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

Abstract

A compound represented by general formula (1). In general formula (1), ring (A) is a monoring, a = b + c + 2, b is an integer of 0-3, d is an integer of 1 or more, ring (B) is a specific heterocyclic group, Y1 is a hydrogen atom or a specific substituent, ArX is a specific substituent, ArZ is a hydrogen atom or a specific substituent, and ArEWG is a specific heterocyclic group or a specific aryl group.

Description

Technical Field

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

[0002] When voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons. At this point, due to the statistical laws of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons at a rate of 75%.

[0003] Although fluorescent organic EL elements that use light emission from singlet excitons are being used in full-color displays such as mobile phones and televisions, their internal quantum efficiency is said to be limited to 25%. In order to improve the performance of organic EL elements, various studies have been conducted on compounds used in organic EL elements (for example, see Patent Documents 1 to 5). Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: International Publication No. 2020 / 111601

[0007] Patent Document 2: International Publication No. 2022 / 031033

[0008] Patent Document 3: Japanese Patent Application Laid-Open No. 2022-14441

[0009] Patent Document 4: International Publication No. 2022 / 270741

[0010] Patent Document 5: Chinese Patent Application Publication No. 112079766 Summary of the Invention

[0011] Problems to be solved by the invention

[0012] In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired.

[0013] An object of the present invention is to provide a compound capable of improving the performance of an organic electroluminescent device. Another object of the present invention is to provide a compound capable of extending the life of an organic electroluminescent device. Another object of the present invention is to provide a material for an organic electroluminescent device containing the compound. Another object of the present invention is to provide an organic electroluminescent device with a long life, and to provide an electronic device equipped with the organic electroluminescent device.

[0014] Means used to solve problems

[0015] According to one embodiment of the present invention, a compound represented by the following general formula (1) is provided.

[0016]

Chemical Formula 1

[0017]

[0018] (In the above general formula (1),

[0019] Ring (A) is a monocyclic ring, and the number of bonding sites of the ring (A) is a,

[0020] a=b+c+2,

[0021] b is 0, 1, 2 or 3, d is an integer greater than 1,

[0022] Ring (B) is a substituted or unsubstituted heterocyclic group having one or more nitrogen atoms in the ring, the nitrogen atom contained in the ring (B) is bonded to the ring (A), and the element constituting the ring (B) is bonded to Y1,

[0023] Y1 is

[0024] hydrogen atoms,

[0025] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0026] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0027] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0028] wherein Y1 is not a substituted or unsubstituted triazine group,

[0029] When there are multiple Y1, the multiple Y1 are the same as or different from each other.

[0030] In the general formula (1), the partial structure formed by the ring (B) and the (Y1)d is not a substituted or unsubstituted biscarbazole ring in which the 3-positions of the carbazole rings are bonded to each other.

[0031] Ar X for

[0032] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0033] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0034] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0035] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0036] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0037] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0038] -O-(R 904 ) shown in the group,

[0039] -S-(R 905 ) shown in the group,

[0040] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0041] -C(=O)R 801 The groups shown,

[0042] -COOR 802 The groups shown,

[0043] Halogen atoms,

[0044] Nitro,

[0045] -P(=O)(R 931 )(R 932 ) shown in the group,

[0046] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0047] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0048] Among them, in Ar X In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0049] Ar X is not any of substituted or unsubstituted triazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl and substituted or unsubstituted benzothiazolyl,

[0050] In Ar X When there are multiple Ar XSame or different from each other,

[0051] Ar Z for

[0052] hydrogen atoms,

[0053] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0054] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0055] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0056] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0057] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0058] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0059] -O-(R 904 ) shown in the group,

[0060] -S-(R 905 ) shown in the group,

[0061] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0062] -C(=O)R 801 The groups shown,

[0063] -COOR 802 The groups shown,

[0064] Halogen atoms,

[0065] Nitro,

[0066] -P(=O)(R 931 )(R 932 ) shown in the group,

[0067] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0068] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0069] Among them, in Ar Z In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Ar Zis not any of a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, and a substituted or unsubstituted carbazolyl group,

[0070] In Ar Z When there are multiple Ar Z Same or different from each other,

[0071] Ar EWG is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms and containing one or more nitrogen atoms in the ring, or an aryl group having 6 to 30 ring carbon atoms and substituted with one or more cyano groups,

[0072] Ar EWG has at least one substituent R, each of which is independently

[0073] substituted or unsubstituted phenyl,

[0074] Substituted or unsubstituted biphenyl,

[0075] substituted or unsubstituted fluorenyl,

[0076] Substituted or unsubstituted N-arylcarbazolyl,

[0077] substituted or unsubstituted indolyl,

[0078] Substituted or unsubstituted benzimidazolyl,

[0079] Substituted or unsubstituted benzimidazolylbenzimidazolyl,

[0080] substituted or unsubstituted thienyl,

[0081] substituted or unsubstituted benzothiophenyl,

[0082] substituted or unsubstituted benzofuranyl, or

[0083] a substituted or unsubstituted furyl group,

[0084] wherein at least one of the substituents R does not contain a protium atom,

[0085] When the substituent R further has a substituent Y2, at least one of the substituent R and the substituent Y2 does not contain a protium atom.

[0086] When there are multiple substituents R, the multiple substituents R are the same as or different from each other.

[0087] When the substituent R further has a substituent Y2, the substituent Y2 is independently

[0088] cyano,

[0089] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0090] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0091] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0092] Wherein, the substituent Y2 is not a substituted or unsubstituted triazine group,

[0093] When there are multiple substituents Y2, the multiple substituents Y2 are the same as or different from each other.

[0094] (In the compound represented by the above general formula (1), R 901 、R 902 、R 903 、R 904 、R 905 、R 801 、R 802 、R 931 and R 932 Each independently

[0095] hydrogen atoms,

[0096] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0097] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0098] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0099] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0100] In R 901 When there are multiple R 901 Same or different from each other,

[0101] In R 902 When there are multiple R 902 Same or different from each other,

[0102] In R 903 When there are multiple R 903 Same or different from each other,

[0103] In R 904 When there are multiple R 904 Same or different from each other,

[0104] In R 905 When there are multiple R 905Same or different from each other,

[0105] In R 801 When there are multiple R 801 Same or different from each other,

[0106] In R 802 When there are multiple R 802 Same or different from each other,

[0107] In R 931 When there are multiple R 931 Same or different from each other,

[0108] In R 932 When there are multiple R 932 Same as or different from each other.)

[0109] According to one embodiment of the present invention, there is provided a material for an organic electroluminescent device, comprising the compound according to one embodiment of the present invention.

[0110] According to one embodiment of the present invention, there is provided an organic electroluminescent device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains the compound according to one embodiment of the present invention as a first host material.

[0111] According to one aspect of the present invention, there is provided an electronic device in which the organic electroluminescent element according to one aspect of the present invention is mounted.

[0112] According to one embodiment of the present invention, a compound capable of improving the performance of an organic electroluminescent element can be provided. According to one embodiment of the present invention, a compound capable of extending the life of an organic electroluminescent element can be provided. According to one embodiment of the present invention, a material for an organic electroluminescent element containing the compound can be provided. According to one embodiment of the present invention, a long-life organic electroluminescent element can be provided, and an electronic device equipped with the organic electroluminescent element can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0113] Figure 1 Schematic diagram of the device for measuring transient PL.

[0114] Figure 2 This is a diagram showing an example of a decay curve of transient PL.

[0115] Figure 3 This is a diagram schematically showing the configuration of an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0116] Figure 4This is a diagram showing the relationship between energy levels and energy transfer between a sensitizing material and a fluorescent material in a light-emitting layer of an example of an organic electroluminescent element according to the third embodiment of the present invention.

[0117] Figure 5 This is a diagram showing the relationship between energy levels and energy transfer among a second host material, a sensitizing material, and a fluorescent material in the light-emitting layer of an example of an organic electroluminescent device according to the fourth embodiment of the present invention. DETAILED DESCRIPTION

[0118] [definition]

[0119] In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0120] In this specification, in chemical structural formulas, any bondable position not explicitly indicating a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, ie, a protium atom, a deuterium atom, or a tritium atom.

[0121] In this specification, the ring carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound and a heterocyclic compound) in which atoms are cyclically bonded. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring carbon number. The "ring carbon number" recorded below is set in the same manner as long as it is not otherwise stated. For example, the ring carbon number of a benzene ring is 6, the ring carbon number of a naphthalene ring is 10, the ring carbon number of a pyridine ring is 5, and the ring carbon number of a furan ring is 4. In addition, for example, the ring carbon number of 9,9-diphenylfluorenyl is 13, and the ring carbon number of 9,9'-spirobifluorenyl is 25.

[0122] Furthermore, when a benzene ring is substituted with, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of a benzene ring substituted with an alkyl group is 6. Furthermore, when a naphthalene ring is substituted with, for example, an alkyl group, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of a naphthalene ring substituted with an alkyl group is 10.

[0123] In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are cyclically bonded. Atoms that do not constitute a ring (such as a hydrogen atom that terminates the bond of the atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not otherwise stated. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. For example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0124] In this specification, "carbon number XX to YY" in the expression "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" refers to the carbon number of the ZZ group when it is unsubstituted and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0125] In this specification, "atomic number XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" indicates the atomic number of the ZZ group when it is unsubstituted and does not include the atomic number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" is an integer greater than 1, and "YY" is an integer greater than 2.

[0126] In this specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0127] In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0128] In this specification, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

[0129] "Substituents described in this specification"

[0130] The substituents described in this specification are described below.

[0131] The number of ring carbon atoms in the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0132] The number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0133] The number of carbon atoms in the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0134] The number of carbon atoms in the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0135] The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.

[0136] The number of ring carbon atoms in the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified in the present specification.

[0137] The number of ring carbon atoms in the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification.

[0138] The number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in the present specification.

[0139] The number of carbon atoms in the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

[0140] "Substituted or unsubstituted aryl"

[0141] Specific examples of the "substituted or unsubstituted aryl group" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Herein, an unsubstituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and a substituted aryl group refers to a case where the "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" alone includes both "unsubstituted aryl groups" and "substituted aryl groups."

[0142] A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include groups in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent, as described in the following specific example group G1A, and examples of substituted aryl groups described in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of an aryl group in the "substituted aryl groups" in the following specific example group G1B is further replaced with a substituent, and groups in which a hydrogen atom of a substituent in a "substituted aryl group" in the following specific example group G1B is further replaced with a substituent.

[0143] Unsubstituted aryl (Specific example group G1A):

[0144] Phenyl,

[0145] p-Biphenyl,

[0146] m-Biphenyl,

[0147] o-biphenyl,

[0148] 4-terphenyl-4-yl,

[0149] 4-terphenyl-3-yl,

[0150] 4-terphenyl-2-yl,

[0151] m-terphenyl-4-yl,

[0152] m-terphenyl-3-yl,

[0153] m-terphenyl-2-yl,

[0154] o-terphenyl-4-yl,

[0155] o-terphenyl-3-yl,

[0156] o-terphenyl-2-yl,

[0157] 1-naphthyl,

[0158] 2-naphthyl,

[0159] Anthracene,

[0160] Benzanthryl,

[0161] Fiki,

[0162] Triphenylene,

[0163] Phenalene,

[0164] Pyrene base,

[0165] base,

[0166] Benzo base,

[0167] triphenylene,

[0168] Benzotriphenylene,

[0169] tetraphenyl,

[0170] Pentaphenyl,

[0171] Fluorenyl,

[0172] 9,9'-spirobifluorenyl,

[0173] Benzofluorenyl,

[0174] Dibenzofluorenyl,

[0175] Fluoranthene group,

[0176] Benzofluoranthene,

[0177] Perylene and

[0178] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0179]

Chemical Formula 2

[0180]

[0181]

Chemical Formula 3

[0182]

[0183] Substituted aryl (Specific example group G1B):

[0184] o-Tolyl,

[0185] m-Tolyl,

[0186] p-Tolyl,

[0187] p-Xylyl,

[0188] m-xylyl,

[0189] o-xylyl,

[0190] p-Isopropylphenyl,

[0191] m-isopropylphenyl,

[0192] o-isopropylphenyl,

[0193] tert-Butylphenyl,

[0194] m-tert-butylphenyl,

[0195] o-tert-butylphenyl,

[0196] 3,4,5-trimethylphenyl,

[0197] 9,9-dimethylfluorenyl,

[0198] 9,9-diphenylfluorenyl,

[0199] 9,9-bis(4-methylphenyl)fluorenyl,

[0200] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0201] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0202] Cyanophenyl,

[0203] triphenylsilylphenyl,

[0204] trimethylsilylphenyl,

[0205] Phenyl naphthyl,

[0206] naphthylphenyl and

[0207] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above-mentioned general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

[0208] "Substituted or unsubstituted heterocyclic group"

[0209] The term "heterocyclic group" as used herein refers to a cyclic group containing at least one heteroatom among the ring atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0210] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0211] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0212] Specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (Specific Example Group G2) include the following unsubstituted heterocyclic groups (Specific Example Group G2A) and substituted heterocyclic groups (Specific Example Group G2B). (Herein, an unsubstituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups."

[0213] A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of the "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are replaced, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

[0214] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0215] Specific example group G2B includes, for example, the following heterocyclic groups containing a substituted nitrogen atom (specific example group G2B1), the following heterocyclic groups containing a substituted oxygen atom (specific example group G2B2), the following heterocyclic groups containing a substituted sulfur atom (specific example group G2B3), and the following groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

[0216] Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0217] Pyrrolyl,

[0218] Imidazole,

[0219] Pyrazolyl,

[0220] triazole,

[0221] Tetrazolyl,

[0222] Oxazolyl,

[0223] Isoxazolyl,

[0224] Oxadiazolyl,

[0225] Thiazolyl,

[0226] Isothiazolyl,

[0227] Thiadiazole,

[0228] Pyridyl,

[0229] Pyridazinyl,

[0230] Pyrimidine group,

[0231] Pyrazinyl,

[0232] Triazine group,

[0233] Indolyl,

[0234] Isoindolyl,

[0235] Indolizinyl,

[0236] Quinolizinyl,

[0237] Quinolinyl,

[0238] Isoquinolinyl,

[0239] Cinnoline,

[0240] Phthalocyanine,

[0241] Quinazoline,

[0242] Quinoxaline,

[0243] Benzimidazole,

[0244] Indazolyl,

[0245] Phenanthroline,

[0246] Phenanthridinyl,

[0247] Acridinyl,

[0248] Phenazine,

[0249] Carbazolyl,

[0250] Benzylcarbazolyl,

[0251] Morpholinyl,

[0252] Phenoxazine,

[0253] Phenothiazine,

[0254] Azacarbazolyl, and

[0255] Diazacarbazolyl.

[0256] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

[0257] furanyl,

[0258] Oxazolyl,

[0259] Isoxazolyl,

[0260] Oxadiazolyl,

[0261] Xanthoxylum,

[0262] Benzofuranyl,

[0263] Isobenzofuranyl,

[0264] dibenzofuranyl,

[0265] naphthobenzofuranyl,

[0266] Benzoxazolyl,

[0267] Benzisoxazolyl,

[0268] Phenoxazine,

[0269] Morpholinyl,

[0270] dinaphthofuranyl,

[0271] Azadibenzofuranyl,

[0272] Diazadibenzofuranyl,

[0273] Azanaphthobenzofuranyl and

[0274] naphthyridinylbenzofuranyl.

[0275] Unsubstituted heterocyclic group containing a sulfur atom (Specific example group G2A3):

[0276] Thiphenyl,

[0277] Thiazolyl,

[0278] Isothiazolyl,

[0279] Thiadiazole,

[0280] benzothienyl,

[0281] Isobenzothienyl,

[0282] dibenzothienyl,

[0283] naphthobenzothienyl,

[0284] Benzothiazolyl,

[0285] Benzisothiazolyl,

[0286] Phenothiazine,

[0287] dinaphthothienyl,

[0288] azadibenzothienyl,

[0289] diazadibenzothienyl,

[0290] azanaphthobenzothienyl and

[0291] diazanaphthobenzothienyl.

[0292] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):

[0293]

Chemical Formula 4

[0294]

[0295]

Chemical Formula 5

[0296]

[0297] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0298] 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 represented by the above general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0299] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0300] (9-phenyl)carbazolyl,

[0301] (9-biphenyl)carbazolyl,

[0302] (9-phenyl)phenylcarbazolyl,

[0303] (9-naphthyl)carbazolyl,

[0304] Diphenylcarbazol-9-yl,

[0305] phenylcarbazol-9-yl,

[0306] Methylbenzimidazole,

[0307] Ethylbenzimidazolyl,

[0308] Phenyltriazine,

[0309] Biphenyl triazine group,

[0310] Diphenyltriazine,

[0311] Phenylquinazolinyl, and

[0312] Biphenylquinazolinyl.

[0313] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0314] Phenyldibenzofuranyl,

[0315] Methyldibenzofuranyl,

[0316] tert-Butyldibenzofuranyl and

[0317] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0318] Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0319] Phenyldibenzothiophene,

[0320] Methyldibenzothiophene,

[0321] tert-Butyldibenzothienyl and

[0322] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0323] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific Example Group G2B4):

[0324] The above-mentioned "one or more hydrogen atoms of the monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms constituting the ring of the monovalent heterocyclic group, X A and Y A When at least one of the nitrogen atoms is NH, the hydrogen atom bonded to the nitrogen atom and X A and Y A When one of them is CH2, one or more hydrogen atoms among the hydrogen atoms of the methylene group.

[0325] "Substituted or unsubstituted alkyl"

[0326] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, unsubstituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "unsubstituted alkyl groups," and substituted alkyl groups refer to "substituted or unsubstituted alkyl groups" being "substituted alkyl groups.") Hereinafter, when simply referring to "alkyl groups," both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0327] "Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0328] Unsubstituted alkyl (Specific example group G3A):

[0329] methyl,

[0330] Ethyl,

[0331] n-propyl,

[0332] Isopropyl,

[0333] n-Butyl,

[0334] Isobutyl,

[0335] sec-butyl and

[0336] tert-butyl.

[0337] Substituted alkyl (Specific example group G3B):

[0338] Heptafluoropropyl (including isomers),

[0339] Pentafluoroethyl,

[0340] 2,2,2-trifluoroethyl and

[0341] trifluoromethyl.

[0342] "Substituted or unsubstituted alkenyl"

[0343] Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (Specific Example Group G4) include the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B). (Herein, the term "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and the term "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" alone includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups."

[0344] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

[0345] Unsubstituted alkenyl (Specific example Group G4A):

[0346] Vinyl,

[0347] Allyl,

[0348] 1-butenyl,

[0349] 2-Butenyl and

[0350] 3-Butenyl.

[0351] Substituted alkenyl (Specific example group G4B):

[0352] 1,3-butadienyl,

[0353] 1-Methylvinyl,

[0354] 1-methylallyl,

[0355] 1,1-dimethylallyl,

[0356] 2-methylallyl and

[0357] 1,2-dimethylallyl.

[0358] "Substituted or unsubstituted alkynyl"

[0359] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Herein, unsubstituted alkynyl groups refer to cases where "substituted or unsubstituted alkynyl groups" are "unsubstituted alkynyl groups.") When simply referring to "alkynyl groups" below, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0360] A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl groups" (Specific Example Group G5A) are replaced with a substituent.

[0361] Unsubstituted alkynyl (Specific example group G5A):

[0362] Ethylene.

[0363] "Substituted or unsubstituted cycloalkyl"

[0364] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups (Specific Example Group G6A) and substituted cycloalkyl groups (Specific Example Group G6B). (Herein, the unsubstituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the substituted cycloalkyl group refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when simply referring to a "cycloalkyl group", both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" are included.

[0365] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

[0366] Unsubstituted cycloalkyl (Specific example group G6A):

[0367] Cyclopropyl,

[0368] Cyclobutyl,

[0369] Cyclopentyl,

[0370] Cyclohexyl,

[0371] 1-adamantyl,

[0372] 2-adamantyl,

[0373] 1-Norbornyl and

[0374] 2-Norbornyl.

[0375] Substituted cycloalkyl (specific example group G6B):

[0376] 4-Methylcyclohexyl.

[0377] ·“-Si(R 901 )(R 902 )(R 903 )”

[0378] As described in this specification, -Si(R 901 )(R 902 )(R 903 ) are shown as specific examples (specific example group G7), and include

[0379] -Si(G1)(G1)(G1),

[0380] -Si(G1)(G2)(G2),

[0381] -Si(G1)(G1)(G2),

[0382] -Si(G2)(G2)(G2),

[0383] -Si(G3)(G3)(G3) and

[0384] -Si(G6)(G6)(G6). Here,

[0385] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0386] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0387] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0388] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0389] A plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0390] A plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0391] A plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0392] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0393] Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0394] A plurality of G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0395] ·“-O-(R 904 )”

[0396] As described in this specification, -O-(R 904 ) are shown as specific examples (specific example group G8), and include

[0397] -O(G1),

[0398] -O(G2),

[0399] -O(G3) and

[0400] -O(G6).

[0401] Here,

[0402] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0403] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0404] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0405] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0406] ·“-S-(R 905 )”

[0407] As -S-(R 905 ) are shown as specific examples (specific example group G9), and include

[0408] -S(G1),

[0409] -S(G2),

[0410] -S(G3) and

[0411] -S(G6).

[0412] Here,

[0413] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0414] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0415] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0416] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0417] ·“-N(R 906 )(R 907 )”

[0418] As described in this specification, -N(R 906 )(R 907 ) are shown as specific examples (specific example group G10), and the following are examples:

[0419] -N(G1)(G1),

[0420] -N(G2)(G2),

[0421] -N(G1)(G2),

[0422] -N(G3)(G3) and

[0423] -N(G6)(G6).

[0424] Here,

[0425] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0426] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0427] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0428] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0429] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0430] - A plurality of G2s in N(G2)(G2) are the same as or different from each other.

[0431] - A plurality of G3's in N(G3)(G3) are the same as or different from each other.

[0432] A plurality of G6's in -N(G6)(G6) are the same as or different from each other.

[0433] "Halogen atoms"

[0434] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0435] "Substituted or unsubstituted fluoroalkyl"

[0436] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

[0437] "Substituted or unsubstituted haloalkyl"

[0438] The “substituted or unsubstituted haloalkyl group” described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the “substituted or unsubstituted alkyl group” is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the “substituted or unsubstituted alkyl group” are replaced with halogen atoms. The number of carbon atoms in the “unsubstituted haloalkyl group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification. The “substituted haloalkyl group” refers to a group in which one or more hydrogen atoms of the “haloalkyl group” are replaced with a substituent. It should be noted that the “substituted haloalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the “substituted haloalkyl group” are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in the “substituted haloalkyl group” are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl groups" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0439] "Substituted or unsubstituted alkoxy"

[0440] A specific example of a "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0441] "Substituted or unsubstituted alkylthio"

[0442] A specific example of a "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. The number of carbon atoms in an "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0443] "Substituted or unsubstituted aryloxy group"

[0444] Specific examples of "substituted or unsubstituted aryloxy groups" described in this specification include groups represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. The number of ring carbon atoms in the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0445] "Substituted or unsubstituted arylthio"

[0446] Specific examples of "substituted or unsubstituted arylthio groups" described in this specification include groups represented by -S(G1), where G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified in this specification, the number of ring carbon atoms in an "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0447] "Substituted or unsubstituted trialkylsilyl"

[0448] A specific example of a "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same or different. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0449] "Substituted or unsubstituted aralkyl"

[0450] A specific example of a "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group." The number of carbon atoms in an "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0451] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

[0452] The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, triphenylene, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

[0453] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthroline group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophenyl, etc.

[0454] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0455]

Chemical Formula 6

[0456]

[0457] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0458]

Chemical Formula 7

[0459]

[0460] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

[0461] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0462]

Chemical Formula 8

[0463]

[0464] In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

[0465] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0466] "Substituted or unsubstituted arylene group"

[0467] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (Specific Example Group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in Specific Example Group G1 by removing one hydrogen atom from the aryl ring.

