phenyl.

[0561] Among the aforementioned substituted or unsubstituted heteroaryl groups with 5 to 13 cyclic atoms, examples of unsubstituted heteroaryl groups include pyrrole, furanyl, thiophene, pyridinyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, indole, isoindole, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, and zolyl. The group includes phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazole, benzoisoxazolyl, benzoisothiazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl (hereinafter the same), isobenzothienyl (hereinafter the same), dibenzothienyl (hereinafter the same), carbazoyl, etc.

[0562] Among them, pyrroloyl, furanyl, thiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl are preferred; more preferably benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl (9-carbazoleyl, or 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, or 4-carbazoleyl).

[0563] Among the heteroaryl groups with 5 to 13 cyclic atoms that are either substituted or unsubstituted, examples of substituted heteroaryl groups include 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuranyl, and phenyldibenzothienyl.

[0564] The aforementioned heteroaryl groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted, include isomer groups in the presence of isomer groups.

[0565] In equation (2A), j is 0, 1, or 2, and k is 0 or 1. The case where j is 2 and k is 0 is excluded.

[0566] • When j=0 and k=0, *23 means *21.

[0567] • When j=0 and k=1, *22 means *21.

[0568] • When j=1 and k=0, *23 means *22.

[0569] In one embodiment of the invention, j is 0 and k is 0. In this case, *23 represents *21, and equation (2A) is represented by the following equation.

[0570] [Chemical Formula 26]

[0571]

[0572] In another embodiment of the invention, j is 0 and k is 1. In this case, *22 represents *21, and equation (2A) is represented by the following equation.

[0573] [Chemical Formula 27]

[0574]

[0575] In another embodiment of the invention, j is 1 and k is 0. In this case, *23 represents *22, and equation (2A) is represented by the following equation.

[0576] [Chemical Formula 28]

[0577]

[0578] In another embodiment of the invention, j is 1 and k is 1. In this case, equation (2A) is represented by the following equation.

[0579] [Chemical Formula 29]

[0580]

[0581] In another embodiment of the invention, j is 2 and k is 1. In this case, equation (2A) is represented by the following equation.

[0582] [Chemical Formula 30]

[0583]

[0584] The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0585] [Chemical Formula 31]

[0586]

[0587] R is not a single bond that bonds with *22. 101 ~R 105 R is not a single bond that bonds with *23. 106 ~R 110 and R 111 ~R 115 Both can be hydrogen atoms.

[0588] [Chemical Formula 32]

[0589]

[0590] In equation (2B), *24 represents the relationship between L and L. 1 Bonded single bonds.

[0591] In equation (2B), the values ​​selected from R 121 ~R 128 One of them is a single bond that bonds with *25.

[0592] R is not the single bond mentioned above. 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0593] Selected from R that is not one of the above single bonds 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0594] In equation (2B), R 121 ~R 128 Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to the above-mentioned R. 21 The records are the same.

[0595] In equation (2B), in R 121 ~R 128 In the substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, the unsubstituted aryl group having 6 to 12 carbon atoms is related to the aforementioned R. 111 The records are the same.

[0596] In one embodiment of the present invention, preferably, the material is selected from R. 121 R 124 R 125 and R 128 One of them is a single bond that bonds with *25.

[0597] In equation (2B), the R that is not bonded to *25 is a single bond.121 ~R 128 Both can be hydrogen atoms.

[0598] [Chemical Formula 33]

[0599]

[0600] In equation (2C), *26 represents the relationship between L and L. 1 Bonded single bonds.

[0601] In equation (2C), the values ​​selected from R 131 ~R 140 One of them is a single bond that bonds with *27.

[0602] R is not the single bond mentioned above. 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0603] Selected from R that is not one of the above single bonds 131 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0604] In equation (2C), R 131 ~R 140 Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to R. 21 The records are the same.

[0605] In equation (2C), in R 131 ~R 140 The details and preferred examples of the unsubstituted or unsubstituted aryl groups with 6 to 12 carbon atoms, as well as those relating to R, are as follows: 111 The records are the same.

[0606] In one embodiment of the present invention, preferably, the material is selected from R. 137 R 138 and R 139 One of them is a single bond bonded to *27, and more preferably, it is selected from R. 137 and R 139 One of them is a single bond that bonds with *27, and R is particularly preferred. 139 This is a single bond that bonds with *27.

[0607] R is not a single bond that bonds with *27. 131 ~R 140 Both can be hydrogen atoms.

[0608] [Chemical Formula 34]

[0609]

[0610] In equation (2D), *28 represents the relationship between L and L. 1 Bonded single bonds.

[0611] In equation (2D), the values ​​selected from R are... 151 ~R 155 One of them is a single bond bonded to *29, selected from R 151 ~R 155 The other one is a single bond that bonds with *30.

[0612] R is not the single bond mentioned above. 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0613] R selected from single bonds not bonded to *29 and not bonded to *30 as described above. 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0614] In equation (2D), R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0615] In equation (2D), the values ​​selected from R are... 161 ~R 165 At least one pair of adjacent two elements in the form are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring.

[0616] In equation (2D), the values ​​selected from R are... 171 ~R 175 At least one pair of adjacent two elements in the form are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring.

[0617] In equation (2D), R 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as indicated above, and for R 21 The records are the same.

[0618] In one embodiment of the invention, the material selected from R 161 ~R 165Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 161 ~R 165 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0619] In one embodiment of the invention, the material selected from R 171 ~R 175 Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 171 ~R 175 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0620] R is not the single bond mentioned above. 151 ~R 155 Both can be hydrogen atoms, R 161 ~R 165 Both can be hydrogen atoms, R 171 ~R 175 Both can be hydrogen atoms.

[0621] [Chemical Formula 35]

[0622]

[0623] In equation (2E), *221 represents the relationship between L and L. 1 Bonded single bonds.

[0624] In equation (2E), the values ​​selected from R 181 ~R 192 One of them is a single bond that bonds with *222.

[0625] R is not the single bond mentioned above. 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0626] Selected from R that is not one of the above single bonds 181 ~R 192 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0627] In equation (2E), R 181 ~R 192 Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to the above-mentioned R. 21 The records are the same.

[0628] In equation (2E), in R 181 ~R 192The details and preferred examples of the unsubstituted or unsubstituted aryl groups with 6 to 12 carbon atoms mentioned above are related to the above-mentioned R 111 The records are the same.

[0629] In one aspect of the invention, R 181 For a single bond that bonds with *222, in another scheme, R 182 This is a single bond that bonds with *222.

[0630] R is not the single bond mentioned above. 181 ~R 192 Both can be hydrogen atoms.

[0631] One aspect of the present invention relates to an inventive compound (2) represented by the following formula (2).

[0632] [Chemical Formula 36]

[0633]

[0634] The symbols in equation (2) and those included in equation (2) in subsequent descriptions will be explained below. Unless otherwise specified, the same symbols have the same meaning.

[0635] In equation (2), R is selected from 31 ~R 33 One of them is a single bond that bonds with *1.

[0636] In equation (2), R is selected from 51 ~R 55 One of them is a single bond that bonds with *a.

[0637] Selected from R that is not one of the above single bonds 31 ~R 33 and R 34 ~R 40 Two adjacent bonds in the bond may bond together to form a ring or not bond together to form a ring. Preferably, R is selected from bonds that are not the single bonds described above. 31 ~R 33 and R 34 ~R 40 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0638] In equation (2), R is selected from 41 ~R 44 Two adjacent elements in the mixture may bond together to form a ring, or they may not bond together to form a ring. Preferably, the element is selected from R... 41 ~R 44 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0639] Selected from R that is not one of the above single bonds51 ~R 55 Two adjacent bonds in the bond may bond together to form a ring or not bond together to form a ring. Preferably, R is selected from bonds that are not the single bonds described above. 51 ~R 55 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0640] In equation (2), R is selected from 61 ~R 68 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0641] The above-mentioned Rs are not mutually bonded and do not form a ring, and are not single bonds. 31 ~R 33 R and non-bonded to form a ring 34 ~R 40 Each is an independent hydrogen atom.

[0642] The above R 41 ~R 44 And R that is not a single bond as described above 51 ~R 55 Each of the atoms is independently a hydrogen atom, a substituted or unsubstituted carbon atom having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms.

[0643] In the above R 41 ~R 44 And R that is not a single bond as described above 51 ~R 55 Among the substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, examples of unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl.

[0644] Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or pentyl are preferred; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl are preferred; and particularly preferably methyl or tert-butyl are preferred.

[0645] In the above R 41 ~R 44 And R that is not a single bond as described above 51 ~R 55Among the substituted or unsubstituted aryl groups with 6 to 30 carbon atoms mentioned above, examples of unsubstituted aryl groups include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzo[anthracene], phenanthryl, benzo[phenanthryl], phenatenyl, styranny, pentyranny, pyrene, styranny, benzo[styranny], fluorenyl, fluoranyl, perylene, triphenylene, benzo[triphenylene], etc.

[0646] Among them, phenyl, biphenyl, terphenyl or naphthyl are preferred; more preferably phenyl or naphthyl.

[0647] The above R 61 ~R 68 Each of the following is independently a hydrogen atom, a substituted or unsubstituted carbon atom having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic carbon atom having 3 to 10 carbon atoms, preferably a cycloalkyl group having 6 to 10 carbon atoms, a substituted or unsubstituted cyclic carbon atom having 6 to 18 carbon atoms, preferably an aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic carbon atom having 5 to 18 carbon atoms, preferably a heteroaryl group having 5 to 13 carbon atoms.

