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

Abstract

The compound shown in formula (1) below. In formulas (1) and (12), Ry is an aryl group, at least one of which is selected from the group consisting of R1 to R3 and is a group shown in formula (12). R1 ​​to R3, which are not groups shown in formula (12), are each independently hydrogen atoms or alkyl groups, m1 + m2 = 4, n1 + n2 = 4, m1 + n1 is 1, 2, 3, 4, 5, 6, 7 or 8, HAr is a heterocyclic group, R 11 ~R 15 R 18 R 19 R 21 ~R 23 R A and R B Each is independently a hydrogen atom or a substituent, wherein R A and R B It cannot be both hydrogen atoms at the same time.

Description

Technical Field

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

[0002] When a voltage is applied to an organic electroluminescent element (hereinafter sometimes referred to as an "organic EL element"), holes are injected from the anode into the emitting layer, and electrons are injected from the cathode into the emitting layer. Then, in the emitting layer, the injected holes recombine with the electrons to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%.

[0003] While fluorescent organic EL devices, which emit light derived from singlet excitons, are being used in full-color displays for mobile phones and televisions, their internal quantum efficiency is reportedly limited to 25%. Various studies have been conducted on compounds used in organic EL devices in an effort to improve their performance (see, for example, Patent Documents 1-2). Performance characteristics of organic EL devices include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Description of Chinese Patent Application Publication No. 114539296

[0007] Patent Document 2: U.S. Patent Application Publication No. 2023-0143071 Summary of the Invention

[0008] The problem the invention aims to solve

[0009] The object of the present invention is to provide a compound that can improve the luminous efficiency of an organic electroluminescent element; to provide a material for an organic electroluminescent element containing the compound; to provide an organic electroluminescent element containing the compound; and to provide an electronic device equipped with the organic electroluminescent element.

[0010] means for solving problems

[0011] According to one aspect of the present invention, a compound represented by the following formula (1) is provided.

[0012] [Chemical Formula 1]

[0013]

[0014] (In equations (1) and (12) above,

[0015] Ry is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[0016] At least one of the groups selected from R1 to R3 is the group shown in formula (12) above.

[0017] R1 to R3 of the groups not shown in formula (12) above are not each independently...

[0018] hydrogen atom, or

[0019] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0020] m1 + m2 = 4,

[0021] m1 is 0, 1, 2, 3, or 4.

[0022] n1 + n2 = 4,

[0023] n1 is 0, 1, 2, 3 or 4.

[0024] Where m1 + n1 is 1, 2, 3, 4, 5, 6, 7, or 8.

[0025] HAr is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0026] R 11 ~R 15 R 18 R 19 R 21 ~R 23 R A and R B Each independently

[0027] hydrogen atom,

[0028] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0029] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0030] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0031] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0032] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0033] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0034] -O-(R 904 The groups shown in the figure,

[0035] -S-(R 905 The groups shown in the figure,

[0036] -N(R 906 (R) 907 The groups shown in the figure,

[0037] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0038] -C(=O)R 801 The groups shown

[0039] -C(=O)(OR 802 The groups shown in the figure,

[0040] Halogen atoms,

[0041] cyano,

[0042] Nitro,

[0043] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0044] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0045] -B(R 936 (R) 937 The groups shown in the figure,

[0046] -B(OR 938 (OR) 939 The groups shown in the figure,

[0047] -OS(=O)2(R 940 The groups shown in the figure,

[0048] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0049] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0050] Among them, R A and R B It cannot be both hydrogen atoms at the same time.

[0051] When there are multiple groups represented by the above formula (12), the multiple groups represented by the above formula (12) may be the same as or different from each other.

[0052] When multiple HArs exist, they may be identical or different from each other.

[0053] In R 18 In the case of multiple Rs, multiple Rs 18 They are the same or different.

[0054] In R 19 In the case of multiple Rs, multiple Rs 19 They are the same or different.

[0055] In equation (12) above, * represents the bonding position.

[0056] (In the compound shown in formula (1) above, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 Each independently

[0057] hydrogen atom,

[0058] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0059] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0060] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0061] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0062] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0063] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0064] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0065] In R 904In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0066] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0067] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0068] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0069] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0070] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[0071] In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different.

[0072] In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different.

[0073] In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different.

[0074] In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different.

[0075] In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different.

[0076] In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different.

[0077] In R 937 In the case of multiple Rs, multiple Rs 937 They are the same or different.

[0078] In R 938 In the case of multiple Rs, multiple Rs 938They are the same or different.

[0079] In R 939 In the case of multiple Rs, multiple Rs 939 They are the same or different.

[0080] In R 940 In the case of multiple Rs, multiple Rs 940 (They may be the same or different.)

[0081] According to one aspect of the present invention, a material for an organic electroluminescent element is provided, which contains a compound according to one aspect of the present invention.

[0082] According to one aspect of the present invention, an organic electroluminescent element is provided, having a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer contains a compound according to one aspect of the present invention as a first compound.

[0083] According to one aspect of the present invention, an electronic device is provided, wherein an organic electroluminescent element according to one aspect of the present invention is incorporated.

[0084] According to one aspect of the present invention, a compound capable of improving the luminous efficiency of an organic electroluminescent element can be provided. According to one aspect of the present invention, a material for an organic electroluminescent element containing the compound can be provided. According to one aspect of the present invention, an organic electroluminescent element containing the compound can be provided, and an electronic device equipped with the organic electroluminescent element can be provided. Attached Figure Description

[0085] Figure 1 This is a diagram showing the general configuration of an example of an organic electroluminescent element according to the third embodiment of the present invention.

[0086] Figure 2 This is a schematic diagram of a device for measuring transient pulses (PL).

[0087] Figure 3 This is a graph showing an example of the decay curve of transient PL.

[0088] Figure 4 This is a diagram showing the energy levels and energy transfer relationships of the first host material, the sensitizing material (phosphorescent metal complex), and the fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the third embodiment of the present invention.

[0089] Figure 5 This is a diagram showing the energy levels and energy transfer relationships of the first host material, the sensitizing material (delayed fluorescence compound), and the fluorescent luminescent material in an example of an organic electroluminescent element according to a third embodiment of the present invention.

[0090] Figure 6 This is a diagram showing the energy levels and energy transfer relationship between the first host material and the fluorescent luminescent material in the light-emitting layer of an example of an organic electroluminescent element according to the fourth embodiment of the present invention.

[0091] Figure 7 This is a diagram showing the relationship between the energy levels and energy transfer of the delayed fluorescence compound and the fluorescent luminescent material in the luminescent layer of an example of an organic electroluminescent element according to the fifth embodiment of the present invention.

[0092] Figure 8 This is a diagram showing the energy levels and energy transfer relationships of the first host material, the second host material, the sensitizing material (phosphorescent metal complex), and the fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the sixth embodiment of the present invention. Detailed Implementation

[0093] [definition]

[0094] In this specification, a hydrogen atom means an isotope containing different numbers of neutrons, namely protium, deuterium, and tritium.

[0095] In this specification, the chemical structural formula does not explicitly show that the bonding positions of symbols such as "R" and "D" representing deuterium atoms are set to be bonded to hydrogen atoms, i.e., protium atoms, deuterium atoms, or tritium atoms.

[0096] In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms in the ring itself of a compound whose atoms are bonded in a ring (e.g., monocyclic compounds, fused-ring compounds, bridged-ring compounds, carbocyclic compounds, and heterocyclic compounds). When the ring is substituted with a substituent, the carbon atoms contained in the substituent are not included in the number of carbon atoms forming the ring. The term "number of carbon atoms forming a ring" is used as such unless otherwise specified. For example, the number of carbon atoms forming a ring is 6 for a benzene ring, 10 for a naphthalene ring, 5 for a pyridine ring, and 4 for a furan ring. Additionally, for example, the number of carbon atoms forming a ring is 13 for 9,9-diphenylfluorene and 25 for 9,9'-spirobifluorene.

[0097] Furthermore, when a benzene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the benzene ring. Therefore, the number of carbon atoms in the cyclic benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, the carbon number of the alkyl group is not included in the number of carbon atoms in the ring-forming process of the naphthalene ring. Therefore, the number of carbon atoms in the cyclic naphthalene ring substituted with an alkyl group is 10.

[0098] In this specification, the number of cyclic atoms refers to the number of atoms constituting the ring itself in compounds with a cyclic structure (e.g., monocyclic, fused-ring, and ring assemblies). Atoms that do not constitute the ring (e.g., hydrogen atoms ending the bonds of the ring-forming atoms) and atoms contained in substituents when the ring is substituted are not included in the number of cyclic atoms. The term "number of cyclic atoms" as used below is the same unless otherwise stated. For example, the number of cyclic atoms in a pyridine ring is 6, in a quinazoline ring it is 10, and in a furan ring it is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents are not included in the number of cyclic atoms in pyridine. Therefore, the number of cyclic atoms in a pyridine ring bonded with hydrogen atoms or substituents is 6. Furthermore, hydrogen atoms bonded to the carbon atoms of the quinazoline ring, or atoms constituting substituents, are not included in the number of cyclic atoms of the quinazoline ring. Therefore, the number of cyclic atoms in a quinazoline ring with bonded hydrogen atoms or substituents is 10.

[0099] In this specification, the phrase "ZZ group with substituted or unsubstituted carbon numbers of XX to YY" indicates the number of carbons when the ZZ group is unsubstituted; the number of carbons in substituents is not included. Here, "YY" is greater than "XX," where "XX" refers to an integer greater than 1, and "YY" refers to an integer greater than 2.

[0100] In this specification, the phrase "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, excluding the number of atoms of substituents when substitution has occurred. Here, "YY" is greater than "XX", where "XX" is an integer greater than or equal to 1, and "YY" is an integer greater than or equal to 2.

[0101] In this specification, "unsubstituted ZZ group" means "substituted or unsubstituted ZZ group" and "substituted ZZ group" means "substituted ZZ group".

[0102] In this specification, "unsubstituted" when referred to as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group has not been substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0103] Furthermore, in this specification, "substitution" when expressed as "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, "substitution" when expressed as "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group have been replaced by an AA group.

[0104] Substituents described in this specification

[0105] The substituents described in this specification are explained below.

[0106] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0107] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0108] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0109] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkenyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0110] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkynyl group" is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.

[0111] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted cycloalkyl group" is 3 to 50, preferably 3 to 20, and more preferably 3 to 6.

[0112] Unless otherwise stated in this specification, the number of carbon atoms in the cyclic formation of the "unsubstituted aryl group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18.

[0113] Unless otherwise stated in this specification, the number of cyclic atoms in the "unsubstituted divalent heterocyclic group" is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0114] Unless otherwise stated in this specification, the number of carbon atoms in the "unsubstituted alkylene group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0115] • "Substituted or unsubstituted aryl groups"

[0116] Specific examples of "substituted or unsubstituted aryl" as described in this specification (specific example group G1) include unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B), etc. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when referred to only as "aryl", both "unsubstituted aryl" and "substituted aryl" are included.

[0117] "Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent. Examples of "substituted aryl" include the group in Specific Example Group G1A below in which one or more hydrogen atoms of an "unsubstituted aryl" group have been substituted with a substituent, and the substituted aryl group in Specific Example Group G1B below. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples. The "substituted aryl" described in this specification also includes the group in Specific Example Group G1B below in which hydrogen atoms bonded to the carbon atom of the aryl group itself have been further substituted with a substituent, and the group in Specific Example Group G1B below in which hydrogen atoms of the substituent have been further substituted with a substituent.