[0468] "Substituted or unsubstituted divalent heterocyclic group"

[0469] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 by removing one hydrogen atom from the heterocyclic ring.

[0470] "Substituted or unsubstituted alkylene"

[0471] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0472] The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

[0473]

Chemical Formula 9

[0474]

[0475]

Chemical Formula 10

[0476]

[0477] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0478] In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

[0479]

Chemical Formula 11

[0480]

[0481] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0482] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0483] In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

[0484]

Chemical Formula 12

[0485]

[0486] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0487] In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

[0488] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0489]

Chemical Formula 13

[0490]

[0491]

Chemical Formula 14

[0492]

[0493]

Chemical Formula 15

[0494]

[0495] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0496]

Chemical Formula 16

[0497]

[0498]

Chemical Formula 17

[0499]

[0500]

Chemical Formula 18

[0501]

[0502]

Chemical Formula 19

[0503]

[0504] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0505] The above is the description of the “substituents described in the present specification”.

[0506] "When bonding to form a ring"

[0507] In this specification, the expression "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

[0508] The following describes the case where "one or more of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "the case where they are bonded to form a ring"). This description uses the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring as an example.

[0509]

Chemical Formula 20

[0510]

[0511] For example, in the 921 ~R 930 In the case of "one or more groups of two or more adjacent groups are bonded to each other to form a ring", the group of two adjacent groups as one group means that R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924 Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0512] The above “one or more groups” means that two or more groups of the above two or more adjacent groups can form a ring at the same time. 921 With R 922 bonded to form ring Q A And at the same time R 925 With R 926 bonded to form ring Q B When the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0513]

Chemical Formula 21

[0514]

[0515] The case where "a group of two or more adjacent groups" forms a ring includes not only the case where adjacent "two" groups are bonded as in the above example, but also the case where adjacent "three or more" groups are bonded. For example, if R 921 With R 922 bonded to form ring Q A , and R 922 With R 923 bonded to form ring Q C , consisting of three adjacent (R 921 、R 922 and R 923) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0516]

Chemical Formula 22

[0517]

[0518] In the formed "monocyclic ring" or "condensed ring", the structure of the ring formed alone may be a saturated ring or an unsaturated ring. Even when "one of the two adjacent groups" forms a "monocyclic ring" or "condensed ring", the "monocyclic ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, in the above general formula (TEMP-104), the ring Q formed A and Ring Q B Each is a "monocyclic" or "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C The ring Q of the above general formula (TMEP-104) is fused to form a fused ring. A If it is a benzene ring, then ring Q A The ring Q of the above general formula (TMEP-104) is A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0519] The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

[0520] Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0521] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified in Specific Example Group G2 are terminated with hydrogen atoms.

[0522] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0523] "Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more other optional elements. For example, R 921 With R 922 The ring Q formed by mutual bonding A Refers to R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 The carbon atom of the anthracene skeleton to which the bonding occurs forms a ring with one or more optional elements. 921 With R 922 Formation of ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton to which the carbon atom is bonded forms a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0524] Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur, as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by a hydrogen atom or the like, or can be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocycle.

[0525] Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0526] Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

[0527] In this specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

[0528] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0529] Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.

[0530] In the case of "one or more groups consisting of two or more adjacent atoms of ..." "bonded to each other to form a substituted or unsubstituted monocyclic ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent atoms of ... bond to each other to form a substituted or unsubstituted "unsaturated ring" formed from multiple atoms of the parent skeleton and one or more and fifteen or less elements selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0531] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in the present specification".

[0532] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

[0533] The above is an explanation of the case where "one or more groups consisting of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

[0534] Substituents when expressed as "substituted or unsubstituted"

[0535] In one embodiment of the present specification, the substituent group described as "substituted or unsubstituted" (in the present specification, sometimes referred to as "optional substituent group") is, for example, selected from

[0536] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0537] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0538] unsubstituted alkynyl having 2 to 50 carbon atoms,

[0539] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0540] -Si(R 901 )(R 902 )(R 903 ),

[0541] -O-(R 904 ),

[0542] -S-(R 905 ),

[0543] -N(R 906 )(R 907 ),

[0544] Halogen atoms, cyano groups, nitro groups,

[0545] unsubstituted aryl group having 6 to 50 ring carbon atoms and

[0546] unsubstituted heterocyclic group having 5 to 50 ring atoms

[0547] The groups in the group etc.

[0548] Here, R 901 ~R 907 Each independently

[0549] hydrogen atoms,

[0550] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0551] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0552] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0553] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0554] In R 901 When there are two or more, two or more R 901 Same or different from each other,

[0555] In R 902 When there are two or more, two or more R 902 Same or different from each other,

[0556] In R 903 When there are two or more, two or more R 903 Same or different from each other,

[0557] In R 904 When there are two or more, two or more R 904 Same or different from each other,

[0558] In R 905 When there are two or more, two or more R 905 Same or different from each other,

[0559] In R 906 When there are two or more, two or more R 906 Same or different from each other,

[0560] In R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0561] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0562] an alkyl group having 1 to 50 carbon atoms,

[0563] an aryl group having 6 to 50 ring carbon atoms and

[0564] A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

[0565] In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

[0566] an alkyl group having 1 to 18 carbon atoms,

[0567] an aryl group having 6 to 18 ring carbon atoms and

[0568] A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

[0569] Specific examples of each of the above optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0570] Unless otherwise specified in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

[0571] Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the optional substituent described above.

[0572] In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit and the numerical value BB described after "AA to BB" as the upper limit.

[0573] In this specification, the mathematical expression represented by “A≥B” means that the value of A is equal to the value of B or the value of A is greater than the value of B.

[0574] In this specification, a mathematical expression represented by “A≤B” means that the value of A is equal to the value of B or the value of A is smaller than the value of B.

[0575] [First embodiment]

[0576] Compounds

[0577] The compound according to this embodiment is a compound represented by the following general formula (1).

[0578]

Chemical Formula 23

[0579]

[0580] (In the above general formula (1),

[0581] Ring (A) is a monocyclic ring, and the number of bonding sites of the ring (A) is a,

[0582] a=b+c+2,

[0583] b is 0, 1, 2 or 3, d is an integer greater than 1,

[0584] Ring (B) is a substituted or unsubstituted heterocyclic group having one or more nitrogen atoms in the ring, the nitrogen atom contained in the ring (B) is bonded to the ring (A), and the element constituting the ring (B) is bonded to Y1,

[0585] Y1 is

[0586] hydrogen atoms,

[0587] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0588] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0589] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0590] wherein Y1 is not a substituted or unsubstituted triazine group,

[0591] When there are multiple Y1, the multiple Y1 are the same as or different from each other.

[0592] In the general formula (1), the partial structure formed by the ring (B) and the (Y1)d is not a substituted or unsubstituted biscarbazole ring in which the 3-positions of the carbazole rings are bonded to each other.

[0593] Ar X for

[0594] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0595] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0596] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0597] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0598] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0599] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0600] -O-(R 904 ) shown in the group,

[0601] -S-(R 905 ) shown in the group,

[0602] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0603] -C(=O)R 801 The groups shown,

[0604] -COOR 802 The groups shown,

[0605] Halogen atoms,

[0606] Nitro,

[0607] -P(=O)(R 931 )(R 932 ) shown in the group,

[0608] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0609] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0610] Among them, in Ar X In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0611] Ar X is not any of substituted or unsubstituted triazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl and substituted or unsubstituted benzothiazolyl,

[0612] In Ar X When there are multiple Ar X Same or different from each other,

[0613] Ar Z for

[0614] hydrogen atoms,

[0615] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0616] a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[0617] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[0618] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0619] a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,

[0620] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[0621] -O-(R 904 ) shown in the group,

[0622] -S-(R 905 ) shown in the group,

[0623] a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,

[0624] -C(=O)R 801 The groups shown,

[0625] -COOR 802 The groups shown,

[0626] Halogen atoms,

[0627] Nitro,

[0628] -P(=O)(R 931 )(R 932 ) shown in the group,

[0629] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0630] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

[0631] Among them, in Ar Z In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Ar Z is not any of a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, and a substituted or unsubstituted carbazolyl group,

[0632] In Ar Z When there are multiple Ar Z Same or different from each other,

[0633] Ar EWGis a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms and containing one or more nitrogen atoms in the ring, or an aryl group having 6 to 30 ring carbon atoms and substituted with one or more cyano groups,

[0634] Ar EWG has at least one substituent R, each of which is independently

[0635] substituted or unsubstituted phenyl,

[0636] Substituted or unsubstituted biphenyl,

[0637] substituted or unsubstituted fluorenyl,

[0638] Substituted or unsubstituted N-arylcarbazolyl,

[0639] substituted or unsubstituted indolyl,

[0640] Substituted or unsubstituted benzimidazolyl,

[0641] Substituted or unsubstituted benzimidazolylbenzimidazolyl,

[0642] substituted or unsubstituted thienyl,

[0643] substituted or unsubstituted benzothiophenyl,

[0644] substituted or unsubstituted benzofuranyl, or

[0645] a substituted or unsubstituted furyl group,

[0646] wherein at least one of the substituents R does not contain a protium atom,

[0647] When the substituent R further has a substituent Y2, at least one of the substituent R and the substituent Y2 does not contain a protium atom.

[0648] When there are multiple substituents R, the multiple substituents R are the same as or different from each other.

[0649] In the case where the substituent R further has a substituent Y2, the substituent Y2 is independently

[0650] cyano,

[0651] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0652] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0653] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0654] Wherein, the substituent Y2 is not a substituted or unsubstituted triazine group,

[0655] When there are multiple substituents Y2, the multiple substituents Y2 are the same as or different from each other.

[0656] (In the compound represented by the above general formula (1), R 901 、R 902 、R 903 、R 904 、R 905 、R 801 、R 802 、R 931 and R 932 Each independently

[0657] hydrogen atoms,

[0658] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0659] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0660] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0661] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[0662] In R 901 When there are multiple R 901 Same or different from each other,

[0663] In R 902 When there are multiple R 902 Same or different from each other,

[0664] In R 903 When there are multiple R 903 Same or different from each other,

[0665] In R 904 When there are multiple R 904 Same or different from each other,

[0666] In R 905 When there are multiple R 905 Same or different from each other,

[0667] In R 801 When there are multiple R 801 Same or different from each other,

[0668] In R 802 When there are multiple R 802 Same or different from each other,

[0669] In R 931 When there are multiple R 931 Same or different from each other,

[0670] In R 932 When there are multiple R 932 Same as or different from each other.)

[0671] In the compound according to this embodiment, c is preferably 1, 2, 3 or 4.

[0672] The present inventors have found that in the above general formula (1), Ar EWG A compound in which at least one of the substituents R and the substituent Y2 of the substituent R is deuterated (i.e., a compound in which at least one of the substituents R and the substituent Y2 does not contain a protium atom) is a compound that can improve the performance of an organic EL device compared to a compound in which neither the substituent R nor the substituent Y2 is deuterated.

[0673] Generally speaking, deuterium atoms have higher bond energy than protium atoms and are less likely to decompose. EWG Since it is the main receptor part, it can EWG At least one of the substituent R bonded to the substituent R and the substituent Y2 of the substituent R is deuterated, whereby the compound according to this embodiment is less likely to decompose even in an excited state.

[0674] Therefore, according to one embodiment of the compound of this embodiment, the performance of an organic EL device can be improved. According to one embodiment of the compound of this embodiment, the life of an organic EL device can be extended.

[0675] In the compound involved in this embodiment, "in the above-mentioned general formula (1), the local structure formed by the above-mentioned ring (B) and the above-mentioned (Y1)d is not a substituted or unsubstituted dicarbazole ring bonded to each other at the 3-position of the carbazole ring" means that in the above-mentioned general formula (1), the local structure represented by the following general formula (10) (equivalent to the local structure formed by the above-mentioned ring (B) and the above-mentioned (Y1)d) is not the local structure represented by the following general formula (10B).

[0676]

Chemical Formula 24

[0677]

[0678] (In the above general formula (10), ring (B), Y1 and d each independently have the same meanings as ring (B), Y1 and d in the above general formula (1), and * represents the bonding position to ring (A) in the above general formula (1).)

[0679]

Chemical Formula 25

[0680]

[0681] (In the above general formula (10B), Rx 20 is a hydrogen atom or an optional substituent, multiple Rx 20 are the same as or different from each other, and * represents the bonding position to the ring (A) in the above general formula (1).

[0682] In the above general formula (1), the "substituted or unsubstituted N-arylcarbazolyl group" in the substituent R is, for example, a group represented by the following general formula (N1), (N20) or (N30).

[0683]

Chemical Formula 26

[0684]

[0685] (In the above general formulas (N1) and (N20), R N Each independently represents a hydrogen atom or a substituent, and R N The substituent Y2 has the same meaning as the substituent Y2 in the general formula (1). N are the same as or different from each other. * represents the same as Ar in the above general formula (1) EWG Specifically, * represents the bonding position of Ar in the above general formula (1). EWG The bonding position of the above-mentioned heterocyclic group having 5 to 30 ring atoms or the above-mentioned aryl group having 6 to 30 ring carbon atoms.

[0686]

Chemical Formula 27

[0687]

[0688] (In the above general formula (N30),

[0689] By multiple R P Among the groups consisting of two or more adjacent groups among , and among the groups consisting of two or more adjacent groups among multiple R0, at least one or more groups are bonded to each other to form a substituted or unsubstituted monocyclic ring or bonded to each other to form a substituted or unsubstituted condensed ring,

[0690] Regarding the bonding position of ** in the above general formula (N30),

[0691] (i) Multiple R P A group of two or more adjacent groups and a group of multiple R Q Among the adjacent groups of two or more, the constituent atoms of the substituted or unsubstituted monocyclic ring formed by one or more groups are bonded to **,

[0692] (ii) By multiple R PA group of two or more adjacent groups and a group of multiple R Q Among the adjacent groups of two or more, the constituent atoms of the substituted or unsubstituted fused ring formed by one or more groups are bonded to **, or

[0693] (iii) R does not form the above-mentioned substituted or unsubstituted monocyclic ring or the above-mentioned substituted or unsubstituted condensed ring P and R Q Any one of is a single bond bonded to **,

[0694] In the above general formula (N30), R which does not form the above substituted or unsubstituted monocyclic ring, does not form the above substituted or unsubstituted condensed ring, and is not a single bond to ** P and R Q Each independently represents a hydrogen atom or a substituent, and R P and R Q Each independently has the same meaning as the substituent Y2 in the above general formula (1), and multiple R P Same or different, multiple R Q Same as or different from each other.

[0695] * represents the same as Ar in the above general formula (1) EWG Specifically, * represents the bonding position of Ar in the above general formula (1). EWG The bonding position of the above-mentioned heterocyclic group having 5 to 30 ring atoms or the above-mentioned aryl group having 6 to 30 ring carbon atoms.

[0696] In the above general formula (1), when the "substituted or unsubstituted N-arylcarbazolyl group" in the substituent R is a group represented by the above general formula (N30), examples of the group represented by the general formula (N30) include the following general formulas (N31) to (N36).

[0697]

Chemical Formula 28

[0698]

[0699] (In the above general formulas (N31) to (N36),

[0700] X 15 is an oxygen atom, a sulfur atom, C(R 1D )(R 2D )、Si(R 3D )(R 4D ) or N(R 5D ),

[0701] R P 、R Q and R 1D ~R 5Dare each independently a hydrogen atom or a substituent,

[0702] R as a substituent P 、R Q and R 1D ~R 5D Each independently has the same meaning as the substituent Y2 in the above general formula (1), and multiple R P Same or different, multiple R Q Same or different from each other,

[0703] Among them, R P 、R Q and R 1D ~R 5D One of them is the same as Ar in the above general formula (1) EWG Single bond bonding.

[0704] Specifically, R P 、R Q and R 1D ~R 5D One of them is the same as Ar in the above general formula (1) EWG A single bond bonded to the above heterocyclic group having 5 to 30 ring atoms or the above aryl group having 6 to 30 ring carbon atoms.

[0705] In the above general formula (1), the "substituted or unsubstituted benzimidazolobenzimidazolyl group" in the substituent R is a group represented by the following general formula (N2), (N3) or (N4).

[0706]

Chemical Formula 29

[0707]

[0708] (In the above general formulas (N2), (N3) and (N4), R N Each independently represents a hydrogen atom or a substituent, and R N The substituent Y2 has the same meaning as the substituent Y2 in the general formula (1). N are the same as or different from each other. * represents the same as Ar in the above general formula (1) EWG Specifically, * represents the bonding position of Ar in the above general formula (1). EWG The bonding position of the above-mentioned heterocyclic group having 5 to 30 ring atoms or the above-mentioned aryl group having 6 to 30 ring carbon atoms.

[0709] In the compound according to this embodiment, when the ring (B) has a substituent, the total number of rings constituting the ring (B) and the number of rings constituting Y1 when Y1 is a ring is preferably 6 or less.

[0710] Here, “the total number of rings constituting the ring (B) when the ring (B) has a substituent and the number of rings constituting Y1 when Y1 is a ring” will be described.

[0711] For example, in the general formula (1), when the partial structure represented by the general formula (10) is a group represented by the general formula (X1) below, the 9-carbazolyl group having a bonding position * at the 9-position in the general formula (X1) corresponds to the ring (B) in the general formula (10), and the other 9-carbazolyl group corresponds to Y1 in the general formula (10). In this case, the total number of rings constituting the ring (B) (3) and the number of rings constituting Y1 (3) is calculated to be 6 rings.

[0712] For example, when the partial structure represented by the general formula (10) is a group represented by the general formula (X2) below, in the general formula (X2) below, the 5,12-dihydroindolo[3,2-a]carbazolyl group having a bonding position * corresponds to the ring (B) in the general formula (10), and the phenyl group in the general formula (X2) below corresponds to Y1 in the general formula (10). In this case, the total number of rings constituting the ring (B) (5) and the number of rings constituting Y1 (1) is calculated to be 6 rings.

[0713]

Chemical Formula 30

[0714]

[0715] On the other hand, when the partial structure represented by the general formula (10) is a group represented by the general formula (X3) below, in the general formula (X3) below, the 9-carbazolyl group having a bonding position * at the 9-position corresponds to the ring (B) in the general formula (10), and the other 9-phenylcarbazolyl group corresponds to Y1 in the general formula (10). In this case, the total number of rings constituting the ring (B) (3) and the number of rings constituting Y1 (4) is calculated to be 7 rings.

[0716]

Chemical Formula 31

[0717]

[0718] The compound according to this embodiment has a structure that easily contributes to the improvement of the performance of a blue organic EL device because "the total number of rings constituting the ring (B) and the number of rings constituting Y1 when Y1 is a ring is 6 or less." The reason for this is as follows.

[0719] When the compound according to this embodiment is used as a delayed fluorescence compound, it is preferred that the energy gap T77K of the compound according to this embodiment at 77[K] is high (preferably 2.90 eV or more). 77KIf the value is less than 2.90 eV, reducing ΔST to achieve high delayed fluorescence may result in a corresponding decrease in the lowest excited singlet state energy S1. This is because, from the perspective of efficient energy transfer to the dopant material, it may be undesirable as a material for blue organic EL systems requiring a high S1.

[0720] In order to increase the T 77K (preferably 2.90 eV or more), it is required to increase the T of the substituent itself possessed by the compound. 77K .

[0721] Therefore, in the main donor portion of the compound according to this embodiment (the portion formed by ring (B) and (Y1)d in the above general formula (1), in order to maintain a high T 77K , it is preferred that the number of rings connected and fused to the ring (B) as a conjugated system is small. Specifically, in the above general formula (1), it is preferred that "the total number of rings constituting the above ring (B) and the number of rings constituting Y1 when Y1 is a ring is less than 6 rings."

[0722] In the compound according to this embodiment, Ar EWG Preferred is a group represented by the following general formula (A1).

[0723]

Chemical Formula 32

[0724]

[0725] (In the above general formula (A1), Y 11 ~Y 15 Each independently represents a nitrogen atom, C-CN or CR, C represents a carbon atom, CN represents a cyano group,

[0726] Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN,

[0727] Each R is independently a hydrogen atom or a substituent. Each R as a substituent has the same meaning as the substituent R in the above general formula (1). A plurality of Rs may be the same as or different from each other.

[0728] * represents the bonding position to the ring (A) in the above general formula (1).

[0729] In the compound according to this embodiment, the group represented by the general formula (A1) is preferably a group represented by any one of the following general formulas (a1) to (a9).

[0730]

Chemical Formula 33

[0731]

[0732]

Chemical Formula 34

[0733]

[0734] (In the above general formulae (a1) to (a9), R each independently has the same meaning as R in the above general formula (A1). * indicates the bonding position to the ring (A) in the above general formula (1).)

[0735] In the compound according to this embodiment, the group represented by the general formula (A1) is more preferably a group represented by any one of the general formulas (a1) to (a3).

[0736] In the compound according to this embodiment, the group represented by the above-mentioned general formula (A1) is more preferably a group represented by any one of the following general formulas (a21) to (a23).

[0737]

Chemical Formula 35

[0738]

[0739] (In the above general formulas (a21) to (a23),

[0740] R is independently the same as R in the above general formula (A1),

[0741] One or more groups of two or more adjacent Rgs

[0742] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0743] bonded to each other to form a substituted or unsubstituted fused ring, or

[0744] Not bonded to each other,

[0745] Each Rg that does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is independently a hydrogen atom or a substituent. Each Rg as a substituent is independently the same as the substituent Y2 in the above-mentioned general formula (1). Multiple Rgs are the same or different. * represents the bonding position to the ring (A) in the above-mentioned general formula (1).

[0746] In the above-mentioned general formulae (a21) to (a23), it is preferred that a group consisting of two or more adjacent Rg groups are not bonded to each other.

[0747] In the general formulas (a21) to (a23), it is also preferred that one or more groups of two or more adjacent Rg groups bond to each other to form a substituted or unsubstituted monocyclic ring, or bond to each other to form a substituted or unsubstituted condensed ring. In this case, the formed monocyclic ring or condensed ring is preferably each independently a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted N-arylcarbazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group, or a substituted or unsubstituted benzofuranyl group.

[0748] In the above general formulas (A1), (a1) to (a9) and (a21) to (a23), R and Rg are each independently preferably a hydrogen atom, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted N-arylcarbazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group or a substituted or unsubstituted benzofuranyl group.

[0749] In the above general formulae (a21) to (a23), it is preferred that at least one of Rg is a deuterium atom.

[0750] In the above general formulae (a22) to (a23), R is preferably a hydrogen atom, and more preferably a deuterium atom.

[0751] In the compound according to this embodiment, in the above-mentioned general formula (1), the partial structure represented by the following general formula (10) is preferably a heterocyclic group represented by any one of the following general formulas (11) to (15).

[0752]

Chemical Formula 36

[0753]

[0754] (In the above general formula (10), ring (B), Y1 and d each independently have the same meanings as ring (B), Y1 and d in the above general formula (1), and * represents the bonding position to ring (A) in the above general formula (1).)

[0755]

Chemical Formula 37

[0756]

[0757]

Chemical Formula 38

[0758]

[0759]

Chemical Formula 39

[0760]

[0761]

Chemical Formula 40

[0762]

[0763] (In the above general formulas (11) to (15), X1 to X 18 Each independently represents a nitrogen atom or C-Y3, where C represents a carbon atom,

[0764] One or more groups of two or more adjacent Y3

[0765] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0766] bonded to each other to form a substituted or unsubstituted fused ring, or

[0767] Not bonded to each other,

[0768] Y3 which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is independently the same as Y1 in the above-mentioned general formula (1).