[0648] In the above R 61 ~R 68 Among the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, examples of unsubstituted alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, etc.

[0649] Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl or hexyl are preferred; more preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl are preferred; methyl or tert-butyl are even more preferred; and tert-butyl is particularly preferred.

[0650] In the above R 61 ~R 68 Among the substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms mentioned above, examples of unsubstituted cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl, and 2-adamantyl.

[0651] Among them, cyclohexyl, 1-norbornyl, 2-norbornyl, 1-adamantyl or 2-adamantyl are preferred; more preferably cyclohexyl, 1-adamantyl or 2-adamantyl are preferred.

[0652] In the above R 61 ~R 68Among the substituted or unsubstituted aryl groups with 6 to 18 carbon atoms mentioned above, examples of unsubstituted aryl groups include phenyl, biphenyl, terphenyl, biphenylenyl, naphthyl, anthracene, benzo[anthracene], phenanthryl, benzo[phenanthryl], phenatenyl, pyrene, phenyl, fluorenyl, fluoranyl, and triphenylene.

[0653] Among them, phenyl, biphenyl, terphenyl or naphthyl are preferred; more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, 2-o-terphenyl, 3-o-terphenyl or 4-o-terphenyl, 2-m-terphenyl, 3-m-terphenyl or 4-m-terphenyl, 2-p-terphenyl, 3-p-terphenyl or 4-p-terphenyl, or 1-naphthyl or 2-naphthyl are preferred; even more preferably phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl are preferred; particularly preferably phenyl.

[0654] In the above R 61 ~R 68 Among the heteroaryl groups with 5 to 18 cyclic atoms that are substituted or unsubstituted as described above, examples of unsubstituted heteroaryl groups include pyrroloyl, furanyl, thiopheneyl, pyridyl, imidazopyridyl, pyridinyl, pyrazinyl, triazinyl, imidazoyl, oxazolyl, thiazoyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazoyl, triazolyl, tetrazolyl, indoleyl, isoyndoleyl, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, terpineyl, phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazoyl, indoleyl, benzoisoxazolyl, benzoisothiazoyl, phenanthidyl, acridineyl, phenanthrololinyl, phenazinyl, phenothiazinyl, phenothiazinyl, xanthonyl, and benzofuranyl. The following groups are included: benzo[a], isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothiophenyl (also known as "benzothienyl"), isobenzothienyl (also known as "isobenzothienyl"), naphthobenzothienyl (also known as "naphthobenzothienyl"), dibenzothienyl (also known as "dibenzothienyl"), carbazoyl (including 9-carbazoyl, or 1-carbazoyl, 2-carbazoyl, 3-carbazoyl, or 4-carbazoyl), dihydroacridyl, phenanthridineyl, acridineyl, phenanthrololinyl, phenazinyl, phenothiazinyl, phenotoxazinyl, acridineyl, xanthonyl, etc.

[0655] Among them, pyrroleyl, furanyl, thiopheneyl, pyridyl, pyrimidinyl, triazineyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothiopheneyl, isobenzothiopheneyl, naphthobenzothiopheneyl, dibenzothiopheneyl, or carbazoleyl are preferred; more preferably dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl are preferred.

[0656] In another embodiment, it is preferred that the aforementioned R... 41 ~R 44 Each is an independent hydrogen atom.

[0657] In another embodiment, it is preferable that the R is not a single bond as described above. 51 ~R 55 Each is an independent hydrogen atom.

[0658] In another embodiment, it is preferred that the aforementioned R... 61 ~R 68 Each is an independent hydrogen atom.

[0659] In another embodiment, it is preferred that, for the aforementioned R... 31 ~R 40 R 41 ~R 44 R 51 ~R 55 and R 61 ~R 68 As far as R is concerned, 31 ~R 40 The hydrogen atoms and R contained therein 41 ~R 44 The hydrogen atoms and R contained therein 51 ~R 55 The hydrogen atoms and R contained therein 61 ~R 68 At least one of the hydrogen atoms contained therein is a protium atom.

[0660] In equation (2), X 3 It is an oxygen atom or a sulfur atom, preferably an oxygen atom.

[0661] In equation (2), L 2 It is a single bond, substituted or unsubstituted cyclic carbon with 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, or a substituted or unsubstituted cyclic carbon with 5 to 30 carbon atoms, preferably 5 to 18 carbon atoms.

[0662] In equation (2), as L 2 The substituted or unsubstituted aryl groups with 6 to 30 cyclic atoms mentioned above can be exemplified by, for example, those derived from the R group mentioned above. 41~R 44 And R that is not a single bond as described above 51 ~R 55 The divalent groups obtained by removing one hydrogen atom from the substituted or unsubstituted aryl groups described herein.

[0663] Among them, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted biphenylene are preferred; more preferably, substituted or unsubstituted phenylene.

[0664] In equation (2), at L 2 Among the substituted or unsubstituted heteroaryl groups with 5 to 30 cyclic atoms mentioned above, examples of unsubstituted heteroaryl groups include pyridine, furyl, thiophene, pyridinyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, and isoxazolyl. Isothiazolyl, Isodiazolel, Isothiadiazolel, Isotriazolel, Isotetrazolyl, Isoindolyl, Isoindolyl, Isoinazinyl, Iquinazinyl, Quinolinyl, Isoquinolinyl, Iso-Itazolyl, Quinolinyl, Iso-Itazolyl, Quinoxolinyl, Benzoimidazolel, Benzoxazolyl, Benzothiazolyl, Isoinazolel, Benzoisoxazolyl, Benzoisothiazolyl, Phenyridinyl Acridineyl, phenanthrolineyl, phenazinyl, phenanthiazinyl, phenoxazinyl, xanthinyl, benzofuranyl, isobenzofuranyl, naphthobenzofuranyl, dibenzofuranyl, benzothienyl (also known as "benzothienylene"), isobenzothienyl (also known as "isobenzothienylene"), naphthobenzothienyl (also known as "naphthobenzothienylene"), dibenzothienyl (also known as "dibenzothienylene"), and carbazoyl (including 9-carbazoyl, 1-carbazoyl, 2-carbazoyl, 3-carbazoyl, or 4-carbazoyl).

[0665] In another option, L is preferred. 2 It is a substituted or unsubstituted arylene group with 6 to 12 carbon atoms, more preferably a substituted or unsubstituted phenylene group.

[0666] In equation (2), Ar 2 The aryl group is a cyclic group with 6 to 30 carbon atoms, preferably 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms, and may be substituted or unsubstituted.

[0667] In equation (2), in Ar 2Among the substituted or unsubstituted aryl groups with 6 to 30 carbon atoms mentioned above, examples of the unsubstituted aryl group include those related to the aforementioned R. 41 ~R 44 And the above R 51 ~R 55 The substituted or unsubstituted aryl groups with 6 to 30 carbon atoms are recorded.

[0668] Among them, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl or substituted or unsubstituted biphenyl are preferred, and substituted or unsubstituted phenyl are more preferred.

[0669] In another scenario, the aforementioned Ar 2 Preferably, it is an aryl group with 6 to 12 carbon atoms that has been substituted or unsubstituted, and more preferably, it is a substituted or unsubstituted phenyl group.

[0670] In another scenario, as described above, Ar 2 It is preferably represented by the following formulas (3A), (3B), (3C), (3D) or (3E).

[0671] [Chemical Formula 37]

[0672]

[0673] In equation (3A), *31 represents the relationship between L and L. 2 Bonded single bonds, in L 2 When it is a single bond, *31 is bonded to the central nitrogen atom.

[0674] In equation (3A), the values ​​selected from R 201 ~R 205 One of them is a single bond bonded to *32, selected from R 206 ~R 210 One of them is a single bond that bonds with *33.

[0675] R is not the single bond mentioned above. 201 ~R 205 and R 206 ~R 210 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0676] Selected from R that is not one of the above single bonds 201 ~R 205 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0677] Selected from R that is not one of the above single bonds 206 ~R 210 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0678] In equation (3A), R211 ~R 215 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms.

[0679] In equation (3A), the values ​​selected from R 211 ~R 215 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0680] Details and preferred examples of the aforementioned unsubstituted alkyl groups having 1 to 10 carbon atoms, and details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms among the aforementioned substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and related information for R. 61 The records are the same.

[0681] Details and preferred examples of the above-mentioned substituted or unsubstituted cycloalkyl groups with 3 to 10 carbon atoms, and for R 61 The records are the same.

[0682] Among the substituted or unsubstituted aryl groups with 6 to 12 carbon atoms, examples of unsubstituted aryl groups include phenyl, biphenyl, and naphthyl.

[0683] Among them, phenyl, 2-biphenyl, 3-biphenyl or 4-biphenyl, or 1-naphthyl or 2-naphthyl are preferred; more preferably phenyl, or 1-naphthyl or 2-naphthyl; particularly preferably phenyl.

[0684] Among the aforementioned substituted or unsubstituted heteroaryl groups with 5 to 13 cyclic atoms, examples of unsubstituted heteroaryl groups include pyrrole, furanyl, thiophene, pyridinyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiazolyl, triazolyl, tetrazolyl, indole, isoindole, indazinyl, quinazinyl, quinolinyl, isoquinolinyl, and zolyl. The group includes phthalazinyl, quinazolinyl, quinoxolinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, indazole, benzoisoxazolyl, benzoisothiazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl (hereinafter the same), isobenzothienyl (hereinafter the same), dibenzothienyl (hereinafter the same), carbazoyl, etc.

