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

Abstract

This invention provides a compound represented by the following formula (I) for further improving the performance of organic EL devices, a material for organic electroluminescent devices comprising said compound, an organic electroluminescent device comprising said compound having further improved device performance, and an electronic device comprising said organic electroluminescent device. (I) (Each symbol in the formula is as defined in the specification.)

Description

Technical Field

[0001] The present invention relates to a compound, a material comprising the above compound for an organic electroluminescent element, an organic electroluminescent element, and an electronic device comprising the above organic electroluminescent element. Background Technology

[0002] Typically, 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 form an excited state, which emits light when it returns to the ground state. Therefore, developing a material that can efficiently transport electrons or holes to the luminescent region and facilitate electron-hole recombination is crucial for obtaining high-performance organic EL devices.

[0003] Patent documents 1 to 7 disclose organic electroluminescent elements and compounds used as materials thereon.

[0004] Existing technical documents

[0005] Patent Document 1: Korean Patent Publication No. 10-1868505 (KR101868505B1)

[0006] Patent Document 2: PCT Publication No. 2019 / 164327 (WO2019164327A1)

[0007] Patent Document 3: PCT Publication No. 2019 / 168367 (WO2019168367A1)

[0008] Patent Document 4: Korean Patent Publication No. 10-2312474 (KR102312474B1)

[0009] Patent Document 5: Korean Patent Publication No. 2021-0047984 (KR20210047984A)

[0010] Patent Document 6: Korean Patent Publication No. 10-2134379 (KR102134379B1)

[0011] Patent Document 7: Korean Patent Publication No. 10-1737212 (KR101737212B1) Summary of the Invention

[0012] The problem that the invention aims to solve

[0013] Previously, although many compounds for organic EL devices have been reported, there is still a need for compounds that can further improve the performance of organic EL devices.

[0014] To address the aforementioned problems, the present invention aims to provide a compound that further improves the performance of organic EL elements, a material for organic electroluminescent elements, an organic electroluminescent element having further improved element performance, and an electronic device comprising the aforementioned organic electroluminescent element.

[0015] Methods for solving problems

[0016] According to one aspect of the present invention, a compound represented by the following formula (I) is provided:

[0017] (I)

[0018] In equation (I),

[0019] Ar1 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms;

[0020] Ar2 and Ar3 are each independently substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic formation;

[0021] L1 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;

[0022] Wherein, L1 is neither a substituted nor an unsubstituted para-phenylene;

[0023] L2 and L3 are each independently a single bond, 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 cyclic atoms.

[0024] In the definition of each substituent in formula (I), "unsubstituted" means that the hydrogen atom is not substituted by the substituent, and the hydrogen atom is a protium atom, a deuterium atom, or a tritium atom;

[0025] At least one of Ar1, Ar2, Ar3, L1, L2 and L3 contains a deuterium atom.

[0026] According to another aspect of the present invention, a material for an organic electroluminescent element is provided, comprising the compound shown in formula (I).

[0027] According to another aspect of the present invention, a hole transport layer material is provided, comprising the compound represented by formula (I).

[0028] An organic electroluminescent element is provided, comprising an anode, a cathode, and an organic layer consisting of a single layer or multiple layers located between the anode and the cathode, the organic layer including a light-emitting layer, at least one of the organic layers comprising a compound represented by formula (I).

[0029] According to another aspect of the present invention, an electronic device is provided, which includes the organic electroluminescent element.

[0030] Invention Effects

[0031] Organic EL elements containing the compound shown in formula (I) exhibit improved element performance. Attached Figure Description

[0032] Figure 1 A simplified diagram illustrating an example of the layer structure of an organic EL element according to one aspect of the present invention.

[0033] Figure 2 A simplified diagram illustrating another example of the layer structure of an organic EL element of one aspect of the present invention.

[0034] Figure 3 A simplified diagram illustrating another example of the layer structure of an organic EL element of one aspect of the present invention. Detailed Implementation

[0035] [definition]

[0036] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0044] 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.

[0045] 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.

[0046] Substituents described in this specification

[0047] The substituents described in this specification are explained below.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] • "Substituted or unsubstituted aryl groups"

[0058] 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.

[0059] "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.

[0060] • Unsubstituted aryl groups (specific example group G1A):

[0061] Phenyl,

[0062] p-phenyl,

[0063] metaphenyl,

[0064] o-phenyl,

[0065] p-terphenyl-4-yl,

[0066] p-terphenyl-3-yl,

[0067] p-terphenyl-2-yl,

[0068] m-terphenyl-4-yl,

[0069] m-terphenyl-3-yl,

[0070] m-terphenyl-2-yl,

[0071] o - terphenyl - 4 - yl,

[0072] o - terphenyl - 3 - yl,

[0073] o - terphenyl - 2 - yl,

[0074] 1 - naphthyl,

[0075] 2 - naphthyl,

[0076] anthryl,

[0077] benzoanthryl,

[0078] phenanthryl,

[0079] benzophenanthryl,

[0080] phenalenyl,

[0081] pyrenyl,

[0082] chrysenyl,

[0083] benzochrysenyl,

[0084] triphenylenyl,<​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​

[0101] p-Tolyl,

[0102] p-Xylyl,

[0103] m-Xylyl,

[0104] o-xylyl,

[0105] p-isopropylphenyl,

[0106] m-Isopropylphenyl,

[0107] o-isopropylphenyl,

[0108] p-tert-butylphenyl,

[0109] m-tert-butylphenyl,

[0110] o-tert-butylphenyl,

[0111] 3,4,5-Trimethylphenyl

[0112] 9,9-Dimethylfluorenyl,

[0113] 9,9-Diphenylfluorenyl

[0114] 9,9-Bis(4-methylphenyl)fluorenyl,

[0115] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0116] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0117] cyanophenyl,

[0118] Triphenylsilylphenyl

[0119] Trimethylsilylphenyl

[0120] Phenynaphthyl,

[0121] Naphthylphenyl and

[0122] 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.

[0123] • "Substituted or unsubstituted heterocyclic groups"

[0124] 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.

[0125] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0126] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0127] 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".

[0128] "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.

[0129] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0130] 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).

[0131] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0132] pyrrole,

[0133] Imidazole group,

[0134] Pyrazolyl,

[0135] Triazole group,

[0136] Tetrazolyl,

[0137] Oxazolyl,

[0138] Isoxazolyl,

[0139] Oxadiazole group,

[0140] Thiazole group,

[0141] Isothiazolyl,

[0142] Thiadiazole group,

[0143] pyridyl,

[0144] pyridazinyl,

[0145] Pyrimidine group,

[0146] Pyrazinyl,

[0147] Triazine group

[0148] Indole,

[0149] Isoindolyl,

[0150] Indazine group

[0151] Quinazine-based

[0152] Quinoline,

[0153] Isoquinoline,

[0154] Crenoline group

[0155] Phthaloazine

[0156] Quinazolinyl,

[0157] Quinoxaloyl,

[0158] Benzimidazole group,

[0159] Indazole group,

[0160] phenanthroline,

[0161] phenanthridine,

[0162] acridine group,

[0163] Phenazine group,

[0164] Carbazolyl,

[0165] Benzocarbazolyl,

[0166] Morpholinyl

[0167] phenoxazine group,

[0168] phenothiazine group,

[0169] Azacarbazolyl, and

[0170] Diazacarbazolyl.

[0171] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0172] furanyl,

[0173] Oxazolyl,

[0174] Isoxazolyl,

[0175] Oxadiazole group,

[0176] Xuton base,

[0177] Benzofuranyl,

[0178] Isobenzofuranyl,

[0179] Dibenzofuranyl,

[0180] Naphthobenzofuranyl,

[0181] Benzoxazolyl,

[0182] Benzisoxazole group,

[0183] phenoxazine group,

[0184] Morpholinyl

[0185] Dinaphthylfuranyl,

[0186] Azadibenzofuranyl,

[0187] diazadibenzofuranyl,

[0188] Azanaphthalenebenzofuranyl and

[0189] Diazanaphthenebenzofuranyl.

[0190] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0191] Thiophene group

[0192] Thiazole group,

[0193] Isothiazolyl,

[0194] Thiadiazole group,

[0195] benzothienyl

[0196] isobenzothienyl

[0197] dibenzothienyl

[0198] Naphthobenzothienyl

[0199] Benzothiazolyl,

[0200] Benzisothiazolyl,

[0201] phenothiazine group,

[0202] dinaphthothienyl

[0203] azadibenzothienyl

[0204] diazadibenzothienyl

[0205] azanaphthobenzothienyl and

[0206] diazanaphthobenzothienyl.

[0207] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0208]

[0209]

[0210] 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.

[0211] 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.

[0212] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0213] (9-phenyl)carbazole group,

[0214] (9-Biphenyl)carbazole,

[0215] (9-Phenyl)phenylcarbazolyl,

[0216] (9-Naphthyl)carbazole,

[0217] Diphenylcarbazole-9-yl,

[0218] Phenylexacarbazole-9-yl,

[0219] Methylbenzimidazole,

[0220] Ethylbenzimidazole,

[0221] Phenylacetyl,

[0222] Biphenyltriazine,

[0223] diphenyltriazine group,

[0224] phenylquinazolinyl, and

[0225] Biphenylquinazolinyl.