[0769] Ara is

[0770] hydrogen atoms,

[0771] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0772] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0773] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0774] Multiple Y3 are the same as or different from each other,

[0775] A1 and A2 are each independently

[0776] single bond,

[0777] oxygen atoms,

[0778] Sulfur atoms,

[0779] C(R 1A )(R 2A ),

[0780] Si(R 3A )(R 4A ),

[0781] C(=O),

[0782] S(=O),

[0783] SO2 or

[0784] N(R 5A ),

[0785] By R 1A and R 2A One or more of the groups

[0786] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0787] bonded to each other to form a substituted or unsubstituted fused ring, or

[0788] Not bonded to each other,

[0789] By R 3A and R 4A One or more of the groups

[0790] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0791] bonded to each other to form a substituted or unsubstituted fused ring, or

[0792] Not bonded to each other,

[0793] R 5A and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 1A ~R 4A Each independently

[0794] hydrogen atoms,

[0795] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0796] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or

[0797] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0798] Among them, R 1A ~R 5A are not substituted or unsubstituted triazine groups,

[0799] * represents the bonding position to the ring (A) in the above general formula (1).

[0800] (In the above general formula (12), any one of X5 to X8 is 12 Any bonded carbon atom in X9~X 12 Any one of is a carbon atom bonded to any one of X5 to X8,

[0801] In the above general formula (13), any one of X5 to X8 is a carbon atom bonded to a nitrogen atom in the ring containing A2,

[0802] In the above general formula (14), any one of X5 to X8 is12 and X 17 Any bonded carbon atom in X9~X 12 and X 17 Any one of is a carbon atom bonded to any one of X5 to X8,

[0803] In the above general formula (15), any one of X5 to X8 is 12 and X 17 The ring containing X 13 ~X 16 and X 18 The carbon atom to which the nitrogen atom of the ring is bonded.)

[0804] In the compound according to this embodiment, the partial structure represented by the general formula (10) is preferably a partial structure represented by any one of the following general formulas (111) to (113).

[0805]

Chemical Formula 41

[0806]

[0807]

Chemical Formula 42

[0808]

[0809] (In the above general formulae (111) to (113), A1, A2 and Ara are independently the same as A1, A2 and Ara in the above general formulae (11) to (13),

[0810] One or more groups of two or more adjacent ones from Rx1 to Rx4

[0811] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0812] bonded to each other to form a substituted or unsubstituted fused ring, or

[0813] Not bonded to each other,

[0814] One or more groups of two or more adjacent ones from Rx5 to Rx8

[0815] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0816] bonded to each other to form a substituted or unsubstituted fused ring, or

[0817] Not bonded to each other,

[0818] From Rx9 to Rx 12 One or more of the adjacent groups of two or more

[0819] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0820] bonded to each other to form a substituted or unsubstituted fused ring, or

[0821] Not bonded to each other,

[0822] By Rx 13 ~Rx 16 One or more of the adjacent groups of two or more

[0823] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0824] bonded to each other to form a substituted or unsubstituted fused ring, or

[0825] Not bonded to each other,

[0826] Rx1 to Rx that do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring 16 Each independently has the same meaning as Y3 in the above general formulae (11) to (13), and * represents the bonding position to the ring (A) in the above general formula (1).

[0827] (In the above general formula (112), any one of the carbon atoms to which Rx5 to Rx8 are bonded is bonded to any one of the carbon atoms to which Rx9 to Rx8 are bonded. 12 Any one of the carbon atoms is bonded to Rx9~Rx 12 Any one of the carbon atoms of is bonded to any one of the carbon atoms to which Rx5 to Rx8 are bonded,

[0828] In the above general formula (113), any one of the carbon atoms to which Rx5 to Rx8 are bonded is bonded to a nitrogen atom in the ring containing A2.

[0829] Among the compounds according to this embodiment, the compound represented by the above-mentioned general formula (1) is preferably a compound represented by any one of the following general formulas (1001) to (1003).

[0830]

Chemical Formula 43

[0831]

[0832]

Chemical Formula 44

[0833]

[0834]

Chemical Formula 45

[0835]

[0836] (In the above general formulas (1001) to (1003),

[0837] A1, A2, Ara, Rx1~Rx 16 Each independently of A1, A2, Ara, Rx1 to Rx in the above general formulas (111) to (113) 16 Same meaning,

[0838] Ar X 、Ar Z , b and c are each independently the same as Ar in the above general formula (1) X 、Ar Z , b and c have the same meaning,

[0839] Y 11 ~Y 15 are each independently a nitrogen atom, C-CN or CR,

[0840] C is a carbon atom, CN is a cyano group,

[0841] Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN,

[0842] R each independently has the same meaning as R in the above general formula (1).

[0843] In the compounds according to this embodiment, Y3 and Rx1 to Rx 16 Each independently preferably represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0844] In the compounds according to this embodiment, Y3 and Rx1 to Rx 16 Each independently is more preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 18 ring atoms, an unsubstituted heterocyclic group having 5 to 18 ring atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, and even more preferably a hydrogen atom or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0845] In the compound according to this embodiment, Ara is preferably a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0846] In the compound according to this embodiment, Ara is more preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and even more preferably an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0847] In the compound according to this embodiment, A1 and A2 are preferably a single bond.

[0848] In the compound according to this embodiment, it is preferred that the partial structure represented by the general formula (10) has at least one deuterium atom.

[0849] In the compound according to this embodiment, in the above-mentioned general formula (1), the partial structure represented by the following general formula (10) is preferably a heterocyclic group represented by the following general formula (12X) or (13X).

[0850]

Chemical Formula 46

[0851]

[0852] (In the above general formula (10), ring (B), Y1 and d each independently have the same meanings as ring (B), Y1 and d in the above general formula (1), and * represents the bonding position to ring (A) in the above general formula (1).)

[0853]

Chemical Formula 47

[0854]

[0855] (In the above general formula (12X), R 11 ~R 18 One or more of the adjacent groups of two or more

[0856] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0857] bonded to each other to form a substituted or unsubstituted fused ring, or

[0858] Not bonded to each other,

[0859] In the above general formula (13X), R 111 ~R 118 One or more of the adjacent groups of two or more

[0860] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0861] bonded to each other to form a substituted or unsubstituted fused ring, or

[0862] Not bonded to each other,

[0863] In the above general formula (12X), R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 11 ~R 18 and R in the above general formula (13X) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 111 ~R 118 Each independently

[0864] hydrogen atoms,

[0865] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0866] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or

[0867] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0868] Among them, R 11 ~R 18 and R 111 ~R 118 are not substituted or unsubstituted triazine groups,

[0869] In the above general formula (12X),

[0870] Ring A1 is a ring structure represented by the following general formula (14X), (15X) or (16X),

[0871] In the above general formula (13X),

[0872] Ring B1 and ring C1 are each independently a ring structure represented by the following general formula (14X) or (15X),

[0873] Ring A1, Ring B1 and Ring C1 are fused with adjacent rings at optional positions,

[0874] p, px and py are each independently 1, 2, 3 or 4,

[0875] When p is 2, 3 or 4, the plurality of rings A1 are identical to or different from each other.

[0876] When px is 2, 3 or 4, the multiple rings B1 are the same as or different from each other.

[0877] When py is 2, 3 or 4, the multiple rings C1 are the same or different from each other.

[0878] * in the above general formulae (11X) to (13X) represents the bonding position to the ring (A) in the above general formula (1).

[0879]

Chemical Formula 48

[0880]

[0881] (In the above general formula (14X),

[0882] r is 0, 2, or 4,

[0883] When r is 2 or 4, multiple R 19 Same or different from each other,

[0884] When r is 2 or 4, multiple R 19Group

[0885] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0886] bonded to each other to form a substituted or unsubstituted fused ring, or

[0887] Not bonded to each other,

[0888] R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 19 Each independently

[0889] hydrogen atoms,

[0890] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0891] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or

[0892] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0893] Among them, R 19 are not substituted or unsubstituted triazine groups,

[0894] In the above general formula (15), X5 is a sulfur atom, an oxygen atom, C(R 1B )(R 2B )、Si(R 3B )(R 4B ) or N(R 5B ),

[0895] By R 1B and R 2B One or more of the groups

[0896] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0897] bonded to each other to form a substituted or unsubstituted fused ring, or

[0898] Not bonded to each other,

[0899] By R 3B and R 4B One or more of the groups

[0900] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0901] bonded to each other to form a substituted or unsubstituted fused ring, or

[0902] Not bonded to each other,

[0903] R 5B and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring1B ~R 4B Each independently

[0904] hydrogen atoms,

[0905] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[0906] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or

[0907] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0908] Among them, R 1B ~R 5B are not substituted or unsubstituted triazine groups,

[0909] Multiple R 19 Same or different from each other,

[0910] When there are multiple X5, the multiple X5 are the same or different from each other.)

[0911] In the compound according to this embodiment, in the general formula (1), the partial structure represented by the general formula (10) is preferably a heterocyclic group represented by any one of the following general formulas (12A) to (12G).

[0912]

Chemical Formula 49

[0913]

[0914]

Chemical Formula 50

[0915]

[0916]

Chemical Formula 51

[0917]

[0918]

Chemical Formula 52

[0919]

[0920]

Chemical Formula 53

[0921]

[0922]

Chemical Formula 54

[0923]

[0924]

Chemical Formula 55

[0925]

[0926] (In the above general formulas (12A), (12B), (12C), (12D), (12E), (12F) and (12G),

[0927] R 11 ~R 18 Each independently of R in the above general formula (12X) 11 ~R 18 Same meaning,

[0928] R 19 and R 20 Each independently of R in the above general formula (14X) 19 Same meaning,

[0929] X5 has the same meaning as X5 in the above general formula (15X),

[0930] In the above general formulae (12A), (12B), (12C), (12D), (12E), (12F), and (12G), * represents the bonding position to the ring (A) in the above general formula (1).

[0931] Among the compounds according to this embodiment, the compound represented by the above-mentioned general formula (1) is preferably a compound represented by the following general formula (1004).

[0932]

Chemical Formula 56

[0933]

[0934] (In the above general formula (1004), Ar X 、Ar Z , b and c are each independently the same as Ar in the above general formula (1) X 、Ar Z , b and c have the same meaning,

[0935] Y 11 ~Y 15 are each independently a nitrogen atom, C-CN or CR,

[0936] C is a carbon atom, CN is a cyano group,

[0937] Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN,

[0938] R is independently the same as R in the above general formula (1),

[0939] R 11 ~R 18 Each independently of R in the above general formula (12X) 11 ~R 18Same meaning,

[0940] R 19 and R 20 Each independently of R in the above general formula (14X) 19 Same meaning,

[0941] X5 has the same meaning as X5 in the above general formula (15X).

[0942] Among the compounds according to this embodiment, the compound represented by the above-mentioned general formula (1) is preferably a compound represented by any one of the following general formulas (1005) to (1008).

[0943]

Chemical Formula 57

[0944]

[0945]

Chemical Formula 58

[0946]

[0947]

Chemical Formula 59

[0948]

[0949]

Chemical Formula 60

[0950]

[0951] (In the above general formulas (1005) to (1008), Ar X 、Ar Z , b and c are each independently the same as Ar in the above general formula (1) X 、Ar Z , b and c have the same meaning,

[0952] Y 11 ~Y 15 Each independently of Y in the above general formula (1004) 11 ~Y 15 Same meaning, R 11 ~R 18 Each independently of R in the above general formula (12X) 11 ~R 18 Same meaning, R 19 and R 20 Each independently of R in the above general formula (14X) 19 X5 has the same meaning as X5 in the above general formula (15X).

[0953] In the compounds according to this embodiment, R 11 ~R 18 、R111 ~R 118 、R 19 and R 20 Each independently preferably represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0954] In the compounds according to this embodiment, R 11 ~R 18 、R 111 ~R 118 、R 19 and R 20 Each independently is more preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 18 ring atoms, an unsubstituted heterocyclic group having 5 to 18 ring atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, and even more preferably a hydrogen atom or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[0955] In the compound according to this embodiment, it is preferred that the partial structure represented by the general formula (10) has at least one deuterium atom.

[0956] In the compound according to this embodiment, in the above-mentioned general formula (1), the partial structure represented by the following general formula (10A) is preferably a group represented by any one of the following general formulas (11A) to (20A).

[0957]

Chemical Formula 61

[0958]

[0959] (In the above general formula (10), ring (A), Ar X 、Ar Z , b and c are each independently the same as the ring (A), Ar X 、Ar Z , b and c have the same meanings, ** represents the bonding position with the ring (B) in the above general formula (1), *** represents the bonding position with Ar in the above general formula (1) EWG bonding position.)

[0960]

Chemical Formula 62

[0961]

[0962]

Chemical Formula 63

[0963]

[0964] (In the above general formulas (11A) to (20A), Ar X and Ar ZEach independently and Ar in the above general formula (10A) X and Ar Z have the same meanings, ** represents the bonding position with the ring (B) in the above general formula (1), *** represents the bonding position with Ar in the above general formula (1) EWG bonding position.)

[0965] Among the compounds represented by the above general formulae (1001) to (1008), it is preferred that (Ar X )b and (Ar Z )c is bonded to a six-membered ring (corresponding to the portion of the partial structure represented by the above general formula (10A)) replaced with a group represented by any one of the above general formulae (11A) to (20A).

[0966] In the compound according to this embodiment, preferably, Ar X Each is independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, a group represented by the following general formula (111A), a group represented by the following general formula (112A), a group represented by the following general formula (113A), a group represented by the following general formula (114A), or a group represented by the following general formula (115A).

[0967] In the compound according to this embodiment, preferably, Ar X are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, a group represented by the following general formula (111A), a group represented by the following general formula (112A), a group represented by the following general formula (113A), a group represented by the following general formula (114A), or a group represented by the following general formula (115A), and Ar Z A hydrogen atom.

[0968]

Chemical Formula 64

[0969]

[0970]

Chemical Formula 65

[0971]

[0972]

Chemical Formula 66

[0973]

[0974] (In the above general formulas (111A) to (115A),

[0975] One or more groups of two or more adjacent ones of Ry1 to Ry4

[0976] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0977] bonded to each other to form a substituted or unsubstituted fused ring, or

[0978] Not bonded to each other,

[0979] One or more groups of two or more adjacent ones of Ry5 to Ry8

[0980] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0981] bonded to each other to form a substituted or unsubstituted fused ring, or

[0982] Not bonded to each other,

[0983] From Ry9~Ry 12 One or more of the adjacent groups of two or more

[0984] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0985] bonded to each other to form a substituted or unsubstituted fused ring, or

[0986] Not bonded to each other,

[0987] By Ry 13 ~Ry 16 One or more of the adjacent groups of two or more

[0988] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0989] bonded to each other to form a substituted or unsubstituted fused ring, or

[0990] Not bonded to each other,

[0991] By Ry 21 ~Ry 25 One or more of the adjacent groups of two or more

[0992] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[0993] bonded to each other to form a substituted or unsubstituted fused ring, or

[0994] Not bonded to each other,

[0995] Arb is

[0996] hydrogen atoms,

[0997] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0998] a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or

[0999] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1000] A 10 and A 20 Each independently

[1001] single bond,

[1002] oxygen atoms,

[1003] Sulfur atoms,

[1004] C(R 1C )(R 2C ),

[1005] Si(R 3C )(R 4C ),

[1006] C(=O),

[1007] S(=O),

[1008] SO2 or

[1009] N(R 5C ),

[1010] By R 1C and R 2C One or more of the groups

[1011] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1012] bonded to each other to form a substituted or unsubstituted fused ring, or

[1013] Not bonded to each other,

[1014] By R 3C and R 4C One or more of the groups

[1015] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1016] bonded to each other to form a substituted or unsubstituted fused ring, or

[1017] Not bonded to each other,

[1018] R 5C and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 1C ~R 4C 、Ry1~Ry16 and Ry 21 ~Ry 25 Each independently

[1019] hydrogen atoms,

[1020] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,

[1021] a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or

[1022] a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[1023] * represents the bonding position to the ring (A) in the above general formula (1).

[1024] (In the above general formula (112A), any one of the carbon atoms to which Ry5 to Ry8 are bonded and any one of the carbon atoms to which Ry9 to Ry8 are bonded 12 Any one of the carbon atoms is bonded to Ry9~Ry 12 Any one of the carbon atoms in Ry is bonded to any one of the carbon atoms to which Ry5 to Ry8 are bonded.

[1025] In the above general formula (113A), any one of the carbon atoms to which Ry5 to Ry8 are bonded is bonded to the carbon atom containing A. 20 The nitrogen atom in the ring is bonded to the

[1026] In the above general formula (114A), any one of the carbon atoms to which Ry1 to Ry4 are bonded is bonded to *1. In the above general formula (115A), Ry 21 ~Ry 25 Any one of the bonded carbon atoms is bonded to *1.)

[1027] In the above general formulas (111A) to (115A), Ry1 to Ry 16 and Ry 21 ~Ry 25 Each of them is independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, more preferably a hydrogen atom, an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted heterocyclic group having 5 to 18 ring atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, and still more preferably a hydrogen atom or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[1028] In the above general formula (112A), Arb is preferably a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and further preferably an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[1029] In the above general formulas (111A) to (115A), A 10 and A 20 It is preferably a single bond.

[1030] In the compound according to this embodiment, preferably, Ar X Having at least one deuterium atom.

[1031] In the compound according to this embodiment, Ar Z Preferred are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

[1032] In the compound according to this embodiment, Ar Z More preferred are a hydrogen atom and an unsubstituted aryl group having 6 to 18 ring carbon atoms, and even more preferred is a hydrogen atom.

[1033] In the compound according to this embodiment, preferably, Ar X are each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, a group represented by the above general formula (111A), a group represented by the above general formula (112A), a group represented by the above general formula (113A), a group represented by the above general formula (114A), or a group represented by the above general formula (115A), Ar Z A hydrogen atom.

[1034] In the compound according to this embodiment, preferably, Ar Z Having at least one deuterium atom.

[1035] In the compound according to this embodiment, it is preferred that the atoms constituting ring (A) do not include a deuterium atom.

[1036] In the compounds involved in this embodiment, when the substituent R further has a substituent Y2, the substituent Y2 is each independently more preferably a cyano group, an unsubstituted alkyl group having 1 to 18 ring atoms, an unsubstituted heterocyclic group having 5 to 18 ring atoms, or an unsubstituted aryl group having 6 to 18 ring carbon atoms, and is further preferably a cyano group or an unsubstituted aryl group having 6 to 18 ring carbon atoms.

[1037] In the compound according to this embodiment, preferably, R901 、R 902 、R 903 、R 904 、R 905 、R 801 、R 802 、R 931 and R 932 Each is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[1038] In the compound according to this embodiment, when the term "substituted or unsubstituted" is used, the substituent is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring atoms.

[1039] In the compound according to this embodiment, when described as "substituted or unsubstituted", the substituent is preferably an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 12 ring atoms.

[1040] In the compound according to this embodiment, it is also preferred that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[1041] In this specification, -O-(R 904 ) in R 904 In the case of a hydrogen atom, it is a hydroxyl group.

[1042] In this specification, -S-(R 905 ) in R 905 When it is a hydrogen atom, it is a mercapto group.

[1043] In this specification, -P(=O)(R 931 )(R 932 ) in R 931 and R 932 When it is a substituent, it is a substituted phosphine oxide group.

[1044] The compound according to this embodiment is preferably a material for a light-emitting layer.

[1045] The compound according to this embodiment is preferably a host material.

[1046] The compound according to this embodiment is preferably a sensitizing material.

[1047] The compound according to this embodiment is preferably a thermally activated delayed fluorescence compound.

[1048] The compound according to this embodiment is preferably a sensitizing material and a thermally activated delayed fluorescence compound.

[1049] In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence.

[1050] (Thermal activated delayed fluorescence)

[1051] Delayed fluorescence is explained in "Device Properties of Organic Semiconductors" (edited by Chiba Andachi, published by Kodansha) on pages 261-268. This document states that if the energy difference ΔE between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, 13 , then reverse energy transfer from the excited triplet state, which has a low transition probability, to the excited singlet state typically occurs efficiently, exhibiting thermally activated delayed fluorescence (TADF). Furthermore, Figure 10.38 in this document illustrates the mechanism of delayed fluorescence. The TADF mechanism utilizes the phenomenon that reverse intersystem crossing from triplet excitons to singlet excitons occurs under the action of heat when using a material with a small energy difference (ΔST) between the singlet and triplet energy levels. Compounds exhibiting thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF compounds) include, for example, compounds having a donor site and an acceptor site bonded within the molecule.

[1052] Generally, delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

[1053] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained by transient PL measurement. Transient PL measurement refers to a method of irradiating a sample with a pulsed laser to excite it and measuring the decay behavior (transition characteristics) of the PL light emission after the irradiation stops. The PL light emission in TADF compounds is classified into a light emission component originating from a singlet exciton generated by the initial PL excitation and a light emission component originating from a singlet exciton generated via a triplet exciton. The lifetime of the singlet exciton generated by the initial PL excitation is in the nanosecond order, which is very short. Therefore, the light emission from the singlet exciton decays rapidly after irradiation with the pulsed laser.

[1054] On the other hand, delayed fluorescence, which originates from singlet excitons generated via long-lived triplet excitons, decays slowly. Thus, there is a significant temporal difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, the intensity of the emission from delayed fluorescence can be determined.

[1055] Figure 1 A schematic diagram of an exemplary apparatus for measuring transient PL is shown. Figure 1 The transient PL measurement method and an example of delayed fluorescence behavior analysis are described.

[1056] Figure 1 The transient PL measurement device 100 comprises a pulse laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectrometer 103 for splitting the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for reading and analyzing the two-dimensional image. It should be noted that the measurement of transient PL is not limited to Figure 1 Recording device.

[1057] The sample contained in the sample chamber 102 can be obtained by forming a thin film on a quartz substrate in which a host material is doped with a dopant material at a concentration of 12% by mass.

[1058] The thin film sample contained in the sample chamber 102 is irradiated with pulsed laser light from the pulsed laser unit 101 to excite the doping material. Luminescence is extracted in a direction 90 degrees relative to the irradiation direction of the excitation light, the extracted light is split by the spectrometer 103, and a two-dimensional image is formed in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to the luminescence intensity. If the two-dimensional image is cut along a predetermined time axis, a luminescence spectrum can be obtained in which the vertical axis is the luminescence intensity and the horizontal axis is the wavelength. In addition, if the two-dimensional image is cut along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of the luminescence intensity and the horizontal axis is time.

[1059] For example, using the following compound HX1 as a host material and the following compound DX1 as a dopant material, a thin film sample A was prepared as described above, and transient PL measurement was performed.

[1060]

Chemical Formula 67

[1061]

[1062] Here, attenuation curves were analyzed using the aforementioned thin film samples A and B. Thin film sample B was prepared by using the following compound HX2 as a host material and the aforementioned compound DX1 as a dopant material in the same manner as described above.

[1063] Figure 2 Shown are decay curves obtained from transient PL measurements of the film samples A and B.

[1064]

Chemical Formula 68

[1065]

[1066] As described above, transient PL measurement produces a luminescence decay curve with luminescence intensity on the vertical axis and time on the horizontal axis. This luminescence decay curve allows the estimation of the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state. In materials exhibiting delayed fluorescence, the intensity of the slowly decaying delayed fluorescence is somewhat greater than the intensity of the rapidly decaying fluorescence.

[1067] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence observed immediately from the excited state after being excited by pulsed light (light irradiated by a pulsed laser) of a wavelength absorbed by the delayed fluorescent material. Delay luminescence is luminescence observed later, not immediately, after excitation by the pulsed light.

[1068] The amount of prompt luminescence and delay luminescence and their ratio can be calculated by the same method as described in "Nature 492, 234-238, 2012" (reference 1). It should be noted that the device used for calculating the amount of prompt luminescence and delay luminescence is not limited to the device described in the above reference 1 or Figure 1 Recording device.

[1069] Furthermore, when the compound involved in this embodiment is a delayed fluorescent compound, the delayed fluorescence of the delayed fluorescent compound is measured using a sample prepared by the following method. For example, the delayed fluorescent compound involved in this embodiment is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. Furthermore, to prevent extinction due to oxygen, the sample solution is freeze-degassed and then sealed in a covered cuvette under an argon atmosphere, thereby creating an oxygen-free sample solution saturated with argon.

[1070] The fluorescence spectrum of the sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation). Separately, the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of the two spectra using equation (1) from Morris et al., J. Phys. Chem., 80 (1976), 969.