[0685] Among them, pyrroloyl, furanyl, thiophene, pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl are preferred; more preferably benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophene, isobenzothiophene, dibenzothiophene, or carbazoleyl (9-carbazoleyl, or 1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, or 4-carbazoleyl).

[0686] Among the heteroaryl groups with 5 to 13 cyclic atoms that are either substituted or unsubstituted, examples of substituted heteroaryl groups include 9-phenylcarbazolyl, 9-biphenylcarbazolyl, 9-phenylphenylcarbazolyl, 9-naphthylcarbazolyl, phenyldibenzofuranyl, and phenyldibenzothienyl.

[0687] The aforementioned heteroaryl groups with 5 to 13 cyclic atoms, whether substituted or unsubstituted, include isomer groups in the presence of isomer groups.

[0688] In equation (3A), jj is 0, 1, or 2, and kk is 0 or 1. The case where jj is 2 and kk is 0 is excluded.

[0689] • When jj=0 and kk=0, *33 means *31.

[0690] • When jj=0 and kk=1, *32 means *31.

[0691] • When jj=1 and kk=0, *33 means *32.

[0692] In one embodiment of the invention, jj is 0 and kk is 0. In this case, *33 represents *31, and equation (3A) is represented by the following equation.

[0693] [Chemical Formula 38]

[0694]

[0695] In another embodiment of the invention, jj is 0 and kk is 1. In this case, *32 represents *31, and equation (3A) is represented by the following equation.

[0696] [Chemical Formula 39]

[0697]

[0698] In another embodiment of the invention, jj is 1 and kk is 0. In this case, *33 represents *32, and equation (3A) is represented by the following equation.

[0699] [Chemical Formula 40]

[0700]

[0701] In another embodiment of the invention, jj is 1 and kk is 1. In this case, equation (3A) is represented by the following equation.

[0702] [Chemical Formula 41]

[0703]

[0704] In another embodiment of the invention, jj is 2 and kk is 1. In this case, equation (3A) is represented by the following equation.

[0705] [Chemical Formula 42]

[0706]

[0707] The group represented by formula (3A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

[0708] [Chemical Formula 43]

[0709]

[0710] R is not a single bond that bonds with *32. 201 ~R 205 R is not a single bond that bonds with *33. 206 ~R 210 and R 211 ~R 215 Both can be hydrogen atoms.

[0711] [Chemical Formula 44]

[0712]

[0713] In equation (3B), *34 represents the relationship between L and L. 2 Bonded single bonds, in L 2 When it is a single bond, *34 is bonded to the central nitrogen atom.

[0714] In equation (3B), the values ​​selected from R 221 ~R 228 One of them is a single bond that bonds with *35.

[0715] R is not the single bond mentioned above. 221 ~R 228 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0716] Selected from R that is not one of the above single bonds221 ~R 228 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0717] In equation (3B), R 221 ~R 228 Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to the above-mentioned R. 61 The records are the same.

[0718] In equation (3B), in R 221 ~R 228 In the substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, the unsubstituted aryl group having 6 to 12 carbon atoms is related to the aforementioned R. 211 The records are the same.

[0719] In one embodiment of the present invention, preferably, the material is selected from R. 221 R 224 R 225 and R 228 One of them is a single bond that bonds with *35.

[0720] In equation (3B), the R that is not bonded to *35 is a single bond. 221 ~R 228 Both can be hydrogen atoms.

[0721] [Chemical Formula 45]

[0722]

[0723] In equation (3C), *36 represents the relationship between L and L. 2 Bonded single bonds, in L 2 When it is a single bond, *36 is bonded to the central nitrogen atom.

[0724] In equation (3C), the values ​​selected from R 231 ~R 240 One of them is a single bond that bonds with *37.

[0725] R is not the single bond mentioned above. 231 ~R 240 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0726] Selected from R that is not one of the above single bonds 231 ~R 240 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0727] In equation (3C), R 231 ~R 240Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to R. 61 The records are the same.

[0728] In equation (3C), in R 231 ~R 240 The details and preferred examples of the unsubstituted or unsubstituted aryl groups with 6 to 12 carbon atoms, as well as those relating to R, are as follows: 211 The records are the same.

[0729] In one embodiment of the present invention, preferably, the material is selected from R. 237 R 238 and R 239 One of them is a single bond bonded to *37, and more preferably, it is selected from R. 237 and R 239 One of them is a single bond that bonds with *37, and R is particularly preferred. 239 This is a single bond that bonds with *37.

[0730] The R that is not bonded to *37 231 ~R 240 Both can be hydrogen atoms.

[0731] [Chemical Formula 46]

[0732]

[0733] In equation (3D), *38 represents the relationship between L and L. 2 Bonded single bonds, in L 2 When it is a single bond, *38 is bonded to the central nitrogen atom.

[0734] In equation (3D), the values ​​selected from R 251 ~R 255 One of them is a single bond that bonds with *39, selected from R 251 ~R 255 The other one is a single bond that bonds with *40.

[0735] R is not the single bond mentioned above. 251 ~R 255 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.

[0736] R selected from single bonds not bonded to *39 and not bonded to *40 as described above. 251 ~R 255 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0737] In equation (3D), R 261 ~R 265 and R271 ~R 275 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.

[0738] In equation (3D), the values ​​selected from R 261 ~R 265 At least one pair of adjacent two elements in the form are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring.

[0739] In equation (3D), the values ​​selected from R 271 ~R 275 At least one pair of adjacent two elements in the form are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring.

[0740] In equation (3D), R 251 ~R 255 R 261 ~R 265 and R 271 ~R 275 Details and preferred examples of the unsubstituted alkyl groups having 1 to 10 carbon atoms as indicated above, and for R 61 The records are the same.

[0741] In one embodiment of the invention, the material selected from R 261 ~R 265 Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 261 ~R 265 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0742] In one embodiment of the invention, the material selected from R 271 ~R 275 Two adjacent benzene rings in the form of a substituted or unsubstituted benzene ring are bonded together. In another embodiment of the invention, the benzene ring is selected from R... 271 ~R 275 The two adjacent ones in the structure do not bond to each other and therefore do not form a ring structure.

[0743] R is not the single bond mentioned above. 251 ~R 255 Both can be hydrogen atoms, R 261 ~R 265 Both can be hydrogen atoms, R 271 ~R 275 Both can be hydrogen atoms.

[0744] [Chemical Formula 47]

[0745]

[0746] In equation (3E), *331 represents the relationship between L and L. 2 Bonded single bonds, in L 2 When it is a single bond, *331 is bonded to the central nitrogen atom.

[0747] In equation (3E), the values ​​selected from R 281 ~R 292 One of them is a single bond that bonds with *332.

[0748] R is not the single bond mentioned above. 281 ~R 292 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms.

[0749] Selected from R that is not one of the above single bonds 281 ~R 292 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

[0750] In equation (3E), R 281 ~R 292 Details and preferred examples of the substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, as indicated above, are related to the above-mentioned R. 61 The records are the same.

[0751] In equation (3E), R 281 ~R 292 Details and preferred examples of the unsubstituted aryl groups with 6 to 12 carbon atoms mentioned above, and related information for the R group mentioned above. 211 The records are the same.

[0752] In one aspect of the invention, R 281 For a single bond that bonds with *332, in another scheme, R 282 This is a single bond that bonds with *332.

[0753] R is not the single bond mentioned above. 281 ~R 292 Both can be hydrogen atoms.

[0754] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, the inventive compounds may contain naturally occurring deuterium atoms.

[0755] Alternatively, deuterium atoms can be intentionally introduced into the inventive compound by using a portion or all of the raw material compound as a deuterated compound. Therefore, in one aspect of the present invention, the inventive compound contains at least one deuterium atom in its molecule. That is, the inventive compound can be a compound represented by formulas (1) and (2), wherein at least one of the hydrogen atoms contained in the compound is a deuterium atom.

[0756] The deuteration rate of the inventive compound depends on the deuteration rate of the raw material compound used. Even when using a raw material with a specified deuteration rate, it may contain a certain proportion of protium isotopes from natural sources. Therefore, for the deuteration rate scheme of the inventive compound shown below, the ratio relative to the ratio obtained by simply counting the number of deuterium atoms represented in the chemical formula includes the ratio that takes into account trace amounts of isotopes from natural sources.

[0757] The deuteration rate of the inventive compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and particularly preferably 50% or more.

[0758] The invented compound can be a deuterium body in which all hydrogen atoms are deuterium atoms (i.e., the deuteration rate of the invented compound is 100%).

[0759] The inventive compound can be a mixture comprising a deuterated compound and an undeuterated compound, or a mixture of two or more compounds with different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, particularly preferably 50% or more, and less than 100%.

[0760] Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, particularly preferably 10% or more, and less than 100%.

[0761] Unless otherwise stated, the details of the substituents (optional substituents) described in the definitions above as “substituted or unsubstituted” are the same as those described in “substituents described as “substituted or unsubstituted””.

[0762] There are no particular limitations on the method of manufacturing the compound. If one is skilled in the art, the compound can be easily manufactured by the method described in the following examples, or by modifying the method with reference to a known synthesis method.

[0763] The following are specific examples of compounds, but are not limited to these.

[0764] In the specific examples below, D represents a deuterium atom.