[0226] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0227] Phenyl dibenzofuranyl,

[0228] Methyldibenzofuranyl,

[0229] tert-butyldibenzofuranyl and

[0230] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0231] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0232] Phenyl dibenzothiophene,

[0233] Methyldibenzothiophene,

[0234] tert-butyldibenzothiophene and

[0235] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0236] • 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):

[0237] 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.

[0238] • "Substituted or unsubstituted alkyl groups"

[0239] 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.

[0240] "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.

[0241] • Unsubstituted alkyl groups (specific example group G3A):

[0242] methyl,

[0243] Ethyl,

[0244] n-propyl,

[0245] Isopropyl,

[0246] n-Butyl,

[0247] Isobutyl,

[0248] sec-butyl and

[0249] tert-butyl.

[0250] • Substituted alkyl groups (specific example group G3B):

[0251] Heptafluoropropyl (including isomers),

[0252] Pentafluoroethyl,

[0253] 2,2,2-Trifluoroethyl and

[0254] Trifluoromethyl

[0255] • "Substituted or unsubstituted alkenyl groups"

[0256] 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.

[0257] "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.

[0258] • Unsubstituted alkenyl groups (specific example group G4A):

[0259] vinyl,

[0260] Allyl

[0261] 1-Butenyl,

[0262] 2-Butenyl and

[0263] 3-Butenyl.

[0264] • Substituted alkenyl groups (specific example group G4B):

[0265] 1,3-Butadienyl,

[0266] 1-Methylvinyl

[0267] 1-Methylallyl,

[0268] 1,1-Dimethylallyl,

[0269] 2-Methylallyl and

[0270] 1,2-Dimethylallyl.

[0271] • "Substituted or unsubstituted alkynyl groups"

[0272] 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".

[0273] "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.

[0274] • Unsubstituted alkynyl group (specific example group G5A):

[0275] Acetylene group.

[0276] • "Substituted or unsubstituted cycloalkyl groups"

[0277] 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.

[0278] "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.

[0279] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0280] Cyclopropyl

[0281] Cyclobutyl,

[0282] Cyclopentyl,

[0283] Cyclohexyl,

[0284] 1-Adamantyl,

[0285] 2-Adamantyl,

[0286] 1-norborneol and

[0287] 2-norborneol.

[0288] • Substituted cycloalkyl groups (specific example group G6B):

[0289] 4-Methylcyclohexyl.

[0290] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0291] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown (specific example group G7) can be given as follows:

[0292] -Si(G1)(G1)(G1),

[0293] -Si(G1)(G2)(G2)

[0294] -Si(G1)(G1)(G2),

[0295] -Si(G2)(G2)(G2),

[0296] -Si(G3)(G3)(G3) and

[0297] -Si(G6)(G6)(G6). Here.

[0298] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0299] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0300] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0301] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0302] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0303] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0304] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0305] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0306] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0307] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0308] ·“-O-(R 904 The group shown in the figure”

[0309] 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:

[0310] -O(G1)

[0311] -O(G2),

[0312] -O(G3) and

[0313] -O(G6).

[0314] Here,

[0315] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0316] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0317] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0318] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0319] ·“-S-(R 905 The group shown in the figure”

[0320] 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:

[0321] -S(G1),

[0322] -S(G2),

[0323] -S(G3) and

[0324] -S(G6).

[0325] Here,

[0326] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0327] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0328] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0329] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0330] ·"-N(R 906 (R) 907 The group shown in the figure”

[0331] 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:

[0332] -N(G1)(G1),

[0333] -N(G2)(G2),

[0334] -N(G1)(G2),

[0335] -N(G3)(G3) and

[0336] -N(G6)(G6).

[0337] Here,

[0338] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0339] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0340] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0341] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0342] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0343] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0344] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0345] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0346] • "Halogen atom"

[0347] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0348] • "Substituted or unsubstituted fluoroalkyl groups"

[0349] 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.

[0350] • "Substituted or unsubstituted haloalkyl groups"

[0351] 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.

[0352] • "Substituted or unsubstituted alkoxy groups"

[0353] 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.

[0354] • "Substituted or unsubstituted alkylthio groups"

[0355] 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.

[0356] • "Substituted or unsubstituted aryloxy groups"

[0357] 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.

[0358] • "Substituted or unsubstituted arylthio groups"

[0359] 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.

[0360] • "Substituted or unsubstituted trialkylsilyl groups"

[0361] 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.

[0362] • "Substituted or unsubstituted aralkyl groups"

[0363] 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.

[0364] 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.

[0365] 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.

[0366] 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.

[0367] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0368]

[0369] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0370]

[0371] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0372] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0373]

[0374] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0375] 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.

[0376] • "Substituted or unsubstituted aryl groups"

[0377] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the 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.

[0378] • "Substituted or unsubstituted divalent heterocyclic groups"

[0379] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is 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.

[0380] • "Substituted or unsubstituted alkylene compounds"

[0381] Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived from "substituted or unsubstituted alkylene groups" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived from "substituted or unsubstituted alkylene groups" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0382] 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).

[0383]

[0384]

[0385] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10Each can be a hydrogen atom or a substituent independently.

[0386] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0387]

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

[0389] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

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

[0391]

[0392] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0393] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0394] 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).

[0395]

[0396]

[0397]

[0398] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0399]

[0400]

[0401]

[0402]

[0403] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0404] The above is an explanation of "substituents described in this specification".

[0405] • "Cases where bonds form rings"

[0406] 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".

[0407] 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.

[0408]

[0409] 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", a group consisting of two adjacent elements is referred to as 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.

[0410] The phrase "one or more groups" refers to the fact that two or more of the aforementioned 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 Q A 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).

[0411]

[0412] 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, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 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 .

[0413]

[0414] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B 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 QC Fusing 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.

[0415] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0416] 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.

[0417] 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.

[0418] 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.

[0419] "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.

[0420] 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.

[0421] 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.

[0422] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0423] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0424] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0425] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0426] In the case of “one or more groups consisting of two or more adjacent elements”, “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 elements are mutually bonded to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0427] 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.

[0428] 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.

[0429] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together" ("the case of forming a ring by bonding").

[0430] Substituents when described as "substituted or unsubstituted"

[0431] 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...

[0432] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0433] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0434] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0435] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0436] -Si(R 901 (R) 902 (R) 903 ),

[0437] -O-(R 904 ),

[0438] -S-(R 905 ),

[0439] -N(R 906 (R) 907 ),

[0440] Halogen atom, cyano group, nitro group,

[0441] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0442] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0443] Groups, etc., in the composition group

[0444] Here, R 901 ~R 907 Each independently

[0445] hydrogen atom,

[0446] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0447] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0448] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0449] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0450] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0451] In R902 When there are more than two, more than two R 902 They are the same or different.

[0452] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0453] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0454] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0455] In R 906 When there are more than two, more than two R 906 They are the same or different.

[0456] In R 907 When there are more than two, more than two R 907 They are the same or different.

[0457] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0458] Alkyl groups with 1 to 50 carbon atoms

[0459] Aryl groups with 6 to 50 carbon atoms and

[0460] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.

[0461] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0462] Alkyl groups having 1 to 18 carbon atoms

[0463] aryl groups with 6 to 18 carbon atoms and

[0464] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.

[0465] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0466] 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.

[0467] 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.

[0468] 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.

[0469] Compound of formula (I)

[0470] The compounds of the present invention are described below.

[0471] The compounds of the present invention are shown in formula (I) above. The symbols in formula (I) and the formulas described below are described below. Unless otherwise stated, the same symbols have the same meaning.

[0472] Hereinafter, the compounds of the present invention represented by formula (I) and those contained in formula (I) described below will sometimes be referred to simply as "compound (I) of the present invention".

[0473] In addition, the compound (I) of the present invention is sometimes simply referred to as "the compound of the present invention".

[0474] The first compound of the present invention (compound (I) of the present invention) is shown in the following formula (I).

[0475] (I)

[0476] In equation (I),

[0477] Ar1 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms;

[0478] Ar2 and Ar3 are each independently substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic formation;

[0479] L1 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;

[0480] Wherein, L1 is neither a substituted nor an unsubstituted para-phenylene;

[0481] L2 and L3 are each independently a single bond, 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 cyclic atoms.

[0482] In the definition of each substituent in formula (I), "unsubstituted" means that the hydrogen atom is not substituted by the substituent, and the hydrogen atom is a protium atom, a deuterium atom, or a tritium atom;

[0483] At least one of Ar1, Ar2, Ar3, L1, L2 and L3 contains a deuterium atom.

[0484] In one specific example, in formula (I), two or more of Ar1, Ar2, Ar3, L1, L2 and L3 contain deuterium atoms.

[0485] In another specific example, in formula (I), Ar1 can be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. More specifically, the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms can be a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. Preferably, the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms can be methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, or tert-butyl, but is not limited thereto.