[1071] In this embodiment, the amount of prompt luminescence (immediate luminescence) of the compound to be measured is set to X P , set the amount of Delay luminescence to X D When X D / X P The value of is preferably 0.05 or more.

[1072] The measurement of the amounts and ratio of Prompt and Delay luminescence of compounds other than the delayed fluorescent compound in this specification is the same as the measurement of the amounts and ratio of Prompt and Delay luminescence of the delayed fluorescent compound according to this embodiment.

[1073] (ΔST)

[1074] In this embodiment, the lowest excited singlet energy S1 is compared with the energy gap T at 77 [K]. 77K The difference (S1-T 77K ) is defined as ΔST.

[1075] When the compound according to this embodiment is a delayed fluorescent compound, the lowest excited singlet energy S1 (GT1) of the delayed fluorescent compound and the energy gap T at 77 [K] of the delayed fluorescent compound are 77K The difference ΔST(GT1) between (GT1) and (GT1) is preferably less than 0.5 eV, more preferably less than 0.3 eV, even more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. Specifically, ΔST(GT1) preferably satisfies the relationship given by the following equations (Equation 2), (Equation 2A), (Equation 2B), (Equation 2C), or (Equation 2D).

[1076] ΔST(GT1)=S1(GT1)-T 77K (GT1)<0.5eV…(Formula 2)

[1077] ΔST(GT1)=S1(GT1)-T 77K (GT1)<0.3eV…(Formula 2A)

[1078] ΔST(GT1)=S1(GT1)-T 77K (GT1)<0.2eV…(Formula 2B)

[1079] ΔST(GT1)=S1(GT1)-T 77K (GT1)<0.1eV…(Mathematical formula 2C)

[1080] ΔST(GT1)=S1(GT1)-T 77K(GT1)<0.01eV…(Mathematical formula 2D)

[1081] (Relationship between triplet energy and energy gap at 77[K])

[1082] Here, the relationship between triplet energy and the energy gap at 77 [K] will be described. In this embodiment, the energy gap at 77 [K] is different from the triplet energy generally defined.

[1083] The triplet energy is measured as follows. First, the compound to be measured is dissolved in an appropriate solvent to obtain a solution, which is then sealed in a quartz glass tube to prepare a sample. The phosphorescence spectrum of this sample is measured at a low temperature (77 [K]) (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength). A tangent line is drawn to the short-wavelength rise of the phosphorescence spectrum, and the triplet energy is calculated using a prescribed conversion formula based on the wavelength at the intersection of this tangent line and the horizontal axis.

[1084] Among the compounds involved in this embodiment, compounds exhibiting thermally activated delayed fluorescence preferably have a small ΔST. A small ΔST facilitates intersystem crossing and reverse intersystem crossing even at low temperatures (77 [K]), allowing the coexistence of excited singlet and triplet states. As a result, the spectrum obtained by measuring in the same manner as above contains emission from both the singlet and triplet states. While it is difficult to distinguish the emission state, the triplet energy is believed to be fundamentally decisive.

[1085] Therefore, in this embodiment, although the measurement method is the same as that of the conventional triplet energy T, in order to distinguish the difference in a strict sense, the value measured as follows is referred to as the energy gap T 77K The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to obtain a solution, which was then added to a quartz colorimetric cell as a measurement sample. The phosphorescence spectrum of this measurement sample was measured at a low temperature (77 [K]) (with the vertical axis representing phosphorescence intensity and the horizontal axis representing wavelength). A tangent line was drawn on the short-wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis was calculated. edge [nm], the energy calculated by the following conversion formula (F1) is the energy gap T when the energy is 77 [K] 77K .

[1086] Conversion formula (F1): T 77K [eV]=1239.85 / λ edge

[1087] The tangent line to the short-wavelength rise of the phosphorescence spectrum is drawn as follows. As the spectrum curve moves from the short-wavelength side of the phosphorescence spectrum to the shortest-wavelength maximum among the spectral maxima, the tangent line at each point on the curve is considered toward the long-wavelength side. The slope of this tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where this slope reaches its maximum (i.e., the tangent line at the inflection point) is used as the tangent line to the short-wavelength rise of the phosphorescence spectrum.

[1088] It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value and is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

[1089] Phosphorescence can be measured using the F-4500 spectrofluorophotometer manufactured by Hitachi High-Technologies Co., Ltd. The measuring device is not limited thereto, and measurement can be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[1090] (Lowest excited singlet state energy S1)

[1091] As a method for measuring the lowest excited singlet energy S1 using a solution (sometimes referred to as a solution method), the following method can be mentioned.

[1092] A 10 μmol / L toluene solution of the compound to be measured was prepared and added to a quartz colorimetric cell. The absorption spectrum of this sample was measured at room temperature (300 K) (absorption intensity on the vertical axis, wavelength on the horizontal axis). A tangent line on the long-wavelength side of the absorption spectrum was drawn, and the wavelength λedge [nm] at the intersection of this tangent line and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the lowest excited singlet energy.

[1093] Conversion formula (F2): S1 [eV] = 1239.85 / λedge

[1094] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310) can be cited, but the device is not limited thereto.

[1095] The tangent line for the long-wavelength drop of the absorption spectrum is derived as follows. As the spectrum curve moves along the long-wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum maximum, the tangent line at each point on the curve is considered. As the curve drops (i.e., as the value on the vertical axis decreases), the slope of this tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope reaches its minimum on the longest wavelength side (excluding absorbance values ​​of 0.1 or less) is considered the tangent line for the long-wavelength drop of the absorption spectrum.

[1096] It should be noted that the maximum point where the absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

[1097] (Method for producing the compound according to this embodiment)

[1098] The compound according to this embodiment (the compound represented by the general formula (1)) can be produced by a known method, or can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[1099] (Specific Examples of Compounds According to This Embodiment)

[1100] Specific examples of the compound according to this embodiment include the following compounds, but the present invention is not limited to these specific examples.

[1101]

[1102]

[1103]

[1104]

[1105]

[1106]

[1107]

[1108]

[1109]

[1110]

[1111]

[1112]

[1113]

[1114]

[1115]

[1116]

[1117]

[1118]

[1119]

[1120]

[1121]

[1122]

[1123]

[1124]

[1125]

[1126]

[1127]

[1128]

[1129]

[1130]

[1131]

[1132]

[1133]

[1134]

[1135]

[1136]

[1137]

[1138]

[1139]

[1140]

[1141]

[1142]

[1143]

[1144]

[1145]

[1146] [Second embodiment]

[1147] Materials for organic electroluminescent devices

[1148] The organic electroluminescent device material involved in this embodiment contains the compound involved in Embodiment 1. As one embodiment, an organic electroluminescent device material containing only the compound involved in Embodiment 1 can be exemplified. As another embodiment, an organic electroluminescent device material containing the compound involved in Embodiment 1 and another compound different from the compound involved in Embodiment 1 can be exemplified.

[1149] In the organic electroluminescent device material of this embodiment, the compound according to the first embodiment is preferably used as a host material.

[1150] In this specification, when the compound according to the first embodiment is a host material, the host material is referred to as a first host material.

[1151] One embodiment of the organic electroluminescent device material may include a first host material (the compound according to the first embodiment) and other compounds such as a dopant material. One embodiment of the organic electroluminescent device material may include a first host material (the compound according to the first embodiment), a second host material different from the first host material, and a dopant material.

[1152] In the organic electroluminescent device material according to one embodiment, the first host material is preferably a sensitizing material. In the organic electroluminescent device material according to one embodiment, it is more preferable that the first host material is a sensitizing material and is a delayed fluorescence compound.

[1153] [Third embodiment]

[1154] Organic electroluminescent devices

[1155] An organic EL element according to a third embodiment will be described.

[1156] The organic EL element according to the third embodiment comprises an organic layer between an anode and a cathode. The organic layer comprises at least one layer composed of an organic compound. Alternatively, the organic layer comprises a plurality of layers composed of organic compounds stacked together. The organic layer may further comprise an inorganic compound. At least one of the organic layers comprises the compound according to the first embodiment.

[1157] (Organic layer)

[1158] In one embodiment of the organic EL element of the third embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound involved in the first embodiment as a first host material. In the organic EL element of the third embodiment, the organic layer may be composed of, for example, a light-emitting layer, or may include a layer that can be used for an organic EL element. The layer that can be used for an organic EL element is not particularly limited, and for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer can be cited.

[1159] One embodiment of the organic EL device includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer includes a first host material (preferably a sensitizing material) and a fluorescent material. The first host material is the compound according to the first embodiment. The first host material and the fluorescent material are different compounds.

[1160] In one embodiment, the light-emitting layer does not contain a metal complex.

[1161] In one embodiment, the light-emitting layer does not contain phosphorescent materials.

[1162] In the organic EL device of the third embodiment, a hole transport layer may be provided between the anode and the light-emitting layer.

[1163] In the organic EL device of the third embodiment, an electron transport layer may be provided between the cathode and the light-emitting layer.

[1164] Figure 3 A schematic configuration of an example of an organic EL element according to this embodiment is shown.

[1165] The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by stacking a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 in this order from the anode 3 side. Figure 3 The structure of the organic EL element shown.

[1166] (Luminescent layer)

[1167] In one embodiment, the first host material and the fluorescent material are contained in a single layer. For example, when the organic EL element has a single light-emitting layer, the first host material and the fluorescent material are contained in the single light-emitting layer. When the organic EL element has multiple light-emitting layers, the first host material and the fluorescent material are contained in a single light-emitting layer of any one of the multiple light-emitting layers.

[1168] In one embodiment, the first host material is a sensitizing material. In one embodiment, the light-emitting layer contains a sensitizing material and a fluorescent material. The sensitizing material is preferably a delayed fluorescent compound.

[1169] In one embodiment, when the light-emitting layer contains a delayed fluorescent compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex. In this specification, the compound used as the first host material (preferably a sensitizing material) is sometimes referred to as the second compound.

[1170] [Sensitized materials]

[1171] In one embodiment, the sensitizing material is a delayed fluorescence compound.

[1172] In one embodiment of the organic EL element, the light-emitting layer contains a sensitizing material and a fluorescent material. The sensitizing material is the compound involved in the first embodiment. In the light-emitting layer, the recombination of holes and electrons easily occurs on the molecules of the sensitizing material rather than the fluorescent material. When the sensitizing material is a delayed fluorescent compound, it is believed that the lowest excited triplet state undergoes reverse intersystem crossing to the lowest excited singlet state. In this way, it is believed that after the energy state transition to the lowest excited singlet state occurs in the sensitizing material, energy transfer occurs from the sensitizing material to the fluorescent material, generating fluorescent light from the lowest excited singlet state of the fluorescent material. In this embodiment, it is believed that the compound involved in the first embodiment used as the sensitizing material (the compound shown in the general formula (1)) is a material that effectively undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, so the energy loss is small, and the fluorescent material that receives its energy emits light with high efficiency.

[1173] [Fluorescent materials]

[1174] In one embodiment, the fluorescent material is a compound that does not exhibit thermally activated delayed fluorescence. In one embodiment, the fluorescent material is a compound that exhibits thermally activated delayed fluorescence. In one embodiment, the fluorescent material is not a phosphorescent metal complex. In one embodiment, the fluorescent material is preferably not a metal complex.

[1175] In this specification, a compound used as a fluorescent material may be referred to as a third compound.

[1176] In the third embodiment, the third compound (fluorescent material) includes, for example, bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylamino Derivatives, aryl substitution derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthenefluoranthene derivatives, compounds containing a boron atom, pyrromethene boron coordination compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives and tetracene derivatives, etc.

[1177] In this embodiment, the fluorescent material is preferably one or more compounds selected from the group consisting of third compounds represented by the following general formula (41).

[1178]

Chemical Formula 69

[1179]

[1180] (In the above general formula (41),

[1181] Ring a, ring b and ring c are each independently

[1182] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or

[1183] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1184] L 401 and L 402 Each independently is O, S, Se, NR 40 、C(R 41 )(R 42 ) or Si(R 43 )(R 44 ),

[1185] L 403 is B, P or P=O,

[1186] R 40 ~R 44 independently

[1187] Bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted monocyclic ring,

[1188] Bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted condensed ring, or

[1189] Not bonded to the above-mentioned a ring, b ring and c ring,

[1190] R 41 and R 42

[1191] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1192] bonded to each other to form a substituted or unsubstituted fused ring, or

[1193] Not bonded to each other,

[1194] R 43 and R 44

[1195] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1196] bonded to each other to form a substituted or unsubstituted fused ring, or

[1197] Not bonded to each other,

[1198] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 40 ~R 44 Each independently

[1199] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1200] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1201] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1202] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1203] -CR 45 = iminyl represented by N,

[1204] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1205] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1206] R 45 for

[1207] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1208] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1209] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

[1210] a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

[1211] In R 40 When there are multiple R 40 Same or different from each other,

[1212] In R 41 When there are multiple R41 Same or different from each other,

[1213] In R 42 When there are multiple R 42 Same or different from each other,

[1214] In R 43 When there are multiple R 43 Same or different from each other,

[1215] In R 44 When there are multiple R 44 Same or different from each other,

[1216] In R 45 When there are multiple R 45 Same as or different from each other.)

[1217] In this embodiment, the compound represented by the general formula (41) is preferably a compound represented by the following general formula (410).

[1218]

Chemical Formula 70

[1219]

[1220] (In the above general formula (410),

[1221] Ring a, ring b and ring c are each independently

[1222] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1223] a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

[1224] R 401 and R 402 independently

[1225] Bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted monocyclic ring,

[1226] Bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted condensed ring, or

[1227] Not bonded to the above-mentioned a ring, b ring and c ring,

[1228] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1229] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1230] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1231] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1232] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1233] -CR 45 = iminyl represented by N,

[1234] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1235] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1236] In this embodiment, the compound represented by the general formula (41) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (41-1) to (41-6).

[1237]

Chemical Formula 71

[1238]

[1239]

Chemical Formula 72

[1240]

[1241]

Chemical Formula 73

[1242]

[1243] (In the above general formula (41-1),

[1244] Xa is O, S, Se, C (R 403 )(R 404 ) or NR 405 ,

[1245] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 424 The group composed of R 424 ~R 427 A group of two or more adjacent 427 With R 412 The group and R 412 With R 411 One or more groups in a group formed by a group

[1246] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1247] bonded to each other to form a substituted or unsubstituted fused ring, or

[1248] Not bonded to each other,

[1249] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1250] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1251] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1252] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1253] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1254] -CR 45 = iminyl represented by N,

[1255] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1256] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1257] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 411 、R 412 and R 421 ~R 427 are each independently a hydrogen atom or a substituent R X ,

[1258] The substituent R X Each independently

[1259] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1260] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1261] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1262] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1263] -Si(R 901 )(R 902 )(R 903) shown in the group,

[1264] -O-(R 904 ) shown in the group,

[1265] -S-(R 905 ) shown in the group,

[1266] -N(R 906 )(R 907 ) shown in the group,

[1267] Halogen atoms,

[1268] cyano,

[1269] Nitro,

[1270] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1271] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1272] R 901 ~R 907 Each independently

[1273] hydrogen atoms,

[1274] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1275] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1276] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1277] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1278] In R 901 When there are multiple R 901 Same or different from each other, in R 902 When there are multiple R 902 Same or different from each other, in R 903 When there are multiple R 903 Same or different from each other, in R 904 When there are multiple R 904 Same or different from each other, in R 905 When there are multiple R 905 Same or different from each other, in R 906 When there are multiple R 906 Same or different from each other, in R 907 When there are multiple R 907Same as or different from each other.)

[1279] (In the above general formula (41-2),

[1280] Xa is O, S, Se, C (R 403 )(R 404 ) or NR 405 ,

[1281] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 424 The group composed of R 424 ~R 427 A group of two or more adjacent 413 With R 414 The group and R 414 With R 401 One or more groups in a group formed by a group

[1282] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1283] bonded to each other to form a substituted or unsubstituted fused ring, or

[1284] Not bonded to each other,

[1285] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1286] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1287] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1288] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1289] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1290] -CR 45 = iminyl represented by N,

[1291] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1292] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1293] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 413 、R 414 and R 421 ~R 427 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning,

[1294] In R 403 When there are multiple R 403 Same or different from each other,

[1295] In R 404 When there are multiple R 404 Same or different from each other,

[1296] In R 405 When there are multiple R 405 Same as or different from each other.)

[1297] (In the above general formula (41-3),

[1298] Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ) or NR 405 ,

[1299] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 415 With R 416 The group composed of R 416 With R 412 The group and R 412 With R 411 One or more groups in a group formed by a group

[1300] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1301] bonded to each other to form a substituted or unsubstituted fused ring, or

[1302] Not bonded to each other,

[1303] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring40 and R 402 Each independently

[1304] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1305] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1306] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1307] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1308] -CR 45 = iminyl represented by N,

[1309] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1310] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1311] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 411 、R 412 、R 415 、R 416 and R 421 ~R 423 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning,

[1312] In R 403 When there are multiple R 403 Same or different from each other,

[1313] In R 404 When there are multiple R 404 Same or different from each other,

[1314] In R 405 When there are multiple R 405 Same as or different from each other.)

[1315] (In the above general formula (41-4),

[1316] Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ) or NR 405 ,

[1317] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 418 The group composed of R 418 With R 417 The group and R 412 With R 411 One or more groups in a group formed by a group

[1318] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1319] bonded to each other to form a substituted or unsubstituted fused ring, or

[1320] Not bonded to each other,

[1321] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1322] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1323] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1324] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1325] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1326] -CR 45 = iminyl represented by N,

[1327] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1328] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1329] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 411 、R 412 、R 417 、R 418 and R 421 ~R 423 are each independently a hydrogen atom or a substituent R X , substituent R Xand the substituent R in the above general formula (41-1) X Same meaning,

[1330] In R 403 When there are multiple R 403 Same or different from each other,

[1331] In R 404 When there are multiple R 404 Same or different from each other,

[1332] In R 405 When there are multiple R 405 Same as or different from each other.)

[1333] (In the above general formula (41-5),

[1334] Xa and Xb are each independently O, S, Se, C(R 403 )(R 404 ) or NR 405 ,

[1335] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 418 The group composed of R 418 With R 417 The group composed of R 413 With R 414 The group and R 414 With R 401 One or more groups in a group formed by a group

[1336] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1337] bonded to each other to form a substituted or unsubstituted fused ring, or

[1338] Not bonded to each other,

[1339] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1340] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1341] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1342] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1343] -CR 45 = iminyl represented by N,

[1344] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1345] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1346] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1347] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 413 、R 414 、R 417 、R 418 and R 421 ~R 423 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning,

[1348] In R 403 When there are multiple R 403 Same or different from each other,

[1349] In R 404 When there are multiple R 404 Same or different from each other,

[1350] In R 405 When there are multiple R 405 Same as or different from each other.)

[1351] (In the above general formula (41-6),

[1352] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 424 The group composed of R 424 ~R 427 A group of two or more adjacent 427 With R 428The group composed of R 428 ~R 431 A group of two or more adjacent ones and R 431 With R 401 One or more groups in a group formed by a group

[1353] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1354] bonded to each other to form a substituted or unsubstituted fused ring, or

[1355] Not bonded to each other,

[1356] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1357] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1358] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1359] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1360] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1361] -CR 45 = iminyl represented by N,

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

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

[1364] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 421 ~R 431 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1365] Among the compounds represented by the above general formulae (41-1) to (41-5), it is also preferred that R 412 With R 411 The group composed of R 413 With R 414 The group composed of R 415 With R 416 The group and R 417 With R 418One or more groups in the group formed by the composed groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring.

[1366] In this embodiment, the compound represented by the above-mentioned general formula (41) is preferably also a compound represented by the following general formula (41-7).

[1367]

Chemical Formula 74

[1368]

[1369] (In the above general formula (41-7),

[1370] Xa is O, S, Se, C (R 403 )(R 404 ) or NR 405 ,

[1371] Choose from R 401 With R 421 The group composed of R 421 ~R 423 A group of two or more adjacent 423 With R 402 The group composed of R 402 With R 424 The group composed of R 424 ~R 427 The adjacent groups of two or more and the groups of R 437 ~R 440 One or more groups of two or more adjacent groups

[1372] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1373] bonded to each other to form a substituted or unsubstituted fused ring, or

[1374] Not bonded to each other,

[1375] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 401 and R 402 Each independently

[1376] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1377] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1378] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1379] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1380] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1381] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1382] R 403 ~R 405 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 421 ~R 427 and R 437 ~R 440 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1383] In this embodiment, R 401 and R 402 Each is independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and further preferably a group represented by the following general formula (42).

[1384]

Chemical Formula 75

[1385]

[1386] (In the above general formula (42),

[1387] By R 432 ~R 436 One or more of the adjacent groups of two or more

[1388] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1389] bonded to each other to form a substituted or unsubstituted fused ring, or

[1390] Not bonded to each other,

[1391] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 432 ~R 436 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning,

[1392] In multiple R 432 In the presence of multiple R 432Same or different from each other,

[1393] In multiple R 433 In the presence of multiple R 433 Same or different from each other,

[1394] In multiple R 434 In the presence of multiple R 434 Same or different from each other,

[1395] In multiple R 435 In the presence of multiple R 435 Same or different from each other,

[1396] In multiple R 436 In the presence of multiple R 436 Same or different from each other,

[1397] *Indicates bonding position.)

[1398] In this embodiment, the compound represented by the above-mentioned general formula (41) is preferably also a compound represented by the following general formula (42-1).

[1399]

Chemical Formula 76

[1400]

[1401] (In the above general formula (42-1),

[1402] R 42 ~R 431 Each of them is the same as R in the above general formula (41-6) 421 ~R 431 Same meaning,

[1403] By R 451 ~R 455 One or more of the adjacent groups of two or more

[1404] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1405] bonded to each other to form a substituted or unsubstituted fused ring, or

[1406] Not bonded to each other,

[1407] By R 456 ~R 460 One or more of the adjacent groups of two or more

[1408] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1409] bonded to each other to form a substituted or unsubstituted fused ring, or

[1410] Not bonded to each other,

[1411] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 451 ~R 455 and R 456 ~R 460 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1412] In this embodiment, the compound represented by the above-mentioned general formula (41) is preferably also a compound represented by the following general formula (42-2).

[1413]

Chemical Formula 77

[1414]

[1415] (In the above general formula (42-2), R 422 、R 426 、R 429 、R 453 and R 458 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1416] In this embodiment, the compound represented by the above-mentioned general formula (41) is preferably also a compound represented by the following general formula (42-3).

[1417]

Chemical Formula 78

[1418]

[1419] (In the above general formula (42-3),

[1420] R 421 ~R 427 、R 437 ~R 440 and Xa are respectively the same as R 421 ~R 427 、R 437 ~R 440 and X a Same meaning,

[1421] By R 451 ~R 455 One or more of the adjacent groups of two or more

[1422] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1423] bonded to each other to form a substituted or unsubstituted fused ring, or

[1424] Not bonded to each other,

[1425] By R 456 ~R 460 One or more of the adjacent groups of two or more

[1426] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1427] bonded to each other to form a substituted or unsubstituted fused ring, or

[1428] Not bonded to each other,

[1429] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 451 ~R 455 and R 456 ~R 460 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1430] In this embodiment, the compound represented by the above-mentioned general formula (41) is preferably also a compound represented by the following general formula (42-4).

[1431]

Chemical Formula 79

[1432]

[1433] (In the above general formula (42-4), Xa has the same meaning as Xa in the above general formula (41-7), and R 422 、R 426 、R 439 、R 453 and R 458 are each independently a hydrogen atom or a substituent R X , substituent R X and the substituent R in the above general formula (41-1) X Same meaning.)

[1434] In this embodiment, R in the third compound 422 、R 426 、R 429 、R 439 、R 453 and R 458Each independently is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and still more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[1435] In this embodiment, Xa and Xb in the third compound are each independently preferably O or S.