[0765] [Chemical Formula 48]

[0766]

[0767] [Chemical Formula 49]

[0768]

[0769] [Chemical Formula 50]

[0770]

[0771] [Chemical Formula 51]

[0772]

[0773] [Chemical Formula 52]

[0774]

[0775] [Chemical Formula 53]

[0776]

[0777] [Chemical Formula 54]

[0778]

[0779] [Chemical Formula 55]

[0780]

[0781] [Chemical Formula 56]

[0782]

[0783] [Chemical Formula 57]

[0784]

[0785] [Chemical Formula 58]

[0786]

[0787] [Chemical Formula 59]

[0788]

[0789] [Chemical Formula 60]

[0790]

[0791] [Chemical Formula 61]

[0792]

[0793] [Chemical Formula 62]

[0794]

[0795] [Chemical Formula 63]

[0796]

[0797] [Chemical Formula 64]

[0798]

[0799] [Chemical Formula 65]

[0800]

[0801] [Chemical Formula 66]

[0802]

[0803] [Chemical Formula 67]

[0804]

[0805] [Chemical Formula 68]

[0806]

[0807] [Chemical Formula 69]

[0808]

[0809] [Chemical Formula 70]

[0810]

[0811] [Chemical Formula 71]

[0812]

[0813] [Chemical Formula 72]

[0814]

[0815] [Chemical Formula 73]

[0816]

[0817] [Chemical Formula 74]

[0818]

[0819] [Chemical Formula 75]

[0820]

[0821] [Chemical Formula 76]

[0822]

[0823] [Chemical Formula 77]

[0824]

[0825] [Chemical Formula 78]

[0826]

[0827] [Chemical Formula 79]

[0828]

[0829] [Chemical Formula 80]

[0830]

[0831] [Chemical Formula 81]

[0832]

[0833] [Chemical Formula 82]

[0834]

[0835] [Chemical Formula 83]

[0836]

[0837] [Chemical Formula 84]

[0838]

[0839] [Chemical Formula 85]

[0840]

[0841] [Chemical Formula 86]

[0842]

[0843] [Chemical Formula 87]

[0844]

[0845] [Chemical Formula 88]

[0846]

[0847] Materials for organic EL components

[0848] The organic EL element material, as one aspect of the present invention, comprises the inventive compound. The content of the inventive compound in the organic EL element material is 1% by mass or more (including 100%), preferably 10% by mass or more (including 100%), more preferably 50% by mass or more (including 100%), further preferably 80% by mass or more (including 100%), and particularly preferably 90% by mass or more (including 100%). The organic EL element material, as one aspect of the present invention, is useful for the manufacture of organic EL elements.

[0849] In one aspect of the present invention, the inventive compound is preferably a hole transport layer material.

[0850] In one aspect of the invention, the material for the organic EL element preferably further comprises a protium form of the inventive compound. The aforementioned protium form refers to a compound in which all hydrogen atoms are protium atoms.

[0851] The molar ratio of the inventive compound to its protium body (inventive compound: protium body) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, even more preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0852] Organic EL components

[0853] An organic EL element, as one aspect of the present invention, has an anode, a cathode, and an organic layer located between the anode and the cathode. The organic layer is composed of a single layer or multiple layers containing a light-emitting layer, and at least one layer selected from the single layer and multiple layers constituting the organic layer contains the inventive compound.

[0854] Examples of organic layers comprising the inventive compound include hole transport regions (hole injection layers, hole transport layers, electron blocking layers, exciton blocking layers, etc.) disposed between the anode and the light-emitting layer, light-emitting layers, spacer layers, and electron transport regions (electron injection layers, electron transport layers, hole blocking layers, etc.) disposed between the cathode and the light-emitting layer, and are not limited thereto. The inventive compound is preferably used as a material for the hole transport region or the light-emitting layer of a fluorescent or phosphorescent EL element, more preferably as a material for the hole transport region, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or the hole transport layer.

[0855] As one aspect of the present invention, the organic EL element can be a monochromatic light-emitting element of the fluorescent or phosphorescent type, or a white light-emitting element of the fluorescent / phosphorescent hybrid type. It can be a simple type with a single light-emitting unit, or a tandem type with multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit that includes an organic layer and is composed of a single layer or multiple layers, at least one of which is selected from the single layer and multiple layers as the light-emitting layer, and emits light by recombination of injected holes and electrons.

[0856] For example, the following are typical component configurations for a simple organic EL element.

[0857] (1) Anode / Light-emitting unit / Cathode

[0858] Alternatively, the aforementioned light-emitting unit can also be a multilayer type with multiple phosphorescent or fluorescent light-emitting layers. In this case, spacer layers may be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer configuration of a simplified light-emitting unit is shown below. The layers within parentheses are optional.

[0859] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0860] (b) (Hole injection layer / ) Hole transport layer / First fluorescent layer / Second fluorescent layer / Electron transport layer ( / Electron injection layer)

[0861] (c)(Hole injection layer / )Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[0862] (d)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[0863] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer( / electron injection layer)

[0864] (f)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0865] (g)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0866] (h)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0867] (h1)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Third Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0868] (i)(hole injection layer / ) first hole transport layer / second hole transport layer / fluorescent layer / first electron transport layer / second electron transport layer( / electron injection layer)

[0869] (i1)(hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent layer / first electron transport layer / second electron transport layer( / electron injection layer)

[0870] (j)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0871] (k)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0872] Each of the aforementioned phosphorescent or fluorescent emitting layers can be configured to display a different emitting color. Specifically, in the aforementioned emitting unit (d), a layer configuration such as (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting light) / second phosphorescent emitting layer (green emitting light) / spacer layer / fluorescent emitting layer (blue emitting light) / electron transport layer can be used.

[0873] It should be noted that electron blocking layers can be appropriately placed between each light-emitting layer and the hole transport layer or spacer layer. Similarly, hole blocking layers can be appropriately placed between each light-emitting layer and the electron transport layer. By placing electron blocking layers and hole blocking layers, electrons or holes can be confined within the light-emitting layer, thereby increasing the recombination probability of charges in the light-emitting layer and thus improving luminous efficiency.

[0874] The following are typical component configurations for tandem organic EL elements.

[0875] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0876] Here, the first light-emitting unit and the second light-emitting unit described above can be selected independently from the light-emitting units described above.

[0877] The aforementioned intermediate layer is generally also referred to as an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, and can be constructed using known materials that supply electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0878] Furthermore, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the aforementioned multilayer structure, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, can function as an electron blocking layer. That is, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the aforementioned multilayer structure can also be used as an electron blocking layer.

[0879] Figure 1 This is a schematic diagram illustrating an example of the configuration of an organic EL element according to one aspect of the present invention. Figure 1 The organic EL element 1 shown has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 10 disposed between the anode 3 and the cathode 4. The light-emitting unit 10 has a light-emitting layer 5. A hole transport region 6 (hole injection layer, hole transport layer, etc.) is provided between the light-emitting layer 5 and the anode 3, and an electron transport region 7 (electron injection layer, electron transport layer, etc.) is provided between the light-emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) can be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) can be provided on the cathode 4 side of the light-emitting layer 5. As a result, electrons and holes can be confined in the light-emitting layer 5, thereby further improving the exciton generation efficiency in the light-emitting layer 5.

[0880] Figure 2 This is a schematic diagram illustrating another configuration of an organic EL element according to one aspect of the present invention. Figure 2 The organic EL element 11 shown has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. In addition, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0881] Figure 3This is a schematic diagram illustrating another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. Furthermore, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0882] Figure 3 This is a schematic diagram illustrating another configuration of an organic EL element according to one aspect of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport region disposed between the anode 3 and the light-emitting layer 5 is formed by a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. Furthermore, the electron transport region disposed between the light-emitting layer 5 and the cathode 4 is formed by a first electron transport layer 7a and a second electron transport layer 7b.

[0883] exist Figures 1-3 In this process, the light-emitting layer 5 comprises at least one light-emitting layer. The light-emitting layer 5 can be a single layer or a layer comprising multiple layers (e.g., multiple light-emitting layers, multiple light-emitting layers and spacer layers).

[0884] It should be noted that in this invention, the host material combined with the fluorescent dopant material (fluorescent emitting material) is called the fluorescent host material, and the host material combined with the phosphorescent dopant material is called the phosphorescent host material. The distinction between fluorescent and phosphorescent hosts is not solely based on molecular structure. That is, a phosphorescent host material refers to the material that forms a phosphorescent emitting layer containing phosphorescent dopant, and does not mean that it cannot be used as a material to form a fluorescent emitting layer. The same applies to fluorescent hosts.

[0885] substrate

[0886] The substrate serves as a support for the organic EL element. Examples of substrates include sheets made of glass, quartz, or plastic. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates formed from polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0887] anode

[0888] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the aforementioned metals (e.g., titanium nitride).

[0889] These materials are typically formed into films using sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 to 10% by mass of zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 to 5% by mass of tungsten oxide and 0.1 to 1% by mass of zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, etc.

[0890] Hole transport region

[0891] As described above, the organic layer may include a hole transport region located between the anode and the light-emitting layer. The hole transport region is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. Preferably, the hole transport region contains the inventive compound. Preferably, the inventive compound is included in at least one of the layers (hole injection layer, hole transport layer, electron blocking layer, etc.) selected from those constituting the hole transport region, and more preferably, the inventive compound is included in the hole transport layer.

[0892] The hole injection layer formed adjacent to the anode is formed using a material that is easy to inject holes into regardless of the work function of the anode. Therefore, materials commonly used as electrode materials (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0893] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, 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. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[0894] Hole injection layer

[0895] A hole injection layer is a layer containing a material with high hole injection properties (hole injection material), which is formed between the anode and the light-emitting layer, or between the hole transport layer and the anode in the presence of a hole transport layer.

[0896] Other than the inventive compound, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc., can be used as hole-injecting materials.

[0897] Examples of hole injection layer materials include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (DN). Aromatic amine compounds such as TPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) are also mentioned.