[0486] In another specific example, in formula (I), Ar1 can be a substituted or unsubstituted aryl group having 6 to 30 cyclic carbons. More specifically, the substituted or unsubstituted aryl group having 6 to 30 cyclic carbons can be a substituted or unsubstituted aryl group having 6 to 20 cyclic carbons, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbons, a substituted or unsubstituted aryl group having 6 to 12 cyclic carbons, or a substituted or unsubstituted aryl group having 6 to 10 cyclic carbons. Preferably, the substituted or unsubstituted aryl group with 6 to 30 carbon atoms can be 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, or 9,9-diphenylfluorene, but is not limited thereto.

[0487] In another specific example, in formula (I), Ar1 can be a heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms. More specifically, the heterocyclic group with 5 to 30 substituted or unsubstituted cyclic atoms can be a heterocyclic group with 5 to 20 substituted or unsubstituted cyclic atoms, a heterocyclic group with 5 to 18 substituted or unsubstituted cyclic atoms, or a heterocyclic group with 5 to 13 substituted or unsubstituted cyclic atoms. The heterocyclic group can be an aromatic heterocyclic group. Preferably, the substituted or unsubstituted heterocyclic group with 5 to 30 cyclic atoms can be pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazoleyl (1-carbazoleyl, 2-carbazoleyl, 3-carbazoleyl, 4-carbazoleyl, or 9-carbazoleyl), benzocarbazoleyl, azacarbazoleyl, diazacarbazoleyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl. 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, or phenyldibenzothiophene, but not limited to these.

[0488] In another specific example, Ar1 in formula (I) can be phenyl, naphthyl, or biphenyl.

[0489] In another specific example, in formula (I), L1 is an unsubstituted arylene group with 6 to 20 cyclic carbon atoms, or an unsubstituted divalent heterocyclic group with 5 to 20 cyclic atoms.

[0490] In another specific example, in equation (I), Ar2 and Ar3 are each independently represented as shown in equations (1-a), (1-b), (1-c), (1-d), or (1-e) below.

[0491]

[0492] (In equation (1-a),

[0493] *21 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *21 is bonded to the central nitrogen atom.

[0494] 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;

[0495] R is not 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;

[0496] 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 aryl group having 6 to 12 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms;

[0497] u is 0 to 2, v is 0 or 1)

[0498]

[0499] (In equation (1-b),

[0500] *24 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *24 is bonded to the central nitrogen atom.

[0501] Selected from R 121 ~R 128 One of them is a single bond that bonds with *25;

[0502] R is not the single bond mentioned 121 ~R 128 Each of the following 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.

[0503]

[0504] (In equation (1-c),

[0505] *26 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *26 is bonded to the central nitrogen atom.

[0506] Selected from R 131 ~R 140 One of them is a single bond that bonds with *27;

[0507] R is not the single bond mentioned 131 ~R 140 Each of the following 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.

[0508]

[0509] (In equation (1-d),

[0510] *28 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *28 is bonded to the central nitrogen atom.

[0511] X 1 For oxygen atoms, sulfur atoms, -CR E R F or -NR G ;

[0512] p is 0 or 1;

[0513] When p is 0, it is selected from R 141 ~R 148 R E R F and R G One of them is a single bond that bonds with *29;

[0514] When p is 1 and X 1 For -CR E R F or -NR G At that time, R 145 and R 146 One of them, R 146 and R 147 One of them, or R 147 and R 148 One of them is a single bond bonded to *d, and the other is a single bond bonded to *e, selected from R that is not a single bond bonded to *d or *e. 145 ~R 148 R 141 ~R 144 R 200 ~R 203 R E R F and R G One of them is a single bond that bonds with *29;

[0515] When p is 1 and X 1 When R is an oxygen atom or a sulfur atom 145 and R 146 One of them, R 146 and R 147 One of them, or R 147 and R 148 One of them is a single bond bonded to *d, and the other is a single bond bonded to *e, selected from R 141 To R 144 One of them is a single bond that bonds with *29;

[0516] R is not the single bond mentioned 141 ~R 148 R is not the single bond mentioned above.200 ~R 203 and R which is not the single bond mentioned above E ~R G Each of the following groups is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 12 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms.

[0517]

[0518] (In equation (1-e),

[0519] *30 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *30 is bonded to the central nitrogen atom.

[0520] Selected from R 151 ~R 155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32;

[0521] R is not 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;

[0522] 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;

[0523] Selected from R which is not a hydrogen atom 161 To R 165 At least one pair of adjacent optional benzene rings are bonded together to form more than one unsubstituted benzene ring;

[0524] Selected from R which is not a hydrogen atom 171 To R 175 (At least one pair of adjacent benzene rings may be optionally bonded to each other to form more than one unsubstituted benzene ring.)

[0525] In one specific example, the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms mentioned in the definition of substituents in formulas (1-a) to (1-e) can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, or heptafluoropropyl, pentafluoroethyl, 2,2,2-trifluoroethyl, or trifluoromethyl.

[0526] In another specific example, the substituted or unsubstituted aryl group with 6 to 12 carbon atoms mentioned in the definition of substituents in formulas (1-a) to (1-e) can be phenyl, biphenyl or naphthyl.

[0527] In another specific example, the substituted or unsubstituted heterocyclic group with 5 to 13 cyclic atoms mentioned in the definition of substituents in formulas (1-a) to (1-e) can be dibenzofuranyl, dibenzothiophenyl, or carbazoyl.

[0528] In another specific example, the group of formula (1-a) may be as shown in any of the following formulas (1-a-1) to (1-a-4).

[0529]

[0530]

[0531]

[0532]

[0533] In equations (1-a-1) to (1-a-4), each symbol is defined as in equation (1-a).

[0534] In another specific example, the group of formula (1-a) can be selected from any of the groups consisting of the following formulas (for simplicity, the symbol R is omitted in the following formulas). 101 ~R 115 ).

[0535]

[0536] In another specific example, in equation (1-a), R is not the single bond described above. 101 ~R 110 and R 111 ~R 115 It can be a hydrogen atom.

[0537] In another specific example, in equation (1-b), R is not the single bond described above. 121 ~R 128 It can be a hydrogen atom.

[0538] In another specific example, in equation (1-c), R is not the single bond described above. 131 ~R 140 It can be a hydrogen atom.

[0539] In another specific example, the group represented by formula (1-d) is any one of the groups represented by formulas (1-d-1) to (1-d-4) below.

[0540]

[0541]

[0542]

[0543]

[0544] In equations (1-d-1) to (1-d-4), each symbol is defined as in equation (1-d).

[0545] In another specific example, in equation (1-d), R is not the single bond described above. 141 ~R 148 And R which is not the single bond mentioned above 200 ~R 203 It can be a hydrogen atom.

[0546] In another specific example, in equation (1-d), X 1 It can be an oxygen atom or a sulfur atom.

[0547] In another specific example, in equation (1-d), R is not the single bond described above. E ~R G It can be a hydrogen atom, a methyl group, or a phenyl group.

[0548] In another specific example, the group represented by formula (1-e) may be represented as any one of the following formulas (1-e-1) to (1-e-5).

[0549]

[0550]

[0551]

[0552]

[0553]

[0554] In equations (1-e-1) to (1-e-5), each symbol is defined as in equation (1-e).

[0555] In another specific example, in equation (1-e), R is not the single bond described above. 151 ~R 155 R 161 ~R 165 and R 171 ~R 175 It can be a hydrogen atom.

[0556] In another specific example, in equation (I), Ar2 is equation (1-a), and Ar3 is equation (1-a). In another specific example, in equation (I), Ar2 is equation (1-a), and Ar3 is equation (1-b). In another specific example, in equation (I), Ar2 is equation (1-a), and Ar3 is equation (1-c). In another specific example, in equation (I), Ar2 is equation (1-a), and Ar3 is equation (1-d). In another specific example, in equation (I), Ar2 is equation (1-a), and Ar3 is equation (1-e).

[0557] In another specific example, in equation (I), Ar2 is equation (1-b), and Ar3 is equation (1-a). In another specific example, in equation (I), Ar2 is equation (1-b), and Ar3 is equation (1-b). In another specific example, in equation (I), Ar2 is equation (1-b), and Ar3 is equation (1-c). In another specific example, in equation (I), Ar2 is equation (1-b), and Ar3 is equation (1-d). In another specific example, in equation (I), Ar2 is equation (1-b), and Ar3 is equation (1-e).

[0558] In another specific example, in equation (I), Ar2 is equation (1-c), and Ar3 is equation (1-a). In another specific example, in equation (I), Ar2 is equation (1-c), and Ar3 is equation (1-b). In another specific example, in equation (I), Ar2 is equation (1-c), and Ar3 is equation (1-c). In another specific example, in equation (I), Ar2 is equation (1-c), and Ar3 is equation (1-d). In another specific example, in equation (I), Ar2 is equation (1-c), and Ar3 is equation (1-e).

[0559] In another specific example, in equation (I), Ar2 is equation (1-d), and Ar3 is equation (1-a). In another specific example, in equation (I), Ar2 is equation (1-d), and Ar3 is equation (1-b). In another specific example, in equation (I), Ar2 is equation (1-d), and Ar3 is equation (1-c). In another specific example, in equation (I), Ar2 is equation (1-d), and Ar3 is equation (1-d). In another specific example, in equation (I), Ar2 is equation (1-d), and Ar3 is equation (1-e).