[1436] (Method for producing the compound represented by general formula (41))

[1437] The compound represented by the general formula (41) can be produced by a known method. Alternatively, the compound represented by the general formula (41) can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[1438] (Specific examples of compounds represented by general formula (41))

[1439] Specific examples of the compound represented by the general formula (41) include the following compounds: In the following specific examples, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[1440]

Chemical Formula 80

[1441]

[1442]

Chemical Formula 81

[1443]

[1444]

Chemical Formula 82

[1445]

[1446]

Chemical Formula 83

[1447]

[1448]

Chemical Formula 84

[1449]

[1450]

Chemical Formula 85

[1451]

[1452]

Chemical Formula 86

[1453]

[1454]

Chemical Formula 87

[1455]

[1456]

Chemical Formula 88

[1457]

[1458]

Chemical Formula 89

[1459]

[1460]

Chemical Formula 90

[1461]

[1462]

Chemical Formula 91

[1463]

[1464]

Chemical Formula 92

[1465]

[1466]

Chemical Formula 93

[1467]

[1468]

Chemical Formula 94

[1469]

[1470]

Chemical Formula 95

[1471]

[1472]

Chemical Formula 96

[1473]

[1474]

Chemical Formula 97

[1475]

[1476]

Chemical Formula 98

[1477]

[1478]

Chemical Formula 99

[1479]

[1480]

Chemical Formula 100

[1481]

[1482] Chemical Formula 101

[1483]

[1484]

Chemical Formula 102

[1485]

[1486]

Chemical Formula 103

[1487]

[1488]

Chemical Formula 104

[1489]

[1490]

Chemical Formula 105

[1491]

[1492]

Chemical Formula 106

[1493]

[1494]

Chemical Formula 107

[1495]

[1496]

Chemical Formula 108

[1497]

[1498]

Chemical Formula 109

[1499]

[1500]

Chemical Formula 110

[1501]

[1502]

Chemical Formula 111

[1503]

[1504]

Chemical Formula 112

[1505]

[1506]

Chemical Formula 113

[1507]

[1508]

Chemical Formula 114

[1509]

[1510]

Chemical Formula 115

[1511]

[1512]

Chemical Formula 116

[1513]

[1514]

Chemical Formula 117

[1515]

[1516]

Chemical Formula 118

[1517]

[1518]

Chemical Formula 119

[1519]

[1520]

Chemical Formula 120

[1521]

[1522]

Chemical Formula 121

[1523]

[1524]

Chemical Formula 122

[1525]

[1526]

Chemical Formula 123

[1527]

[1528]

Chemical Formula 124

[1529]

[1530]

Chemical Formula 125

[1531]

[1532]

Chemical Formula 126

[1533]

[1534]

Chemical Formula 127

[1535]

[1536]

Chemical Formula 128

[1537]

[1538]

Chemical Formula 129

[1539]

[1540]

Chemical Formula 130

[1541]

[1542]

Chemical Formula 131

[1543]

[1544]

Chemical Formula 132

[1545]

[1546]

Chemical Formula 133

[1547]

[1548]

Chemical Formula 134

[1549]

[1550]

Chemical Formula 135

[1551]

[1552]

Chemical Formula 136

[1553]

[1554]

Chemical Formula 137

[1555]

[1556]

Chemical Formula 138

[1557]

[1558]

Chemical Formula 139

[1559]

[1560]

Chemical Formula 140

[1561]

[1562]

Chemical Formula 141

[1563]

[1564]

Chemical Formula 142

[1565]

[1566]

Chemical Formula 143

[1567]

[1568]

Chemical Formula 144

[1569]

[1570]

Chemical Formula 145

[1571]

[1572]

Chemical Formula 146

[1573]

[1574] In this embodiment, the fluorescent material is preferably one or more compounds selected from the group consisting of third compounds represented by the following general formula (31) or (32). The third compound serving as the fluorescent material may be a compound represented by the following general formula (31) or a compound represented by the following general formula (32).

[1575]

Chemical Formula 147

[1576]

[1577] [(In the above general formula (31),

[1578] C1 ring and D1 ring

[1579] Single bonded to each other,

[1580] Mutual via O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ) bonded, or not bonded to each other,

[1581] They are not bonded to each other by single bonds and are not bonded to each other via O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ) The C1 ring and the D1 ring, as well as the A1 ring and the B1 ring bonded to each other are independently

[1582] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or

[1583] a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms,

[1584] R E or R E Substituents

[1585] is bonded to at least one of the A1 ring, the A1 ring substituent, the B1 ring, and the B1 ring substituent to form a substituted or unsubstituted monocyclic ring,

[1586] is bonded to at least one of the A1 ring, the A1 ring substituent, the B1 ring, and the B1 ring substituent to form a substituted or unsubstituted condensed ring, or

[1587] It is not bonded to the aforementioned A1 ring, the substituent of the aforementioned A1 ring, the aforementioned B1 ring, and the substituent of the aforementioned B1 ring.)

[1588] (In the above general formula (32),

[1589] Ring A2, Ring B2 and Ring C2 are each independently

[1590] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 ring carbon atoms, or

[1591] a substituted or unsubstituted heterocyclic ring having 5 to 60 ring atoms,

[1592] The D2 ring is a substituted or unsubstituted monocyclic ring having 5 to 7 ring atoms, which may be fused with at least one substituted or unsubstituted non-aromatic ring having 5 to 60 ring atoms.

[1593] The C2 ring and the D2 ring share a single bond or a double bond and are fused.

[1594] A2 ring and D2 ring

[1595] Single bonded to each other,

[1596] Mutual via O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ) bonded, or not bonded to each other,

[1597] R F or R F Substituents

[1598] is bonded to at least one of the A2 ring, the A2 ring substituent, the B2 ring, and the B2 ring substituent to form a substituted or unsubstituted monocyclic ring,

[1599] is bonded to at least one of the A2 ring, the A2 ring substituent, the B2 ring, and the B2 ring substituent to form a substituted or unsubstituted condensed ring, or

[1600] It is not bonded to the aforementioned A2 ring, the substituent of the aforementioned A2 ring, the aforementioned B2 ring, and the substituent of the aforementioned B2 ring.)

[1601] (In the above general formula (31) or (32),

[1602] R not bonded to the A1 ring, the substituent of the A1 ring, the B1 ring, and the substituent of the B1 ring E and R not bonded to the A2 ring, the substituent of the A2 ring, the B2 ring, and the substituent of the B2 ring F Each independently

[1603] hydrogen atoms,

[1604] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1605] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1606] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

[1607] a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

[1608] a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms,

[1609] -CR 39 = iminyl represented by N, or

[1610] a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms,

[1611] Y E and Y F Each independently represents a single bond, O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ),

[1612] In Y E When it is a single bond, the B1 ring and the C1 ring are connected via O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ) bonded or not bonded,

[1613] In YF When it is a single bond, the B2 ring and the C2 ring are connected via O, S, NR 33 、Si(R 34 )(R 35 ) or C(R 37 )(R 38 ) bonded or not bonded,

[1614] R 34 With R 35

[1615] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1616] bonded to each other to form a substituted or unsubstituted fused ring, or

[1617] Not bonded to each other,

[1618] R 37 With R 38

[1619] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1620] bonded to each other to form a substituted or unsubstituted fused ring, or

[1621] Not bonded to each other,

[1622] In the above general formula (31), R 33 、R 34 、R 35 、R 37 and R 38 independently

[1623] is bonded to at least one of the A1 ring and the B1 ring to form a substituted or unsubstituted monocyclic ring,

[1624] is bonded to at least one of the A1 ring and the B1 ring to form a substituted or unsubstituted condensed ring, or

[1625] Not bonded to the A1 ring and the B1 ring,

[1626] In the above general formula (32), R 33 、R 34 、R 35 、R 37 and R 38 independently

[1627] is bonded to at least one of the A2 ring and the B2 ring to form a substituted or unsubstituted monocyclic ring,

[1628] is bonded to at least one of the A2 ring and the B2 ring to form a substituted or unsubstituted condensed ring, or

[1629] Not bonded to the A2 ring and the B2 ring,

[1630] R 39 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 33 、R 34 、R 35 、R 35 and R 38 Each independently

[1631] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1632] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1633] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

[1634] a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

[1635] In R 33 When there are multiple R 33 Same or different from each other,

[1636] In R 34 When there are multiple R 34 Same or different from each other,

[1637] In R 35 When there are multiple R 35 Same or different from each other,

[1638] In R 37 When there are multiple R 37 Same or different from each other,

[1639] In R 38 When there are multiple R 38 the same as or different from each other. )]

[1640] In this embodiment, the compound represented by the above-mentioned general formula (31) is preferably also a compound represented by the following general formula (35).

[1641]

Chemical Formula 148

[1642]

[1643] (In the above general formula (35),

[1644] By R 1 ~R 3A group of two or more adjacent ones, consisting of R 4 ~R 6 A group of two or more adjacent ones, consisting of R 12 ~R 15 The adjacent groups of two or more and the groups of R 16 ~R 19 One or more of the adjacent groups of two or more

[1645] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1646] bonded to each other to form a substituted or unsubstituted fused ring, or

[1647] Not bonded to each other,

[1648] By R 7 ~R 11 One or more of the adjacent groups of two or more

[1649] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1650] bonded to each other to form a substituted or unsubstituted fused ring, or

[1651] Not bonded to each other,

[1652] R 7 and R 6 Group

[1653] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1654] bonded to each other to form a substituted or unsubstituted fused ring, or

[1655] Not bonded to each other,

[1656] R 11 and R 12 Group

[1657] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1658] bonded to each other to form a substituted or unsubstituted fused ring, or

[1659] Not bonded to each other,

[1660] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 1 ~R 19 Each independently

[1661] hydrogen atoms,

[1662] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1663] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1664] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,

[1665] a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms,

[1666] a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

[1667] cyano,

[1668] N(R 22 )2.

[1669] OR 20 、

[1670] SR 20 、

[1671] B(R 21 )2.

[1672] SiR 24 R 25 R 26 or

[1673] halogen atoms,

[1674] By 2 R 22 The group consists of 2 R 21 One or more of the groups

[1675] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1676] bonded to each other to form a substituted or unsubstituted fused ring, or

[1677] Not bonded to each other,

[1678] R 20 With adjacent R 1 ~R 19 At least any one of them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

[1679] R 21 Each independently and adjacent R 1 ~R 19 At least any one of them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

[1680] R 22 Each independently and adjacent R 1 ~R 19At least any one of them are bonded to each other to form a substituted or unsubstituted monocyclic ring, are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other,

[1681] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 20 ~R 22 Each independently

[1682] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1683] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1684] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

[1685] a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,

[1686] 2 adjacent R 24 and R 25 Group

[1687] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1688] bonded to each other to form a substituted or unsubstituted fused ring, or

[1689] Not bonded to each other,

[1690] R 26 and R which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 24 and R 25 Each independently

[1691] a substituted or unsubstituted aryl group having 6 to 60 ring carbon atoms,

[1692] a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms,

[1693] a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or

[1694] A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.

[1695] In this embodiment, the compound represented by the general formula (31) is preferably any one compound selected from the group consisting of compounds represented by the following general formulas (351), (352), and (353).

[1696]

Chemical Formula 149

[1697]

[1698] (In the above general formulas (351) and (352),

[1699] By R 1 ~R 3 A group of two or more adjacent ones, R 4 and R 5 The group, by R 8 ~R 11 A group of two or more adjacent ones, consisting of R 12 ~R 15 The adjacent groups of two or more and the groups of R 16 ~R 19 One or more of the adjacent groups of two or more

[1700] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1701] bonded to each other to form a substituted or unsubstituted fused ring, or

[1702] Not bonded to each other,

[1703] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 1 ~R 5 and R 8 ~R 19 Each independently of R in the above general formula (35) 1 ~R 5 and R 8 ~R 19 Same meaning.)

[1704]

Chemical Formula 150

[1705]

[1706] (In the above general formula (353),

[1707] By R 1 ~R 3 A group of two or more adjacent ones, consisting of R 4 ~R 6 A group of two or more adjacent ones, consisting of R 7 ~R 10 A group of two or more adjacent ones, consisting of R 13 ~R 15 The adjacent groups of two or more and the groups of R 16 ~R 19 One or more of the adjacent groups of two or more

[1708] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1709] bonded to each other to form a substituted or unsubstituted fused ring, or

[1710] Not bonded to each other,

[1711] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 1 ~R 10 and R 13 ~R 19 Each independently of R in the above general formula (35) 1 ~R 10 and R 13 ~R 19 Same meaning.)

[1712] (Method for producing the compound represented by general formula (31))

[1713] The compound represented by the general formula (31) can be produced by a known method. Alternatively, the compound represented by the general formula (31) can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[1714] (Specific examples of compounds represented by general formula (31))

[1715] Specific examples of the compound represented by the general formula (31) include the following compounds.

[1716]

Chemical Formula 151

[1717]

[1718]

Chemical Formula 152

[1719]

[1720]

Chemical Formula 153

[1721]

[1722]

Chemical Formula 154

[1723]

[1724]

Chemical Formula 155

[1725]

[1726]

Chemical Formula 156

[1727]

[1728]

Chemical Formula 157

[1729]

[1730] In one embodiment, the substituents in the third compound described as "substituted or unsubstituted" are unsubstituted alkyl groups having 1 to 50 carbon atoms, unsubstituted alkenyl groups having 2 to 50 carbon atoms, unsubstituted alkynyl groups having 2 to 50 carbon atoms, unsubstituted cycloalkyl groups having 3 to 50 ring carbon atoms, -Si(R 901a )(R 902a )(R 903a )、-O-(R 904a )、-S-(R 905a )、-N(R 906a )(R 907a ), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1731] R 901a ~R 907a are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1732] In R 901a If there are two or more, two or more R 901a Same or different from each other, in R 902a If there are two or more, two or more R 902a Same or different from each other, in R 903a If there are two or more, two or more R 903a Same or different from each other, in R 904a If there are two or more, two or more R 904a Same or different from each other, in R 905a If there are two or more, two or more R 905a Same or different from each other, in R 906a If there are two or more, two or more R 906a Same or different from each other, in R 907a If there are two or more, two or more R 907a Same as or different from each other.

[1733] In one embodiment, the substituent in the third compound described as "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1734] In one embodiment, the substituent in the third compound described as "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.

[1735] (Maximum peak wavelength)

[1736] In the third embodiment, the maximum peak wavelength of the third compound as the fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less.

[1737] In the third embodiment, the maximum peak wavelength of the third compound as the fluorescent material is preferably 430 nm or longer, more preferably 440 nm or longer.

[1738] In this specification, the maximum peak wavelength of fluorescent light may be referred to as the fluorescent light maximum peak wavelength.

[1739] In the organic EL device of the third embodiment, the third compound preferably emits blue light. In this specification, blue light emission refers to light emission having a maximum peak wavelength in a fluorescence spectrum within a range of 430 nm to 480 nm.

[1740] (Full width at half maximum of luminescence spectrum)

[1741] In the third embodiment, the emission spectrum half-maximum width (FWHM) of the third compound as the fluorescent material is preferably 40 nm or less, more preferably 30 nm or less.

[1742] In this specification, the maximum peak wavelength of fluorescence refers to the maximum peak wavelength of the compound to be measured at 10 -6 mol / L and above 10 -5 The maximum peak wavelength of the fluorescence spectrum at which the luminescence intensity in the fluorescence spectrum measured by dissolving the toluene solution at a concentration of 1 mol / L or less reaches the maximum. The luminescence spectrum half-width (FWHM) is the full width at half-maximum in the maximum peak of the fluorescence spectrum. As an apparatus for measuring the fluorescence spectrum, a fluorescence spectrometer can be used. For example, a fluorescence spectrometer manufactured by JASCO Corporation (device name: FP-8300) can be used. It should be noted that the fluorescence spectrometer is not limited to the apparatus exemplified here.

[1743] (Stokes shift)

[1744] In this embodiment, the Stokes shift of the third compound as the fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less.

[1745] In this embodiment, the Stokes shift of the third compound as the fluorescent material is preferably 5 nm or more, more preferably 10 nm or more.

[1746] When the Stokes shift of the third compound is 20 nm or less, the excitation energy can be reduced.

[1747] When the Stokes shift of the third compound is 10 nm or more, self-absorption can be suppressed and efficiency loss can be reduced.

[1748] The Stokes shift can be measured by the following method. The compound to be measured is subjected to 2.0×10 -5 mol / L concentration was dissolved in toluene to prepare a sample for measurement. The sample for measurement placed in a quartz colorimetric cell was irradiated with continuous light in the ultraviolet-visible region at room temperature (300K) and the absorption spectrum was measured (vertical axis: absorbance, horizontal axis: wavelength). The absorption spectrum can be measured using a spectrophotometer, for example, the spectrophotometer U-3900 / 3900H model of Hitachi High-Tech Science Co., Ltd. In addition, the compound to be measured was diluted with 4.9×10 -6 A sample for measurement is prepared by dissolving it in toluene at a concentration of 1 mol / L. The sample placed in a quartz colorimetric cell is irradiated with excitation light at room temperature (300K), and the fluorescence spectrum is measured (vertical axis: fluorescence intensity, horizontal axis: wavelength). Fluorescence spectrum measurement can be performed using a spectrophotometer, such as the F-7000 spectrofluorometer from Hitachi High-Technologies Corporation. Based on these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength is calculated to determine the Stokes shift (SS). The unit of the Stokes shift SS is nm.

[1749] (Relationship between the Sensitizing Material and the Fluorescent Material in the Light-Emitting Layer)

[1750] In one embodiment, the sensitizing material (compound according to the first embodiment) serving as the first host material is the delayed fluorescent compound described above. In one embodiment, when the light-emitting layer contains the delayed fluorescent compound as the sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.

[1751] Figure 4 This is a diagram showing an example of the energy level relationship between the sensitizing material and the fluorescent material when the light-emitting layer contains a delayed fluorescent compound (second compound) as a sensitizing material and a fluorescent material (third compound). Figure 4In the formula ( ), S0 represents the ground state. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. Figure 4 The dotted arrow from S1 (M2) toward S1 (M3) in represents the Forster-type energy transfer from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material.

[1752] like Figure 4 As shown, if a compound with a small ΔST(M2) is used as a delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) with the help of thermal energy. Then, Forster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[1753] In the organic EL device according to the third embodiment, the lowest excited singlet energy S1(GT2) of the sensitizing material and the lowest excited singlet energy S1(D) of the fluorescent material preferably satisfy the relationship represented by the following equation (Equation 4).

[1754] S1(GT2)>S1(D)…(Formula 4)

[1755] In one embodiment, the energy gap T of the sensitizing material at 77 [K] 77K (GT2) and the energy gap T of the fluorescent material at 77[K] 77K (D) also preferably satisfies the relationship of the following mathematical formula (Mathematical formula 6A).

[1756] T 77K (GT2)>T 77K (D)…(Mathematical Formula 6A)

[1757] When the organic EL element of the third embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer.

[1758] The maximum peak wavelength of light emitted from the organic EL element is measured as follows.

[1759] A voltage was applied to the organic EL element so that the current density was 10 mA / cm 2The spectral emission brightness spectrum at 1 ℃ was measured using a spectral emission brightness meter CS-2000 (manufactured by Konica Minolta Co., Ltd.).

[1760] In the obtained spectroscopic emission luminance spectrum, the peak wavelength of the emission spectrum at which the emission intensity reaches the maximum is measured and defined as the maximum peak wavelength (unit: nm).

[1761] (Content of Compound in Light Emitting Layer)

[1762] The content ratios of the first host material (second compound) and the fluorescent material (third compound) contained in the light-emitting layer are preferably within the following ranges, for example.

[1763] The content of the second compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. In addition, the content of the second compound may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or 99% by mass or more and 99.9% by mass or less.

[1764] The content of the third compound is preferably 0.01% by mass to 10% by mass, more preferably 0.01% by mass to 5% by mass, and even more preferably 0.01% by mass to 1% by mass.

[1765] It should be noted that this embodiment does not exclude the inclusion of materials other than the second compound and the third compound in the light-emitting layer.

[1766] In the light-emitting layer, the second compound may be contained in one type or in two or more types. In the light-emitting layer, the third compound may be contained in one type or in two or more types.

[1767] The structure of the organic EL element will be further described.

[1768] (Substrate)

[1769] The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, and plastic can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent. For example, a plastic substrate can be mentioned. As materials forming the plastic substrate, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

[1770] (anode)

[1771] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or mixture thereof having a large work function (specifically, 4.0 eV or greater). Specifically, examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metal materials (e.g., titanium nitride).

[1772] These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target to which zinc oxide is added at 1% by mass or more and 10% by mass or less relative to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target to which tungsten oxide is added at 0.5% by mass or less and 5% by mass or less relative to indium oxide and zinc oxide is added at 0.1% by mass or less and 1% by mass or less relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

[1773] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is easy to conduct holes (hol e )-injected composite material, and therefore, materials that can serve as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

[1774] It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), and ytterbium (Yb), and alloys thereof. It should be noted that when forming the anode using alkali metals, alkaline earth metals, and alloys thereof, vacuum evaporation or sputtering can be used. In addition, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.

[1775] In bottom-emitting organic EL devices, the anode is preferably formed from a translucent or semi-translucent metal material that transmits light from the light-emitting layer. In this specification, translucent or semi-translucent properties refer to properties that transmit at least 50% (preferably at least 80%) of the light emitted by the light-emitting layer. Translucent or semi-translucent metal materials can be appropriately selected from the materials listed above for the anode.

[1776] In top-emission organic EL devices, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a light-reflective metal material. In this specification, light reflectivity refers to the property of reflecting at least 50% (preferably at least 80%) of the light emitted by the light-emitting layer. The light-reflective metal material can be appropriately selected from the materials listed above for the anode.

[1777] The anode may consist solely of a reflective layer or may have a multilayer structure comprising a reflective layer and a conductive layer (preferably a transparent conductive layer). In the case where the anode comprises a reflective layer and a conductive layer, the conductive layer is preferably disposed between the reflective layer and the hole transport region. The conductive layer may be appropriately selected from the materials listed above for the anode.

[1778] (cathode)

[1779] The cathode is preferably made of a metal, alloy, conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group I or Group II of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1780] It should be noted that when an alkali metal, an alkaline earth metal, or an alloy thereof is used to form the cathode, vacuum evaporation or sputtering can be used. In addition, when a silver paste is used, coating or inkjet methods can be used.

[1781] It should be noted that by providing an electron injection layer, a variety of conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide can be used to form the cathode regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

[1782] In the case of a bottom-emitting organic EL element, the cathode is a reflective electrode. The reflective electrode is preferably formed of a light-reflective metal material. The light-reflective metal material can be appropriately selected from the materials listed in the section on the cathode.

[1783] In the case of a top-emission organic EL element, the cathode is preferably formed of a translucent or semi-translucent metal material that transmits light from the light-emitting layer. The translucent or semi-translucent metal material can be appropriately selected from the materials listed in the above section on the cathode.

[1784] The organic EL element according to this embodiment may be a bottom emission type organic EL element. Alternatively, the organic EL element according to this embodiment may be a top emission type organic EL element.

[1785] When the organic EL element is a bottom emission type, it is preferable that the anode is a light-transmitting electrode having light transmission properties, and the cathode is a light-reflecting electrode having light reflection properties.

[1786] When the organic EL element is a top emission type, it is preferable that the anode is a light reflective electrode having light reflectivity, and the cathode is a light transmissive electrode having light transmissivity.

[1787] (Capping layer)

[1788] When the organic EL element is a top emission type, the organic EL element generally includes a capping layer on the upper portion of the cathode.

[1789] The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide).

[1790] Furthermore, the capping layer may contain at least one compound selected from, for example, aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives.

[1791] Furthermore, a laminate in which layers containing these substances are laminated can also be used as a capping layer.

[1792] (Hole Injection Layer)

[1793] The hole injection layer is a layer containing a substance with high hole injectability. Examples of substances with high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

[1794] In addition, examples of substances with high hole-injecting properties include low-molecular-weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCNl) and other aromatic amine compounds.

[1795] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD) and the like polymer compounds. In addition, a polymer compound to which an acid is added, such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly (styrene sulfonic acid) (PAni / PSS) can also be used.