[0118] • Unsubstituted aryl groups (specific example group G1A):

[0119] Phenyl,

[0120] p-phenyl,

[0121] metaphenyl,

[0122] o-phenyl,

[0123] p-terphenyl-4-yl,

[0124] p-terphenyl-3-yl,

[0125] p-terphenyl-2-yl,

[0126] m-terphenyl-4-yl,

[0127] m-terphenyl-3-yl,

[0128] m-terphenyl-2-yl,

[0129] o-terphenyl-4-yl

[0130] o-terphenyl-3-yl

[0131] o-terphenyl-2-yl,

[0132] 1-Naphthyl,

[0133] 2-naphthyl,

[0134] anthryl,

[0135] benzanthryl,

[0136] phenanthryl,

[0137] triphenylene,

[0138] phenalenyl,

[0139] pyrenyl,

[0140] chrysenyl,

[0141] benzochrysenyl,

[0142] triphenylenyl,

[0143] benzotriphenylenyl,

[0144] tetracenyl,

[0145] pentacenyl,

[0146] fluorenyl,

[0147] 9,9'-spirobifluorenyl,

[0148] benzofluorenyl,

[0149] dibenzofluorenyl,

[0150] fluoranthenyl,

[0151] benzofluoranthenyl,

[0152] perylenyl, and

[0153] a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0154]

Chemical Formula 2

[0155]

[0156]

Chemical Formula 3

[0157]

[0158] ·Substituted aryl (specific example group G1B):

[0159] o-tolyl,

[0160] m-tolyl,

[0161] p-tolyl,

[0162] p-xylyl,

[0163] m-Xylyl,

[0164] o-xylyl,

[0165] p-isopropylphenyl,

[0166] m-Isopropylphenyl,

[0167] o-isopropylphenyl,

[0168] p-tert-butylphenyl,

[0169] m-tert-butylphenyl,

[0170] o-tert-butylphenyl,

[0171] 3,4,5-Trimethylphenyl

[0172] 9,9-Dimethylfluorenyl,

[0173] 9,9-Diphenylfluorenyl

[0174] 9,9-Bis(4-methylphenyl)fluorenyl,

[0175] 9,9-Bis(4-isopropylphenyl)fluorenyl,

[0176] 9,9-Bis(4-tert-butylphenyl)fluorenyl,

[0177] cyanophenyl,

[0178] Triphenylsilylphenyl

[0179] Trimethylsilylphenyl

[0180] Phenynaphthyl,

[0181] Naphthylphenyl and

[0182] A group derived from the ring structure shown in the above general formulas (TEMP-1) to (TEMP-15) is a group in which one or more hydrogen atoms of a monovalent group have been replaced by substituents.

[0183] • "Substituted or unsubstituted heterocyclic groups"

[0184] The term "heterocyclic group" as used in this specification refers to a cyclic group whose cyclic atoms contain at least one heteroatom. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0185] The term "heterocyclic group" as used in this specification refers to a monocyclic group or a fused-ring group.

[0186] The term "heterocyclic group" as used in this specification refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0187] Specific examples of "substituted or unsubstituted heterocyclic groups" described in this specification (specific example group G2) include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B), etc. (Here, unsubstituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and substituted heterocyclic group refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group".) In this specification, the term "heterocyclic group" includes both "unsubstituted heterocyclic group" and "substituted heterocyclic group".

[0188] "Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" have been substituted with a substituent. Specific examples of "substituted heterocyclic groups" include the group in example group G2A below where the hydrogen atoms of the "unsubstituted heterocyclic group" have been substituted, and the example of a substituted heterocyclic group in example group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are only examples. The "substituted heterocyclic groups" described in this specification also include the group in example group G2B where the hydrogen atoms bonded to the cyclic atoms of the heterocyclic group itself have been further substituted with a substituent, and the group in example group G2B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0189] Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0190] Specific example group G2B includes, for example, the following: a nitrogen-containing substituted heterocyclic group (specific example group G2B1), an oxygen-containing substituted heterocyclic group (specific example group G2B2), a sulfur-containing substituted heterocyclic group (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) have been substituted with a substituent (specific example group G2B4).

[0191] • Unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1):

[0192] pyrrole,

[0193] Imidazole group,

[0194] pyrazolyl,

[0195] Triazole group,

[0196] Tetrazolyl,

[0197] Oxazolyl,

[0198] Isoxazolyl,

[0199] Oxadiazole group,

[0200] Thiazole group,

[0201] Isothiazolyl,

[0202] Thiadiazole group,

[0203] pyridyl,

[0204] pyridazinyl,

[0205] Pyrimidine group,

[0206] Pyrazinyl,

[0207] Triazine group

[0208] Indole,

[0209] Isoindolyl,

[0210] Indazine-based

[0211] Quinazine-based

[0212] Quinoline,

[0213] Isoquinoline,

[0214] Crenoline group

[0215] Phthaloazine

[0216] Quinazolinyl,

[0217] Quinoxaloyl,

[0218] Benzimidazole group,

[0219] Indazole group,

[0220] phenanthroline,

[0221] phenanthridine,

[0222] acridine group,

[0223] Phenazine group,

[0224] Carbazolyl,

[0225] Benzocarbazolyl,

[0226] Morpholinyl,

[0227] phenoxazine group,

[0228] phenothiazine group,

[0229] Azacarbazolyl, and

[0230] Diazacarbazolyl.

[0231] • Unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2):

[0232] furanyl,

[0233] Oxazolyl,

[0234] Isoxazolyl,

[0235] Oxadiazole group,

[0236] Xuton base,

[0237] Benzofuranyl,

[0238] Isobenzofuranyl,

[0239] Dibenzofuranyl,

[0240] Naphthobenzofuranyl,

[0241] Benzoxazolyl,

[0242] Benzisoxazole group,

[0243] phenoxazine group,

[0244] Morpholinyl,

[0245] Dinaphthylfuranyl,

[0246] Azadibenzofuranyl,

[0247] diazadibenzofuranyl,

[0248] Azanaphthalenebenzofuranyl and

[0249] Diazanaphthenebenzofuranyl.

[0250] • Unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3):

[0251] Thiophene group

[0252] Thiazole group,

[0253] Isothiazolyl,

[0254] Thiadiazole group,

[0255] benzothienyl

[0256] isobenzothienyl

[0257] dibenzothienyl

[0258] Naphthobenzothienyl

[0259] Benzothiazolyl,

[0260] Benzisothiazolyl,

[0261] phenothiazine group,

[0262] dinaphthothienyl

[0263] azadibenzothienyl

[0264] diazadibenzothienyl

[0265] azanaphthobenzothienyl and

[0266] diazanaphthobenzothienyl.

[0267] • A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure shown in the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0268] [Chemical Formula 4]

[0269]

[0270] [Chemical Formula 5]

[0271]

[0272] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each can be independently composed of an oxygen atom, a sulfur atom, NH, or CH2. Among them, X... A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0273] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y AWhen at least one of them is NH or CH2, the monovalent heterocyclic group derived from the ring structure shown in the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0274] • Heterocyclic groups containing nitrogen atoms (specific example group G2B1):

[0275] (9-phenyl)carbazole group,

[0276] (9-Biphenyl)carbazolyl,

[0277] (9-Phenyl)phenylcarbazolyl,

[0278] (9-Naphthyl)carbazole,

[0279] Diphenylcarbazole-9-yl,

[0280] Phenylexacarbazole-9-yl,

[0281] Methylbenzimidazole,

[0282] Ethylbenzimidazole,

[0283] Phenylacetyl,

[0284] Biphenyltriazine

[0285] diphenyltriazine group,

[0286] phenylquinazolinyl, and

[0287] Biphenylquinazolinyl.

[0288] • Heterocyclic groups containing oxygen atoms (specific example group G2B2):

[0289] Phenyl dibenzofuranyl,

[0290] Methyldibenzofuranyl,

[0291] tert-butyldibenzofuranyl and

[0292] The monovalent residue of [9H-xanton-9,9'-[9H]fluorene].

[0293] • Heterocyclic groups containing sulfur atoms (specific example group G2B3):

[0294] Phenyl dibenzothiophene,

[0295] Methyldibenzothiophene,

[0296] tert-butyldibenzothiophene and

[0297] The monovalent residue of [9H-thiophene-9,9'-[9H]fluorene].

[0298] • Groups derived from the ring structures shown in the above general formulas (TEMP-16) to (TEMP-33) in which one or more hydrogen atoms of a monovalent heterocyclic group have been substituted with substituents (specific example group G2B4):

[0299] The aforementioned "one or more hydrogen atoms in a monovalent heterocyclic group" refers to hydrogen atoms bonded to the cyclic carbon atoms of the monovalent heterocyclic group, X A and Y A The hydrogen atom bonded to the nitrogen atom when at least one of them is NH and X A and Y A One of them is one or more hydrogen atoms in the methylene group when CH2 is present.

[0300] • "Substituted or unsubstituted alkyl groups"

[0301] As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when referred to as "alkyl", both "unsubstituted alkyl" and "substituted alkyl" are included.

[0302] "Substituted alkyl" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl" have been substituted with a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms of an "unsubstituted alkyl" (specific example group G3A) have been substituted with a substituent, and examples of substituted alkyl (specific example group G3B). In this specification, "unsubstituted alkyl" refers to a chain-like alkyl group. Therefore, "unsubstituted alkyl" includes both straight-chain and branched-chain unsubstituted alkyl groups. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples; the "substituted alkyl" described in this specification also includes groups in which the hydrogen atoms of the alkyl group in specific example group G3B have been further substituted with a substituent, and groups in which the hydrogen atoms of the substituents in specific example group G3B have been further substituted with a substituent.

[0303] • Unsubstituted alkyl groups (specific example group G3A):

[0304] methyl,

[0305] Ethyl,

[0306] n-propyl,

[0307] Isopropyl,

[0308] n-Butyl,

[0309] Isobutyl,

[0310] sec-butyl and

[0311] tert-butyl.

[0312] • Substituted alkyl groups (specific example group G3B):

[0313] Heptafluoropropyl (including isomers),

[0314] Pentafluoroethyl,

[0315] 2,2,2-Trifluoroethyl and

[0316] Trifluoromethyl

[0317] • "Substituted or unsubstituted alkenyl groups"

[0318] Specific examples of "substituted or unsubstituted alkenyl groups" (specific example group G4) described in this specification include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "substituted alkenyl group".) In this specification, when simply referred to as "alkenyl group", both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0319] "Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" group have been substituted with a substituent. Specific examples of "substituted alkenyl" include the "unsubstituted alkenyl" group (specific example group G4A) having a substituent and examples of substituted alkenyl groups (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples; the "substituted alkenyl" described in this specification also includes groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the alkenyl itself have been further substituted with a substituent, and groups in the "substituted alkenyl" group of specific example group G4B where the hydrogen atoms of the substituent have been further substituted with a substituent.

[0320] • Unsubstituted alkenyl groups (specific example group G4A):

[0321] vinyl,

[0322] Allyl

[0323] 1-Butenyl,

[0324] 2-Butenyl and

[0325] 3-Butenyl.

[0326] • Substituted alkenyl groups (specific example group G4B):

[0327] 1,3-Butadienyl,

[0328] 1-Methylvinyl

[0329] 1-Methylallyl,

[0330] 1,1-Dimethylallyl,

[0331] 2-Methylallyl and

[0332] 1,2-Dimethylallyl.

[0333] • "Substituted or unsubstituted alkynyl groups"

[0334] As specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (specific example group G5), the following unsubstituted alkynyl groups (specific example group G5A) can be cited. (Here, unsubstituted alkynyl group refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group".) The following description of "alkynyl group" includes both "unsubstituted alkynyl group" and "substituted alkynyl group".

[0335] "Substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" have been replaced by a substituent. Specific examples of "substituted alkynyl group" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) have been replaced by a substituent.

[0336] • Unsubstituted alkynyl group (specific example group G5A):

[0337] Acetylene group.

[0338] • "Substituted or unsubstituted cycloalkyl groups"

[0339] Specific examples of "substituted or unsubstituted cycloalkyl" described in this specification (specific example group G6) include unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B), etc. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In this specification, when referred to only as "cycloalkyl", both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

[0340] "Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group have been substituted with a substituent. Specific examples of "substituted cycloalkyl" include the group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" group (specific example group G6A) have been substituted with a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples. The "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" group of specific example group G6B have been substituted with a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl" group of specific example group G6B have been further substituted with a substituent.

[0341] • Unsubstituted cycloalkyl groups (specific example group G6A):

[0342] Cyclopropyl,

[0343] Cyclobutyl,

[0344] Cyclopentyl,

[0345] Cyclohexyl,

[0346] 1-Adamantyl,

[0347] 2-Adamantyl,

[0348] 1-norborneol and

[0349] 2-norborneol.