[0560] In another specific example, in equation (I), Ar2 is equation (1-e), and Ar3 is equation (1-a). In another specific example, in equation (I), Ar2 is equation (1-e), and Ar3 is equation (1-b). In another specific example, in equation (I), Ar2 is equation (1-e), and Ar3 is equation (1-c). In another specific example, in equation (I), Ar2 is equation (1-e), and Ar3 is equation (1-d). In another specific example, in equation (I), Ar2 is equation (1-e), and Ar3 is equation (1-e).

[0561] In another specific example, in formula (I), when L2 is a para-linked phenylene (i.e., 1,4-phenylene), Ar2 is not... (Including cases where the group is deuterated or not).

[0562] In another specific example, in formula (I), when L3 is a para-linked phenylene (i.e., 1,4-phenylene), Ar3 is not... (Including cases where the group is deuterated or not).

[0563] In another specific example, in equation (I), -L2-Ar2 and / or -L3-Ar3 are not Groups (including whether the group is deuterated or not).

[0564] In another specific example, in equation (I), Fiki ( It does not have any substituents other than Ar1.

[0565] In another specific example, in formula (I), two or more of L1, L2 and L3 contain deuterium atoms.

[0566] In another specific example, in formula (I), L1 and L2 contain deuterium atoms.

[0567] In another specific example, in formula (I), L1 and L3 contain deuterium atoms.

[0568] In another specific example, in formula (I), L2 and L3 contain deuterium atoms.

[0569] In another specific example, in formula (I), L1, L2 and L3 contain deuterium atoms.

[0570] In another specific example, in formula (I), L1 is an unsubstituted aryl group with 6 to 20 cyclic carbon atoms; L2 and L3 are each independently a single bond or an unsubstituted aryl group with 6 to 20 cyclic carbon atoms.

[0571] In another specific example, in formula (I), L1, L2 and L3 are each independently a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene, and in the case of substitution, the substituent is an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or an unsubstituted phenyl group.

[0572] In another specific example, in formula (I), L1 is an unsubstituted phenylene, an unsubstituted biphenylene (i.e., a divalent biphenyl), or an unsubstituted naphthylene.

[0573] In another specific example, in formula (I), L2 and L3 are each independently a single bond, an unsubstituted phenylene, an unsubstituted biphenylene, or an unsubstituted naphthylene.

[0574] In another specific example, in formula (I), Ar1 is an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted aryl group having 6 to 20 cyclic carbon atoms, or an unsubstituted heterocyclic group having 5 to 20 cyclic atoms; L1 is an unsubstituted arylene group having 6 to 20 cyclic carbon atoms; and L2 and L3 are each independently a single bond or an unsubstituted arylene group having 6 to 20 cyclic carbon atoms.

[0575] In another specific example, in the formula (I), Ar1 is an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted cyclic group having 6 to 12 carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 cyclic atoms.

[0576] In another specific example, in formula (I), Ar1 is an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, or an unsubstituted heterocyclic group having 5 to 12 cyclic atoms.

[0577] In another specific example, in formula (I), Ar1 is an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl.

[0578] In another specific example, in formula (I), Ar1 is an unsubstituted alkyl group having 1 to 12 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, or an unsubstituted heterocyclic group having 5 to 12 cyclic atoms; L1 is an unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted naphthylene group; and L2 and L3 are each independently a single bond, an unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted naphthylene group.

[0579] In another specific example, in formula (I), Ar1 is an unsubstituted phenyl, an unsubstituted biphenyl, or an unsubstituted naphthyl; L1 is an unsubstituted phenylene, an unsubstituted biphenylene, or an unsubstituted naphthylene; and L2 and L3 are each independently a single bond, an unsubstituted phenylene, an unsubstituted biphenylene, or an unsubstituted naphthylene.

[0580] As mentioned in the definition of formula (I) above, the case where L1 is a substituted or unsubstituted para-phenylene (i.e., L1 is a phenylene, and its adjacent phenanthrene group and nitrogen atom are attached to the para position of the phenylene) is not within the scope of this invention. Therefore, in the specific examples above, when L1 is a substituted or unsubstituted aryl group with 6 to 20 carbon atoms in a cyclic ring, or when L1 is a substituted or unsubstituted phenylene, the case where L1 is a substituted or unsubstituted para-phenylene is not within the scope of this invention. In one specific example, L1 can be a substituted or unsubstituted ortho-phenylene, or a substituted or unsubstituted meta-phenylene, more specifically, it can be an unsubstituted ortho-phenylene, or an unsubstituted meta-phenylene.

[0581] As stated above, the term "hydrogen atom" as used in this specification includes protium, deuterium, and tritium atoms. Therefore, the compounds of this invention may contain naturally occurring deuterium atoms.

[0582] Furthermore, by using a deuterated compound as part or all of the starting compound, deuterium atoms can be intentionally introduced into the compounds of the present invention. Therefore, in one aspect of the present invention, the compounds of the present invention contain at least one deuterium atom. That is, the compounds of the present invention are compounds represented by formula (I), and can be compounds in which at least one of the hydrogen atoms contained is a deuterium atom.

[0583] The deuteration rate of the compounds of the present invention depends on the deuteration rate of the raw material compounds used. Even when using raw materials with a certain deuteration rate, they may still contain a certain proportion of naturally occurring protium isotopes. Therefore, the deuteration rates of the compounds of the present invention shown below, compared to the proportions obtained by simply calculating the number of deuterium atoms shown in the chemical formula, include a proportion that takes into account trace amounts of naturally occurring isotopes.

[0584] The deuteration rate of the compound of the present invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and even more preferably 50% or more.

[0585] The compounds of the present invention can be deuterated forms in which all hydrogen atoms are deuterated atoms (i.e., the deuteration rate of the compounds of the present invention is 100%).

[0586] The compounds of the present invention can be mixtures comprising deuterated and non-deuterated compounds, or mixtures of two or more compounds with different deuteration rates. The deuteration rate of such mixtures is preferably 1% or more, more preferably 3% or more, further preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and less than 100%.

[0587] Furthermore, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the present invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more, and less than 100%.

[0588] The details of substituents (any substituents) expressed as “substituted or unsubstituted” in the above definitions are as described in “Substituents expressed as “substituted or unsubstituted””, unless otherwise stated.

[0589] There are no particular limitations on the preparation method of the compounds of the present invention. Those skilled in the art can easily prepare them by the methods described in the following examples, or by modifying the method with reference to known synthetic methods.

[0590] Specific examples of the compounds of the present invention are shown below, but the compounds of the present invention are not limited to the following exemplary compounds.

[0591] In the following specific examples, D represents a deuterium atom.

[0592] Exemplary compounds of formula (I)

[0593]

[0594]

[0595]

[0596]

[0597]

[0598]

[0599]

[0600]

[0601]

[0602]

[0603]

[0604]

[0605]

[0606]

[0607]

[0608]

[0609]

[0610]

[0611]

[0612]

[0613]

[0614]

[0615]

[0616]

[0617]

[0618]

[0619]

[0620]

[0621]

[0622]

[0623]

[0624]

[0625]

[0626]

[0627]

[0628]

[0629]

[0630]

[0631]

[0632]

[0633]

[0634]

[0635]

[0636]

[0637]

[0638]

[0639]

[0640]

[0641]

[0642]

[0643]

[0644]

[0645]

[0646]

[0647]

[0648]

[0649]

[0650]

[0651]

[0652]

[0653]

[0654]

[0655]

[0656]

[0657]

[0658]

[0659]

[0660]

[0661]

[0662]

[0663]

[0664]

[0665]

[0666]

[0667]

[0668]

[0669]

[0670]

[0671]

[0672]

[0673]

[0674]

[0675]

[0676]

[0677]

[0678]

[0679]

[0680]

[0681]

[0682]

[0683]

[0684]

[0685]

[0686]

[0687]

[0688]

[0689]

[0690]

[0691]

[0692]

[0693]

[0694]

[0695]

[0696]

[0697]

[0698] Materials for organic EL elements

[0699] The material for an organic EL element according to one aspect of the present invention preferably comprises the compound of the present invention.

[0700] The content of the compound of the present invention in the material used for organic EL elements 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 material for organic EL elements, as one aspect of the present invention, can be used to manufacture organic EL elements.

[0701] The hole transport layer material of one aspect of the present invention preferably comprises the compound of the present invention.

[0702] In one aspect of the invention, the compounds of the invention can also be used in hole injection layer materials.

[0703] In one aspect of the invention, the material for the organic EL element preferably further comprises a protium form of the compound of the invention. The protium form refers to a compound of the invention in which all hydrogen atoms are protium atoms.

[0704] The molar ratio of the compound of the present invention to the protium body of the compound of the present invention (compound of the present invention: protium body) is preferably 10:90 to 90:10, more preferably 20:80 to 80:20, further preferably 30:70 to 70:30, and particularly preferably 40:60 to 60:40.

[0705] Organic EL components

[0706] An organic EL element as an aspect of the present invention includes an anode, a cathode, and an organic layer consisting of a single layer or multiple layers located between the anode and the cathode, the organic layer including a light-emitting layer, and at least one of the organic layers containing a compound of the present invention.