[1796] (Hole Transport Layer)

[1797] The hole transport layer is a layer containing a substance with high hole transport properties. The hole transport layer can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N -phenylamino]biphenyl (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), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) and the like. The substances described here are mainly aromatic amine compounds having 10 -6 cm 2 / Vs or higher hole mobility.

[1798] Carbazole derivatives such as CBP, CzPA, and PCzPA, and anthracene derivatives such as t-BuDNA, DNA, and DPAnth can also be used in the hole transport layer. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used.

[1799] It should be noted that any substance other than these may also be used as long as it has a higher hole transport property than electrons. It should be noted that the layer containing a substance with a high hole transport property may not only be a single layer but also a layer formed by stacking two or more layers formed of the above substances.

[1800] (Electron Transport Layer)

[1801] The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer can use 1) metal complexes such as aluminum complexes, beryllium complexes, zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as: Almq3), bis (10-hydroxybenzo [h] quinoline) beryllium (abbreviated as: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. The substances described here are mainly heteroaromatic compounds having 10 -6 cm 2 / Vs or more. It should be noted that as long as the electron transport property is higher than the hole transport property of the substance, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can be a single layer or a layer formed by stacking two or more layers of the above substances.

[1802] Furthermore, polymer compounds may be used in the electron transport layer. Examples 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).

[1803] (Electron Injection Layer)

[1804] The electron injection layer is a layer comprising a substance having high electron injection. Alkali metals, alkaline earth metals or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx) etc. can be used in the electron injection layer. In addition, a material formed by containing an alkali metal, alkaline earth metal or a compound thereof in a substance having electron transportability can also be used, specifically a material formed by containing magnesium (Mg) in Alq etc. can be used. It should be noted that electron injection from the cathode can be more efficiently performed at this time.

[1805] Alternatively, a composite material mixed with an organic compound and an electron donor (donor) can also be used in the electron injection layer. Such a composite material has excellent electron injection and electron transport properties because it generates electrons in the organic compound through the electron donor. At this time, as an organic compound, it is preferably a material with excellent transport of the generated electrons. Specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, it is as long as it is a substance that shows electron donating properties for the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be mentioned. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be mentioned. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

[1806] (Layer Formation Method)

[1807] The method for forming each layer of the organic EL element involved in any of the embodiments described above is not limited except for those specifically mentioned above, and well-known methods such as dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film-forming methods such as spin coating, immersion, flow coating, and inkjet can be used.

[1808] (film thickness)

[1809] The thickness of each organic layer of the organic EL element according to the third embodiment is not limited except as specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are likely to occur, while if the film thickness is too thick, a high applied voltage is required, resulting in reduced efficiency. Therefore, the film thickness of each organic layer of the organic EL element is generally preferably within the range of several nanometers to 1 μm.

[1810] According to one aspect of the third embodiment, it is possible to achieve higher performance of the organic EL element.

[1811] According to one aspect of the third embodiment, the life of the organic EL element can be extended.

[1812] The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1813] [Fourth embodiment]

[1814] The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, components identical to those in the third embodiment are denoted by the same reference numerals and names, and the description thereof will be omitted or simplified. In the fourth embodiment, materials and compounds not specifically mentioned may be the same as those described in the third embodiment.

[1815] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a second host material.

[1816] In this specification, a compound used as a second host material may be referred to as a first compound.

[1817] In one embodiment, the light-emitting layer contains a second host material (first compound), a first host material (second compound), and a fluorescent material (third compound).

[1818] (Luminescent layer)

[1819] In one embodiment, the second host material, the first host material (the compound according to the first embodiment), and the fluorescent material are contained in a single layer.

[1820] In one embodiment, a second host material, a sensitizing material serving as the first host material, and a fluorescent material are contained in a single layer. For example, in an organic EL device having a single light-emitting layer, the second host material, the sensitizing material, and the fluorescent material are contained in the single light-emitting layer. In a device having multiple light-emitting layers, the second host material, the sensitizing material, and the fluorescent material are contained in any single light-emitting layer among the multiple light-emitting layers.

[1821] In one embodiment, when the light-emitting layer contains a delayed fluorescence compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.

[1822] [Second main material]

[1823] In the fourth embodiment, the second host material is a first compound containing one or more partial structures selected from the partial structures represented by the following general formulae (101) to (118) in one molecule.

[1824]

Chemical Formula 158

[1825]

[1826]

Chemical Formula 159

[1827]

[1828] (In the above general formula (101),

[1829] A 11 ~A 16 Each independently is a nitrogen atom, CR 11 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound,

[1830] Among them, A 11 ~A 16 At least one of them is a carbon atom bonded to other atoms or other structures in the molecule of the first compound,

[1831] In R 11 When there are multiple R 11 Same or different from each other, composed of multiple R 11 One or more of the adjacent groups of two or more

[1832] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1833] bonded to each other to form a substituted or unsubstituted fused ring, or

[1834] Not bonded to each other,

[1835] In the above general formula (102),

[1836] A1 to A4 are each independently a nitrogen atom, CR 12 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound,

[1837] R 12 are each independently a hydrogen atom or a substituent, or adjacent R 12 One or more of the groups formed by each other are bonded to each other to form a ring,

[1838] In R 12 When there are multiple R 12 Same or different from each other, composed of multiple R 12 One or more of the adjacent groups of two or more

[1839] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1840] bonded to each other to form a substituted or unsubstituted fused ring, or

[1841] Not bonded to each other,

[1842] X 10 NR 13 、C(R 14 )(R 15 )、Si(R 16 )(R 17 ), oxygen atoms, sulfur atoms, nitrogen atoms bonded to other atoms or other structures in the molecule of the first compound, and R 18 and carbon atoms respectively bonded to other atoms or other structures in the molecule of the first compound, or to R 19 silicon atoms bonded to other atoms or other structures in the molecule of the first compound,

[1843] Among them, the carbon atoms in A1 to A4, X 10 The nitrogen atoms, X 10 The carbon atoms and X 10 At least one of the silicon atoms in the first compound is bonded to other atoms or other structures in the molecule of the first compound,

[1844] By R 14 and R 15 Group

[1845] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1846] bonded to each other to form a substituted or unsubstituted fused ring, or

[1847] Not bonded to each other,

[1848] By R 16 and R 17 Group

[1849] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1850] bonded to each other to form a substituted or unsubstituted fused ring, or

[1851] Not bonded to each other,

[1852] In the above general formula (103),

[1853] By R 115 and R 116 Group

[1854] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[1855] bonded to each other to form a substituted or unsubstituted fused ring, or

[1856] Not bonded to each other,

[1857] In the above general formulas (101) to (104),

[1858] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 11 、R 12 、R 14 、R 15 、R 16 、R 17 、R 115 and R 116 , and R 13 、R 18 、R 19 and R 117 Each independently

[1859] hydrogen atoms,

[1860] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1861] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[1862] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1863] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1864] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1865] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[1866] -O-(R 904 ) shown in the group,

[1867] -S-(R 905 ) shown in the group,

[1868] -N(R 906 )(R 907 ) shown in the group,

[1869] -C(=O)R 908 The groups shown,

[1870] -COOR 909 The groups shown,

[1871] -P(=O)(R 910 )(R 911 ) shown in the group,

[1872] -P(=O)(OR912 )(OR 913 ) shown in the group,

[1873] -Ge(R 914 )(R 915 )(R 916 ) shown in the group,

[1874] -B(R 917 )(R 918 ) shown in the group,

[1875] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[1876] Halogen atoms,

[1877] cyano,

[1878] Nitro,

[1879] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1880] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1881] In the above general formulas (103) to (118),

[1882] * represents a bonding site with other atoms or other structures in the molecule of the first compound,

[1883] When the first compound has a plurality of partial structures represented by the general formulae (101) to (104),

[1884] The partial structures represented by the general formula (101) are the same as or different from each other.

[1885] The partial structures represented by the above general formula (102) are the same as or different from each other,

[1886] The partial structures represented by the above general formula (103) are the same as or different from each other,

[1887] The partial structures represented by the above general formula (104) may be the same as or different from each other.

[1888] (In the above first compound, R 901 ~R 918 Each independently

[1889] hydrogen atoms,

[1890] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1891] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1892] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1893] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[1894] In R 901 When there are multiple R 901 Same or different from each other,

[1895] In R 902 When there are multiple R 902 Same or different from each other,

[1896] In R 903 When there are multiple R 903 Same or different from each other,

[1897] In R 904 When there are multiple R 904 Same or different from each other,

[1898] In R 905 When there are multiple R 905 Same or different from each other,

[1899] In R 906 When there are multiple R 906 Same or different from each other,

[1900] In R 907 When there are multiple R 907 Same or different from each other,

[1901] In R 908 When there are multiple R 908 Same or different from each other,

[1902] In R 909 When there are multiple R 909 Same or different from each other,

[1903] In R 910 When there are multiple R 910 Same or different from each other,

[1904] In R 911 When there are multiple R 911 Same or different from each other,

[1905] In R 912 When there are multiple R 912 Same or different from each other,

[1906] In R913 When there are multiple R 913 Same or different from each other,

[1907] In R 914 When there are multiple R 914 Same or different from each other,

[1908] In R 915 When there are multiple R 915 Same or different from each other,

[1909] In R 916 When there are multiple R 916 Same or different from each other,

[1910] In R 917 When there are multiple R 917 Same or different from each other,

[1911] In R 918 When there are multiple R 918 Same as or different from each other.)

[1912] In the above general formula (102), X 10 In the case of "a nitrogen atom bonded to another atom or another structure in the molecule of the first compound", the above general formula (102) is represented by the following general formula (102-1).

[1913] In the above general formula (102), X 10 For "with R 18 In the case of "a carbon atom that is respectively bonded to other atoms or other structures in the molecule of the first compound", the above general formula (102) is represented by the following general formula (102-2).

[1914] In the above general formula (102), X 10 For "with R 19 In the case of "a silicon atom that is respectively bonded to other atoms or other structures in the molecule of the first compound", the above general formula (102) is represented by the following general formula (102-3).

[1915] In the general formulae (102-1) to (102-3), A1 to A4 are independently the same as A1 to A4 in the general formula (102), and R 18 and R 19 Each independently of R in the above general formula (102) 12 The meanings are the same, and * represents a bonding site with other atoms or other structures in the molecule of the first compound.

[1916]

Chemical Formula 160

[1917]

[1918] In one embodiment, the second host material has at least one partial structure represented by the above general formula (101).

[1919] In one embodiment, the partial structure represented by the general formula (101) is at least one selected from the partial structures represented by the following general formulas (A11) to (A19).

[1920]

Chemical Formula 161

[1921]

[1922]

Chemical Formula 162

[1923]

[1924] (In the above general formulas (A11) to (A16), A 12 ~A 16 Each independently is a nitrogen atom or CR 11 , R 11 and R in the above general formula (101) 11 have the same meaning, * represents the bonding site with other atoms or other structures in the molecule of the first compound,

[1925] In the above general formulas (A17) and (A18), A 11 ~A 22 Each independently is a nitrogen atom or CR 11 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, R 11 Each independently of R in the above general formula (101) 11 Same meaning, A 11 ~A 22 At least one of them is a carbon atom bonded to other atoms or other structures in the molecule of the first compound,

[1926] In the above general formula (A19), A 11 ~A 18 Each independently is a nitrogen atom or CR 11 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, R 11 Each independently of R in the above general formula (101) 11 Same meaning, X 11 and X 12 Each independently of X in the above general formula (102) 10 The meaning is the same, and A 11 ~A18 The carbon atoms in 11 and X 12 The nitrogen atoms, X 11 and X 12 The carbon atoms in 11 and X 12 At least one of the silicon atoms in the compound is bonded to another atom or other structure in the molecule of the first compound. In the general formulae (A11) to (A19), * represents a bonding site to another atom or other structure in the molecule of the first compound.

[1927] In one embodiment, the second host material has at least one partial structure represented by the above general formula (102).

[1928] In one embodiment, the partial structure represented by the general formula (102) is at least one selected from the partial structures represented by the following general formulas (B11) to (B24).

[1929]

Chemical Formula 163

[1930]

[1931] (In the above general formulas (B11) to (B16), Ax1 to Ax4 are each independently a nitrogen atom or CR 12 , R 12 Each independently of R in the above general formula (102) 12 Same meaning, X 10 and X in the above general formula (102) 10 have the same meaning, * represents the bonding site with other atoms or other structures in the molecule of the first compound,

[1932] In the above general formula (B17), Ax1, Ax2 and Ay1 to Ay4 are each independently a nitrogen atom or CR 12 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, R 12 Each independently of R in the above general formula (102) 12 Same meaning, X 10 and X in the above general formula (102) 10 The same meaning, wherein the carbon atoms in Ax1, Ax2 and Ay1 to Ay4, X 10 The nitrogen atoms, X 10 The carbon atoms and X 10 At least one of the silicon atoms in the first compound is bonded to other atoms or other structures in the molecule of the first compound,

[1933] In the above general formula (B18), Ay1 to Ay8 are each independently a nitrogen atom or CR 12 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, R 12 Each independently of R in the above general formula (102) 12 Same meaning, X 10 and X in the above general formula (102) 10 The same meaning, the carbon atoms in Ay1~Ay8, X 10 The nitrogen atoms, X 10 The carbon atoms and X 10 At least one of the silicon atoms in the first compound is bonded to other atoms or other structures in the molecule of the first compound,

[1934] In the above general formulas (B11) to (B18), * represents a bonding site with other atoms or other structures in the molecule of the above first compound.

[1935]

Chemical Formula 164

[1936]

[1937] (In the above general formulas (B19) to (B24), Ay1 to Ay8 and Ay9 to Ay 12 Each independently is a nitrogen atom or CR 12 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, R 12 Each independently of R in the above general formula (102) 12 Same meaning, X9 and X 10 Each independently of X in the above general formula (102) 10 Same meaning,

[1938] Ay1~Ay8 and Ay9~Ay 12 The carbon atoms, X9 and X 10 The nitrogen atoms, X9 and X 10 The carbon atoms in X9 and X 10 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the first compound.

[1939] In the first compound of the fourth embodiment, preferably, R 11 、R 12 and R 115 ~R 117Each of them is independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 ring carbon atoms, an unsubstituted haloalkyl group having 1 to 30 ring carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 ring carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 30 ring carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 30 ring carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a mercapto group, an unsubstituted alkylthio group having 1 to 30 ring carbon atoms, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms.

[1940] In the first compound of the fourth embodiment, more preferably, R 11 、R 12 and R 115 ~R 117 Each of them is independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 ring carbon atoms, an unsubstituted haloalkyl group having 1 to 6 ring carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 ring carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, an unsubstituted alkoxy group having 1 to 6 ring carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 12 ring carbon atoms, an unsubstituted arylamino group having 6 to 60 ring carbon atoms, a mercapto group, an unsubstituted alkylthio group having 1 to 6 ring carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[1941] In the first compound of the fourth embodiment, it is further preferred that R 11 、R 12 and R 115 ~R 117 A hydrogen atom.

[1942] In the first compound of the fourth embodiment, preferably, X 10 R in 13 ~R 19 and R in X9 13 ~R 19 (with X 10 R in 13 ~R 19 have the same meaning) are each independently a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms.

[1943] In the first compound of the fourth embodiment, more preferably, X 10 R in 13 ~R 19 and R in X9 13 ~R 19 Each is independently a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms.

[1944] In the first compound of the fourth embodiment, it is further preferred that X 10 R in 13 ~R 19 and R in X9 13 ~R 19 Each is independently an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 ring carbon atoms.

[1945] Examples of the partial structure represented by any of the general formulae (101) to (118) include partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125).

[1946] The first compound also preferably contains at least one of the partial structures represented by the following general formulae (A101) to (A121) and (B101) to (B125) in one molecule.

[1947]

Chemical Formula 165

[1948]

[1949] In the above general formulas (A101) to (A107), R 101 ~R 106 Each independently of R in the above general formula (101) 11 Same meaning, R 101 ~R 106 At least one of them is a single bond to another atom or other structure in the molecule of the first compound.

[1950] In the above general formulas (A101) to (A107), adjacent R 101 With R 102 Group, R 102 With R 103 Group, R 103 With R 104 Group, R 104 With R 105 Group, R 105 With R 106 The group and R106 With R 101 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1951]

Chemical Formula 166

[1952]

[1953] In the above general formulas (A108) to (A109), R 110 Each independently of R in the above general formula (101) 11 Same meaning, R 110 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, and the plurality of R 110 Same or different from each other, composed of multiple R 110 Among the groups of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1954]

Chemical Formula 167

[1955]

[1956] In the above general formulas (A110) to (A114), R 110 and R 112 ~R 114 Each independently of R in the above general formula (101) 11 Same meaning, X 110 Each independently of X in the above general formula (102) 10 The same meaning, where R 110 and R 112 ~R 114 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, or X 110 At least one of the nitrogen atoms, carbon atoms and silicon atoms in the first compound is bonded to other atoms or other structures in the molecule of the first compound, and multiple R 110 Same as or different from each other.

[1957] In the above general formulas (A110) to (A114), multiple R 110 A group of two or more adjacent 112 With R 113 Group and X 110 R in 14 With R 15 The group (with X 10 R in14 With R 15 The same meaning as the group), X 110 R in 16 With R 17 The group (with X 10 R in 16 With R 17 One or more groups in the group (groups denoted as ' and ' have the same meaning) may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1958]

Chemical Formula 168

[1959]

[1960] In the above general formulas (A115) to (A119), R 110 and R 112 ~R 114 Each independently of R in the above general formula (101) 11 The same meaning, where R 110 and R 112 ~R 114 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, and the plurality of R 110 Same as or different from each other.

[1961] In the above general formulas (A115) to (A119), a plurality of R 110 A group of two or more adjacent ones and R 112 and R 113 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1962]

Chemical Formula 169

[1963]

[1964] In the above general formulas (A120) to (A121), R 110 Each independently of R in the above general formula (101) 11 The same meaning, where R 110 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, and the plurality of R 110 Same as or different from each other.

[1965] In the above general formulas (A120) to (A121), multiple R 110Among the groups of two or more adjacent ones, one or more groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1966]

Chemical Formula 170

[1967]

[1968] In the above general formulas (B101) to (B109), R 114 and R 121 ~R 131 Each independently of R in the above general formula (102) 12 The same meaning, where R 114 and R 121 ~R 131 At least one of them is a single bond to another atom or other structure in the molecule of the first compound.

[1969] In the above general formulas (B101) to (B102), R 122 With R 123 Group, R 123 With R 114 The group and R 114 With R 121 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1970] In the above general formulas (B105) to (B106), R 124 With R 125 Group, R 125 With R 126 Group, R 126 With R 127 Group, R 127 With R 128 The group and R 128 With R 129 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1971] In the above general formula (B107), R 124 With R 125 Group, R 125 With R 126 Group, R 126 With R 127 Group, R 127 With R 128 Group, R 128 With R 129 Group, R 129With R 114 The group and R 114 With R 124 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1972] In the above general formulas (B108) to (B109), R 124 With R 125 Group, R 125 With R 126 Group, R 130 With R 131 The group and R 131 With R 129 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1973]

Chemical Formula 171

[1974]

[1975] In the above general formulas (B110) to (B117), R 110 and R 132 ~R 135 Each independently of R in the above general formula (102) 12 The same meaning, where R 110 and R 132 ~R 135 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, and the plurality of R 110 Same as or different from each other.

[1976] In the above general formulas (B110) to (B117), multiple R 110 A group of two or more adjacent ones and R 132 With R 133 One or more of the groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1977]

Chemical Formula 172

[1978]

[1979] In the above general formulas (B118) to (B123), R 110 Each independently of R in the above general formula (102) 12 Xa and Xb are independently the same as X in the above general formula (102). 10 The same meaning, where R110 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, or at least one of the nitrogen atoms, carbon atoms and silicon atoms in Xa and Xb is bonded to other atoms or other structures in the molecule of the first compound, and multiple R 110 Same as or different from each other.

[1980] In the above general formulas (B118) to (B123), multiple R 110 A group of two or more adjacent ones, X a R in 14 With R 15 The group and R in Xb 14 With R 15 The group (with X 10 R in 14 With R 15 The same meaning as the group), and X a R in 16 With R 17 The group and R in Xb 16 With R 17 The group (with X 10 R in 16 With R 17 One or more groups in the group (groups denoted as ' and ' have the same meaning) may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1981]

Chemical Formula 173

[1982]

[1983] In the above general formulas (B124) to (B125), R 110 Each independently of R in the above general formula (102) 12 Xa, Xb and Xc are independently the same as X in the above general formula (102). 10 The same meaning, where R 110 At least one of them is a single bond to other atoms or other structures in the molecule of the first compound, or X a , Xb and X c At least one of the nitrogen atoms, carbon atoms and silicon atoms in the first compound is bonded to other atoms or other structures in the molecule of the first compound, and multiple R 110 Same as or different from each other.

[1984] In the above general formulas (B124) to (B125), multiple R 110 A group of two or more adjacent ones, R in Xa, Xb and Xc14 With R 15 The group (with X 10 R in 14 With R 15 and R in Xa, Xb, and Xc 16 With R 17 The group (with X 10 R in 16 With R 17 One or more groups in the group (groups denoted as ' and ' have the same meaning) may be bonded to each other to form a substituted or unsubstituted monocyclic ring, may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1985] In the above general formulas (A101) to (A121) and (B101) to (B125), R 110 、R 101 ~R 106 、R 112 ~R 114 、R 121 ~R 131 and R 132 ~R 135 Each of them is independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1986] More preferably, it is a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted haloalkyl group having 1 to 6 carbon atoms.

[1987] More preferably, it is a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, or an unsubstituted alkyl group having 1 to 6 ring carbon atoms.

[1988] In the above general formulas (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X 110 R in 13 ~R 19 (with X 10 R in 13 ~R 19 have the same meaning) are each independently preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted haloalkyl group having 1 to 30 carbon atoms,

[1989] More preferably, it is a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted haloalkyl group having 1 to 6 carbon atoms.

[1990] More preferably, it is an unsubstituted aryl group having 6 to 14 ring carbon atoms or an unsubstituted alkyl group having 1 to 6 ring carbon atoms.

[1991] In the fourth embodiment, it is preferred that the first compound (I) has at least one group selected from a cyano group, an amino group, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, or (II) has at least one monovalent or higher residue derived from any one of substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, and substituted or unsubstituted triphenylene.

[1992] In the fourth embodiment, it is more preferred that the first compound (III) has at least one cyano group, or (IV) has at least one monovalent or higher residue derived from any one of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[1993] In the fourth embodiment, it is further preferred that the first compound has at least one monovalent or higher residue derived from any one of substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted pyrimidine.

[1994] In the fourth embodiment, the first compound preferably has at least one monovalent or higher-valent residue derived from a substituted or unsubstituted carbazole.

[1995] In the fourth embodiment, the first compound preferably has at least one partial structure represented by the following general formula (150).

[1996]

Chemical Formula 174

[1997]

[1998] (In the above general formula (150), R 150 ~R 158 At least one of them is a single bond to another atom or other structure in the molecule of the first compound,

[1999] R is not a single bond 150 ~R 158 Each independently

[2000] hydrogen atoms,

[2001] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2002] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[2003] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2004] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2005] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2006] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2007] -O-(R 904 ) shown in the group,

[2008] -S-(R 905 ) shown in the group,

[2009] -N(R 906 )(R 907 ) shown in the group,

[2010] -C(=O)R 908 The groups shown,

[2011] -COOR 909 The groups shown,

[2012] -P(=O)(R 910 )(R 911 ) shown in the group,

[2013] -Ge(R 912 )(R 913 )(R 914 ) shown in the group,

[2014] -B(R 915 )(R 916 ) shown in the group,

[2015] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[2016] Halogen atoms,

[2017] cyano,

[2018] Nitro,

[2019] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2020] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2021] In the above general formula (150), R 150 Preferred are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 30 ring atoms, substituted or unsubstituted alkyl groups having 1 to 30 ring atoms, or substituted or unsubstituted haloalkyl groups having 1 to 30 ring atoms; more preferred are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, or substituted or unsubstituted alkyl groups having 1 to 30 ring atoms; and even more preferred are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms.