[0350] • Substituted cycloalkyl groups (specific example group G6B):

[0351] 4-Methylcyclohexyl.

[0352] ·"-Si(R 901 (R) 902 (R) 903 The group shown in the figure”

[0353] As described in this specification, -Si(R) 901 (R) 902 (R) 903 Specific examples of the group shown in the figure (specific example group G7) can be given as follows:

[0354] -Si(G1)(G1)(G1),

[0355] -Si(G1)(G2)(G2)

[0356] -Si(G1)(G1)(G2),

[0357] -Si(G2)(G2)(G2),

[0358] -Si(G3)(G3)(G3) and

[0359] -Si(G6)(G6)(G6). Here.

[0360] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0361] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0362] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0363] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0364] In -Si(G1)(G1)(G1), multiple G1s may be identical or different from each other.

[0365] In -Si(G1)(G2)(G2), multiple G2s may be the same or different from each other.

[0366] In -Si(G1)(G1)(G2), multiple G1s may be the same or different from each other.

[0367] In -Si(G2)(G2)(G2), multiple G2s may be the same or different from each other.

[0368] In -Si(G3)(G3)(G3), multiple G3s may be identical or different from each other.

[0369] In -Si(G6)(G6)(G6), multiple G6s may be identical or different from each other.

[0370] ·“-O-(R 904 The group shown in the figure”

[0371] As described in this specification, -O-(R) 904 Specific examples of the group shown in the figure (specific example group G8) can be given as follows:

[0372] -O(G1)

[0373] -O(G2),

[0374] -O(G3) and

[0375] -O(G6).

[0376] Here,

[0377] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0378] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0379] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0380] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0381] ·“-S-(R 905 The group shown in the figure”

[0382] As described in this specification, -S-(R) 905 Specific examples of the group shown in the figure (specific example group G9) can be given as follows:

[0383] -S(G1)

[0384] -S(G2),

[0385] -S(G3) and

[0386] -S(G6).

[0387] Here,

[0388] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0389] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0390] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0391] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0392] ·"-N(R 906 (R) 907 The group shown in the figure”

[0393] As described in this specification, -N(R) 906 (R) 907 Specific examples of the group shown (specific example group G10) can be given as follows:

[0394] -N(G1)(G1),

[0395] -N(G2)(G2),

[0396] -N(G1)(G2),

[0397] -N(G3)(G3) and

[0398] -N(G6)(G6).

[0399] Here,

[0400] G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1.

[0401] G2 refers to the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.

[0402] G3 refers to "substituted or unsubstituted alkyl group" as described in the specific example group G3.

[0403] G6 refers to "substituted or unsubstituted cycloalkyl" as described in the specific example group G6.

[0404] In -N(G1)(G1), multiple G1s may be the same or different from each other.

[0405] In -N(G2)(G2), multiple G2s may be the same or different from each other.

[0406] In -N(G3)(G3), multiple G3s may be the same or different from each other.

[0407] In -N(G6)(G6), multiple G6s may be the same or different from each other.

[0408] • "Halogen atom"

[0409] Specific examples of "halogen atoms" described in this specification (specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0410] • "Substituted or unsubstituted fluoroalkyl groups"

[0411] The term "substituted or unsubstituted fluoroalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by fluorine atoms (perfluorinated groups). Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted fluoroalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted fluoroalkyl" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl" group have been replaced by a substituent. It should be noted that the term "substituted fluoroalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted fluoroalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted fluoroalkyl", examples can be given of groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) have been replaced by fluorine atoms.

[0412] • "Substituted or unsubstituted haloalkyl groups"

[0413] The term "substituted or unsubstituted haloalkyl" as used in this specification refers to a group in which at least one hydrogen atom bonded to the carbon atom constituting the alkyl group has been replaced by a halogen atom, and also includes a group in which all hydrogen atoms bonded to the carbon atom constituting the alkyl group have been replaced by halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in an "unsubstituted haloalkyl" group is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. "Substituted haloalkyl" refers to a group in which one or more hydrogen atoms of a "haloalkyl" group have been replaced by a substituent. It should be noted that "substituted haloalkyl" as used in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in a "substituted haloalkyl" group have been further replaced by a substituent, and groups in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl" group have been further replaced by a substituent. As a specific example of "unsubstituted haloalkyl", examples can be given of groups in which one or more hydrogen atoms of the above-mentioned "alkyl" (specific example group G3) have been substituted with halogen atoms. Haloalkyl is sometimes called haloalkyl.

[0414] • "Substituted or unsubstituted alkoxy groups"

[0415] As a specific example of "substituted or unsubstituted alkoxy group" as described in this specification, it is the group indicated by -O (G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0416] • "Substituted or unsubstituted alkylthio groups"

[0417] As a specific example of "substituted or unsubstituted alkylthio group" as described in this specification, it is the group indicated by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The number of carbon atoms of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.

[0418] • "Substituted or unsubstituted aryloxy groups"

[0419] As a specific example of "substituted or unsubstituted aryloxy group" as described in this specification, it is the group indicated by -O (G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0420] • "Substituted or unsubstituted arylthio groups"

[0421] As a specific example of "substituted or unsubstituted arylthio group" as described in this specification, it is the group indicated by -S(G1), where G1 refers to the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of carbon atoms in the ring of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in this specification.

[0422] • "Substituted or unsubstituted trialkylsilyl groups"

[0423] As a specific example of "trialkylsilyl" as described in this specification, it is the group represented by -Si(G3)(G3)(G3), where G3 refers to the "substituted or unsubstituted alkyl" described in the specific example group G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0424] • "Substituted or unsubstituted aralkyl groups"

[0425] As a specific example of "substituted or unsubstituted aralkyl" as described in this specification, it is the group shown as -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl" described in specific example group G1. Therefore, "aralkyl" is a group in which the hydrogen atom of "alkyl" is replaced by "aryl" as a substituent, and is one embodiment of "substituted alkyl". "Unsubstituted aralkyl" is an "unsubstituted alkyl" that is substituted with "unsubstituted aryl", and the number of carbon atoms of "unsubstituted aralkyl" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0426] Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0427] Unless otherwise specified in this specification, the substituted or unsubstituted aryl groups described herein are preferably phenyl, p-biphenyl, meta-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, meta-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthraceneyl, phenanthryl, pyrene, phenyl, triphenylene, fluorene, 9,9'-spirobisfluorene, 9,9-dimethylfluorene, and 9,9-diphenylfluorene, etc.

[0428] Unless otherwise specified in this specification, the substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinel, carbazole (1-carbazole, 2-carbazole, 3-carbazole, 4-carbazole or 9-carbazole), benzocarbazole, azacarbazole, diazacarbazole, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophene, and naphtho-benzofuranyl. Benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazoyl ((9-phenyl)carbazo-1-yl, (9-phenyl)carbazo-2-yl, (9-phenyl)carbazo-3-yl or (9-phenyl)carbazo-4-yl), (9-biphenyl)carbazoyl, (9-phenyl)phenylcarbazoyl, diphenylcarbazo-9-yl, phenylcarbazo-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

[0429] In this specification, the carbazoyl group, unless otherwise specified herein, specifically refers to any one of the following groups.

[0430]

Chemical Formula 6

[0431]

[0432] In this specification, (9-phenyl)carbazolyl refers specifically to any one of the following groups unless otherwise specified herein.

[0433] [Chemical Formula 7]

[0434]

[0435] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0436] In this specification, dibenzofuranyl and dibenzothiopheneyl are specifically any one of the following groups unless otherwise stated in this specification.

[0437] [Chemical Formula 8]

[0438]

[0439] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0440] Unless otherwise specified in this specification, the substituted or unsubstituted alkyl groups described herein are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0441] • "Substituted or unsubstituted aryl groups"

[0442] Unless otherwise stated, the "substituted or unsubstituted aryl group" described in this specification is a divalent group derived from the "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aryl ring. Specific examples of "substituted or unsubstituted aryl group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom from the aryl ring.

[0443] • "Substituted or unsubstituted divalent heterocyclic groups"

[0444] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the aforementioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocycle. Specific examples of "substituted or unsubstituted divalent heterocyclic groups" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom from the heterocycle.

[0445] • "Substituted or unsubstituted alkylene compounds"

[0446] Unless otherwise stated, "substituted or unsubstituted alkylene groups" as described in this specification are divalent groups derived from "substituted or unsubstituted alkylene groups" by removing one hydrogen atom from the alkyl chain. Specific examples of "substituted or unsubstituted alkylene groups" (specific example group G14) include divalent groups derived from "substituted or unsubstituted alkylene groups" described in specific example group G3 by removing one hydrogen atom from the alkyl chain.

[0447] Unless otherwise specified in this specification, the substituted or unsubstituted aryl group described herein is preferably any one of the groups in the following general formulas (TEMP-42) to (TEMP-68).

[0448] [Chemical Formula 9]

[0449]

[0450]

Chemical Formula 10

[0451]

[0452] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0453] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0454]

Chemical Formula 11

[0455]

[0456] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each can be a hydrogen atom or a substituent independently.

[0457] Formulas Q9 and Q 10 They can form rings by bonding with each other via single bonds.

[0458] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0459]

Chemical Formula 12

[0460]

[0461] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0462] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0463] Unless otherwise specified in this specification, the substituted or unsubstituted divalent heterocyclic group described herein is preferably any group of the following general formulas (TEMP-69) to (TEMP-102).

[0464]

Chemical Formula 13

[0465]

[0466]

Chemical Formula 14

[0467]

[0468]

Chemical Formula 15

[0469]

[0470] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0471] [Chemical Formula 16]

[0472]

[0473]

Chemical Formula 17

[0474]

[0475] [Chemical Formula 18]

[0476]

[0477] [Chemical Formula 19]

[0478]

[0479] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0480] The above is an explanation of "substituents described in this specification".

[0481] • "Cases where bonds form rings"

[0482] In this specification, the description of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring, or bonded together to form a substituted or unsubstituted fused ring, or not bonded together" refers to the cases of "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted monocyclic ring", "one or more groups of two or more adjacent elements bonded together to form a substituted or unsubstituted fused ring", and "one or more groups of two or more adjacent elements not bonded together".

[0483] The following description addresses the cases described in this specification as "forming a substituted or unsubstituted monocyclic ring by bonding one or more groups of two or more adjacent elements together" and "forming a substituted or unsubstituted fused ring by bonding one or more groups of two or more adjacent elements together" (hereinafter, these cases are sometimes collectively referred to as "forming a ring by bonding"). The case of anthracene compounds represented by the following general formula (TEMP-103) with an anthracene ring as the parent skeleton will be used as an example.

[0484]

Chemical Formula 20

[0485]

[0486] For example, in the case of R 921 ~R 930 In the case of "one or more groups of two or more adjacent elements bonded together to form a loop", a group consisting of two adjacent elements is referred to as R. 921 With R 922 group, R 922 With R 923 group, R 923 With R 924 group, R 924 With R 930 group, R 930 With R 925 group, R 925 With R 926 group, R 926 With R 927 group, R 927 With R 928 group, R 928 With R 929 The group, and R 929 With R 921 The group.

[0487] The phrase "one or more groups" refers to the fact that two or more of the aforementioned groups consisting of two or more adjacent elements can simultaneously form a loop. For example, in R... 921 With R 922 They bond together to form a ring Q A Moreover, R 925 With R 926 They bond together to form a ring Q B In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0488]

Chemical Formula 21

[0489]

[0490] The formation of rings from "groups consisting of two or more adjacent elements" includes not only the case of bonds formed by groups consisting of "two" adjacent elements, as in the previous example, but also the case of bonds formed by groups consisting of "three or more" adjacent elements. For example, it refers to R... 921 With R 922 They bond together to form a ring Q A And R 922 With R 923 They bond together to form a ring Q C , consisting of 3 adjacent (R) 921 R 922 and R 923When the groups of components Q bond together to form a ring and fuse to the anthracene matrix, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q... A and ring Q C There are a total of R 922 .