[0707] Examples of organic layers comprising the compounds of the present invention may include, but are not limited to: 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. The compounds of the present invention are preferably used as materials for hole transport regions or light-emitting layers in fluorescent or phosphorescent EL elements, more preferably as materials for hole transport regions, even more preferably as materials for hole injection layers, hole transport layers, electron blocking layers, or exciton blocking layers, and particularly preferably as materials for hole injection layers or hole transport layers.

[0708] As an aspect of the present invention, the organic EL element can be a fluorescent or phosphorescent monochromatic light-emitting element, a fluorescent / phosphorescent hybrid white light-emitting element, a simple element having a single light-emitting unit, or a series-connected element having multiple light-emitting units, wherein a fluorescent light-emitting element is preferred. Here, "light-emitting unit" refers to the smallest unit comprising an organic layer (at least one of which is a light-emitting layer) and emitting light through recombination of injected holes and electrons.

[0709] For example, the following are representative element structures for simple organic EL elements.

[0710] (1) Anode / Light-emitting unit / Cathode

[0711] Furthermore, the light-emitting unit can be a multilayer type with multiple phosphorescent or fluorescent light-emitting layers. In this case, spacer layers can be provided between the light-emitting layers to prevent excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer. The following lists representative layer structures of simple light-emitting units. The layers in parentheses are arbitrary.

[0712] (a)(hole injection layer / )hole transport layer / fluorescent layer / electron transport layer( / electron injection layer)

[0713] (b) (Hole injection layer / ) Hole transport layer / First fluorescent emissive layer / Second fluorescent emissive layer / Electron transport layer ( / Electron injection layer)

[0714] (c)(Hole injection layer / )Hole transport layer / phosphorescent layer / spacer layer / fluorescent layer / electron transport layer( / electron injection layer)

[0715] (d)(Hole injection layer / )Hole transport layer / First phosphorescent layer / Second phosphorescent layer / Spacer layer / Fluorescent layer / Electron transport layer( / Electron injection layer)

[0716] (e)(hole injection layer / )hole transport layer / phosphorescent layer / spacer layer / first fluorescent layer / second fluorescent layer / electron transport layer ( / electron injection layer)

[0717] (f)(hole injection layer / )hole transport layer / electron blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0718] (g)(hole injection layer / )hole transport layer / exciton blocking layer / fluorescent layer / electron transport layer( / electron injection layer)

[0719] (h)(Hole Injection Layer / )First Hole Transport Layer / Second Hole Transport Layer / Fluorescent Layer / Electron Transport Layer( / Electron Injection Layer)

[0720] (h1)(hole injection layer / ) first hole transport layer / second hole transport layer / third hole transport layer / fluorescent layer / electron transport layer( / electron injection layer).

[0721] (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)

[0722] (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)

[0723] (j)(hole injection layer / )hole transport layer / fluorescent layer / hole blocking layer / electron transport layer( / electron injection layer)

[0724] (k)(hole injection layer / )hole transport layer / fluorescent layer / exciton blocking layer / electron transport layer( / electron injection layer)

[0725] Each phosphorescent or fluorescent emitting layer can exhibit a different emitting color. Specifically, for the emitting unit (d), the following layer structure can be described: (hole injection layer / ) hole transport layer / first phosphorescent emitting layer (red emitting) / second phosphorescent emitting layer (green emitting) / spacer layer / fluorescent emitting layer (blue emitting) / electron transport layer.

[0726] On the other hand, electron blocking layers can be appropriately placed between each light-emitting layer and the hole transport layer or spacer layer. Additionally, hole blocking layers can also be appropriately placed between each light-emitting layer and the electron transport layer. By placing electron blocking layers or hole blocking layers, electrons or holes can be confined within the light-emitting layer, thereby increasing the probability of charge recombination within the light-emitting layer and improving luminous efficiency.

[0727] The following are representative element structures that serve as examples of tandem organic EL elements.

[0728] (2) Anode / First Light-Emitting Unit / Intermediate Layer / Second Light-Emitting Unit / Cathode

[0729] Here, the first light-emitting unit and the second light-emitting unit can each be independently selected from the aforementioned light-emitting units.

[0730] The intermediate layer, also commonly referred to as the intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connecting layer, or intermediate insulating layer, can be composed of known materials that provide electrons to the first light-emitting unit and holes to the second light-emitting unit.

[0731] Furthermore, when the hole transport layer is a multilayer structure comprising two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure, such as the second hole transport layer in a two-layer structure or the third hole transport layer in a three-layer structure, can be used as an electron blocking layer. That is, when the hole transport layer is a multilayer structure comprising two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure can be used as an electron blocking layer.

[0732] Figure 1 This is a simplified diagram illustrating an example of the structure of the organic EL element of the present invention. The organic EL element 1 includes 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) may be provided on the anode 3 side of the light-emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light-emitting layer 5. As a result, electrons or holes can be confined within the light-emitting layer 5, thereby improving the exciton generation efficiency in the light-emitting layer 5.

[0733] Figure 2 This is a simplified diagram illustrating another structure of the organic EL element of the present invention. The organic EL element 11 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. 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.

[0734] Figure 3 This is a simplified diagram illustrating another structure of the organic EL element 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.

[0735] exist Figures 1 to 3 In this process, the light-emitting layer 5 includes at least one light-emitting layer. The light-emitting layer 5 can be a single layer or can include multiple layers (e.g., multiple light-emitting layers, multiple light-emitting layers and a space layer).

[0736] On the other hand, in this invention, the substrate combined with a fluorescent dopant material (fluorescent emitting material) is called a fluorescent substrate, and the substrate combined with a phosphorescent dopant material is called a phosphorescent substrate. The difference between a fluorescent substrate and a phosphorescent substrate lies not only in their molecular structure. That is, a phosphorescent substrate refers to a material that forms a phosphorescent emitting layer containing a phosphorescent dopant, but this does not mean that the material cannot be used to form a fluorescent emitting layer. The same applies to fluorescent substrates.

[0737] substrate

[0738] The substrate serves as a support for the organic EL element. For example, substrates made of glass, quartz, or plastic can be used. Flexible substrates can also be used. Examples of flexible substrates include plastic substrates selected from the group consisting of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Furthermore, inorganic vapor-deposited films can also be used.

[0739] anode

[0740] For the anode formed on the substrate, metals, alloys, conductive compounds, and mixtures thereof with a high work function (specifically 4.0 eV or higher) are preferred. Specifically, examples 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. Furthermore, 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 above metals (e.g., titanium nitride).

[0741] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1–10 wt% zinc oxide relative to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5–5 wt% tungsten oxide and 0.1–1 wt% zinc oxide relative to indium oxide. Alternatively, they can be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, etc.

[0742] Hole transport region

[0743] As described above, the organic layer may include a hole transport region between the anode and the light-emitting layer. The hole transport region is preferably composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. The hole transport region preferably contains the compound of the present invention. Preferably, at least one of these layers constituting the hole transport region contains the compound of the present invention; more preferably, the hole transport layer contains the compound of the present invention.

[0744] The hole injection layer formed in contact with the anode is formed using materials that are independent of the work function of the anode and are easy to inject holes. Therefore, materials commonly used as electrode materials can be used (e.g., metals, alloys, conductive compounds and mixtures thereof, elements belonging to Group 1 or Group 2 of the periodic table).

[0745] Elements belonging to Group 1 or Group 2 of the periodic table can also be used. These elements are materials with low work functions, namely alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and their alloys (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb) and their alloys. On the other hand, 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.

[0746] Hole injection layer

[0747] The hole injection layer is a layer containing a material with high hole injection properties (hole injection material) and is formed between the anode and the light-emitting layer, or, if a hole transport layer is present, it is formed between the hole transport layer and the anode.

[0748] In addition to the compounds of this invention, 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.

[0749] 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 (DNT), all of which are low-molecular-weight organic compounds. Aromatic amine compounds such as PD), 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).

[0750] Polymers (oligomers, dendrimers, 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.

[0751] In addition, acceptor materials such as hexaazabenzophenanthrene (HAT) compounds represented by the following formula (K) are preferred.

[0752]

[0753] (In the above equation (K), R) 221 ~R 226 Each can independently represent a cyano group, -CONH2, a carboxyl group, or -COOR. 227 (R 227 (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... 221 and R 222 R 223 and R 224 and R 225 and R 226 Two adjacent groups can bond with each other to form a group represented by -CO-O-CO-.

[0754] As R 227 Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, and cyclohexyl.

[0755] Hole transport layer

[0756] The 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, if a hole injection layer is present, formed between the hole injection layer and the light-emitting layer. The compounds of this invention can be used alone or in combination with the following compounds in the hole transport layer.

[0757] The hole transport layer can be a single-layer structure or a multi-layer structure comprising two or more layers. For example, the hole transport layer can also be a two-layer structure comprising a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport region can also include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. Alternatively, the hole transport layer can also 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 also be disposed between the second hole transport layer and the light-emitting layer.

[0758] In one aspect of the invention, the hole transport layer of the single-layer structure is preferably adjacent to the light-emitting layer. Furthermore, in the multilayer structure, the hole transport layer closest to the cathode (e.g., the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure) is preferably adjacent to the light-emitting layer. In one example, the light-emitting layer may be in direct contact with the second hole transport layer.