[0898] Polymers (oligomers, dendritic polymers, polymers, etc.) can also be used. Examples include: poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Additionally, polymers containing acids, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), can also be used.

[0899] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are also preferred.

[0900] [Chemical Formula 89]

[0901]

[0902] (In the above formula, R) K221 ~R K226 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. K227 (R K227 (Refers to alkyl groups having 1 to 20 carbon atoms or cycloalkyl groups having 3 to 20 carbon atoms). Additionally, it is selected from R... K221 With R K222 R K223 With R K224 and R K225 With R K226 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[0903] As R K227 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[0904] Hole transport layer

[0905] A hole transport layer is a layer containing a material with high hole transportability (hole transport material) formed between the anode and the light-emitting layer, or between the hole injection layer and the light-emitting layer in the presence of a hole injection layer. The inventive compound can be used alone or in combination with the compounds described below for use in the hole transport layer.

[0906] The hole transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the hole transport layer can be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the aforementioned hole transport region can include a first hole transport region on the anode side and a second hole transport layer on the cathode side. Alternatively, the hole transport layer can be a three-layer structure comprising a first hole transport layer, a second hole transport layer, and a third hole transport layer sequentially from the anode side. That is, a third hole transport layer can be disposed between the second hole transport layer and the light-emitting layer.

[0907] In one aspect of the present invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Alternatively, the hole transport layer closest to the cathode in the multilayer structure, such as the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the present invention, an electron blocking layer (described later) may be sandwiched between the hole transport layer and the light-emitting layer in the single-layer structure, or between the hole transport layer closest to the light-emitting layer in the multilayer structure. Furthermore, as described above, when the hole transport layer is a multilayer structure containing two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can also be used as an electron blocking layer.

[0908] In one embodiment of the organic electroluminescent device of the present invention, at least one of the first hole transport layer and the second hole transport layer comprises the inventive compound. Specifically, in the two-layer hole transport layer structure, the inventive compound may be contained in one or both of the first and second hole transport layers. In another embodiment, at least one of the first to third hole transport layers comprises the inventive compound. Specifically, in the three-layer hole transport layer structure, the inventive compound may be contained in only one of the first to third hole transport layers, only in any two layers, or in all layers.

[0909] In one aspect of the present invention, it is preferred that the inventive compound is contained in the second hole transport layer. More specifically, it is preferred that the inventive compound is contained only in the second hole transport layer, or that the inventive compound is contained in both the first hole transport layer and the second hole transport layer.

[0910] In one aspect of the present invention, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer, or the inventive compound contained in at least one or more of the first to third hole transport layers, is preferably protium from the viewpoint of manufacturing cost.

[0911] The aforementioned protium refers to an inventive compound in which all hydrogen atoms are protium atoms.

[0912] Therefore, one aspect of the present invention includes: an organic EL element comprising one or both of the first hole transport layer and the second hole transport layer described above, which contains an inventive compound substantially composed solely of protium; and an organic EL element comprising one or more layers of the first to third hole transport layers described above, which contains an inventive compound substantially composed solely of protium. The term "inventive compound substantially composed solely of protium" means that, relative to the total amount of the inventive compound, the proportion of protium is 90 mol% or more, preferably 95 mol% or more, and more preferably 99 mol% or more (each including 100%).

[0913] Other hole transport layer materials besides the inventive compound can be, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc.

[0914] Examples of aromatic amine compounds include: 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethyl]... [fluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB). The above compounds have 10 -6 cm 2 Hole mobility above / Vs.

[0915] Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA).

[0916] Examples of anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), and 9,10-diphenylanthracene (abbreviated as DPAnnth).

[0917] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[0918] Among them, any compound whose hole transport capability is higher than its electron transport capability can use compounds other than those mentioned above.

[0919] In one embodiment of the organic EL element involved in this invention, the first hole transport layer comprises a compound represented by formula (21) or formula (22).

[0920] [Chemical Formula 90]

[0921]

[0922] In equations (21) and (22) above,

[0923] L A1 L B1 L C1 L A2 L B2 L C2 and L D2 Each is independently a single bond, a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a divalent heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0924] k can be 1, 2, 3, or 4.

[0925] When k is 1, L E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[0926] When k is 2, 3, or 4, multiple L E2 They are the same or different.

[0927] When k is 2, 3, or 4, multiple L E2 They can bond together to form substituted or unsubstituted monocyclic rings, bond together to form substituted or unsubstituted fused rings, or not bond together at all.

[0928] L does not form the aforementioned single ring and does not form the aforementioned fused ring E2 It is a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in the cyclic ring, or a substituted or unsubstituted divalent heterocyclic group with 5 to 50 carbon atoms in the cyclic ring.

[0929] A 1 B 1 C 1 A 2 B 2 C 2 and D 2 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group with 5 to 50 cyclic atoms, or a -Si(R') group. 901 )(R' 902 )(R' 903 ),

[0930] R' 901 、R' 902 and R' 903 Each is independently a substituted or unsubstituted aryl group with 6 to 50 carbon atoms in a cyclic formation.

[0931] In R' 901In the case of multiple R's, multiple R's 901 They are the same or different.

[0932] In R' 902 In the case of multiple R's, multiple R's 902 They are the same or different.

[0933] In R' 903 In the case of multiple R's, multiple R's 903 They are the same or different.

[0934] It should be noted that the first hole transport layer described above may contain one compound represented by formula (21) and formula (22), or it may contain multiple compounds represented by formula (21) and formula (22).

[0935] In equations (21) and (22), it is preferred that A 1 B 1 C 1 A 2 B 2 C 2 and D 2 Each is independently selected from substituted or unsubstituted phenylene, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl and substituted or unsubstituted carbazoleyl.

[0936] Furthermore, more preferably, the part selected from A in formula (21) is... 1 B 1 and C 1 At least one of them, and the ones selected from A in equation (22) 2 B 2 C 2 and D 2 At least one of them is a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazoyl.

[0937] A 1 B 1 C 1 A 2 B 2 C 2 and D 2 The optional fluorenyl group may have a substituent at the 9-position, such as 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl. Alternatively, the substituents at the 9-position may form a ring with each other, for example, a fluorenyl skeleton or a thallium skeleton may be formed by the substituents at the 9-position.

[0938] L A1 L B1 L C1 L A2 L B2 L C2 and L D2 Preferably, each arylene group is a single bond, substituted or unsubstituted, and has 6 to 12 carbon atoms in the cyclic group.

[0939] As specific examples of the compounds shown in formulas (21) and (22), the following compounds can be cited.

[0940] [Chemical Formula 91]

[0941]

[0942] dopant material of the light-emitting layer

[0943] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent luminescent materials and phosphorescent luminescent materials can be used as dopant materials. Fluorescent luminescent materials are compounds that emit light using a singlet excited state, while phosphorescent luminescent materials are compounds that emit light using a triplet excited state.

[0944] In one embodiment of the organic EL element involved in this invention, the light-emitting layer is a single layer.

[0945] In another embodiment of the organic EL element involved in this invention, the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer.

[0946] As blue fluorescent materials that can be used in the luminescent layer, pyrene derivatives, styrylamine derivatives, phenanthrene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, azaborane derivatives, and arylborane derivatives can be used. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenyl sphine-4,4'-diamine (abbreviated as YGA2S), 4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as YGAPA), and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (abbreviated as PCPA).

[0947] As green fluorescent materials that can be used in the luminescent layer, aromatic amine derivatives can be used. Specifically, examples include N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), and N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPA). PA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine (abbreviated as: 2YGABPhA), N,N,9-triphenylanthracene-9-amine (abbreviated as: DPhAPhA), etc.

[0948] As red-based fluorescent materials that can be used in the luminescent layer, tetraphenyl derivatives, diamine derivatives, etc., can be used. Specifically, examples include N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (abbreviated as p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (abbreviated as p-mPhAFD).

[0949] In one embodiment of the present invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[0950] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes can be used. Specifically, examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (abbreviated as Fir6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Firpic), bis[2-(3',5'-bistrifluoromethylphenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (abbreviated as Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (abbreviated as Firacac).

[0951] As a green phosphorescent material that can be used in the luminescent layer, iridium complexes can be used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)).

[0952] As red phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes can be used. Specifically, organometallic complexes such as bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP) can be used.

[0953] In addition, rare earth metal complexes such as tri(acetylacetonyl)(monophenanthrene)terbium(III) (abbreviated as Tb(acac)3(Phen)), tri(1,3-diphenyl-1,3-propanedione)(monophenanthrene)eupium(III) (abbreviated as Eu(DBM)3(Phen)), and tri[1-(2-thiophenecarboxyl)-3,3,3-trifluoroacetone](monophenanthrene)eupium(III) (abbreviated as Eu(TTA)3(Phen)) can be used as phosphorescent materials because their luminescence originates from the luminescence of rare earth metal ions (electronic transitions between different multiplicity levels).

[0954] The main material of the light-emitting layer

[0955] The light-emitting layer can be configured by dispersing the aforementioned dopant material within other materials (the host material). Preferably, a material with a lower unoccupied orbital level (LUMO level) higher than that of the dopant material and a higher occupied orbital level (HOMO level) lower than that of the dopant material is used.