[0491]

Chemical Formula 22

[0492]

[0493] In the formed "single ring" or "fused ring," the structure of the ring alone can be either a saturated ring or an unsaturated ring. Even when a "single ring" or "fused ring" is formed from "one group of two adjacent rings," the "single ring" or "fused ring" can still form a saturated ring or an unsaturated ring. For example, the ring Q formed in the above general formula (TEMP-104) A and ring Q B Each is either a "single ring" or a "fused ring". Additionally, the ring Q formed in the above general formula (TEMP-105) A and Q ring C It is a "fused ring". The ring Q of the above general formula (TEMP-105) A With ring Q C Through ring Q A With ring Q C Fusing together forms a fused ring. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A It is a single ring. The ring Q in the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0494] "Unsaturated rings" refer to aromatic hydrocarbon rings or aromatic heterocycles. "Saturated rings" refer to aliphatic hydrocarbon rings or non-aromatic heterocycles.

[0495] As a specific example of an aromatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G1 can be cited.

[0496] As a specific example of an aromatic heterocycle, one can cite the structure formed by end-capping an aromatic heterocycle group with hydrogen atoms in specific example group G2.

[0497] As a specific example of an aliphatic hydrocarbon ring, the structure formed by the hydrogen atom-terminated group in specific example group G6 can be cited.

[0498] "Ring formation" refers to the formation of a ring solely by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton forming a ring with one or more other optional elements. For example, R shown in the above general formula (TEMP-104) 921 With R 922 The ring Q formed by mutual bonding A It refers to R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 The carbon atoms of the bonded anthracene framework form rings with one or more optional elements. As a specific example, in the case of R... 921 With R 922 Forming ring Q A In the case of R 921 The carbon atoms and R atoms of the bonded anthracene skeleton 922 When the bonded anthracene skeleton carbon atoms and 4 carbon atoms form a monocyclic unsaturated ring, R 921 With R 922 The resulting ring is a benzene ring.

[0499] Here, "optional element" is preferably selected from at least one element chosen from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified in this specification. In the case of optional elements (e.g., carbon or nitrogen), non-ring bonds can be capped by hydrogen atoms or replaced by "optional substituents" described later. When optional elements other than carbon are included, the resulting ring is a heterocycle.

[0500] Unless otherwise specified in this specification, the "one or more optional elements" constituting a monocyclic or fused ring are preferably two or more and 15 or less, more preferably three or more and 12 or less, and even more preferably three or more and 5 or less.

[0501] Unless otherwise stated in this specification, "monocyclic" is preferred over "fused-ring".

[0502] Unless otherwise stated in this specification, "unsaturated ring" is preferred over "saturated ring".

[0503] Unless otherwise stated in this specification, "monocyclic" is preferably a benzene ring.

[0504] Unless otherwise stated in this specification, the "unsaturated ring" is preferably a benzene ring.

[0505] In the case of “one or more groups consisting of two or more adjacent elements”, “forming a substituted or unsubstituted monocyclic ring by mutual bonding”, or “forming a substituted or unsubstituted fused ring by mutual bonding”, unless otherwise stated in this specification, it is preferred that one or more groups consisting of two or more adjacent elements are mutually bonded to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of a parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

[0506] When the aforementioned "monocyclic" or "fused-ring" rings have substituents, the substituents are, for example, the "optional substituents" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused-ring" rings have substituents are the substituents described in the section "Substituents Represented in This Specification" above.

[0507] When the aforementioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of substituents when the aforementioned "monocyclic" or "fused ring" has a substituent are the substituents described in the section "Substituents Represented in This Specification" above.

[0508] The above explains the cases of "a single ring formed by bonding one or more groups of two or more adjacent elements together" and "a fused ring formed by bonding one or more groups of two or more adjacent elements together" ("the case of forming a ring by bonding").

[0509] Substituents when described as "substituted or unsubstituted"

[0510] In one embodiment of this specification, the substituents described above as "substituted or unsubstituted" (sometimes referred to as "optional substituents" in this specification) are, for example, selected from...

[0511] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0512] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0513] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0514] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0515] -Si(R 901 (R) 902 (R) 903 ),

[0516] -O-(R 904 ),

[0517] -S-(R 905 ),

[0518] -N(R 906 (R) 907 ),

[0519] Halogen atom, cyano group, nitro group,

[0520] Unsubstituted aryl groups with 6 to 50 carbon atoms and

[0521] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0522] Groups, etc., in the composition group

[0523] Here, R 901 ~R 907 Each independently

[0524] hydrogen atom,

[0525] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0526] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0527] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0528] A heterocyclic group with 5 to 50 cyclic atoms, either substituted or unsubstituted.

[0529] In R 901 When there are more than two, more than two R 901 They are the same or different.

[0530] In R 902 When there are more than two, more than two R 902 They are the same or different.

[0531] In R 903 When there are more than two, more than two R 903 They are the same or different.

[0532] In R 904 When there are more than two, more than two R 904 They are the same or different.

[0533] In R 905 When there are more than two, more than two R 905 They are the same or different.

[0534] In R 906 When there are more than two, more than two R 906 They are the same or different.

[0535] In R 907 When there are more than two, more than two R 907 They are the same or different.

[0536] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0537] Alkyl groups with 1 to 50 carbon atoms

[0538] Aryl groups with 6 to 50 carbon atoms and

[0539] Groups in the group consisting of heterocyclic groups with 5 to 50 cyclic atoms.

[0540] In one embodiment, the substituent when described as "substituted or unsubstituted" is selected freely.

[0541] Alkyl groups having 1 to 18 carbon atoms

[0542] aryl groups with 6 to 18 carbon atoms and

[0543] Groups in the group consisting of heterocyclic groups with 5 to 18 cyclic atoms.

[0544] Specific examples of the substituents mentioned above are those described in the section "Substituents as set forth in this specification".

[0545] Unless otherwise stated in this specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably forming a benzene ring.

[0546] Unless otherwise stated in this specification, optional substituents may also have other substituents. Any further substituents that may be present as optional substituents are the same as those described above.

[0547] In this specification, the numerical range represented by "AA~BB" refers to the range included by taking the value AA, which is written before "AA~BB", as the lower limit and the value BB, which is written after "AA~BB", as the upper limit.

[0548] [First Implementation]

[0549] <Compound>

[0550] The compound involved in the first embodiment is the compound shown in the following formula (1).

[0551]

Chemical Formula 23

[0552]

[0553] (In equations (1) and (12) above,

[0554] Ry is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure.

[0555] At least one of the groups selected from R1 to R3 is the group shown in formula (12) above.

[0556] R1 to R3 of the groups not shown in formula (12) above are not each independently...

[0557] hydrogen atom, or

[0558] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0559] m1 + m2 = 4,

[0560] m1 is 0, 1, 2, 3, or 4.

[0561] n1 + n2 = 4,

[0562] n1 is 0, 1, 2, 3 or 4.

[0563] Where m1 + n1 is 1, 2, 3, 4, 5, 6, 7, or 8.

[0564] HAr is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms.

[0565] R 11 ~R 15 R 18 R 19 R 21 ~R 23 R A and R B Each independently

[0566] hydrogen atom,

[0567] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0568] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0569] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0570] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0571] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0572] -Si(R 901 (R)902 (R) 903 The groups shown in the figure,

[0573] -O-(R 904 The groups shown in the figure,

[0574] -S-(R 905 The groups shown in the figure,

[0575] -N(R 906 (R) 907 The groups shown in the figure,

[0576] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0577] -C(=O)R 801 The groups shown

[0578] -C(=O)(OR 802 The groups shown in the figure,

[0579] Halogen atoms,

[0580] cyano,

[0581] Nitro,

[0582] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0583] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0584] -B(R 936 (R) 937 The groups shown in the figure,

[0585] -B(OR 938 (OR) 939 The groups shown in the figure,

[0586] -OS(=O)2(R 940 The groups shown in the figure,

[0587] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0588] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0589] Among them, R A and R B It cannot be both hydrogen atoms at the same time.

[0590] When there are multiple groups represented by the above formula (12), the multiple groups represented by the above formula (12) may be the same as or different from each other.

[0591] When multiple HArs exist, they may be identical or different from each other.

[0592] In R 18 In the case of multiple Rs, multiple Rs 18 They are the same or different.

[0593] In R 19 In the case of multiple Rs, multiple Rs 19 They are the same or different.

[0594] In equation (12) above, * represents the bonding position.

[0595] (In the compound shown in formula (1) above, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 Each independently

[0596] hydrogen atom,

[0597] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0598] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0599] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0600] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0601] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[0602] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[0603] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[0604] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[0605] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[0606] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[0607] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[0608] In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different.

[0609] In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different.

[0610] In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different.

[0611] In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different.

[0612] In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different.

[0613] In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different.

[0614] In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different.

[0615] In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different.

[0616] In R 937In the case of multiple Rs, multiple Rs 937 They are the same or different.

[0617] In R 938 In the case of multiple Rs, multiple Rs 938 They are the same or different.

[0618] In R 939 In the case of multiple Rs, multiple Rs 939 They are the same or different.

[0619] In R 940 In the case of multiple Rs, multiple Rs 940 (They may be the same or different.)

[0620] According to the compound involved in this embodiment, the luminous efficiency of organic electroluminescent elements can be improved.

[0621] In one embodiment of the compound, Ry is preferably a substituted or unsubstituted aryl group having 6 to 18 cyclic carbons, more preferably a substituted or unsubstituted aryl group having 6 to 14 cyclic carbons, and even more preferably a substituted phenyl group.

[0622] In this embodiment, the compound represented by formula (1) above is preferably the compound represented by formula (10) below.

[0623] [Chemical Formula 24]

[0624]

[0625] (In the above formula (10), R1~R3, R 11 ~R 15 R 18 R 19 The meanings of HAr, m1, m2, n1, and n2 are respectively the same as R1~R3, R in the above formula (1). 11 ~R 15 R 18 R 19 HAr, m1, m2, n1, and n2 have the same meaning.

[0626] R4 to R6 are each independent of each other.

[0627] hydrogen atom,

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

[0629] The group shown in formula (12) above,

[0630] R 16 and R 17 Each independently

[0631] hydrogen atom,

[0632] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0633] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0634] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0635] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0636] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0637] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0638] -O-(R 904 The groups shown in the figure,

[0639] -S-(R 905 The groups shown in the figure,

[0640] -N(R 906 (R) 907 The groups shown in the figure,

[0641] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0642] -C(=O)R 801 The groups shown

[0643] -C(=O)(OR 802 The groups shown in the figure,

[0644] Halogen atoms,

[0645] cyano,

[0646] Nitro,

[0647] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0648] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0649] -B(R 936 (R) 937 The groups shown in the figure,

[0650] -B(OR 938 (OR)939 The groups shown in the figure,

[0651] -OS(=O)2(R 940 The groups shown in the figure,

[0652] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0653] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0654] When there are multiple groups represented by formula (12) above, the multiple groups represented by formula (12) above may be the same as or different from each other.

[0655] (In the above equation (10), R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 The meanings of each are independently related to R in the above formula (1). 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 The meanings are the same.

[0656] In one embodiment of the compound, m1 is 1 and n1 is 0.

[0657] In one embodiment of the compound, m1 is 0 and n1 is 1.

[0658] In one embodiment of the compound, m1 is 1 and n1 is 1.

[0659] In one embodiment of the compound, when multiple HArs are present, the multiple HArs are identical to each other.

[0660] In one embodiment of the compound, the group represented by the following formula (1a) in the compound shown in the above formula (1) is the same group as Ry.

[0661] In one embodiment of the compound, the group represented by formula (1a) in the compound shown in formula (10) above is the same group as the group represented by formula (1b) below. In this case, in the compound shown in formula (10) above, the groups of R1 and R6, R2 and R5, R3 and R4, and R... 14 and R 16 The group and R 15 and R 17 Each group consists of the same functional groups.

[0662] [Chemical Formula 25]

[0663]

[0664] (In the above formula (1a), R1~R3 and R 14 ~R 15 The meanings are respectively the same as R1~R3 and R in the above formula (1). 14 ~R 15 The meanings are the same.