[0759] In another aspect of the invention, the electron blocking layer, etc., described later, may be positioned between the hole transport layer and the light-emitting layer of the single-layer structure, or between the hole transport layer and the light-emitting layer closest to the light-emitting layer in the multilayer structure. Furthermore, as described above, when the hole transport layer is a multilayer structure comprising two or more hole transport layers, the hole transport layer adjacent to the light-emitting layer in the multilayer structure may also be used as an electron blocking layer.

[0760] In one embodiment of the organic electroluminescent element of the present invention, one of the first hole transport layer and the second hole transport layer contains the compound of the present invention, or both contain the compound of the present invention. Specifically, in the two-layer hole transport layer structure, the compound of the present invention may be contained in either the first hole transport layer or the second hole transport layer, or simultaneously in both. In another embodiment, at least one of the first to third hole transport layers contains the compound of the present invention. Specifically, when the hole transport layer is a three-layer structure, the compound of the present invention may be contained in only one of the first to third hole transport layers, or in any two of them, or in all of them.

[0761] In one aspect of the invention, the second hole transport layer preferably comprises the compound of the present invention. Specifically, preferably, the compound of the present invention is contained only in the second hole transport layer, or the compound of the present invention is contained in both the first hole transport layer and the second hole transport layer.

[0762] In one aspect of the invention, from the perspective of manufacturing cost, the inventive compound contained in one or both of the first hole transport layer and the second hole transport layer, or contained in at least one of the first hole transport layer to the third hole transport layer, can be protium.

[0763] The term "protium" refers to the compound of the present invention in which all hydrogen atoms are protium atoms.

[0764] Therefore, the present invention includes an organic EL element comprising a compound of the present invention consisting substantially only of protium in one or both of the first and second hole transport layers, or in at least one of the first to third hole transport layers. "A compound of the present invention consisting substantially only of protium" means that the protium content relative to the total amount of the compound of the present invention is 90 mol percent or more, preferably 95 mol percent or more, and more preferably 99 mol percent or more (all including 100%).

[0765] In addition to the compounds of this invention, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used as hole transport layer materials.

[0766] Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethyl]biphenylamino]triphenylamine (BAFLP). The compounds are: 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 hole mobility of these compounds is 10. -6 cm 2 / Vs and above.

[0767] 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).

[0768] 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).

[0769] Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) or poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[0770] Other compounds besides those mentioned above can also be used, as long as the hole transport property of the compound is higher than that of the electron transport property.

[0771] In one aspect of the organic EL element of the present invention, the first hole transport layer comprises a compound represented by formula (21) or formula (22).

[0772]

[0773] In equations (21) and (22) above,

[0774] 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.

[0775] k is 1, 2, 3, or 4.

[0776] 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.

[0777] When k is 2, 3, or 4, multiple L E2 They are the same or different.

[0778] When k is 2, 3, or 4, multiple L E2 They may bond together to form substituted or unsubstituted monocyclic rings, or they may bond together to form substituted or unsubstituted fused rings, or they may not bond together.

[0779] L does not form the single ring and does not form the 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.

[0780] A 1 B 1 C 1 A 2 B 2 C 2 and D 2Each 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 ),

[0781] 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.

[0782] In R' 901 When there are multiple R's, multiple R's 901 They are the same or different.

[0783] In R' 902 When there are multiple R's, multiple R's 902 They are the same or different.

[0784] In R' 903 When there are multiple R's, multiple R's 903 They are the same or different.

[0785] In addition, the first hole transport layer may contain one compound represented by formula (21) and formula (22), or may contain multiple compounds represented by formula (21) and formula (22).

[0786] Preferably, in equations (21) and (22), 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 carbazoyl.

[0787] Furthermore, more preferably, A in equation (21) 1 B 1 and C 1 At least one of them and A in equation (22) 2 B 2 C 2 and D 2At least one of them is a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl or a substituted or unsubstituted carbazoyl.

[0788] A 1 B 1 C 1 A 2 B 2 C 2 and D 2 The preferred fluorenyl group may have a substituent at the 9-position, for example, it may be 9,9-dimethylfluorenyl or 9,9-diphenylfluorenyl. Alternatively, the substituent at the 9-position may form a ring, for example, a fluorenyl skeleton or a zeolite skeleton.

[0789] 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.

[0790] Specific examples of the compounds shown in formulas (21) and (22) may include, for example, the following compounds.

[0791]

[0792] dopant material of the light-emitting layer

[0793] The luminescent layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, fluorescent or phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, while phosphorescent materials are compounds that emit light from a triplet excited state.

[0794] In one aspect of the organic EL element of the present invention, the light-emitting layer is preferably a single layer.

[0795] In another aspect of the organic EL element of the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

[0796] As blue fluorescent materials that can be used in the luminescent layer, pyrene derivatives, styrylamine derivatives, phenylene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. Specifically, examples include N,N'-bis[4-(9H-carbazole-9-yl)phenyl]-N,N'-diphenylstilbene-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 PCPAPA).

[0797] 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.

[0798] 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).

[0799] In one aspect of the invention, the light-emitting layer preferably comprises a fluorescent light-emitting material (fluorescent dopant material).

[0800] As blue phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are employed. 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).

[0801] As a green phosphorescent material that can be used in the luminescent layer, iridium complexes are 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)).

[0802] As red-based phosphorescent materials that can be used in the luminescent layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are employed. Specifically, examples include 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).

[0803] 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).

[0804] The main material of the light-emitting layer

[0805] The light-emitting layer can be constructed by dispersing the aforementioned dopant material in other materials (the host material). Preferably, a material with a higher lowest unoccupied molecular orbital energy level (LUMO level) and a lower highest occupied molecular orbital energy level (HOMO level) than the dopant material is used.

[0806] As the main material, for example, the following compounds can be used:

[0807] (1) Metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes,

[0808] (2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives.

[0809] (3) Fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or β-carbazole derivatives.

[0810] (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives.

[0811] For example, the following compounds can be used:

[0812] 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), bis[2-(2-benzothiazolyl)phenol]zinc(II) (abbreviated as ZnBTZ) and other metal complexes;

[0813] 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);

[0814] 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'-(stilbene-3,3'-diyl)phenanthrene (DPNS), 9,9'-(stilbene-4,4'-diyl)phenanthrene (DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene (DPAnth), and 6,12-dimethoxy-5,11-diphenylanthracene; and others; and

[0815] 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. A variety of host materials can be employed.

[0816] In particular, in the case of blue fluorescent elements, the following anthracene compounds are preferred as the host material.

[0817]

[0818]

[0819]

[0820]

[0821] In one aspect of the organic EL element of the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the component constituting the second light-emitting layer. For example, cases can be given where the dopant material contained in the first light-emitting layer is different from the dopant material contained in the second light-emitting layer, or cases can be given where the host material contained in the first light-emitting layer is different from the host material contained in the second light-emitting layer.

[0822] In the organic EL element of the present invention, the light-emitting layer may also contain a luminescent compound that exhibits fluorescence emission with a main peak wavelength of less than 500 nm.

[0823] The method for measuring the main peak wavelength of a compound is as follows: Prepare a 5 μmol / L toluene solution of the compound to be tested, place it in a quartz dish, and measure the emission spectrum of the sample at room temperature (300 K) (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a fluorescence spectrophotometer (equipment name: F-7000) manufactured by Hitachi Advanced Technology Co., Ltd. However, the emission spectrum measurement device is not limited to the device used herein.

[0824] In a emission spectrum, the peak wavelength of the emission spectrum with the highest emission intensity is called the main peak wavelength. On the other hand, in this specification, the main peak wavelength is sometimes also referred to as the fluorescence emission main peak wavelength (FL-peak).

[0825] The luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm can be either the dopant material or the host material.

[0826] When the light-emitting layer is a single layer, only one of the dopant material and the host material can be a luminescent compound exhibiting fluorescence emission with a main peak wavelength below 500 nm, or both can be luminescent compounds exhibiting fluorescence emission with a main peak wavelength below 500 nm.

[0827] Furthermore, when the luminescent layer includes 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 below 500 nm, or both luminescent layers may contain luminescent compounds exhibiting fluorescence with a main peak wavelength below 500 nm. When the first luminescent layer contains a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm, 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 below 500 nm, or both may be luminescent compounds exhibiting fluorescence with a main peak wavelength below 500 nm. Similarly, when the second luminescent layer contains a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm, only one of the dopant material and the host material contained in the second luminescent layer may be a luminescent compound exhibiting fluorescence with a main peak wavelength below 500 nm, or both materials may be luminescent compounds exhibiting fluorescence with a main peak wavelength below 500 nm.

[0828] Electron transport layer

[0829] The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light-emitting layer and the cathode, or, if an electron injection layer is present, it is formed between the electron injection layer and the light-emitting layer.

[0830] The electron transport layer can be a single-layer structure or a multi-layer structure comprising two or more layers. For example, the electron transport layer can be a bilayer structure comprising 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. Furthermore, in the multi-layer structure, the electron transport layer closest to the anode, such as the first electron transport layer in the bilayer structure, is preferably adjacent to the light-emitting layer. In another aspect of the invention, a hole-blocking layer, etc., as described later, may be placed between the electron transport layer and the light-emitting layer of the single-layer structure, or between the electron transport layer closest to the light-emitting layer and the light-emitting layer in the multi-layer structure.