[0956] As the main material, use, for example

[0957] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;

[0958] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives;

[0959] (3) Carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or pyroxene derivatives, etc., fused aromatic compounds

[0960] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[0961] For example, metal complexes such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), and bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) can be used;

[0962] Heterocyclic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), phenanthrene-rhein (abbreviation: BPhen), and copper bath (abbreviation: BCP);

[0963] 9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviation: t-BuDN) A) fused aromatic compounds such as 9,9'-bianthracite (BANT), 9,9'-(bruhn-3,3'-diyl)diphenanthrene (DPNS), 9,9'-(bruhn-4,4'-diyl)diphenanthrene (DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), and 6,12-dimethoxy-5,11-diphenylanthracene; and,

[0964] N,N-Diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthrayl)phenyl]phenyl}-9H-carbazole-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl- Aromatic amine compounds such as 9H-carbazole-3-amine (abbreviated as 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used as the main material.

[0965] In particular, in the case of blue fluorescent elements, the following anthracene compounds are preferred as the main material.

[0966] [Chemical Formula 92]

[0967]

[0968] [Chemical Formula 93]

[0969]

[0970] [Chemical Formula 94]

[0971]

[0972] [Chemical Formula 95]

[0973]

[0974] In one embodiment of the organic EL element of the present invention, when the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer, at least one component constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, embodiments in which the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, and embodiments in which the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer, can be cited.

[0975] In the organic EL element involved in this embodiment, the light-emitting layer may contain a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm.

[0976] The method for determining the peak wavelength of the compound's main peak is as follows. A 5 μmol / L toluene solution of the compound to be measured is prepared and added to a quartz cuvette. The emission spectrum of the sample is measured at room temperature (300 K) (vertical axis is set as emission intensity, and horizontal axis is set as wavelength). The emission spectrum can be measured using a spectrophotometer (device name: F-7000) manufactured by Hitachi Advanced Scientific Corporation. It should be noted that the emission spectroscopy measuring device is not limited to the device used here.

[0977] In the emission spectrum, the peak wavelength at which the emission intensity reaches its maximum is defined as the main peak wavelength. It should be noted that, in this specification, the main peak wavelength is sometimes referred to as the fluorescence emission main peak wavelength (FL-peak).

[0978] The luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm can be either the dopant material or the host material mentioned above.

[0979] When the luminescent layer is a single layer, either the dopant material or the host material can be a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm, or both materials can be luminescent compounds exhibiting fluorescence with a main peak wavelength below 500 nm.

[0980] Furthermore, when the luminescent layer comprises a first luminescent layer and a second luminescent layer, only one of the first and second luminescent layers may contain a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, or both luminescent layers may contain a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less. Moreover, when the first luminescent layer contains a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, only one of the dopant material and the host material contained in the first luminescent layer may be a luminescent compound exhibiting fluorescence with a main peak wavelength of 500 nm or less, or both materials may be luminescent compounds exhibiting fluorescence with a main peak wavelength of 500 nm or less. Alternatively, if the second luminescent layer contains a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm, either the dopant material or the host material contained in the second luminescent layer may be a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm, or both materials may be luminescent compounds that exhibit fluorescence emission with a main peak wavelength of less than 500 nm.

[0981] Electron transport layer

[0982] An electron transport layer is a layer containing a material with high electron transport properties (electron transport material), which is formed between the light-emitting layer and the cathode, or between the electron injection layer and the light-emitting layer in the presence of an electron injection layer.

[0983] The electron transport layer can be a single-layer structure or a multi-layer structure containing two or more layers. For example, the electron transport layer can be a two-layer structure containing a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one aspect of the invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, or the electron transport layer closest to the anode in the multi-layer structure, such as the first electron transport layer in the two-layer structure, is preferably adjacent to the light-emitting layer. In another aspect of the invention, a hole-blocking layer, as described later, may be sandwiched between the electron transport layer and the light-emitting layer in the single-layer structure, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure.

[0984] For example, an electron transport layer can be used

[0985] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;

[0986] (2) Imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[0987] (3) Polymer compounds.

[0988] Examples of metal complexes include: tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ), and (8-hydroxyquinoline)lithium (abbreviated as Liq).

[0989] Examples of heteroaromatic compounds include: 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs).

[0990] Examples of high molecular weight compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy).

[0991] The above material has 10 -6 cm 2 Materials with an electron mobility of / Vs or higher. It should be noted that any material with electron transport capacity higher than hole transport capacity can be used for the electron transport layer, even if it is not mentioned above. Furthermore, the electron transport layer can be a single layer or a stack of two or more layers, each containing the aforementioned materials. When the electron transport layer is a two-layer structure, the layer on the anode side is called the first electron transport layer, and the layer on the cathode side is called the second electron transport layer.

[0992] Electron injection layer

[0993] An electron injection layer is a layer containing materials with high electron injection capability. The electron injection layer can use alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu) and ytterbium (Yb), and compounds containing these metals. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes such as (8-hydroxyquinoline)lithium (Liq), alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. Furthermore, multiple such compounds can be used in combination.

[0994] Furthermore, materials containing alkali metals, alkaline earth metals, or their compounds in an electron-transporting material can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.

[0995] Alternatively, the electron injection layer can be a composite material made by mixing an organic compound and an electron donor. Such a composite material exhibits excellent electron injection and electron transport properties because the organic compound accepts electrons from the electron donor. In this case, the organic compound is preferably a material that excels in the transport of the accepted electrons; specifically, materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) as described above can be used. The electron donor can be any material that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[0996] cathode

[0997] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV). 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.

[0998] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[0999] It should be noted that by setting an electron injection layer, a wide variety of conductive materials, such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide, can be used to form cathodes regardless of the work function. These conductive materials can be deposited using methods such as sputtering, inkjet printing, and spin coating.

[1000] Insulation layer

[1001] Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to the ultrathin film. To prevent this, an insulating layer formed by an insulating thin film can be inserted between a pair of electrodes.

[1002] Examples of materials that can be used as insulating layers include alumina, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, and vanadium oxide. It should be noted that mixtures or laminates of these materials can also be used.

[1003] Spacer layer

[1004] In the case of a stacked fluorescent and phosphorescent layer, the spacer layer refers to a layer disposed between the fluorescent and phosphorescent layers to prevent excitons generated in the phosphorescent layer from diffusing to the fluorescent layer or to adjust carrier balance. Alternatively, the spacer layer may be disposed between multiple phosphorescent layers.

[1005] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that has both electron transport and hole transport properties. Furthermore, to prevent the diffusion of triplet energy within adjacent phosphorescent light-emitting layers, the triplet energy is preferably 2.6 eV or higher. Materials similar to those used for the hole transport layer can be used as examples of materials for the spacer layer.

[1006] Barrier layer

[1007] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can also be placed adjacent to the light-emitting layer. An electron blocking layer prevents electrons from leaking from the light-emitting layer to the hole transport layer, while a hole blocking layer prevents holes from leaking from the light-emitting layer to the electron transport layer. An exciton blocking layer prevents excitons generated in the light-emitting layer from diffusing to surrounding layers, thus confining the excitons within the light-emitting layer.

[1008] The layers of the aforementioned organic EL element can be formed using conventional vapor deposition or coating methods. For example, they can be formed using vapor deposition methods such as vacuum vapor deposition or molecular beam vapor deposition (MBE), or using known coating methods based on solutions of the compound forming the layer, such as dip coating, spin coating, casting, rod coating, and roll coating.

[1009] There are no particular restrictions on the thickness of each layer. Generally speaking, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if the film thickness is too thick, a high driving voltage is required and the efficiency will be reduced. Therefore, the thickness is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[1010] In one embodiment of the organic EL element of the present invention, the combined thickness of the first hole transport layer and the second hole transport layer is 30 nm or more and 150 nm or less. In this case, it is preferably 40 nm or more and 130 nm or less.

[1011] Furthermore, in one embodiment of the organic EL element of the present invention, the thickness of the second hole transport layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably 35 nm or more, and further preferably 100 nm or less.

[1012] Furthermore, in one embodiment of the organic EL element of the present invention, the hole transport layer adjacent to the light-emitting layer is 20 nm or more. Preferably, it is 25 nm or more, more preferably 30 nm or more, and further preferably 100 nm or less.

[1013] Furthermore, in one embodiment of the organic EL element of the present invention, the film thickness D1 of the first hole transport layer and the film thickness D2 of the second hole transport layer satisfy the relationship 0.3 < D2 / D1 < 4.0. Preferably, the relationship is 0.5 < D2 / D1 < 3.5, and more preferably, the relationship is 0.75 < D2 / D1 < 3.0.

[1014] Examples of embodiments of the organic EL element of the present invention include:

[1015] As an organic EL element having the hole transport layer composed of the above two layers and

[1016] • A first embodiment in which the second hole transport layer contains the compound of the present invention and the first hole transport layer does not contain the compound of the present invention;

[1017] • Both the first hole transport layer and the second hole transport layer comprise the second embodiment of the compound of the present invention;

[1018] • A third embodiment in which the first hole transport layer contains the compound of the present invention and the second hole transport layer does not contain the compound of the present invention;

[1019] As an organic EL element having a hole transport layer consisting of the above three layers and

[1020] • A fourth embodiment in which the first hole transport layer contains the compound of the present invention and the second and third hole transport layers do not contain the compound of the present invention;

[1021] • A fifth embodiment in which the second hole transport layer contains the compound of the present invention and the first and third hole transport layers do not contain the compound of the present invention;

[1022] • A sixth embodiment in which the third hole transport layer contains the compound of the present invention and the first and second hole transport layers do not contain the compound of the present invention;

[1023] • A seventh embodiment in which the first and second hole transport layers contain the compounds of the present invention and the third hole transport layer does not contain the compounds of the present invention;

[1024] • An eighth embodiment in which the first and third hole transport layers contain the compounds of the present invention and the second hole transport layer does not contain the compounds of the present invention;

[1025] • A ninth embodiment in which the second and third hole transport layers contain the compounds of the present invention and the first hole transport layer does not contain the compounds of the present invention;

[1026] • The first to third hole transport layers all contain the compound of the present invention in the tenth embodiment; etc.