[0665] (In equations (1a) and (1b) above, R1~R6 and R 14 ~R 17 The meanings are respectively the same as R1~R6 and R in the above formula (10). 14 ~R 17 The meanings are the same.

[0666] The preferred compound in this embodiment is a compound having a symmetrical structure, in which the structure bonded to the right side of the heterocycle containing 2 nitrogen atoms and 1 boron atom is the same as the structure bonded to the left side.

[0667] In one embodiment of the compound, the group represented by formula (1a) in the compound represented by formula (1) is a different group from Ry.

[0668] In one embodiment of the compound, the group represented by formula (1a) in the compound represented by formula (10) is a different group from the group represented by formula (1b). In this case, in the compound represented by formula (10), the groups R1 and R6, R2 and R5, R3 and R4, and R... 14 and R 16 The group and R 15 and R 17 At least one group in the group consists of mutually distinct groups.

[0669] The compounds involved in this embodiment are preferably compounds with an asymmetric structure in which the structure bonded to the right side of the heterocycle containing 2 nitrogen atoms and 1 boron atom is different from the structure bonded to the left side.

[0670] In the compounds involved in this embodiment, the group represented by the above formula (12) is preferably a group represented by any one of the following formulas (12A) to (12H).

[0671]

Chemical Formula 26

[0672]

[0673] (In the above equations (12A) to (12D), R) A and R 21 ~R 23 The meanings are respectively the same as R in the above formula (12). A and R 21 ~R 23 The meanings are the same, R 211 ~R 220 and R 241 ~R 245 The meanings of each are independently related to R in the above equation (12). 21 ~R 23 The meaning is the same.

[0674] When multiple groups are represented in formula (12A), the multiple groups represented in formula (12A) are identical or different from each other. When multiple groups are represented in formula (12B), the multiple groups represented in formula (12B) are identical or different from each other. When multiple groups are represented in formula (12C), the multiple groups represented in formula (12C) are identical or different from each other. When multiple groups are represented in formula (12D), the multiple groups represented in formula (12D) are identical or different from each other. In formulas (12A) to (12D), * indicates a bonding position.

[0675] [Chemical Formula 27]

[0676]

[0677] (In the above equations (12E)~(12H), R) A and R 21 ~R 23 The meanings are respectively the same as R in the above formula (12). A and R 21 ~R 23 The meanings are the same; Ak1, Ak2, and Ak3 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0678] When multiple groups are represented by formula (12E), the multiple groups represented by formula (12E) may be the same as or different from each other. When multiple groups are represented by formula (12F), the multiple groups represented by formula (12F) may be the same as or different from each other. When multiple groups are represented by formula (12G), the multiple groups represented by formula (12G) may be the same as or different from each other. When multiple groups are represented by formula (12H), the multiple groups represented by formula (12H) may be the same as or different from each other. In formulas (12E) to (12H), * indicates a bonding position.

[0679] In the above equations (12A) to (12D), R A R 21 ~R 23 R 211 ~R 220 and R 241 ~R 245 Each is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 14 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms.

[0680] In the above equations (12E) to (12H), R A R 21 ~R 23 R 211 ~R 220 and R 241 ~R 245 Each is preferably a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, or -Si(R 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, more preferably a hydrogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 14 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms.

[0681] In the above formulas (12E) to (12H), Ak1, Ak2 and Ak3 are each preferably substituted or unsubstituted alkyl groups having 1 to 18 carbon atoms, more preferably substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and even more preferably unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0682] In the compounds involved in this embodiment, the group represented by the above formula (12) is preferably a group represented by any one of the following formulas (120a) to (120k).

[0683] [Chemical Formula 28]

[0684]

[0685] In the above formulas (120d), (120e), (120g), and (120h), the meanings of Ak1, Ak2, and Ak3 are the same as those of Ak1, Ak2, and Ak3 in formulas (12E) to (12H).

[0686] In equations (120b) and (120i) above, the meaning of Ak4 is the same as the meaning of Ak1 in equation (12F) above.

[0687] In the above equation (120j), R 901 R 902 and R 903The meaning of R is the same as in equation (1) above. 901 R 902 and R 903 The meaning is the same.

[0688] In the above equations (120a) to (120k), * denotes the bonding position.

[0689] In the compounds involved in this embodiment, it is preferred that at least one of the groups selected from the group consisting of R1 and R3 is a group represented by the above formula (12).

[0690] In the compounds involved in this embodiment, it is also preferred that R1 or R3 is a group represented by the above formula (12).

[0691] In the compounds involved in this embodiment, it is also preferred that R2 is a group represented by the above formula (12).

[0692] In the compounds involved in this embodiment, it is also preferred that one of the groups selected from R1 to R3 is the group shown in the above formula (12), and one of the groups selected from R4 to R6 is the group shown in the above formula (12).

[0693] In the compounds involved in this embodiment, it is also preferred that R3 and R4 are each independently a group represented by the above formula (12).

[0694] In the compounds involved in this embodiment, it is also preferred that R2 and R5 are each independently a group represented by the above formula (12).

[0695] In the compounds involved in this embodiment, it is also preferred that one of the groups selected from R1 to R3 is the group shown in the above formula (12), and that R4 to R6 are not the groups shown in the above formula (12).

[0696] In the compounds involved in this embodiment, R1 to R6, which are not groups shown in the above formula (12), are each preferably hydrogen atoms or substituted or unsubstituted alkyl groups having 1 to 18 carbon atoms, more preferably hydrogen atoms or substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, and even more preferably hydrogen atoms or unsubstituted alkyl groups having 1 to 6 carbon atoms.

[0697] In the compounds involved in this embodiment, the compound represented by formula (10) above is preferably the compound represented by formula (112) or (113) below. The compound represented by formula (112) or (113) below is a scheme of the compound represented by formula (1) above.

[0698] [Chemical Formula 29]

[0699]

[0700]

Chemical Formula 30

[0701]

[0702] (In the above equations (112) and (113), R1~R3, R 11 ~R 15 R 18 R 19 The meanings of HAr, m1, m2, n1, and n2 are respectively the same as R1~R3, R in the above formula (1). 11 ~R 15 R 18 R 19 HAr, m1, m2, n1, and n2 have the same meaning.

[0703] R4~R6 and R 16 ~R 17 The meanings are respectively the same as R4~R6 and R in the above formula (10). 16 ~R 17 The meaning is the same.

[0704] R 21 ~R 23 R A and R B The meanings are respectively the same as R in the above formula (12). 21 ~R 23 R A and R B The meanings are the same, multiple R 21 Multiple Rs that are the same or different 22 Multiple Rs that are the same or different 23 Multiple Rs that are the same or different A Multiple Rs that are the same or different B (They may be the same or different.)

[0705] In the compounds involved in this embodiment, R 11 ~R 19 and R 21 ~R 23 Each is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms.

[0706] In the compounds involved in this embodiment, R 11 ~R 19 and R 21 ~R 23Each of the following is more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 18 carbon atoms.

[0707] In the compounds involved in this embodiment, R 11 ~R 19 and R 21 ~R 23 Each of the following is further preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 14 carbon atoms.

[0708] In the compounds involved in this embodiment, the compound represented by formula (10) above is preferably the compound represented by formula (110) or (111) below. The compound represented by formula (110) or (111) below is a scheme of the compound represented by formula (1) above.

[0709]

Chemical Formula 31

[0710]

[0711] (In the above equations (110) and (111), R1~R6, R 11 ~R 17 The meanings of HAr are respectively the same as R1~R6 and R in the above formula (10). 11 ~R 17 The meaning of HAr is the same as that of HAr; multiple HArs may be the same or different from each other.

[0712] R 181 R 183 R 184 R 191 R 192 R 193 and R 194 Each independently

[0713] hydrogen atom,

[0714] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0715] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0716] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0717] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0718] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0719] -Si(R 901 (R) 902 (R)903 The groups shown in the figure,

[0720] -O-(R 904 The groups shown in the figure,

[0721] -S-(R 905 The groups shown in the figure,

[0722] -N(R 906 (R) 907 The groups shown in the figure,

[0723] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0724] -C(=O)R 801 The groups shown

[0725] -C(=O)(OR 802 The groups shown in the figure,

[0726] Halogen atoms,

[0727] cyano,

[0728] Nitro,

[0729] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0730] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0731] -B(R 936 (R) 937 The groups shown in the figure,

[0732] -B(OR 938 (OR) 939 The groups shown in the figure,

[0733] -OS(=O)2(R 940 The groups shown in the figure,

[0734] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0735] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0736] R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively the same as R in the above formula (1).901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

[0737] Of the compounds involved in this embodiment, R is preferred. A and R B At least one of them is a substituent. In the compounds involved in this embodiment, R is preferred. A and R B Each is an independent substituent.

[0738] Of the compounds involved in this embodiment, R is preferred. A and R B One of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms, R A and R B The other party is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 50 carbon atoms.

[0739] Of the compounds involved in this embodiment, R is more preferably preferred. A and R B One of them is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms, R A and R B The other party is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms.

[0740] Of the compounds involved in this embodiment, R is preferred. A and R B Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 50 carbon atoms.

[0741] Of the compounds involved in this embodiment, R is more preferably preferred. A and R B Each is independently a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 18 carbon atoms.

[0742] Of the compounds involved in this embodiment, R is further preferred. A and R B Each is independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted cyclic aryl group having 6 to 14 carbon atoms.

[0743] In the compounds involved in this embodiment, R 181 R 183 R 184 R 191 R 192 R 193 and R 194 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms; more preferably 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 cyclic carbon atoms; and even more preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 14 cyclic carbon atoms.

[0744] In the compounds involved in this embodiment, it is preferred that HAr is a monovalent group derived from the ring structure shown in the following formula (13).

[0745]

Chemical Formula 32

[0746]

[0747] (In the above formula (13),

[0748] X3 represents oxygen atoms, sulfur atoms, and N(R) atoms. 39 ) or Si(R 39A (R) 39B ),

[0749] By R 351 and R 352 Groups

[0750] They bond together to form substituted or unsubstituted monocyclic rings.

[0751] They bond together to form substituted or unsubstituted fused rings, or

[0752] They do not bond with each other.

[0753] By R 39A and R 39B Groups

[0754] They bond together to form substituted or unsubstituted monocyclic rings.

[0755] They bond together to form substituted or unsubstituted fused rings, or

[0756] They do not bond with each other.

[0757] By R 31 ~R 34 One or more groups consisting of two or more adjacent elements.

[0758] They bond together to form substituted or unsubstituted monocyclic rings.

[0759] They bond together to form substituted or unsubstituted fused rings, or

[0760] They do not bond with each other.

[0761] R 39 R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 31 ~R 34 R 39A R 39B R 351 and R 352 Each independently

[0762] hydrogen atom,

[0763] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0764] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0765] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0766] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0767] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0768] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0769] -O-(R 904 The groups shown in the figure,

[0770] -S-(R 905 The groups shown in the figure,

[0771] -N(R 906 (R) 907 The groups shown in the figure,

[0772] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0773] -C(=O)R 801 The groups shown

[0774] -C(=O)(OR 802 The groups shown in the figure,

[0775] Halogen atoms,

[0776] cyano,

[0777] Nitro,

[0778] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0779] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0780] -B(R 936 (R) 937 The groups shown in the figure,

[0781] -B(OR 938 (OR) 939 The groups shown in the figure,

[0782] -OS(=O)2(R 940 The groups shown in the figure,

[0783] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0784] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0785] R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively the same as R in the above formula (1). 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

[0786] In the compounds involved in this embodiment, "a monovalent group derived from the ring structure shown in formula (13)" refers to a monovalent group derived from the ring structure shown in formula (13) (selected from R... 351 With R 352 The group, and the group by R 31 ~R 34 In the case where two or more adjacent groups are bonded together to form a substituted or unsubstituted monocyclic ring, or a substituted or unsubstituted fused ring, the monovalent group derived by removing one hydrogen atom from the monocyclic or fused ring is also included.