[2022] (First compound represented by general formula (161) or (162))

[2023] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (161) or the following general formula (162).

[2024]

Chemical Formula 175

[2025]

[2026] (In the above general formula (161), Ar 161 for

[2027] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or

[2028] a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms,

[2029] m1 is 1, 2, 3, 4, 5 or 6,

[2030] R 161 is an electron-donating group, R 161 Each of them constitutes Ar 161 The element bonding,

[2031] When m1 is 2 or more, multiple R 161 Same or different from each other,

[2032] Among them, Ar 161 Aromatic hydrocarbon rings and heterocyclic rings that are not electron-withdrawing, Ar161 When there is a substituent, the substituent is not an electron-withdrawing group.

[2033] In the above general formula (162), Ar 162 for

[2034] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or

[2035] a substituted or unsubstituted heterocyclic ring having 5 to 30 ring atoms,

[2036] n1 is 1, 2, 3, 4, 5 or 6,

[2037] R 162 is an electron-withdrawing group, R 162 Each of them constitutes Ar 162 The element bonding,

[2038] When n1 is 2 or more, multiple R 162 Same or different from each other,

[2039] Among them, Ar 162 Aromatic hydrocarbon rings and heterocyclic rings that are not electron-donating, Ar 162 When there is a substituent, the substituent is not an electron-donating group.)

[2040] In the above general formulas (161) and (162), Ar 161 and Ar 162 Each independently is preferably a monovalent or higher-valent residue derived from any one of the compounds represented by the following general formulae (A61) and (A62).

[2041]

Chemical Formula 176

[2042]

[2043] In the fourth embodiment, R in the above general formula (161) 161 Each independently is preferably a monovalent or higher-valent residue derived from any one of the compounds represented by the following general formulae (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following general formula (DN7).

[2044]

Chemical Formula 177

[2045]

[2046] (In the above general formula (DN7), * represents each of the following: 161 The bonding site of the element.)

[2047] In the fourth embodiment, R in the above general formula (162) 162Each is independently preferably a monovalent or higher residue derived from any of the compounds represented by the following general formulas (AC4) to (AC18) and (AC22) to (AC23), or any of the groups represented by the following general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24).

[2048]

Chemical Formula 178

[2049]

[2050]

Chemical Formula 179

[2051]

[2052] (In the above general formula (AC1), nA is 1, 2 or 3,

[2053] In the above general formulas (AC22) to (AC23), X1 to X8 are each independently CR 163 , or a carbon atom bonded to other atoms or other structures in the molecule of the first compound, wherein at least one of the carbon atoms in X1 to X8 is bonded to the carbon atom constituting Ar 162 The element bonding,

[2054] In the above general formula (AC24), X1 to X8 are each independently a nitrogen atom or CR 163 , or with the composition Ar 162 The elements bonded to the carbon atoms,

[2055] In the above general formulas (AC22) to (AC24), R 163 When there are multiple R 163 Same or different from each other, composed of multiple R 163 One or more of the adjacent groups of two or more

[2056] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[2057] bonded to each other to form a substituted or unsubstituted fused ring, or

[2058] Not bonded to each other,

[2059] R does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring 163 Each independently of R in the above general formula (102) 12 Same meaning,

[2060] In the above general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24), * represents a group consisting of Ar 162The bonding site of the element.)

[2061] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (130).

[2062]

Chemical Formula 180

[2063]

[2064] (In the above general formula (130),

[2065] X 13 is an oxygen atom, a sulfur atom or a group represented by N-Rb,

[2066] Z1~Z 12 Each independently is a nitrogen atom or CR c The groups shown,

[2067] Ar 14 and Ar 15 Each independently

[2068] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2069] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2070] L 14 and L 15 Each independently

[2071] single bond,

[2072] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[2073] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[2074] Rb and Rc are each independently

[2075] hydrogen atoms,

[2076] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2077] a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

[2078] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2079] a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

[2080] -Si(R 901 )(R 902 )(R 903 ) shown in the group,

[2081] -C(=O)R 908 The groups shown,

[2082] -COOR 909 The groups shown,

[2083] -P(=O)(R 910 )(R 911 ) shown in the group,

[2084] -Ge(R 912 )(R 913 )(R 914 ) shown in the group,

[2085] cyano,

[2086] Nitro,

[2087] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2088] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2089] When there are multiple Rc's, the multiple Rc's may be the same or different from each other.)

[2090] In the compound represented by the above general formula (130), in -L 14 -Ar 14 The groups shown are the same as -L 15 -Ar 15 When the groups shown are the same substituents, it is also preferred that Z1 and Z 12 , Z2 and Z 11 , Z3 and Z 10 , Z4 and Z9, Z5 and Z8, and Z6 and Z7 are not all identical groups. In this case, in the above general formula (130), 13 The structure of the right side of the five-membered ring fused with X 13 The structure of the left condensed five-membered ring is different, and the compound represented by the above general formula (130) has an asymmetric structure.

[2091] Among the compounds represented by the above general formula (130), preferably, -L 14 -Ar 14 The groups shown are the same as -L 15 -Ar 15 The groups represented are different from each other. In this case, as in the above, the compound represented by the general formula (130) is a compound having an asymmetric structure.

[2092] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (120).

[2093]

Chemical Formula 181

[2094]

[2095] (In the above general formula (120),

[2096] Ar 11 and Ar 12 Each independently

[2097] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2098] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2099] L 11 and L 12 Each independently

[2100] single bond,

[2101] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

[2102] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[2103] L 13 for

[2104] a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring carbon atoms, or

[2105] a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring atoms,

[2106] m is 0, 1, 2 or 3, multiple L 13 Same or different from each other,

[2107] X1 to X8 and Y1 to Y8 are each independently N or CRa,

[2108] Among them, one of X5 to X8 and one of Y1 to Y4 are connected via L 13 The bonded carbon atoms, or directly bonded carbon atoms,

[2109] Ra is independently

[2110] hydrogen atoms,

[2111] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2112] -Si(R 901 )(R 902 )(R903 ) shown in the group,

[2113] Halogen atoms,

[2114] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2115] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2116] When there are multiple Ra, the multiple Ra are the same as or different from each other.

[2117] The compound represented by the general formula (120) satisfies one or both of the following (i) and (ii).

[2118] (i)Ar 11 and Ar 12 At least one of them is an aryl group having 6 to 50 ring carbon atoms substituted by a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted by a cyano group.

[2119] (ii) At least one of X1 to X4 and Y5 to Y8 is CRa, and at least one of Ra among X1 to X4 and Y5 to Y8 is an aryl group having 6 to 50 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 50 ring atoms substituted with a cyano group.

[2120] In the compound represented by the general formula (120), the aromatic hydrocarbon group having 6 to 50 ring carbon atoms substituted with a cyano group and the heterocyclic group having 5 to 50 ring atoms substituted with a cyano group may further have a substituent other than a cyano group.

[2121] In the compound represented by the general formula (120), m is preferably 0, 1 or 2, more preferably 0 or 1. In the compound represented by the general formula (120), when m is 0, one of X5 to X8 is directly bonded to one of Y1 to Y4 via a single bond.

[2122] In the compound represented by the above general formula (120), it is preferred that any one of the groups selected from the group consisting of X6 and Y3, the group of X6 and Y2, and the group of X7 and Y3 is a carbon atom bonded via L13 or a directly bonded carbon atom.

[2123] The combination of X6 and Y3 is through L 13 In the case of a bonded carbon atom or a directly bonded carbon atom, the compound represented by the above general formula (120) is represented by the following general formula (121).

[2124]

Chemical Formula 182

[2125]

[2126] (In the above general formula (121), Ar 11 、Ar 12 , L 11 , L 12 , L 13 , m, X1-X5, X7-X8, Y1-Y2 and Y4-Y8 are each the same as Ar in the above general formula (120) 11 、Ar 12 , L 11 , L 12 , L 13 , m, X1 to X5, X7 to X8, Y1 to Y2 and Y4 to Y8 have the same meanings, and the compound represented by the above general formula (121) satisfies at least one of the above conditions (i) and (ii).

[2127] Among the compounds represented by the above general formula (120), preferably, -Ar 11 -L 11 The groups shown are the same as -Ar 12 -L 12 The groups shown are different from each other.

[2128] As L 13 The monocyclic hydrocarbon group having 6 or less ring carbon atoms is preferably at least one group selected from the group consisting of phenylene, cyclopentenylene, cyclopentadienylene, cyclohexylene and cyclopentylene, and more preferably phenylene.

[2129] As L 13 The monocyclic heterocyclic group having 6 or less ring atoms is preferably at least one group selected from, for example, a pyrrolylene group, a pyrazinylene group, a pyridylene group, a furylene group, and a thienylene group.

[2130] In one embodiment, the light-emitting layer may contain two or more first compounds having different molecular structures. By mixing different charge-transporting compounds, the charge balance within the light-emitting layer is improved, and the luminous efficiency is expected to be improved. Moreover, by forming an exciplex by two or more first compounds (second host materials), the excitation energy is reduced, and compared to the case where the light-emitting layer contains a single second host material, it can be driven at a lower voltage.

[2131] (Method for producing the first compound)

[2132] The first compound can be produced by a known method. Alternatively, the first compound can be produced by following a known method using a known substitution reaction and raw materials corresponding to the target substance.

[2133] (Specific example of the first compound)

[2134] Specific examples of the first compound of the fourth embodiment include the following compounds. However, the present invention is not limited to these specific examples of the compounds.

[2135]

Chemical Formula 183

[2136]

[2137]

Chemical Formula 184

[2138]

[2139]

Chemical Formula 185

[2140]

[2141]

Chemical Formula 186

[2142]

[2143]

Chemical Formula 187

[2144]

[2145]

Chemical Formula 188

[2146]

[2147]

Chemical Formula 189

[2148]

[2149]

Chemical Formula 190

[2150]

[2151]

Chemical Formula 191

[2152]

[2153]

Chemical Formula 192

[2154]

[2155]

Chemical Formula 193

[2156]

[2157]

Chemical Formula 194

[2158]

[2159]

Chemical Formula 195

[2160]

[2161]

Chemical Formula 196

[2162]

[2163]

Chemical Formula 197

[2164]

[2165]

Chemical Formula 198

[2166]

[2167]

Chemical Formula 199

[2168]

[2169]

Chemical Formula 200

[2170]

[2171]

Chemical Formula 201

[2172]

[2173]

Chemical Formula 202

[2174]

[2175]

Chemical Formula 203

[2176]

[2177]

Chemical Formula 205

[2178]

[2179]

Chemical Formula 206

[2180]

[2181]

Chemical Formula 207

[2182]

[2183]

Chemical Formula 208

[2184]

[2185]

Chemical Formula 209

[2186]

[2187]

Chemical Formula 210

[2188]

[2189]

Chemical Formula 211

[2190]

[2191]

Chemical Formula 212

[2192]

[2193]

Chemical Formula 213

[2194]

[2195]

Chemical Formula 214

[2196]

[2197]

Chemical Formula 215

[2198]

[2199]

Chemical Formula 216

[2200]

[2201]

Chemical Formula 217

[2202]

[2203]

Chemical Formula 218

[2204]

[2205]

Chemical Formula 219

[2206]

[2207]

Chemical Formula 220

[2208]

[2209]

Chemical Formula 221

[2210]

[2211]

Chemical Formula 222

[2212]

[2213]

Chemical Formula 223

[2214]

[2215]

Chemical Formula 224

[2216]

[2217]

Chemical Formula 225

[2218]

[2219]

Chemical Formula 226

[2220]

[2221]

Chemical Formula 227

[2222]

[2223]

Chemical Formula 228

[2224]

[2225]

Chemical Formula 229

[2226]

[2227]

Chemical Formula 230

[2228]

[2229]

Chemical Formula 231

[2230]

[2231]

Chemical Formula 232

[2232]

[2233]

Chemical Formula 233

[2234]

[2235]

Chemical Formula 234

[2236]

[2237]

Chemical Formula 235

[2238]

[2239]

Chemical Formula 236

[2240]

[2241]

Chemical Formula 237

[2242]

[2243]

Chemical Formula 238

[2244]

[2245]

Chemical Formula 239

[2246]

[2247]

Chemical Formula 240

[2248]

[2249]

Chemical Formula 241

[2250]

[2251]

Chemical Formula 242

[2252]

[2253]

Chemical Formula 243

[2254]

[2255]

Chemical Formula 244

[2256]

[2257]

Chemical Formula 245

[2258]

[2259]

Chemical Formula 246

[2260]

[2261]

Chemical Formula 247

[2262]

[2263]

Chemical Formula 248

[2264]

[2265]

Chemical Formula 249

[2266]

[2267]

Chemical Formula 250

[2268]

[2269]

Chemical Formula 251

[2270]

[2271]

Chemical Formula 252

[2272]

[2273]

Chemical Formula 253

[2274]

[2275]

Chemical Formula 254

[2276]

[2277]

Chemical Formula 255

[2278]

[2279]

Chemical Formula 256

[2280]

[2281]

Chemical Formula 257

[2282]

[2283]

Chemical Formula 258

[2284]

[2285]

Chemical Formula 259

[2286]

[2287]

Chemical Formula 260

[2288]

[2289]

Chemical Formula 261

[2290]

[2291]

Chemical Formula 262

[2292]

[2293]

Chemical Formula 263

[2294]

[2295]

Chemical Formula 264

[2296]

[2297]

Chemical Formula 265

[2298]

[2299]

Chemical Formula 266

[2300]

[2301] (Relationship between the Second Host Material, Sensitizing Material, and Fluorescent Material in the Light-Emitting Layer)

[2302] In one embodiment, the sensitizing material serving as the first host material is the aforementioned delayed fluorescence compound.

[2303] Figure 5 This is a diagram showing an example of the energy level relationship among the second host material (first compound), the delayed fluorescence compound (second compound) as a sensitizing material, and the fluorescent material (third compound) when the light-emitting layer contains the second host material (first compound), the delayed fluorescence compound (second compound) as a sensitizing material, and the fluorescent material. Figure 5 In the formula ( ), S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the second host material, and T1(M1) represents the lowest excited triplet state of the second host material. S1(M2) represents the lowest excited singlet state of the delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of the delayed fluorescent compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. Figure 5 The dotted arrow from S1(M2) toward S1(M3) in FIG represents the Forster transition from the lowest excited singlet state of the delayed fluorescent compound to the lowest excited singlet state of the fluorescent material. r Type energy transfer.

[2304] like Figure 5 As shown, if a compound with a small ΔST(M2) is used as a delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) with the help of thermal energy. Then, Forster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence based on this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[2305] In one embodiment, the energy gap T of the second host material at 77 [K] 77K (H2) and the energy gap T of the sensitized material at 77[K] 77K(G2) preferably satisfies the relationship of the following mathematical formula (Mathematical formula 1).

[2306] T 77K (H2)>T 77K (G2)…(Formula 1)

[2307] In one embodiment, the lowest excited singlet energy S1(2) of the second host material and the lowest excited singlet energy S1(GT2) of the sensitizing material also preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 4A).

[2308] S1(H2)>S1(GT2)…(Formula 4A)

[2309] In one embodiment, the lowest excited singlet energy S1 of the second host material, the sensitizing material, and the fluorescent material also preferably satisfies the relationship of the following mathematical formula (Mathematical Formula 4B).

[2310] S1(H2)>S1(GT2)>S1(D)…(Formula 4B)

[2311] In one embodiment, the energy gap T of the second host material, the sensitizing material, and the fluorescent material at 77 [K] is 77K It is also preferable to satisfy the relationship of the following mathematical formula (Mathematical formula 6B).

[2312] T 77K (H2)>T 77K (GT2)>T 77K (D)…(Mathematical formula 6B)

[2313] (Content of Compound in Light Emitting Layer)

[2314] The content ratios of the second host material (first compound), the first host material (second compound), and the fluorescent material (third compound) contained in the light-emitting layer are preferably within the following ranges, for example.

[2315] The content of the first compound in the light-emitting layer is preferably 50% by mass or more, more preferably 70% by mass or more.

[2316] The content of the first compound in the light-emitting layer is preferably 95% by mass or less, more preferably 90% by mass or less.

[2317] The content of the second compound is preferably 5% by mass or more, more preferably 10% by mass or more.

[2318] The content of the second compound is preferably 50% by mass or less, more preferably 30% by mass or less.

[2319] The content of the third compound in the light-emitting layer is preferably 0.5% by mass or more, more preferably 1% by mass or more.

[2320] The content of the third compound in the light-emitting layer is preferably 10% by mass or less, more preferably 5% by mass or less.

[2321] The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. It should be noted that the present embodiment does not exclude the inclusion of materials other than the first compound, the second compound, and the third compound in the light-emitting layer. In the present embodiment, in the light-emitting layer, the first compound may include only one kind or more than two kinds. In the present embodiment, in the light-emitting layer, the second compound may include only one kind or more than two kinds. In the present embodiment, in the light-emitting layer, the third compound may include only one kind or more than two kinds.

[2322] According to one aspect of the fourth embodiment, it is possible to achieve higher performance of the organic EL element.

[2323] According to one aspect of the fourth embodiment, the life of the organic EL element can be extended.

[2324] The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[2325] [Fifth embodiment]

[2326] (Electronic equipment)

[2327] The electronic device involved in the fifth embodiment is equipped with one or more organic EL elements selected from the group consisting of the organic EL elements involved in the above-mentioned embodiment and the organic EL elements involved in other embodiments described later. The electronic device involved in the fifth embodiment can be equipped with any organic EL element in the other embodiments described later. As electronic devices, for example, display devices and light-emitting devices can be mentioned. As display devices, for example, display components (such as organic EL panel modules, etc.), televisions, mobile phones, tablet computers and personal computers can be mentioned. As light-emitting devices, for example, lighting and vehicle lamps can be mentioned. The light-emitting device can also be used in a display device, for example, it can also be used as a backlight for a display device.

[2328] The display device of the electronic device according to the fifth embodiment is preferably an organic EL display device equipped with organic EL elements as red pixels, green pixels, and blue pixels. In this organic EL display device, the blue pixel is preferably the organic EL element according to the third embodiment or the fourth embodiment.

[2329] [Other Implementation Methods]

[2330] An organic EL device according to one embodiment includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer may include the compound according to the first embodiment as a first host material and a phosphorescent metal complex as a dopant material.

[2331] An organic EL element involved in one embodiment includes an anode, a cathode and a light-emitting layer arranged between the anode and the cathode. The light-emitting layer can include the compound involved in the first embodiment as a first host material, a phosphorescent metal complex as a sensitizing material and a fluorescent material (third compound) as a dopant material.

[2332] (Phosphorescent Metal Complex)

[2333] In one embodiment, the phosphorescent metal complex preferably contains a heavy metal atom.

[2334] In one embodiment, the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm).

[2335] In one embodiment, the phosphorescent metal complex is preferably a compound represented by the following general formula (21).

[2336] M(L1) n1 (L2) n2 …(twenty one)

[2337]

Chemical Formula 267

[2338]

[2339] (In the above general formulas (21), (211), (212), and (213),

[2340] M is a transition metal selected from the group consisting of a first transition metal, a second transition metal and a third transition metal,

[2341] L1 is at least one ligand selected from the group consisting of the ligand represented by the above general formula (211), the ligand represented by the above general formula (212), and the ligand represented by the above general formula (213),

[2342] n1 is 1, 2 or 3,

[2343] L2 is at least one ligand selected from the group consisting of a monodentate ligand, a bidentate ligand, and a tridentate ligand,

[2344] n2 is 0, 1, 2, 3 or 4,

[2345] The CY1 ring, the CY2 ring, the CY3 ring, and the CY4 ring are each independently selected from the group consisting of a carbocyclic group having 5 to 30 ring carbon atoms and a heterocyclic group having 1 to 30 ring carbon atoms.

[2346] Y1 to Y4 are each independently selected from

[2347] single bond,

[2348] Double bond,

[2349] a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

[2350] a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

[2351] *aO-*b,

[2352] *aS-*b,

[2353] *aC(=O)-*b,

[2354] *aS(=O)-*b、

[2355] *aC(R5)(R6)-*b,

[2356] *aC(R5)=C(R6)-*b、

[2357] *aC(R5)=*b、

[2358] *a-Si(R5)(R6)-*b,

[2359] *aB(R5)-*b,

[2360] *aN(R5)-*b, and

[2361] The group consisting of *aP(R5)-*b,

[2362] a1, a2 and a3 are each independently 1, 2 or 3,

[2363] a4 is 0, 1, 2 or 3. When a4 is 0, the CY1 ring and the CY4 ring are not connected to each other.

[2364] T1, T2, T3 and T4 are each independently selected from

[2365] Chemical bonds,

[2366] *aO-*b,

[2367] *aS-*b,

[2368] *aB(R7)-*b,

[2369] *aN(R7)-*b,

[2370] *aP(R7)-*b,

[2371] *aC(R7)(R8)-*b,

[2372] *a-Si(R7)(R8)-*b,

[2373] *a-Ge(R7)(R8)-*b,

[2374] *aC(=O)-*b and

[2375] *aC(=S)-*b group,

[2376] *a and *b are each independently the bonding position to the adjacent atom,

[2377] *1, *2, *3 and *4 are the bonding positions with M,

[2378] R1 to R8 are each independently selected from

[2379] hydrogen atoms,

[2380] Halogen atoms,

[2381] cyano,

[2382] Nitro,

[2383] amidino group,

[2384] Hydrazine,

[2385] Hydrazonyl,

[2386] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2387] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2388] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2389] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2390] a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms,

[2391] a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms,

[2392] a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms,

[2393] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2394] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2395] a substituted or unsubstituted monovalent non-aromatic fused polycyclic group,

[2396] a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group,

[2397] -Si(R 251 )(R 252 )(R 253 ) shown in the group,

[2398] -O-(R 254 ) shown in the group,

[2399] -S-(R 255 ) shown in the group,

[2400] -N(R 256 )(R 257 ) shown in the group,

[2401] -C(=O)R 258 The groups shown,

[2402] -C(=O)(OR 259 ) shown in the group,

[2403] -S(=O)2(OR 260 ) shown in the group,

[2404] -OP(=O)(OR 261 )(OR 262 ) shown in the group,

[2405] -C(R 263 )(R 264 )(R 265 ) shown in the group,

[2406] -B(R 266 )(R 267 ) shown in the group,

[2407] -P(R 268 )(R 269 ) shown in the group,

[2408] -S(=O)(R 270 ) shown in the group,

[2409] -S(=O)2(R 271 ) shown in the group,

[2410] -P(=O)(R 272 )(R 273 ) shown in the group, and

[2411] -P(=S)(R 274 )(R 275 ),

[2412] One or more groups of two or more adjacent ones of R1 to R8

[2413] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[2414] bonded to each other to form a substituted or unsubstituted fused ring, or

[2415] Not bonded to each other,

[2416] One or more groups consisting of two or more adjacent ones of R1 to R8 and Y1 to Y4

[2417] bonded to each other to form a substituted or unsubstituted monocyclic ring,

[2418] bonded to each other to form a substituted or unsubstituted fused ring, or

[2419] Not bonded to each other,

[2420] b1, b2, b3 and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

[2421] R 251 ~R 275 Independently choose freedom

[2422] hydrogen atoms,

[2423] Halogen atoms,

[2424] -O-(R 276 ) shown in the group,

[2425] -N(R 277 )(R 278 ) shown in the group,

[2426] cyano,

[2427] Nitro,

[2428] amidino group,

[2429] Hydrazine,

[2430] Hydrazonyl,

[2431] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2432] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[2433] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[2434] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2435] a substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms,

[2436] a substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms,

[2437] a substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms,

[2438] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2439] an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2440] an aryl group having 6 to 50 ring carbon atoms substituted with a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[2441] a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

[2442] a substituted or unsubstituted monovalent non-aromatic fused polycyclic group,

[2443] a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group,

[2444] The group consisting of biphenyl and terphenyl,

[2445] R 276 ~R 278 Each independently

[2446] hydrogen atoms,

[2447] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[2448] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[2449] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[2450] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[2451] In this specification, a carbocyclic group having 5 to 30 ring carbon atoms refers to a monocyclic or polycyclic group having 5 to 30 carbon atoms containing only carbon as ring atoms. A carbocyclic group having 5 to 30 ring carbon atoms may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. A carbocyclic group having 5 to 30 ring carbon atoms may be a ring such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. Alternatively, a carbocyclic group having 5 to 30 ring carbon atoms can be variously modified, such as to form a trivalent group or a tetravalent group, depending on the number of substituents attached to the carbocyclic group having 5 to 30 ring carbon atoms.