[1027] electronic devices

[1028] The aforementioned organic EL elements can be used in display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, as well as electronic devices such as lighting and vehicle lamps.

[1029] Example

[1030] The present invention will be described in more detail below using examples, but the present invention is not limited to the following examples.

[1031] Compounds Inv-1 to Inv-11 used in the manufacture of the organic EL elements in Examples 1 to 11

[1032] [Chemical Formula 96]

[1033]

[1034] [Chemical Formula 97]

[1035]

[1036] Compounds Ref-1 to Ref-3 used in the manufacture of the organic EL elements of Comparative Examples 1 to 3

[1037] [Chemical Formula 98]

[1038]

[1039] [Chemical Formula 99]

[1040]

[1041] Other compounds used in the manufacture of organic EL elements in Examples 1-11 and Comparative Examples 1-3

[1042] [Chemical Formula 100]

[1043]

[1044] Fabrication of organic EL components

[1045] Example 1

[1046] A 25mm × 75mm × 1.1mm glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was set to 130nm.

[1047] The cleaned glass substrate with transparent electrodes was mounted on the substrate holder of a vacuum evaporation apparatus. First, compounds HT-1 and HA were co-deposited on the side where the transparent electrodes were formed, covering the transparent electrodes, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compounds HT-1 to HA (HT-1:HA) was 97:3.

[1048] Next, compound HT-1 was deposited on the hole injection layer to form the first hole transport layer with a thickness of 85 nm.

[1049] Next, compound Inv-1, which is compound HT-2, was deposited on the first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1050] Next, compounds BH-1 (the host material) and BD-1 (the dopant material) were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 20 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 99:1.

[1051] Next, compound ET-1 was deposited on the light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[1052] Next, a second electron transport layer with a thickness of 31 nm was formed by co-evaporating compounds ET-2 and Liq on the first electron transport layer. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50.

[1053] Next, Liq was deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[1054] Then, metallic Al was deposited on the electron-injecting electrode to form a metal cathode with a film thickness of 80 nm.

[1055] The following shows the layer configuration of the organic EL element of Example 1 obtained by such operation.

[1056] ITO(130) / HT-1:HA=97:3(10) / HT-1(85) / HT-2(5) / BH-1:BD-1=99:1(20) / ET-1(5) / ET-2:Liq=50:50(31) / Liq(1) / Al(80)

[1057] It should be noted that in the above layer composition, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

[1058] Examples 2-11 and Comparative Examples 1-3

[1059] In Example 1, the compounds shown in Table 1 below were used instead of Compound Inv-1, which was used as the material for the second hole transport layer. Otherwise, the organic EL elements of Examples 2 to 11 and Comparative Examples 1 to 3 were prepared in the same manner as in Example 1.

[1060] Component lifetime (LT95) determination

[1061] For each of the above organic EL devices, a voltage is applied such that the current density reaches 50 mA / cm². 2 The organic EL device was evaluated for 95% lifetime (LT95). Here, 95% lifetime (LT95) refers to the time (hr) during constant current drive before the brightness drops to 95% of the initial brightness.

[1062] The results are shown in Table 1.

[1063] Measurement of external quantum efficiency (EQE)

[1064] The above organic EL elements were subjected to a current density of 10 mA / cm² at room temperature. 2 A DC constant current drive was used, and the brightness was measured using a luminance meter (Minolta CS-1000 spectroluminance-emissivity meter). The external quantum efficiency (%) was calculated based on the measurement results.

[1065] The results are shown in Table 1.

[1066] [Table 1]

[1067]

[1068] As can be clearly seen from the results in Table 1, the compounds that meet the requirements of the present invention (compound Inv-1 of Example 1 to compound Inv-11 of Example 11) exhibit improved LT95 values ​​compared to the monoamines that do not meet the requirements of the present invention (compound Ref-1 of Comparative Example 1 to compound Ref-3 of Comparative Example 3).

[1069] Furthermore, it is known that compounds that meet the requirements of the present invention (compound Inv-1 of Example 1 to compound Inv-11 of Example 11) exhibit improved EQE values ​​while having higher LT95 values ​​compared to monoamines that do not meet the requirements of the present invention (compound Ref-1 of Comparative Example 1 to compound Ref-3 of Comparative Example 3).

[1070] Synthesis of Intermediate A: Example A-1: ​​Synthesis of Intermediate A-1

[1071] [Chemical Formula 101]

[1072]

[1073] The mixture of [Ingredient 1] naphtho[1,2-b]benzofuran-10-ylboronic acid (2.62 g, 10 mmol), [Ingredient 2] 1-bromo-4-iodobenzene (2.87 g, 10 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.14 g, 0.2 mmol), 2M potassium carbonate aqueous solution (15 mL), and 1,2-dimethoxyethane (50 mL) was subjected to boiling point reflux for 3 hours.

[1074] The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3.55 g of a white solid. The yield was 95%.

[1075] Synthesis examples of intermediate A: A-2 to A-4

[1076] Except for using the compounds shown in Table 2 below as raw material 1 and raw material 2, intermediates A-2 to A-4 were synthesized using the same steps as the synthesis of intermediate A-1.

[1077] Intermediates A-1 to A-4, along with raw materials 1, 2, and yields, are shown in Table 2.

[1078] [Table 2]

[1079]

[1080] Synthesis of Intermediate B Example B-1: Synthesis of Intermediate B-1

[1081] [Chemical Formula 102]

[1082]

[1083] The mixture of [Recipe 3] dibenzo[b,d]furan-1-amine (2.75 g, 15 mmol), [Recipe 4] 4-bromo-1,1':4',1''-terphenyl (4.64 g, 15 mmol), tris(dibenzylacetone)dipalladium(0) (0.275 g, 0.3 mmol), BINAP (0.374 g, 0.6 mmol), sodium tert-butoxide (1.586 g, 16.5 mmol), and toluene (75 mL) was subjected to boiling point reflux for 3 hours.

[1084] The reaction solution was cooled to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 5.22 g of a white solid. The yield was 85%.

[1085] Synthesis examples of intermediates B-2 to B-9: Synthesis of intermediates B-2 to B-9

[1086] Except for using the compounds shown in Table 3 below as raw materials 3 and 4, intermediates B-2 to B-9 were synthesized using the same steps as those for intermediate B-1.

[1087] Intermediates B-1 to B-9, along with raw materials 3 and 4 and their yields, are shown in Table 3.

[1088] [Table 3]

[1089]

[1090] Example 1: Synthesis of Compound 1

[1091] [Chemical Formula 103]

[1092]

[1093] Under an argon atmosphere, a mixture of intermediate A-1 (3.73 g, 10 mmol), intermediate B-1 (4.12 g, 10 mmol), tris(dibenzylacetone)dipalladium(0) (0.183 g, 0.2 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.232 g, 0.8 mmol), sodium tert-butoxide (1.44 g, 15 mmol), and xylene (50 mL) was stirred at 110 °C for 5 hours.

[1094] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 4.12 g of a white solid. The yield was 58%.

[1095] Mass spectrometry analysis of the obtained substance revealed it to be compound 1, with a molecular weight of 703.84 and an m / e ratio of 704.

[1096] Synthesis Examples 2-11: Synthesis of Compounds 2-11

[1097] Except for using the compounds shown in Table 4 below as intermediates A and B, compounds 2 to 11 were synthesized using the same steps as those used in the synthesis of compound 1.

[1098] Compounds 1 to 11, along with intermediates A and B used as raw materials and their yields, are shown in Table 4.

[1099] [Table 4]

[1100]

[1101] Symbol Explanation

[1102] 1, 11, 12 Organic EL elements

[1103] 2 substrate

[1104] 3 Anode

[1105] 4 Cathode

[1106] 5. Light-emitting layer

[1107] 6. Hole transport region (hole transport layer)

[1108] 6a Hole injection layer

[1109] 6b Hole Transport Layer 1

[1110] 6c Hole transport layer 2

[1111] 6d Third Hole Transport Layer

[1112] 7. Electron transport region (electron transport layer)

[1113] 7a First electron transport layer

[1114] 7b Second electron transport layer

[1115] 10, 20, 30 light-emitting units

Claims

1. The compound represented by the following formula (1), wherein, In equation (1), • Selected from R 1 ~R 9 Two adjacent elements in the structure may bond together to form a ring, or they may not bond together to form a ring. • Selected from R 11 ~R 14 Two adjacent elements in the structure may bond together to form a ring, or they may not bond together to form a ring. • Selected from R 21 ~R 27 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • The R that does not bond with each other and does not form a ring 1 ~R 9 Each is an independent hydrogen atom. The R 11 ~R 14 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms. The R 21 ~R 27 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms. ·X 1 and X 2 Each can be independently an oxygen atom or a sulfur atom. ·L 1 It is a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic ring, or a substituted or unsubstituted heteroaryl group with 5 to 30 cyclic atoms in the cyclic ring. ·Ar 1 It is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