[0787] In the compounds involved in this embodiment, it is preferred that the monovalent group derived from the ring structure shown in formula (13) is a monovalent group derived from the ring structure shown in formulas (13A), (13B), (13C), (13D), (13E) or (13F).

[0788]

Chemical Formula 33

[0789]

[0790] (In the above equations (13A), (13B) and (13C),

[0791] R 31 ~R 34 R 39 R 351 and R 352 The meanings are respectively the same as R in the above formula (13). 31 ~R 34 R 39 R 351 and R 352 The meanings are the same.

[0792] (In the above equations (13D), (13E) and (13F),

[0793] R 31 ~R 34 and R 39 The meanings are respectively the same as R in the above formula (13). 31 ~R 34 and R 39 The meaning is the same.

[0794] By R 35 ~R 38 One or more groups consisting of two or more adjacent elements.

[0795] They bond together to form substituted or unsubstituted monocyclic rings.

[0796] They bond together to form substituted or unsubstituted fused rings, or

[0797] They do not bond with each other.

[0798] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 35 ~R 38 Each independently

[0799] hydrogen atom,

[0800] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[0801] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[0802] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0803] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[0804] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0805] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0806] -O-(R 904 The groups shown in the figure,

[0807] -S-(R 905 The groups shown in the figure,

[0808] -N(R 906 (R) 907 The groups shown in the figure,

[0809] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0810] -C(=O)R 801 The groups shown

[0811] -C(=O)(OR 802 The groups shown in the figure,

[0812] Halogen atoms,

[0813] cyano,

[0814] Nitro,

[0815] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0816] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0817] -B(R 936 (R) 937 The groups shown in the figure,

[0818] -B(OR 938 (OR) 939 The groups shown in the figure,

[0819] -OS(=O)2(R 940 The groups shown in the figure,

[0820] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0821] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[0822] R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively the same as R in the above formula (1). 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

[0823] Of the compounds involved in this embodiment, the preferred one is...

[0824] By R 351 and R 352 The groups formed are not mutually bonded.

[0825] By R 31 ~R 34 Two or more adjacent groups are not bonded to each other.

[0826] By R 35 ~R 38 Two or more adjacent groups are not bonded to each other.

[0827] In the compounds involved in this embodiment, it is preferred that the monovalent group derived from the ring structure shown in formula (13) is a monovalent group derived from the ring structure shown in formula (13D).

[0828] Of the compounds involved in this embodiment, R in (13D) is preferred. 39 It is a single bond that bonds with the above formula (1).

[0829] In the compounds involved in this embodiment, R 21 ~R 23 Each of these is also preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 carbon atoms, or a -Si(R) group. 901 (R) 902 (R) 903 The radical shown in the diagram, or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, is also preferred to be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 14 carbon atoms, or a -Si(R) group. 901 (R)902 (R) 903 The group indicated by ) or a substituted or unsubstituted aryl group having 6 to 14 carbon atoms.

[0830] Among the compounds involved in this embodiment, R is also preferred. 21 ~R 23 It is a hydrogen atom.

[0831] In the compounds involved in this embodiment, R 31 ~R 39 R 39A R 39B R 351 and R 352 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms. More preferably, it is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 18 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 cyclic atoms. Further preferably, it is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 cyclic atoms.

[0832] Preferably, the compound involved in this embodiment has at least one deuterium atom.

[0833] Preferably, the hydrogen atoms in the compounds involved in this embodiment are all deuterium atoms.

[0834] Among the compounds involved in this embodiment, R1 to R6 and R are also preferred. 11 ~R 19 At least one of them is a deuterium atom. In the compound involved in this embodiment, in R1 to R6 and R 11 ~R 19 In the case of substituents, R1 to R6 and R are preferred. 11 ~R 19 At least one of the hydrogen atoms is a deuterium atom.

[0835] Among the compounds involved in this embodiment, R is also preferred. 21 ~R 23 R A and R B At least one of them is a deuterium atom. In the compound involved in this embodiment, in R 21 ~R23 R A and R B In the case of substituents, R is also preferred. 21 ~R 23 R A and R B At least one of the hydrogen atoms is a deuterium atom.

[0836] In the compounds involved in this embodiment, it is also preferred that at least one of the hydrogen atoms in HAr is a deuterium atom. In the compounds involved in this embodiment, it is also preferred that all hydrogen atoms in HAr are deuterium atoms.

[0837] In the compounds involved in this embodiment, it is preferred that the substituents, when described as "substituted or unsubstituted", are...

[0838] Unsubstituted alkyl groups having 1 to 50 carbon atoms

[0839] Unsubstituted alkenyl groups with 2 to 50 carbon atoms

[0840] Unsubstituted acetylinyl groups with 2 to 50 carbon atoms

[0841] Unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[0842] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[0843] -O-(R 904 The groups shown in the figure,

[0844] -S-(R 905 The groups shown in the figure,

[0845] -N(R 906 (R) 907 The groups shown in the figure,

[0846] Unsubstituted aralkyl groups with 7 to 50 carbon atoms

[0847] -C(=O)R 801 The groups shown

[0848] -C(=O)(OR 802 The groups shown in the figure,

[0849] cyano,

[0850] Nitro,

[0851] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[0852] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[0853] -B(R 936 (R) 937 The groups shown in the figure,

[0854] -B(OR 938 (OR) 939 The groups shown in the figure,

[0855] -OS(=O)2(R 940 The groups shown in the figure,

[0856] Unsubstituted aryl groups with 6 to 50 carbon atoms, or

[0857] Unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[0858] R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 Each independently

[0859] hydrogen atom,

[0860] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[0861] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[0862] Unsubstituted heterocyclic groups with 5 to 25 cyclic atoms.

[0863] In this specification, -O-(R 904 The group shown in R 904 In the case of hydrogen atoms, it is a hydroxyl group.

[0864] In this specification, -S-(R 905 The group shown in R 905 In the case of hydrogen atoms, it is a thiol group.

[0865] In this specification, -P(=O)(R 931 (R) 932 The group shown in R 931 and R 932 In the case of a substituent, it is a substituted phosphine oxide group.

[0866] In this specification, -Ge(R) 933 (R) 934 (R) 935 The group shown in R 933 R 934 and R 935 In the case of a substituent, it is a substituted germanium group.

[0867] In this specification, -B(R) 936 (R) 937 The group shown in R 936 and R 937 In the case of a substituent, it is a substituted methylborane.

[0868] In the compounds involved in this embodiment, it is preferred that the substituents described as "substituted or unsubstituted" are unsubstituted alkyl groups having 1 to 25 carbon atoms, unsubstituted cycloalkyl groups having 3 to 10 cyclic carbon atoms, unsubstituted aryl groups having 6 to 25 cyclic carbon atoms, or unsubstituted heterocyclic groups having 5 to 25 cyclic atoms.

[0869] In the compounds involved in this embodiment, it is preferred that the substituents described as "substituted or unsubstituted" are unsubstituted alkyl groups having 1 to 6 carbon atoms, unsubstituted cycloalkyl groups having 3 to 10 cyclic carbon atoms, unsubstituted aryl groups having 6 to 14 cyclic carbon atoms, or unsubstituted heterocyclic groups having 5 to 14 cyclic atoms.

[0870] In the compounds involved in this embodiment, it is preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[0871] The compound involved in this embodiment is preferably a material used for the light-emitting layer.

[0872] The compounds involved in this embodiment are preferably dopant materials.

[0873] The compounds involved in this embodiment are preferably fluorescent materials.

[0874] In this specification, the compound involved in the first embodiment is sometimes referred to as the first compound.

[0875] (Maximum peak wavelength of fluorescence emission)

[0876] In this specification, the maximum peak wavelength of fluorescence emission is sometimes referred to as the maximum peak wavelength of fluorescence emission.

[0877] The maximum peak wavelength of fluorescence emission of the compound involved in this embodiment is preferably below 480 nm, and more preferably below 475 nm.

[0878] The maximum peak wavelength of fluorescence emission of the compound involved in this embodiment is preferably 430 nm or more, and more preferably 440 nm or more.

[0879] In this specification, the maximum peak wavelength of fluorescence emission refers to the wavelength at which the compound being measured reaches its maximum emission value at 10 nm. -6 moles per liter and above and 10 -5 The fluorescence spectrum obtained by measuring a toluene solution with a concentration of less than mol / L yields the maximum peak wavelength of the fluorescence spectrum, where the emission intensity reaches its maximum. The full width at half maximum (FWHM) of the emission spectrum is the full width at half maximum (FWHM) of the maximum peak in the fluorescence spectrum. A fluorescence spectrometer can be used as the apparatus for measuring the fluorescence spectrum. For example, a fluorescence spectrometer manufactured by Nippon Spectroscopy Corporation (device name: FP-8300) can be used. It should be noted that the fluorescence spectrometer is not limited to the apparatus illustrated here.

[0880] (The method for manufacturing the compound involved in this embodiment)

[0881] The compounds involved in this embodiment can be manufactured according to the synthesis method described in the examples below, or they can be manufactured by using known alternative reactions and raw materials corresponding to the target substance, following the synthesis method.

[0882] (Specific examples of compounds involved in this embodiment)

[0883] Specific examples of compounds involved in this embodiment include the following compounds. However, the present invention is not limited to these specific examples.

[0884] [Chemical Formula 34]

[0885]

[0886]

Chemical Formula 35

[0887]

[0888]

Chemical Formula 36

[0889]

[0890]

Chemical Formula 37

[0891]

[0892] [Chemical Formula 38]

[0893]

[0894] [Chemical Formula 39]

[0895]

[0896]

Chemical Formula 40

[0897]

[0898]

Chemical Formula 41

[0899]

[0900]

Chemical Formula 42

[0901]

[0902]

Chemical Formula 43

[0903]

[0904]

Chemical Formula 44

[0905]

[0906] [Chemical Formula 45]

[0907]

[0908]

Chemical Formula 46

[0909]

[0910] [Chemical Formula 47]

[0911]

[0912] [Chemical Formula 48]

[0913]

[0914] [Chemical Formula 49]

[0915]

[0916] [Chemical Formula 50]

[0917]

[0918]

Chemical Formula 51

[0919]

[0920]

Chemical Formula 52

[0921]

[0922]

Chemical Formula 53

[0923]

[0924] [Chemical Formula 54]

[0925]

[0926]

Chemical Formula 55

[0927]

[0928] [Chemical Formula 56]

[0929]

[0930] [Chemical Formula 57]

[0931]

[0932] [Chemical Formula 58]

[0933]

[0934] [Chemical Formula 59]

[0935]

[0936] [Chemical Formula 60]

[0937]

[0938]

Chemical Formula 61

[0939]

[0940]

Chemical Formula 62

[0941]

[0942]

Chemical Formula 63

[0943]

[0944]

Chemical Formula 64

[0945]

[0946]

Chemical Formula 65

[0947]

[0948]

Chemical Formula 66

[0949]

[0950] [Chemical Formula 67]

[0951]

[0952]

Chemical Formula 68

[0953]

[0954]

Chemical Formula 69

[0955]

[0956] [Chemical Formula 70]

[0957]

[0958]

Chemical Formula 71

[0959]

[0960]

Chemical Formula 72

[0961]

[0962]

Chemical Formula 73

[0963]

[0964] [Chemical Formula 74]

[0965]

[0966] [Chemical Formula 75]

[0967]

[0968] [Chemical Formula 76]

[0969]

[0970]

Chemical Formula 77

[0971]

[0972] [Chemical Formula 78]

[0973]

[0974] [Chemical Formula 79]

[0975]

[0976] [Chemical Formula 80]

[0977]

[0978]

Chemical Formula 81

[0979]

[0980]

Chemical Formula 82

[0981]

[0982]

Chemical Formula 83

[0983]

[0984]

Chemical Formula 84

[0985]

[0986]

Chemical Formula 85

[0987]

[0988]

Chemical Formula 86

[0989]

[0990] [Chemical Formula 87]

[0991]

[0992]

Chemical Formula 88

[0993]

[0994]

Chemical Formula 89

[0995]

[0996] [Chemical Formula 90]

[0997]

[0998]

Chemical Formula 91

[0999]