[2452] In this specification, a heterocyclic group having 1 to 30 ring carbon atoms refers to a group having the same structure as a carbocyclic group having 5 to 30 ring carbon atoms, but containing, as a ring atom, at least one heteroatom selected from N (carbon atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom) and S (sulfur atom), in addition to carbon (the carbon number can be 1 to 30).

[2453] In this specification, a heterocycloalkyl group having 3 to 50 ring atoms refers to a monovalent monocyclic group having 3 to 50 ring atoms and containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom. Specific examples include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothienyl. In this specification, a heterocycloalkylene group having 3 to 50 ring atoms refers to a divalent group having the same structure as a heterocycloalkyl group having 3 to 50 ring atoms.

[2454] In this specification, a cycloalkenyl group having 3 to 50 ring carbon atoms refers to a monovalent monocyclic group having 3 to 50 ring carbon atoms, having at least one double bond in the ring, but not being aromatic. Specific examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. In this specification, a cycloalkenylene group having 3 to 50 ring carbon atoms refers to a divalent group having the same structure as a cycloalkenyl group having 3 to 50 ring carbon atoms.

[2455] In this specification, a heterocycloalkenyl group having 3 to 50 ring atoms is a monovalent monocyclic group having 3 to 50 ring atoms, containing at least one heteroatom selected from N, O, Si, P, and S as a ring atom, and having at least one double bond within the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring atoms include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. In this specification, a heterocycloalkenylene group having 3 to 50 ring atoms refers to a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring atoms.

[2456] According to one embodiment, in the compound represented by the above general formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring carbon atoms preferably has 3 to 10 ring carbon atoms, and the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring atoms preferably has 3 to 10 ring atoms.

[2457] In this specification, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together and the molecule as a whole is non-aromatic. In this specification, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[2458] In this specification, a monovalent non-aromatic hetero-fused polycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together, the ring atoms include at least one heteroatom selected from N, O, Si, P, and S in addition to carbon, and the molecule as a whole is non-aromatic. In this specification, a divalent non-aromatic hetero-fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic hetero-fused polycyclic group.

[2459] In this specification, "biphenyl group" means "phenyl group substituted with phenyl group." "Biphenyl group" belongs to "substituted phenyl group" whose substituent is "aryl group having 6 to 50 ring carbon atoms."

[2460] In this specification, "terphenyl" refers to a "phenyl group substituted with a biphenyl group." "Terphenyl" belongs to a "substituted phenyl group" whose substituent is an "aryl group having 6 to 50 ring carbon atoms substituted with an aryl group having 6 to 50 ring carbon atoms."

[2461] In the compound represented by the above general formula (21), the chemical bond between T1, T2, T3 and T4 is preferably a single bond.

[2462] In the compound represented by the above general formula (21), M is preferably one or more metal atoms selected from platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), more preferably platinum (Pt) or iridium (Ir).

[2463] According to one embodiment, in the compound represented by the general formula (21), the CY1 ring to the CY4 ring can be independently selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, Cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenophene, indole, benzoborole, benzophosphole, indene, benzosilole, benzogermanol, benzothiophene, benzoselenophene, benzofuran, carbazole, dibenzoborole, dibenzophosphole, fluorene, dibenzosilole, dibenzo Germanopentadiene, dibenzothiophene, dibenzoselenophene, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzoborole, azabenzophosphole, azaindene, azabenzosilole, azabenzogermanopentadiene, azabenzothiophene, azabenzoselenophene, azabenzene Furan, azacarbazole, azadibenzoborole, azadibenzophosphole, azafluorene, azadibenzosilole, azadibenzogermanyl, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluorene-9-one, azadibenzothiophene 5,5-dioxide, pyridine , pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[2464] According to one embodiment, at least one of the CY1 and CY2 rings in the general formula (211), at least one of the CY1 to CY3 rings in the general formula (212), and at least one of the CY1 to CY4 rings in the general formula (213) may be a carbene.

[2465] According to one embodiment, Y1 to Y4 in general formulae (211) to (213) can each independently be at least one selected from a single bond, a double bond, *aO-*b, *aS-*b, *aC(R5)(R6)-*b and *aN(R5)-*b.

[2466] According to one embodiment, at least one of R1 and R2 in general formula (211), at least one of R1 to R3 in general formula (212), and at least one of R1 to R4 in general formula (213) may be an electron donating group.

[2467] For example, the electron-donating group may be a substituent selected from an isopropyl group, a tert-butyl group, and the following general formulae (10-1) to (10-61).

[2468]

Chemical Formula 268

[2469]

[2470]

Chemical Formula 269

[2471]

[2472] In the above general formulae (10-1) to (10-61), * represents a bonding position with an adjacent atom.

[2473] In this specification, deuterium atoms are represented by D in chemical formulas, and protium atoms are represented by H or omitted. In this specification, in chemical formulas, methyl groups may be represented by Me, phenyl groups may be represented by Ph, isopropyl groups may be represented by i-Pr, and tert-butyl groups may be represented by t-Bu.

[2474] According to one embodiment, at least one of R1 and R2 in the general formula (211) is a substituent other than hydrogen, and / or Y1 is *aN(R5)-*b, and R5 is a substituted aromatic group having 6 to 50 ring carbon atoms.

[2475] According to one embodiment, at least one of R1 to R3 in the above general formula (212) is a substituent other than hydrogen, and / or at least one of Y1 and Y2 is *aN(R5)-*b, and R5 is a substituted aromatic group having 6 to 50 ring carbon atoms.

[2476] According to one embodiment, at least one of R1 to R4 in the above general formula (213) is a substituent other than hydrogen, and / or at least one of Y1 to Y4 is *aN(R5)-*b, and R5 is a substituted aromatic group having 6 to 50 ring carbon atoms.

[2477] Since the organic EL element according to the other embodiment includes the compound (second compound) according to the first embodiment in the light-emitting layer, the efficiency of the organic EL element can be improved according to the other embodiment.

[2478] Organic EL elements according to other embodiments can be used in electronic devices such as display devices and light-emitting devices.

[2479] [Changes in Implementation Methods]

[2480] It should be noted that the present invention is not limited to the above-described embodiment, and modifications, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

[2481] For example, the light-emitting layer is not limited to a single layer, and multiple light-emitting layers may be stacked. In the case of an organic EL element having multiple light-emitting layers, at least one light-emitting layer may satisfy the conditions described in the above embodiment. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission based on direct electron transition from a triplet excited state to a ground state.

[2482] When the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem organic EL element may be used in which a plurality of light-emitting units are stacked with an intermediate layer interposed therebetween.

[2483] Furthermore, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably provided in contact with the light-emitting layer to block at least one of holes, electrons, and excitons.

[2484] For example, when a blocking layer is disposed in contact with the cathode side of a light-emitting lay...

Claims

1. A compound represented by the following general formula (1), In the general formula (1), Ring (A) is a monocyclic ring, and the number of bonding sites of said ring (A) is a, a=b+c+2, b is 0, 1, 2 or 3, d is an integer greater than 1, Ring (B) is a substituted or unsubstituted heterocyclic group having one or more nitrogen atoms in the ring, the nitrogen atom contained in the ring (B) is bonded to the ring (A), and the element constituting the ring (B) is bonded to Y1, Y1 is hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, in, Y1 is not a substituted or unsubstituted triazine group, When there are multiple Y1, the multiple Y1 are the same as or different from each other. In the general formula (1), the local structure formed by the ring (B) and the (Y1)d is not a substituted or unsubstituted bicarbazole ring in which the 3-positions of the carbazole ring are bonded to each other. Ar X for a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, Nitro, vP(=O)(R 931 )(R 932 ) shown in the group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Among them, in Ar X In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Ar X is not any of substituted or unsubstituted triazinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl and substituted or unsubstituted benzothiazolyl, In Ar X When there are multiple Ar X Same or different from each other, Ar v for hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, -Si(R 901 )(R 902 )(R 903 ) shown in the group, -O-(R 904 ) shown in the group, -S-(R 905 ) shown in the group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, -C(=O)R 801 The groups shown, -COOR 802 The groups shown, Halogen atoms, Nitro, -P(=O)(R 931 )(R 932 ) shown in the group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Among them, in Ar Z In the case of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Ar Z is not any of a substituted or unsubstituted triazine group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzothiazolyl group, and a substituted or unsubstituted carbazolyl group, In Ar Z When there are multiple Ar Z Same or different from each other, Ar EWG is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms and containing one or more nitrogen atoms in the ring, or an aryl group having 6 to 30 ring carbon atoms and substituted with one or more cyano groups, Ar EWG has at least one substituent R, each of which is independently substituted or unsubstituted phenyl, Substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, Substituted or unsubstituted N-arylcarbazolyl, substituted or unsubstituted indolyl, Substituted or unsubstituted benzimidazolyl, Substituted or unsubstituted benzimidazolylbenzimidazolyl, substituted or unsubstituted thienyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, or a substituted or unsubstituted furyl group, wherein at least one of the substituents R does not contain a protium atom, When the substituent R further has a substituent Y2, at least one of the substituent R and the substituent Y2 does not contain a protium atom. When there are multiple substituents R, the multiple substituents R are the same as or different from each other. In the case where the substituent R further has a substituent Y2, the substituent Y2 is independently cyano, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Wherein, the substituent Y2 is not a substituted or unsubstituted triazine group, When there are multiple substituents Y2, the multiple substituents Y2 are the same as or different from each other. In the compound represented by the general formula (1), R 901 、R 902 、R 903 、R 904 、R 905 、R 801 、R 802 、R 931 and R 932 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In R 901 When there are multiple R 901 Same or different from each other, In R 902 When there are multiple R 902 Same or different from each other, In R 903 When there are multiple R 903 Same or different from each other, In R 904 When there are multiple R 904 Same or different from each other, In R 905 When there are multiple R 905 Same or different from each other, In R 801 When there are multiple R 801 Same or different from each other, In R 802 When there are multiple R 802 Same or different from each other, In R 931 When there are multiple R 931 Same or different from each other, In R 932 When there are multiple R 932 Same as or different from each other.

2. The compound according to claim 1, wherein Ar EWG is a group represented by the following general formula (A1), In the general formula (A1), Y 11 ~Y 15 Each independently represents a nitrogen atom, C-CN or CR, C represents a carbon atom, CN represents a cyano group, Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN, R is independently a hydrogen atom or a substituent, and each R as a substituent has the same meaning as the substituent R in the general formula (1), and multiple Rs are the same or different from each other. * represents the bonding position to the ring (A) in the general formula (1).

3. The compound according to claim 2, wherein The group represented by the general formula (A1) is a group represented by any one of the following general formulas (a1) to (a9), In the general formulae (a1) to (a9), R each independently has the same meaning as R in the general formula (A1), and * indicates the bonding position to the ring (A) in the general formula (1).

4. The compound according to any one of claims 1 to 3, wherein When the ring (B) has a substituent, the total number of rings constituting the ring (B) and the number of rings constituting Y1 when Y1 is a ring is 6 or less.

5. The compound according to any one of claims 1 to 4, wherein In the general formula (1), the partial structure represented by the following general formula (10) is a heterocyclic group represented by any one of the following general formulas (11) to (15), In the general formula (10), ring (B), Y1 and d are independently the same as ring (B), Y1 and d in the general formula (1), * represents the bonding position with ring (A) in the general formula (1), In the general formulas (11) to (15), X1 to X 18 Each independently represents a nitrogen atom or C-Y3, where C represents a carbon atom, One or more groups of two or more adjacent Y3 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Y3 that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring is independently the same as Y1 in the general formula (1). Ara is hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, Multiple Y3 are the same as or different from each other, A1 and A2 are each independently single bond, oxygen atoms, Sulfur atoms, C(R 1A )(R 2A )、 Si(R 3A )(R 4A )、 C(=O), S(=O), SO2 or N(R 5A ), By R 1A and R 2A One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By R 3A and R 4A One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 5A and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 1A ~R 4A Each independently hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Among them, R 1A ~R 5A are not substituted or unsubstituted triazine groups, * represents the bonding position to the ring (A) in the general formula (1), In the general formula (12), any one of X5 to X8 is 12 Any bonded carbon atom in X9~X 12 Any one of is a carbon atom bonded to any one of X5 to X8, In the general formula (13), any one of X5 to X8 is a carbon atom bonded to a nitrogen atom in the ring containing A2, In the general formula (14), any one of X5 to X8 is 12 and X 17 Any bonded carbon atom in X9~X 12 and X 17 Any one of is a carbon atom bonded to any one of X5 to X8, In the general formula (15), any one of X5 to X8 is 12 and X 17 The ring containing X 13 ~X 16 and X 18 The ring is connected to a nitrogen atom bonded to a carbon atom.

6. The compound according to claim 5, wherein The partial structure represented by the general formula (10) is a partial structure represented by any one of the following general formulas (111) to (113), In the general formulae (111) to (113), A1, A2 and Ara are independently the same as A1, A2 and Ara in the general formulae (11) to (13). One or more groups of two or more adjacent ones from Rx1 to Rx4 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, One or more groups of two or more adjacent ones from Rx5 to Rx8 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, From Rx9 to Rx 12 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By Rx 13 ~Rx 16 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Rx1 to Rx that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring 16 Each independently has the same meaning as Y3 in the general formulae (11) to (13), * represents the bonding position to the ring (A) in the general formula (1), In the general formula (112), any one of the carbon atoms to which Rx5 to Rx8 are bonded is bonded to any one of the carbon atoms to which Rx9 to Rx8 are bonded. 12 Any one of the carbon atoms is bonded to Rx9~Rx 12 Any one of the carbon atoms of is bonded to any one of the carbon atoms to which Rx5 to Rx8 are bonded, In the general formula (113), any one of the carbon atoms to which Rx5 to Rx8 are bonded is bonded to a nitrogen atom in the ring including A2.

7. The compound according to claim 6, wherein The compound represented by the general formula (1) is a compound represented by any one of the following general formulas (1001) to (1003), In the general formulas (1001) to (1003), A1, A2, Ara, Rx1~Rx 16 Each independently and A1, A2, Ara, Rx1 to Rx in the general formula (111) to (113) 16 Same meaning, Ar X 、Ar Z , b and c are each independently the same as Ar in the general formula (1) X 、Ar Z , b and c have the same meaning, Y 11 ~Y 15 are each independently a nitrogen atom, C-CN or CR, C is a carbon atom, CN is a cyano group, Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN, R each independently has the same meaning as R in the general formula (1).

8. The compound according to any one of claims 5 to 7, wherein Y3 and Rx1~Rx 16 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, Ara is a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or A substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

9. The compound according to any one of claims 5 to 8, wherein A1 and A2 are single bonds.

10. The compound according to any one of claims 5 to 9, wherein The partial structure represented by the general formula (10) has at least one deuterium atom.

11. The compound according to any one of claims 1 to 3, wherein In the general formula (1), the partial structure represented by the following general formula (10) is a heterocyclic group represented by the following general formula (12X) or (13X), In the general formula (10), ring (B), Y1 and d are independently the same as ring (B), Y1 and d in the general formula (1), * represents the bonding position with ring (A) in the general formula (1), In the general formula (12X), R 11 ~R 18 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, In the general formula (13X), R 111 ~R 118 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R in the general formula (12X) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. 11 ~R 18 and R in the general formula (13X) does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 111 ~R 118 Each independently hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Among them, R 11 ~R 18 and R 111 ~R 118 are not substituted or unsubstituted triazine groups, In the general formula (12X), Ring A1 is a ring structure represented by the following general formula (14X), (15X) or (16X), In the general formula (13X), Ring B1 and ring C1 are each independently a ring structure represented by the following general formula (14X) or (15X), Ring A1, Ring B1 and Ring C1 are fused to adjacent rings at optional positions, p, px and py are each independently 1, 2, 3 or 4, When p is 2, 3 or 4, the plurality of rings A1 are identical to or different from each other. When px is 2, 3 or 4, the multiple rings B1 are the same as or different from each other. When py is 2, 3 or 4, the multiple rings C1 are the same or different from each other. * in the general formulae (11X) to (13X) indicates the bonding position to the ring (A) in the general formula (1), In the general formula (14X), r is 0, 2, or 4, When r is 2 or 4, multiple R 19 Same or different from each other, When r is 2 or 4, multiple R 19 Group bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring 19 Each independently hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Among them, R 19 are not substituted or unsubstituted triazine groups, In the general formula (15), X5 is a sulfur atom, an oxygen atom, C(R 1B )(R 2B )、Si(R 3B )(R 4B ) or N(R 5B ), By R 1B and R 2B One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By R 3B and R 4B One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 5B and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 1B ~R 4B Each independently hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Among them, R 1B ~R 5B are not substituted or unsubstituted triazine groups, Multiple R 19 Same or different from each other, When there are multiple X5, the multiple X5 are the same as or different from each other.

12. The compound according to claim 11, wherein In the general formula (1), the partial structure represented by the general formula (10) is a heterocyclic group represented by any one of the following general formulas (12A) to (12G), In the general formulae (12A), (12B), (12C), (12D), (12E), (12F) and (12G), R 11 ~R 18 Each independently of R in the general formula (12X) 11 ~R 18 Same meaning, R 19 and R 20 Each independently of R in the general formula (14X) 19 Same meaning, X5 has the same meaning as X5 in the general formula (15X), * in the general formulae (12A), (12B), (12C), (12D), (12E), (12F) and (12G) represents the bonding position to the ring (A) in the general formula (1).

13. The compound according to claim 12, wherein The compound represented by the general formula (1) is a compound represented by the following general formula (1004), In the general formula (1004), Ar X 、Ar Z , b and c are each independently the same as Ar in the general formula (1) X 、Ar Z , b and c have the same meaning, Y 11 ~Y 15 are each independently a nitrogen atom, C-CN or CR, C is a carbon atom, CN is a cyano group, Y 11 ~Y 15 At least one of them is a nitrogen atom or C-CN, R is independently the same as R in the general formula (1), R 11 ~R 18 Each independently of R in the general formula (12X) 11 ~R 18 Same meaning, R 19 and R 20 Each independently of R in the general formula (14X) 19 Same meaning, X5 has the same meaning as X5 in the general formula (15X).

14. The compound according to any one of claims 11 to 13, wherein R 11 ~R 18 、R 111 ~R 118 、R 19 and R 20 Each independently hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, or A substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

15. The compound according to any one of claims 11 to 14, wherein The partial structure represented by the general formula (10) has at least one deuterium atom.

16. The compound according to any one of claims 1 to 15, wherein In the general formula (1), the partial structure represented by the following general formula (10A) is a group represented by any one of the following general formulas (11A) to (20A), In the general formula (10), ring (A), Ar X 、Ar Z , b and c are each independently the same as the ring (A), Ar X 、Ar Z , b and c have the same meanings, ** represents the bonding position with the ring (B) in the general formula (1), *** represents the bonding position with Ar in the general formula (1) EWG bonding position. In the general formulas (11A) to (20A), Ar X and Ar Z Each independently and Ar in the general formula (10A) X and Ar Z have the same meanings, ** represents the bonding position with the ring (B) in the general formula (1), *** represents the bonding position with Ar in the general formula (1) EWG bonding position.

17. The compound according to any one of claims 1 to 16, wherein Ar X Each independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms, The group represented by the following general formula (11 1A), The group represented by the following general formula (112A), The group represented by the following general formula v113A), A group represented by the following general formula (114A), or The group represented by the following general formula (115A) In the general formulas (111A) to (115A), One or more groups of two or more adjacent ones of Ry1 to Ry4 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, One or more groups of two or more adjacent ones of Ry5 to Ry8 bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, From Ry9~Ry 12 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By Ry 13 ~Ry 16 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By Ry 21 ~Ry 25 One or more of the adjacent groups of two or more bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, Arb is hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A 10 and A 20 Each independently single bond, oxygen atoms, Sulfur atoms, C(R 1C )(R 2C )、 Si(R 3C )(R 4C )、 C(=O), S(=O), SO2 or N(R 5C ), By R 1C and R 2C One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, By R 3C and R 4C One or more of the groups bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted fused ring, or Not bonded to each other, R 5C and R which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 1C ~R 4C 、Ry1~Ry 16 and Ry 21 ~Ry 25 Each independently hydrogen atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, * represents the bonding position to the ring (A) in the general formula (1), In the general formula (112A), any one of the carbon atoms to which Ry5 to Ry8 are bonded is bonded to any one of the carbon atoms to which Ry9 to Ry 12 Any one of the carbon atoms is bonded to Ry9~Ry 12 Any one of the carbon atoms of is bonded to any one of the carbon atoms to which Ry5 to Ry8 are bonded, In the general formula (113A), any one of the carbon atoms to which Ry5 to Ry8 are bonded is bonded to the carbon atom containing A 20 The nitrogen atom in the ring is bonded to In the general formula (114A), any one of the carbon atoms to which Ry1 to Ry4 are bonded is bonded to *1. In the general formula (115A), any one of the carbon atoms to which Ry1 to Ry4 are bonded is bonded to *1. 21 ~Ry 25 Any one of the carbon atoms is bonded to *1.

18. The compound according to any one of claims 1 to 17, wherein Ar X Having at least one deuterium atom.

19. The compound according to any one of claims 1 to 18, wherein Ar Z for hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or A substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

20. The compound according to any one of claims 1 to 19, wherein Ar Z Having at least one deuterium atom.

21. The compound according to any one of claims 1 to 20, wherein The atoms constituting the ring (A) do not include a deuterium atom.

22. A material for an organic electroluminescent device, comprising the compound according to any one of claims 1 to 21.

23. An organic electroluminescent element comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. The light-emitting layer contains the compound according to any one of claims 1 to 21 as a first host material.

24. The organic electroluminescent element according to claim 23, wherein The light-emitting layer contains the first host material and a fluorescent material. The first host material and the fluorescent material are different compounds.

25. The organic electroluminescent element according to claim 24, wherein The first host material and the fluorescent material are contained in a single layer.

26. The organic electroluminescent element according to claim 24 or 25, wherein The first host material is a sensitizing material.

27. The organic electroluminescent element according to claim 26, wherein The sensitizing material is a delayed fluorescence compound.

28. The organic electroluminescent element according to claim 26 or 27, wherein The lowest excited singlet energy S1(GT2) of the sensitizing material and the lowest excited singlet energy S1(D) of the fluorescent material satisfy the relationship of the following mathematical formula (Mathematical formula 3): S1(GT2)>S1(D)...(Mathematical formula 3).

29. The organic electroluminescent element according to any one of claims 26 to 28, wherein The light-emitting layer further contains a second host material, The energy gap T of the second host material at 77[K] 77K (H2) and the energy gap T of the sensitizing material at 77 [K] 77K (G2) satisfies the following mathematical formula (Mathematical formula 1), The second host material and the first host material are different compounds from each other, T 77K (H2)>T 77K (G2)...(Mathematical formula 1).

30. The organic electroluminescent element according to claim 29, wherein The sensitizing material, the fluorescent material, and the second host material are contained in a single layer.

31. The organic electroluminescent element according to any one of claims 23 to 30, wherein The light-emitting layer does not contain a metal complex.

32. The organic electroluminescent element according to any one of claims 23 to 31, wherein The light-emitting layer does not contain a phosphorescent material.

33. The organic electroluminescent element according to any one of claims 23 to 32, wherein A hole transport layer is included between the anode and the light-emitting layer.

34. The organic electroluminescent element according to any one of claims 23 to 33, wherein An electron transport layer is included between the cathode and the light-emitting layer. 35 . An electronic device comprising the organic electroluminescent element according to claim 23 .

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