[0831] In the electron transport layer, for example, the following compounds can be used:

[0832] (1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes.

[0833] (2) Imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, phenanthroline derivatives, and other heteroaromatic compounds.

[0834] (3) Polymer compounds.

[0835] 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).

[0836] 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)stilbene (abbreviated as BzOs).

[0837] 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).

[0838] The material has a content of 10 -6 cm 2 Materials with an electron mobility of / Vs or higher. On the other hand, materials other than those mentioned above can also be used in the electron transport layer, as long as the electron transport property is higher than the hole transport property. 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 has 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.

[0839] Electron injection layer

[0840] The electron injection layer is a layer containing materials with high electron injection capability. 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 can be used in the electron injection layer. Examples of such compounds include alkali metal oxides, alkali metal halides, organic complexes containing alkali metals such as (8-hydroxyquinoline)lithium (Liq), alkaline earth metal oxides, alkaline earth metal halides, organic complexes containing alkaline earth metals, rare earth metal oxides, rare earth metal halides, and organic complexes containing rare earth metals. Furthermore, multiple mixtures of these compounds can be used.

[0841] Furthermore, alkali metals, alkaline earth metals, or compounds containing them can be used as materials with electron transport properties; specifically, materials containing magnesium (Mg) in Alq can also be used. On the other hand, in this case, electron injection from the cathode can be performed more efficiently.

[0842] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. This composite material exhibits excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that exhibits excellent transport properties for the received electrons; specifically, materials constituting the aforementioned electron transport layer (e.g., metal complexes or heteroaromatic compounds) can be used. As the electron donor, any material that has electron-donating properties to the organic compound is acceptable. 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 or 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.

[0843] cathode

[0844] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with a low work function (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) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr) and their alloys (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb) and their alloys.

[0845] On the other hand, when using alkali metals, alkaline earth metals, and alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[0846] On the other hand, by setting an electron injection layer, various conductive materials such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide can be used to form the cathode, regardless of their work function. These conductive materials can be deposited using sputtering, inkjet printing, spin coating, or other methods.

[0847] Insulation layer

[0848] Organic EL elements are prone to pixel defects caused by leakage or short circuits due to the application of an electric field to the ultrathin film. To prevent this, an insulating layer consisting of an insulating thin film can be inserted between a pair of electrodes.

[0849] Examples of materials used in the insulating layer include aluminum oxide, 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. Alternatively, mixtures or laminates of these materials may also be used.

[0850] Spacer layer

[0851] The spacer layer, for example, is disposed between the fluorescent emitting layer and the phosphorescent emitting layer. Its purpose is to prevent excitons generated in the phosphorescent emitting layer from diffusing into the fluorescent emitting layer when the fluorescent emitting layer and the phosphorescent emitting layer are stacked, or to regulate the carrier balance. Alternatively, the spacer layer may also be disposed between multiple phosphorescent emitting layers.

[0852] Since the spacer layer is disposed between the light-emitting layers, it is preferably made of a material that simultaneously possesses 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. The same materials used in the spacer layer as those used in the aforementioned hole transport layer can be cited as examples.

[0853] Barrier layer

[0854] Electron blocking layers, hole blocking layers, exciton blocking layers, and other blocking layers can 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 into surrounding layers, thus confining the excitons within the light-emitting layer.

[0855] The layers of the organic EL element can be formed using existing known methods such as vapor deposition and coating. For example, they can be formed using known methods, such as vapor deposition, vacuum vapor deposition, molecular beam epitaxy (MBE), etc.; or coating methods using solutions of compounds for forming the layers, such as dip coating, spin coating, casting, rod coating, roll coating, etc.

[0856] There are no particular restrictions on the thickness of each layer, but 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 higher driving voltage is required, which leads to reduced efficiency. Therefore, the film thickness is usually 5nm to 10μm, and more preferably 10nm to 0.2μm.

[0857] In the organic EL element with a hole transport layer of the present invention, the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is preferably 30 nm to 150 nm, more preferably 40 nm to 130 nm.

[0858] Further, in one aspect of the organic EL device of the present invention, the thickness of the second hole transport layer is preferably 5 nm or more and preferably 100 nm or less.

[0859] Further, in one aspect of the organic EL device of the present invention, the thickness of the hole transport layer adjacent to the light emitting layer is preferably 5 nm or more and preferably 100 nm or less.

[0860] Further, in one aspect of the organic EL device 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 relational expression 0.3 < D2 / D1 < 4.0. Preferably, the relational expression 0.5 < D2 / D1 < 3.5 is satisfied, and more preferably, the relational expression 0.75 < D2 / D1 < 3.0 is satisfied.

[0861] Preferred embodiments of the organic EL device of the present invention may include, for example, the following embodiments:

[0862] For an organic EL device having a hole transport layer with a two-layer structure,

[0863] · First embodiment: 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;

[0864] · Second embodiment: Both the first hole transport layer and the second hole transport layer contain the compound of the present invention;

[0865] · Third embodiment: 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;

[0866] For an organic EL device having a hole transport layer with a three-layer structure,

[0867] · Fourth embodiment: 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;

[0868] · Fifth embodiment: 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;

[0869] · Sixth embodiment: 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;

[0870] · Seventh embodiment: The first and second hole transport layers contain the compound of the present invention, and the third hole transport layer does not contain the compound of the present invention;

[0871] · Eighth embodiment: The first and third hole transport layers contain the compound of the present invention, and the second hole transport layer does not contain the compound of the present invention;

[0872] • Ninth embodiment: The second hole transport layer and the third hole transport layer contain the compound of the present invention, while the first hole transport layer does not contain the compound of the present invention;

[0873] • Tenth embodiment: The first hole transport layer to the third hole transport layer all contain the compound of the present invention, etc.

[0874] electronic devices

[0875] The organic EL element can be used in electronic devices, such as display components like organic EL panel modules, display devices like televisions, mobile phones, and personal computers, as well as light-emitting devices like lighting and vehicle lamps.

[0876] Therefore, an electronic device according to one embodiment includes the organic electroluminescent element.

[0877] Example

[0878] The present invention will be described in more detail below through embodiments, but the present invention is not limited to the following embodiments.

[0879] The compounds of formula (I) used in the manufacture of the organic EL elements of Examples 1 to 10 are shown below.

[0880]

[0881]

[0882]

[0883]

[0884]

[0885] The comparative compounds used in the manufacture of the organic EL elements of Comparative Examples 1 to 5 are shown below.

[0886]

[0887]

[0888]

[0889] Other compounds used in the manufacture of the organic EL elements of Examples 1 to 10 and Comparative Examples 1 to 5 are shown below.

[0890]

[0891]

[0892]

[0893] <Manufacturing of Organic EL Components>

[0894] The fabrication and evaluation of organic EL components are as follows.

[0895] Example 1

[0896] A glass substrate (manufactured by Geomatec Corporation) with an ITO transparent electrode (anode) attached, measuring 25mm × 75mm × 1.1mm, was ultrasonically cleaned in isopropanol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The ITO film thickness was 130nm.

[0897] The cleaned glass substrate with the ITO transparent electrode attached was mounted on the substrate holder of the vacuum evaporation apparatus. First, compound HT-1 and compound HA were co-deposited on the side where the transparent electrode was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 to compound HA was 97:3.

[0898] Next, compound HT-1 is deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm.

[0899] Next, compound Inv-1 is deposited on the first hole transport layer to form a second hole transport layer with a thickness of 10 nm.

[0900] Next, compounds BH-1 and BD-1 were co-deposited on the second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The mass ratio of compound BH-1 to compound BD-1 (BH-1:BD-1) was 96:4.

[0901] Next, compound ET-1 is deposited on the above-mentioned light-emitting layer to form a first electron transport layer with a thickness of 5 nm.

[0902] Next, compounds ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer with a thickness of 20 nm. The mass ratio of compound ET-2 to Liq (ET-2:Liq) was 50:50. Liq is an abbreviation for (8-hydroxyquinoline) lithium.

[0903] Next, LiF is deposited on the second electron transport layer to form an electron injection electrode with a film thickness of 1 nm.

[0904] Furthermore, Al metal is deposited on the aforementioned electron-injecting electrode to form a metal cathode with a film thickness of 50 nm.

[0905] The following is a brief description of the structure of the organic EL element in Example 1.

[0906] ITO(130) / HT-1:HA=97:3(10) / HT-1(80) / Inv-1(10) / BH-1:BD-1=96:4(25) / ET-1(5) / ET-2:Liq=50:50(20) / LiF(1) / Al(50)

[0907] In the above component structures, the numbers in parentheses represent film thickness (nm), and the ratios represent the mass ratio of the compounds used.

[0908] Examples 2 to 10

[0909] The organic EL elements of Examples 2 to 10 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of compound Inv-1 in Example 1.

[0910] Comparative Examples 1 to 5

[0911] The organic EL elements of Comparative Examples 1 to 5 were manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of compound Inv-1 in Example 1.

[0912] Evaluation of Organic EL Components

[0913] The manufactured organic EL devices were evaluated as follows. The evaluation results are shown in Table 1.