[1000]

Chemical Formula 92

[1001]

[1002] [Chemical Formula 93]

[1003]

[1004] [Chemical Formula 94]

[1005]

[1006] [Chemical Formula 95]

[1007]

[1008] [Chemical Formula 96]

[1009]

[1010] [Chemical Formula 97]

[1011]

[1012]

Chemical Formula 98

[1013]

[1014]

Chemical Formula 99

[1015]

[1016]

Chemical Formula 100

[1017]

[1018]

Chemical Formula 101

[1019]

[1020]

Chemical Formula 102

[1021]

[1022]

Chemical Formula 103

[1023]

[1024] [Chemical Formula 104]

[1025]

[1026] [Chemical Formula 105]

[1027]

[1028] [Chemical Formula 106]

[1029]

[1030] [Chemical Formula 107]

[1031]

[1032] [Chemical Formula 108]

[1033]

[1034] [Chemical Formula 109]

[1035]

[1036]

Chemical Formula 110

[1037]

[1038]

Chemical Formula 111

[1039]

[1040]

Chemical Formula 112

[1041]

[1042]

Chemical Formula 113

[1043]

[1044]

Chemical Formula 114

[1045]

[1046]

Chemical Formula 115

[1047]

[1048]

Chemical Formula 116

[1049]

[1050]

Chemical Formula 117

[1051]

[1052]

Chemical Formula 118

[1053]

[1054]

Chemical Formula 119

[1055]

[1056]

Chemical Formula 120

[1057]

[1058]

Chemical Formula 121

[1059]

[1060]

Chemical Formula 122

[1061]

[1062]

Chemical Formula 123

[1063]

[1064] [Chemical Formula 124]

[1065]

[1066] [Chemical Formula 125]

[1067]

[1068] [Chemical Formula 126]

[1069]

[1070] [Chemical Formula 127]

[1071]

[1072] [Chemical Formula 128]

[1073]

[1074] [Chemical Formula 129]

[1075]

[1076]

Chemical Formula 130

[1077]

[1078]

Chemical Formula 131

[1079]

[1080]

Chemical Formula 132

[1081]

[1082]

Chemical Formula 133

[1083]

[1084] [Chemical Formula 134]

[1085]

[1086] [Chemical Formula 135]

[1087]

[1088]

Chemical Formula 136

[1089]

[1090]

Chemical Formula 137

[1091]

[1092] [Chemical Formula 138]

[1093]

[1094]

Chemical Formula 139

[1095]

[1096] [Chemical Formula 140]

[1097]

[1098]

Chemical Formula 141

[1099]

[1100] [Chemical Formula 142]

[1101]

[1102] [Chemical Formula 143]

[1103]

[1104] [Chemical Formula 144]

[1105]

[1106] [Chemical Formula 145]

[1107]

[1108] [Chemical Formula 146]

[1109]

[1110] [Chemical Formula 147]

[1111]

[1112] [Chemical Formula 148]

[1113]

[1114] [Chemical Formula 149]

[1115]

[1116] [Chemical Formula 150]

[1117]

[1118]

Chemical Formula 151

[1119]

[1120]

Chemical Formula 152

[1121]

[1122]

Chemical Formula 153

[1123]

[1124]

Chemical Formula 154

[1125]

[1126]

Chemical Formula 155

[1127]

[1128] [Chemical Formula 156]

[1129]

[1130] [Chemical Formula 157]

[1131]

[1132] [Chemical Formula 158]

[1133]

[1134] [Chemical Formula 159]

[1135]

[1136] [Chemical Formula 160]

[1137]

[1138]

Chemical Formula 161

[1139]

[1140] [Chemical Formula 162]

[1141]

[1142] [Chemical Formula 163]

[1143]

[1144] [Chemical Formula 164]

[1145]

[1146] [Chemical Formula 165]

[1147]

[1148]

Chemical Formula 166

[1149]

[1150] [Chemical Formula 167]

[1151]

[1152] [Chemical Formula 168]

[1153]

[1154] [Chemical Formula 169]

[1155]

[1156] [Chemical Formula 170]

[1157]

[1158]

Chemical Formula 171

[1159]

[1160] [Chemical Formula 172]

[1161]

[1162]

Chemical Formula 173

[1163]

[1164] [Chemical Formula 174]

[1165]

[1166] [Chemical Formula 175]

[1167]

[1168] [Chemical Formula 176]

[1169]

[1170] [Chemical Formula 177]

[1171]

[1172] [Chemical Formula 178]

[1173]

[1174] [Chemical Formula 179]

[1175]

[1176] [Chemical Formula 180]

[1177]

[1178]

Chemical Formula 181

[1179]

[1180] [Chemical Formula 182]

[1181]

[1182]

Chemical Formula 183

[1183]

[1184] [Chemical Formula 184]

[1185]

[1186] [Chemical Formula 185]

[1187]

[1188] [Chemical Formula 186]

[1189]

[1190] [Chemical Formula 187]

[1191]

[1192]

Chemical Formula 188

[1193]

[1194] [Chemical Formula 189]

[1195]

[1196] [Chemical Formula 190]

[1197]

[1198]

Chemical Formula 191

[1199]

[1200] [Chemical Formula 192]

[1201]

[1202] [Chemical Formula 193]

[1203]

[1204] [Chemical Formula 194]

[1205]

[1206] [Chemical Formula 195]

[1207]

[1208] [Chemical Formula 196]

[1209]

[1210] [Chemical Formula 197]

[1211]

[1212] [Chemical Formula 198]

[1213]

[1214]

Chemical Formula 199

[1215]

[1216] [Chemical Formula 200]

[1217]

[1218]

Chemical Formula 201

[1219]

[1220]

Chemical Formula 202

[1221]

[1222]

Chemical Formula 203

[1223]

[1224] [Chemical Formula 204]

[1225]

[1226]

Chemical Formula 205

[1227]

[1228]

Chemical Formula 206

[1229]

[1230] [Chemical Formula 207]

[1231]

[1232] [Chemical Formula 208]

[1233]

[1234]

Chemical Formula 209

[1235]

[1236]

Chemical Formula 210

[1237]

[1238]

Chemical Formula 211

[1239]

[1240]

Chemical Formula 212

[1241]

[1242]

Chemical Formula 213

[1243]

[1244]

Chemical Formula 214

[1245]

[1246]

Chemical Formula 215

[1247]

[1248]

Chemical Formula 216

[1249]

[1250]

Chemical Formula 217

[1251]

[1252]

Chemical Formula 218

[1253]

[1254]

Chemical Formula 219

[1255]

[1256]

Chemical Formula 220

[1257]

[1258]

Chemical Formula 221

[1259]

[1260]

Chemical Formula 222

[1261]

[1262]

Chemical Formula 223

[1263]

[1264] [Chemical Formula 224]

[1265]

[1266] [Chemical Formula 225]

[1267]

[1268]

Chemical Formula 226

[1269]

[1270] [Chemical Formula 227]

[1271]

[1272] [Chemical Formula 228]

[1273]

[1274] [Chemical Formula 229]

[1275]

[1276]

Chemical Formula 230

[1277]

[1278]

Chemical Formula 231

[1279]

[1280]

Chemical Formula 232

[1281]

[1282]

Chemical Formula 233

[1283]

[1284] [Chemical Formula 234]

[1285]

[1286] [Chemical Formula 235]

[1287]

[1288] [Chemical Formula 236]

[1289]

[1290] [Chemical Formula 237]

[1291]

[1292] [Chemical Formula 238]

[1293]

[1294] [Chemical Formula 239]

[1295]

[1296] [Chemical Formula 240]

[1297]

[1298]

Chemical Formula 241

[1299]

[1300]

Chemical Formula 242

[1301]

[1302] [Chemical Formula 243]

[1303]

[1304] [Chemical Formula 244]

[1305]

[1306] [Chemical Formula 245]

[1307]

[1308] [Chemical Formula 246]

[1309]

[1310] [Chemical Formula 247]

[1311]

[1312] [Chemical Formula 248]

[1313]

[1314] [Chemical Formula 249]

[1315]

[1316] [Second Implementation]

[1317] Materials for Organic Electroluminescent Devices

[1318] The organic electroluminescent element material according to the second embodiment contains the compound according to the first embodiment. As one embodiment, an organic electroluminescent element material containing only the compound according to the first embodiment can be cited; as another embodiment, an organic electroluminescent element material containing the compound according to the first embodiment and other compounds different from those in the first embodiment can be cited.

[1319] In the organic electroluminescent element material of the second embodiment, the compound involved in the first embodiment is preferably a fluorescent material.

[1320] One approach involves materials for organic electroluminescent elements that may include fluorescent materials (the compounds involved in the first embodiment) and other compounds such as host materials.

[1321] [Third Implementation Method]

[1322] Organic electroluminescent devices

[1323] One embodiment of the organic EL element includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises at least one layer containing an organic compound. Alternatively, the organic layer is composed of multiple layers containing organic compounds stacked together. Each organic compound-containing layer constituting the organic layer may independently further contain an inorganic compound.

[1324] (Organic layer)

[1325] In one embodiment of the third implementation, the organic layer may be composed of one light-emitting layer or two or more light-emitting layers.

[1326] In one embodiment of the third embodiment, when the organic layer is composed of a single light-emitting layer, that single light-emitting layer contains the compound involved in the first embodiment. In one embodiment of the third embodiment, when the organic layer is composed of two or more light-emitting layers, at least one of the two or more light-emitting layers contains the compound involved in the first embodiment. In one embodiment of the third embodiment, when the organic layer is composed of two or more light-emitting layers, all of the two or more light-emitting layers contain the compound involved in the first embodiment.

[1327] In one embodiment of the third implementation, the organic layer may include at least one light-emitting layer and a layer that can be used in an organic EL element.

[1328] As a layer that can be used in organic EL devices, there is no particular limitation. For example, at least one layer selected from the group consisting of hole injection layer, hole transport layer, electron blocking layer, hole blocking layer, electron transport layer and electron injection layer can be mentioned.

[1329] In one embodiment of the third implementation, a hole transport layer is included between the anode and the light-emitting layer closest to the anode among the at least one light-emitting layer.

[1330] In one embodiment of the third implementation, an electron transport layer is included between the cathode and the light-emitting layer closest to the cathode among the at least one light-emitting layer.

[1331] Figure 1 The general configuration of an example of an organic EL element according to the third embodiment is shown.

[1332] 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 constructed by stacking, in sequence from the anode 3 side, 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. This invention is not limited to... Figure 1 The structure of the organic EL element shown.

[1333] (Emitting layer)

[1334] In one embodiment of the third embodiment, the organic layer comprises the compound involved in the first embodiment as the first compound.

[1335] In one embodiment of the third embodiment, the organic layer has at least one light-emitting layer, and at least one of the light-emitting layers contains a first compound (the compound involved in the first embodiment).

[1336] In one embodiment of the third implementation, at least one of the at least one light-emitting layers contains the first compound as a dopant material.

[1337] In one embodiment of the third embodiment, at least one of the at least one light-emitting layers contains the first compound as a fluorescent light-emitting material.

[1338] In one embodiment of the third method, at least one of the at least one light-emitting layers contains a fluorescent light-emitting material, a sensitizing material, and a host material.

[1339] In this specification, the host material contained in at least one light-emitting layer is sometimes referred to as the first host material.

[1340] In one embodiment of the third method, a single layer contains a first host material, a sensitizing material, and a fluorescent luminescent material. For example, when the organic EL element has one luminescent layer, the first host material, the sensitizing material, and the fluorescent luminescent material are contained in that single luminescent layer; when the organic EL element has multiple luminescent layers, they are contained in any single luminescent layer among the multiple luminescent layers.

[1341] In one embodiment of the third implementation, the light-emitting layer contains a first host material, a sensitizing material, and a fluorescent light-emitting material as a first compound.

[1342] In the third embodiment, the sensitizing material is preferably one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescence compounds, and more preferably phosphorescent metal complexes.

[1343] In the third embodiment, when the light-emitting layer contains a delayed fluorescence compound as a sensitizing material, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex.