2. The compound according to claim 1, wherein, The Ar 1 Represented by the following formulas (2A), (2B), (2C), (2D), or (2E), In equation (2A), ·*21 is related to L 1 Bonded single bonds, • Selected from R 101 ~R 105 One of them is a single bond bonded to *22, selected from R 106 ~R 110 One of them is a single bond that bonds with *23. • Not the R of the single bond mentioned 101 ~R 105 and R 106 ~R 110 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. • Selected from R that is not the single bond described 101 ~R 105 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • Selected from R that is not the single bond described 106 ~R 110 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. ·R 111 ~R 115 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms. • Selected from R 111 ~R 115 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • j is 0, 1, or 2, and k is 0 or 1, excluding the case where j is 2 and k is 0. • When j=0 and k=0, *23 represents *21. • When j=0 and k=1, *22 represents *21. • When j=1 and k=0, *23 means *22. In equation (2B), ·*24 is related to L 1 Bonded single bonds, • Selected from R 121 ~R 128 One of them is a single bond that bonds with *25. • Not the R of the single bond mentioned 121 ~R 128 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 121 ~R 128 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2C), ·*26 is related to L 1 Bonded single bonds, • Selected from R 131 ~R 140 One of them is a single bond that bonds with *27. • Not the R of the single bond mentioned 131 ~R 140 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 131 ~R 140 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (2D), ·*28 is related to L 1 Bonded single bonds, • Selected from R 151 ~R 155 One of them is a single bond bonded to *29, selected from R 151 ~R 155 The other one is a single bond that bonds with *30. • Not the R of the single bond mentioned 151 ~R 155 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. • Selected from R that is not the single bond bonded to *29 and the single bond bonded to *30. 151 ~R 155 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. ·R 161 ~R 165 and R 171 ~R 175 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. • Selected from R 161 ~R 165 At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring. • Selected from R 171 ~R 175 At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring. In equation (2E), ·*221 is related to L 1 Bonded single bonds, • Selected from R 181 ~R 192 One of them is a single bond bonded to *222. • Not the R of the single bond mentioned 181 ~R 192 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 181 ~R 192 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

3. The compound according to claim 1 or 2, wherein, Ar 1 It is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.

4. The compound according to any one of claims 1 to 3, wherein, Ar 1 It can be a substituted or unsubstituted biphenyl.

5. The compound according to any one of claims 1 to 4, wherein, L 1 It is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic structure.

6. The compound according to any one of claims 1 to 5, wherein, L 1 It can be a substituted or unsubstituted phenylene.

7. The compound according to any one of claims 1 to 6, wherein, R 11 ~R 14 Each is an independent hydrogen atom.

8. The compound according to any one of claims 1 to 7, wherein, R 21 ~R 27 Each is an independent hydrogen atom.

9. The compound according to any one of claims 1 to 8, wherein, R 1 ~R 9 The hydrogen atoms and R contained therein 11 ~R 14 The hydrogen atoms and R contained therein 21 ~R 27 At least one of the hydrogen atoms contained therein is a protium atom.

10. The compound represented by the following formula (2), wherein, In equation (2), • Selected from R 31 ~R 33 One of them is a single bond that bonds with *1. • Selected from R 51 ~R 55 One of them is a single bond bonded to *a. • Selected from R that is not the single bond described 31 ~R 33 and R 34 ~R 40 Two adjacent elements in the structure may bond together to form a ring, or they may not bond together to form a ring. • Selected from R 41 ~R 44 Two adjacent elements in the structure may bond together to form a ring, or they may not bond together to form a ring. • Selected from R that is not the single bond described 51 ~R 55 Two adjacent elements in the structure may bond together to form a ring, or they may not bond together to form a ring. • Selected from R 61 ~R 68 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • The R that is not mutually bonded and does not form a ring and is not a single bond 31 ~R 33 R and non-bonded to form a ring 34 ~R 40 Each is an independent hydrogen atom. The R 41 ~R 44 And R which is not the single bond 51 ~R 55 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms. The R 61 ~R 68 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms. ·X 3 It consists of oxygen or sulfur atoms. ·L 2 It is a single bond, a substituted or unsubstituted aryl group with 6 to 30 carbon atoms in the cyclic ring, or a substituted or unsubstituted heteroaryl group with 5 to 30 cyclic atoms. ·Ar 2 It is an aryl group with 6 to 30 carbon atoms, either substituted or unsubstituted.

11. The compound according to claim 10, wherein, The Ar 2 Represented by the following formulas (3A), (3B), (3C), (3D), or (3E), In equation (3A), ·*31 is related to L 2 Bonded single bonds, in L 2 When it is a single bond, *31 is bonded to the central nitrogen atom. • Selected from R 201 ~R 205 One of them is a single bond bonded to *32, selected from R 206 ~R 210 One of them is a single bond that bonds with *33. • Not the R of the single bond mentioned 201 ~R 205 and R 206 ~R 210 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. • Selected from R that is not the single bond described 201 ~R 205 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • Selected from R that is not the single bond described 206 ~R 210 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. ·R 211 ~R 215 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 13 carbon atoms. • Selected from R 211 ~R 215 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. • jj is 0, 1, or 2, and kk is 0 or 1, excluding the case where jj is 2 and kk is 0. • When jj=0 and kk=0, *33 means *31. • When jj=0 and kk=1, *32 means *31. • When jj=1 and kk=0, *33 means *32. In equation (3B), ·*34 is related to L 2 Bonded single bonds, in L 2 When it is a single bond, *34 is bonded to the central nitrogen atom. • Selected from R 221 ~R 228 One of them is a single bond that bonds with *35. • Not the R of the single bond mentioned 221 ~R 228 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 221 ~R 228 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (3C), ·*36 is related to L 2 Bonded single bonds, in L 2 When it is a single bond, *36 is bonded to the central nitrogen atom. • Selected from R 231 ~R 240 One of them is a single bond that bonds with *37. • Not the R of the single bond mentioned 231 ~R 240 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 231 ~R 240 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. In equation (3D), ·*38 is related to L 2 Bonded single bonds, in L 2 When it is a single bond, *38 is bonded to the central nitrogen atom. • Selected from R 251 ~R 255 One of them is a single bond bonded to *39, selected from R 251 ~R 255 The other one is a single bond that bonds with *40. • Not the R of the single bond mentioned 251 ~R 255 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group. • Selected from R that is not the single bond bonded to *39 and the single bond bonded to *40. 251 ~R 255 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop. ·R 261 ~R 265 and R 271 ~R 275 Each is independently a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms. • Selected from R 261 ~R 265 At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring. • Selected from R 271 ~R 275 At least one pair of adjacent two atoms in the form of a benzene ring are bonded to each other to form one or more unsubstituted benzene rings, or they are not bonded to each other and do not form a ring. In equation (3E), ·*331 is related to L 2 Bonded single bonds, in L 2 When it is a single bond, *331 is bonded to the central nitrogen atom. • Selected from R 281 ~R 292 One of them is a single bond that bonds with *332. • Not the R of the single bond mentioned 281 ~R 292 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms. • Selected from R that is not the single bond described 281 ~R 292 Two adjacent elements in the loop do not bond to each other and therefore do not form a loop.

12. The compound according to claim 10 or 11, wherein, Ar 2 It is an aryl group with 6 to 12 carbon atoms, either substituted or unsubstituted.

13. The compound according to any one of claims 10 to 12, wherein, Ar 2 The phenyl group can be substituted or unsubstituted.

14. The compound according to any one of claims 10 to 13, wherein, L 2 It is a substituted or unsubstituted aryl group with 6 to 12 carbon atoms in a cyclic structure.

15. The compound according to any one of claims 10 to 14, wherein, L 2 It can be a substituted or unsubstituted phenylene.

16. The compound according to any one of claims 10 to 15, wherein, R 41 ~R 44 Each is an independent hydrogen atom.

17. The compound according to any one of claims 10 to 16, wherein, Not the R of the single bond 51 ~R 55 Each is an independent hydrogen atom.

18. The compound according to any one of claims 10 to 17, wherein, R 61 ~R 68 Each is an independent hydrogen atom.

19. The compound according to any one of claims 10 to 18, wherein, R 31 ~R 40 The hydrogen atoms and R contained therein 41 ~R 44 The hydrogen atoms and R contained therein 51 ~R 55 The hydrogen atoms and R contained therein 61 ~R 68 At least one of the hydrogen atoms contained therein is a protium atom.

20. The compound according to any one of claims 1 to 19, wherein, The molecule contains at least one deuterium atom.

21. A material for an organic electroluminescent device, comprising any one of claims 1 to 20.

22. The material for organic electroluminescent devices according to claim 21, in, The compound according to any one of claims 1 to 20 is a hole transport layer material.

23. An organic electroluminescent element having an anode, a cathode, and an organic layer located between the anode and the cathode, the organic layer comprising a light-emitting layer, at least one layer of the organic layer comprising a compound according to any one of claims 1 to 20.

24. The organic electroluminescent element according to claim 23, wherein, The organic layer includes a hole transport region located between the anode and the light-emitting layer, and the hole transport region contains the compound.

25. The organic electroluminescent element according to claim 24, wherein, The hole transport region includes a first hole transport layer and a second hole transport layer, and one or both of the first hole transport layer and the second hole transport layer contain the compound.

26. The organic electroluminescent element according to claim 25, wherein, The light-emitting layer is directly connected to the second hole transport layer.

27. The organic electroluminescent element according to claim 25 or 26, wherein, The combined thickness of the first hole transport layer and the second hole transport layer is more than 30 nm and less than 150 nm.

28. The organic electroluminescent element according to claim 25, wherein, The hole transport region, starting from the anode side, sequentially comprises a first hole transport layer, a second hole transport layer, and a third hole transport layer, wherein only one layer selected from the first to the third hole transport layers, only two layers selected from the first to the third hole transport layers, or all layers of the first to the third hole transport layers contain the compound.

29. An electronic device comprising an organic electroluminescent element according to any one of claims 23 to 28.

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