[0914] Measurement of 95% lifespan (LT95)

[0915] A voltage is applied to the organic EL element such that the current density is 50 mA / cm². 2 And a 95% lifetime (LT95) assessment is performed. Here, LT95 refers to the time (in hours) required for the brightness to drop to 95% of the initial brightness under constant current drive.

[0916] External quantum efficiency (EQE)

[0917] For organic EL devices, at room temperature, a spectroradiometer (Konica Minolta CS-1000) was used to measure the current density when a voltage was applied to the device to achieve a current density of 10 mA / cm². 2 The spectroradiance spectrum obtained at that time. Based on the obtained spectroradiance spectrum, assuming that Lambertian radiation was performed, the external quantum efficiency (EQE, %) was obtained.

[0918] Table 1

[0919]

[0920] As can be seen from the results in Table 1, compared with organic EL elements containing any one of the comparative compounds Ref-1 to Ref-5, organic EL elements containing any one of the compounds of the present invention Inv-1 to Inv-10 have a longer lifetime of 95% and a better external quantum efficiency.

[0921] Synthesis of Second Hole Transport Layer Compounds

[0922] Synthesis Example 1: Synthesis of Compound Inv-1

[0923]

[0924] Raw material 1: 9-(3-bromophenyl)-10-phenylphenanthrene (4.09 g, 10 mmol)

[0925] Raw material 2: N-([1,1'-biphenyl]-4-yl-2,3,5,6-d4)-[1,1':4',1''-terphenyl]-2,3,5,6-d4-4-amine (4.06 g, 10 mmol)

[0926] Catalyst: Tris(dibenzylacetone)dipalladium(0) (0.183 g, 0.2 mmol)

[0927] Ligand: tert-butylphosphine tetrafluoroborate (0.232 g, 0.8 mmol)

[0928] Base: Sodium tert-butoxide (1.44 g, 15 mmol)

[0929] Solvent: Xylene (50 mL)

[0930] The mixture of the above components was refluxed at boiling point for 3 hours. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to give 4.62 g of a white solid. The yield was 63%. Mass spectrometry analysis confirmed that the obtained substance was compound Inv-1, with a molecular weight of 733.98 and m / e = 734.

[0931] Synthetic Examples 2 to 10: Synthesis of Compounds Inv-2 to Inv-10

[0932] Except that raw materials 1 and 2 in Synthesis Example 1 were replaced with the compounds shown in Table 2 below, compounds Inv-2 to Inv-10 were synthesized in the same manner as in Synthesis Example 1.

[0933] Table 2

[0934]

[0935]

[0936]

[0937] Explanation of reference numerals in the attached figures

[0938] 1, 11, 12: Organic EL element; 2: Substrate; 3: Anode; 4: Cathode; 5: Light-emitting layer; 6: Hole transport region (hole transport layer); 6a: Hole injection layer; 6b: First hole transport layer; 6c: Second hole transport layer; 6d: Third hole transport layer; 7: Electron transport region (electron transport layer); 7a: First electron transport layer; 7b: Second electron transport layer; 10, 20, 30: Light-emitting unit.

Claims

1. A compound, which is represented by the following formula (I): (I) In equation (I), Ar1 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms; Ar2 and Ar3 are each independently substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in a cyclic formation; L1 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; in, L1 is neither a substituted nor an unsubstituted para-phenylene; L2 and L3 are each independently a single bond, 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 cyclic atoms. In the definition of each substituent in formula (I), "unsubstituted" means that the hydrogen atom is not substituted by the substituent, and the hydrogen atom is a protium atom, a deuterium atom, or a tritium atom; At least one of Ar1, Ar2, Ar3, L1, L2 and L3 contains a deuterium atom.

2. The compound according to claim 1, wherein, Two or more of Ar1, Ar2, Ar3, L1, L2 and L3 contain deuterium atoms.

3. The compound according to claim 1, wherein, L1 is an unsubstituted aryl group with 6 to 20 carbon atoms in the cyclic ring, or an unsubstituted divalent heterocyclic group with 5 to 20 carbon atoms in the cyclic ring.

4. The compound according to claim 1, wherein, Ar2 and Ar3 are each independently represented as shown in equations (1-a), (1-b), (1-c), (1-d), or (1-e) below: In equation (1-a), *21 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *21 is bonded to the central nitrogen atom. 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; R is not 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; 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 aryl group having 6 to 12 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms; u is between 0 and 2, and v is 0 or 1. In equation (1-b), *24 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *24 is bonded to the central nitrogen atom. Selected from R 121 ~R 128 One of them is a single bond that bonds with *25; R is not 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. In equation (1-c), *26 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *26 is bonded to the central nitrogen atom. Selected from R 131 ~R 140 One of them is a single bond that bonds with *27; R is not 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. In equation (1-d), *28 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *28 is bonded to the central nitrogen atom. X 1 For oxygen atoms, sulfur atoms, -CR E R F or -NR G ; p is 0 or 1; When p is 0, it is selected from R 141 ~R 148 R E R F and R G One of them is a single bond that bonds with *29; When p is 1 and X 1 For -CR E R F or -NR G At that time, R 145 and R 146 One of them, R 146 and R 147 One of them, or R 147 and R 148 One of them is a single bond bonded to *d, and the other is a single bond bonded to *e, selected from R that is not a single bond bonded to *d or *e. 145 ~R 148 R 141 ~R 144 R 200 ~R 203 R E R F and R G One of them is a single bond that bonds with *29; When p is 1 and X 1 When R is an oxygen atom or a sulfur atom 145 and R 146 One of them, R 146 and R 147 One of them, or R 147 and R 148 One of them is a single bond bonded to *d, and the other is a single bond bonded to *e, selected from R 141 To R 144 One of them is a single bond that bonds with *29; R is not the single bond mentioned 141 ~R 148 R is not the single bond mentioned above. 200 ~R 203 and R which is not the single bond mentioned above E ~R G Each of the following groups is independently composed of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 cyclic atoms. In equation (1-e), *30 is a single bond bonded to L2 or L3. When L2 or L3 is a single bond, *30 is bonded to the central nitrogen atom. Selected from R 151 ~R 155 One of them is a single bond bonded to *31, selected from R 151 ~R 155 The other one is a single bond that bonds with *32; R is not 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; 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 which is not a hydrogen atom 161 To R 165 At least one pair of adjacent optional benzene rings are bonded together to form more than one unsubstituted benzene ring; Selected from R which is not a hydrogen atom 171 To R 175 At least one pair of adjacent optional benzene rings are bonded together to form more than one unsubstituted benzene ring.

5. The compound according to claim 1, wherein, Two or more of L1, L2, and L3 contain deuterium atoms.

6. The compound according to claim 1, wherein, L1 is an unsubstituted arylene group with 6 to 20 cyclic carbon atoms; L2 and L3 are each independently a single bond or an unsubstituted aryl group with 6 to 20 carbon atoms in a cyclic ring.

7. The compound according to claim 4, wherein, Ar1 is an unsubstituted alkyl group with 1 to 20 carbon atoms, an unsubstituted aryl group with 6 to 20 cyclic carbon atoms, or an unsubstituted heterocyclic group with 5 to 20 cyclic atoms; L1 is an unsubstituted arylene group with 6 to 20 cyclic carbon atoms; L2 and L3 are each independently a single bond or an unsubstituted aryl group with 6 to 20 carbon atoms in a cyclic ring.

8. The compound according to claim 1, wherein, L1, L2, and L3 are each independently a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted biphenylene, and in the case of substitution, the substituent is an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or an unsubstituted phenyl group.

9. The compound according to claim 1, wherein, L1 is a substituted or unsubstituted ortho-phenylene or a substituted or unsubstituted meta-phenylene.

10. A material for an organic electroluminescent element comprising any one of claims 1 to 9.

11. A hole transport layer material comprising any one of claims 1 to 9.

12. An organic electroluminescent element comprising an anode, a cathode, and an organic layer consisting of one or more layers located between the anode and the cathode, wherein, The organic layer includes a light-emitting layer. At least one of the organic layers comprises a compound according to any one of claims 1 to 9.

13. The organic electroluminescent element according to claim 12, wherein, The organic layer includes a hole transport region between the anode and the light-emitting layer, and the hole transport region contains the compound.

14. The organic electroluminescent element according to claim 13, wherein, The hole transport region includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, wherein one of the first hole transport layer and the second hole transport layer contains the compound or both contain the compound.

15. The organic electroluminescent element according to claim 14, wherein, The second hole transport layer contains the compound.

16. The organic electroluminescent element according to claim 14, wherein, The light-emitting layer is in direct contact with the second hole transport layer.

17. The organic electroluminescent element according to claim 14, wherein, The sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30nm to 150nm.

18. The organic electroluminescent element according to claim 12, wherein, The light-emitting layer is a single layer.

19. The organic electroluminescent element according to claim 12, wherein, The luminescent layer contains a luminescent compound that exhibits fluorescence with a main peak wavelength below 500 nm.

20. The organic electroluminescent element according to claim 12, wherein, The light-emitting layer contains fluorescent dopant material.

21. An electronic device comprising the organic electroluminescent element of claim 12.

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