[1344] [Fluorescent materials (first compound)]

[1345] In the third embodiment, the fluorescent material is not a phosphorescent metal complex. Preferably, the fluorescent material is not a metal complex.

[1346] (Maximum peak wavelength)

[1347] In the third embodiment, the maximum peak wavelength of the fluorescent material (first compound) is preferably 480 nm or less, more preferably 475 nm or less.

[1348] In the third embodiment, the maximum peak wavelength of the fluorescent luminescent material is preferably 430 nm or more, and more preferably 440 nm or more.

[1349] In the third embodiment, it is preferred that the fluorescent material exhibits blue luminescence. In this specification, blue luminescence refers to luminescence with a maximum peak wavelength in the fluorescence spectrum ranging from 430 nm to 480 nm.

[1350] (Full width at half maximum of emission spectrum)

[1351] In the third embodiment, the full width at half maximum (FWHM) of the emission spectrum of the fluorescent luminescent material is preferably less than 40 nm, and more preferably less than 30 nm.

[1352] In the third embodiment, the full width at half maximum (FWHM) of the emission spectrum of the fluorescent luminescent material is preferably 5 nm or more, and more preferably 10 nm or more. FWHM is short for full width at half maximum.

[1353] (Stokes displacement)

[1354] In the third embodiment, the Stokes shift of the fluorescent luminescent material is preferably 25 nm or less, and more preferably 20 nm or less.

[1355] In the third embodiment, the Stokes shift of the fluorescent luminescent material is preferably 5 nm or more, and more preferably 10 nm or more.

[1356] In the third embodiment, the excitation energy can be reduced by using a Stokes shift of less than 20 nm for the fluorescent luminescent material.

[1357] In the third embodiment, by using a Stokes shift of 10 nm or more for the fluorescent luminescent material, self-absorption can be suppressed to reduce efficiency loss.

[1358] The Stokes shift can be determined using the method described below. The compound to be measured is subjected to a concentration of 2.0 × 10⁻⁶. -5The sample was prepared by dissolving it in toluene at a concentration of mol / L. The sample, placed in a quartz cuvette, was irradiated with continuous light in the ultraviolet-visible region at room temperature (300 K) to measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength). Absorption spectroscopy can be performed using a spectrophotometer, such as the Hitachi Advanced Scientific U-3900 / 3900H spectrophotometer. Additionally, the compound to be measured was analyzed at 4.9 × 10⁻⁶ mol / L. -6 The sample for analysis is prepared by dissolving it in toluene at a concentration of mol / L. The sample, added to a quartz cuvette, is then irradiated with excitation light at room temperature (300 K) to measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). Fluorescence spectroscopy can be performed using a spectrophotometer, such as the Hitachi Advanced Scientific Spectrophotometer F-7000. Based on these absorption and fluorescence spectra, the difference between the wavelengths of absorption maximum and fluorescence maximum is calculated to determine the Stokes shift (SS). The unit of the Stokes shift SS is nm.

[1359] [Sensitized Materials]

[1360] In this specification, the compound used as a sensitizing material is sometimes referred to as the second compound.

[1361] (Phosphorescent metal complex)

[1362] In the third embodiment, preferably, the phosphorescent metal complex contains heavy metal atoms.

[1363] In the third embodiment, preferably, the phosphorescent metal complex comprises 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).

[1364] In the third embodiment, it is preferred that the phosphorescent metal complex is a compound represented by the following general formula (21).

[1365] M(L1) n1 (L2) n2 …(twenty one)

[1366] [Chemical Formula 250]

[1367]

[1368] (In the above general formulas (21), (211), (212), (213),

[1369] M is a transition metal selected from the first, second, and third transition metals.

[1370] L1 is a ligand selected from at least one of the ligands shown in general formula (211), general formula (212), and general formula (213).

[1371] n1 is 1, 2, or 3.

[1372] L2 is a ligand selected from at least one of monodentate, bidentate, and tripentate ligands.

[1373] n2 is 0, 1, 2, 3 or 4.

[1374] The CY1, CY2, CY3, and CY4 rings are each independently selected from carbocyclic groups with 5 to 30 carbon atoms and heterocyclic groups with 1 to 30 carbon atoms.

[1375] Y1 to Y4 are each selected independently.

[1376] single bond,

[1377] Double bond,

[1378] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms

[1379] Substituted or unsubstituted divalent heterocyclic groups with 5 to 50 cyclic atoms

[1380] *aO-*b、

[1381] *aS-*b、

[1382] *aC(=O)-*b、

[1383] *aS(=O)-*b、

[1384] *aC(R5)(R6)-*b、

[1385] *aC(R5)=C(R6)-*b、

[1386] *aC(R5)=*b、

[1387] *a-Si(R5)(R6)-*b、

[1388] *aB(R5)-*b、

[1389] *aN(R5)-*b、and

[1390] *aP(R5)-*b,

[1391] a1, a2, and a3 are each independently 1, 2, or 3.

[1392] a4 can be 0, 1, 2, or 3. When a4 is 0, the CY1 ring and the CY4 ring are not connected.

[1393] T1, T2, T3, and T4 are each independently selected from...

[1394] Chemical bonds

[1395] *aO-*b、

[1396] *aS-*b、

[1397] *aB(R7)-*b、

[1398] *aN(R7)-*b、

[1399] *aP(R7)-*b、

[1400] *aC(R7)(R8)-*b、

[1401] *a-Si(R7)(R8)-*b、

[1402] *a-Ge(R7)(R8)-*b、

[1403] *aC(=O)-*b and

[1404] *aC(=S)-*b,

[1405] *a and *b are each an independent bonding position with an adjacent atom.

[1406] *1, *2, *3, and *4 are the bonding positions with M.

[1407] R1 to R8 are each selected independently.

[1408] hydrogen atom,

[1409] Halogen atoms,

[1410] cyano,

[1411] Nitro,

[1412] amidoyl,

[1413] hydrazine group,

[1414] Hydrazine

[1415] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1416] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1417] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1418] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1419] Substituted or unsubstituted heterocyclic alkyl groups with 3 to 50 cyclic atoms

[1420] Substituted or unsubstituted cycloalkenyl groups with 3 to 50 carbon atoms

[1421] Substituted or unsubstituted heterocyclic alkenyl groups with 3 to 50 cyclic atoms

[1422] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1423] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[1424] Substituted or unsubstituted monovalent nonaromatic fused polycyclic groups

[1425] Substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups

[1426] -Si(R 251 (R) 252 (R) 253 The groups shown in the figure,

[1427] -O-(R 254 The groups shown in the figure,

[1428] -S-(R 255 The groups shown in the figure,

[1429] -N(R 256 (R) 257 The groups shown in the figure,

[1430] -C(=O)R 258 The groups shown

[1431] -C(=O)(OR 259 The groups shown in the figure,

[1432] -S(=O)2(OR 260 The groups shown in the figure,

[1433] -OP(=O)(OR 261 (OR) 262 The groups shown in the figure,

[1434] -C(R 263 (R) 264 (R) 265 The groups shown in the figure,

[1435] -B(R 266 (R) 267 The groups shown in the figure,

[1436] -P(R 268 (R) 269 The groups shown in the figure,

[1437] -S(=O)(R 270 The groups shown in the figure,

[1438] -S(=O)2(R 271 The groups shown in the figure,

[1439] -P(=O)(R 272 (R) 273 The groups and shown in the figure

[1440] -P(=S)(R 274 (R) 275 The group shown in the figure,

[1441] One or more groups consisting of two or more adjacent elements from R1 to R8.

[1442] They bond together to form substituted or unsubstituted monocyclic rings.

[1443] They bond together to form substituted or unsubstituted fused rings, or

[1444] They do not bond with each other.

[1445] One or more groups consisting of two or more adjacent elements from R1 to R8 and Y1 to Y4.

[1446] They bond together to form substituted or unsubstituted monocyclic rings.

[1447] They bond together to form substituted or unsubstituted fused rings, or

[1448] They do not bond with each other.

[1449] b1, b2, b3, and b4 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[1450] R 251 ~R 275 Each independently selected

[1451] hydrogen atom,

[1452] Halogen atoms,

[1453] -O-(R 276 The groups shown in the figure,

[1454] -N(R 277 (R) 278 The groups shown in the figure,

[1455] cyano,

[1456] Nitro,

[1457] amidoyl,

[1458] hydrazine group,

[1459] Hydrazine

[1460] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1461] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1462] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1463] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1464] Substituted or unsubstituted heterocyclic alkyl groups with 3 to 50 cyclic atoms

[1465] Substituted or unsubstituted cycloalkenyl groups with 3 to 50 carbon atoms

[1466] Substituted or unsubstituted heterocyclic alkenyl groups with 3 to 50 cyclic atoms

[1467] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms

[1468] Alkyl groups with 1 to 50 carbon atoms that are substituted or unsubstituted, and aryl groups with 6 to 50 carbon atoms that are substituted with alkyl groups.

[1469] Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted,

[1470] Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms

[1471] Substituted or unsubstituted monovalent nonaromatic fused polycyclic groups

[1472] Substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups

[1473] Biphenyl and terphenyl

[1474] R 276 ~R 278 Each independently

[1475] hydrogen atom,

[1476] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1477] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1478] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1479] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[1480] In this specification, a carbocyclic group having 5 to 30 carbon atoms refers to a monocyclic or polycyclic group having 5 to 30 carbon atoms as the cyclic atom. The carbocyclic group having 5 to 30 carbon atoms can be an aromatic or non-aromatic carbocyclic group. It can be a ring such as benzene, a monovalent group such as phenyl, or a divalent group such as phenylene. Alternatively, the carbocyclic group having 5 to 30 carbon atoms can undergo various transformations, such as becoming a trivalent or tetravalent group, depending on the number of substituents attached to it.

[1481] In this specification, a heterocyclic group having 1 to 30 carbon atoms refers to a group that, although having the same structure as a carbocyclic group having 5 to 30 carbon atoms, contains at least one heteroatom selected from N (nitrogen atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom) and S (sulfur atom) in addition to carbon (which can be 1 to 30 carbon atoms) as the cyclic atom.

[1482] In this specification, a heterocyclic alkyl group with 3 to 50 cyclic atoms refers to a monovalent monocyclic group with 3 to 50 cyclic atoms, containing at least one heteroatom selected from N, O, Si, P, and S as the cyclic atom. Specific examples include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, and tetrahydrothiopheneyl. In this specification, a heterocyclic alkyl subgroup with 3 to 50 cyclic atoms refers to a divalent group having the same structure as a heterocyclic alkyl group with 3 to 50 cyclic atoms.

[1483] In this specification, a cycloalkenyl group with 3 to 50 carbon atoms refers to a monovalent monocyclic group with at least one double bond within the ring, but which lacks aromaticity. Specific examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. In this specification, a cycloene-alkenyl group with 3 to 50 carbon atoms refers to a divalent group having the same structure as a cycloalkenyl group with 3 to 50 carbon atoms.

[1484] In this specification, a heterocyclic alkenyl group with 3 to 50 cyclic atoms is a monovalent monocyclic group with 3 to 50 cyclic atoms, comprising at least one heteroatom selected from N, O, Si, P, and S as a cyclic atom, and having at least one double bond within the ring. Specific examples of heterocyclic alkenyl groups with 3 to 50 cyclic atoms include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiopheneyl. In this specification, a heterocyclic alkenyl group with 3 to 50 cyclic atoms refers to a divalent group having the same structure as a heterocyclic alkenyl group with 3 to 50 cyclic atoms.

[1485] According to one embodiment, in the compound shown in the above general formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 cyclic carbon atoms preferably has 3 to 10 cyclic carbon atoms, the substituted or unsubstituted heterocyclic alkyl group having 3 to 50 cyclic carbon atoms preferably has 3 to 10 cyclic carbon atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 cyclic carbon atoms preferably has 3 to 10 cyclic carbon atoms, and the substituted or unsubstituted heterocyclic alkenyl group having 3 to 50 cyclic carbon atoms preferably has 3 to 10 cyclic carbon atoms.

[1486] In this specification, a monovalent nonaromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) with two or more rings fused together, containing only carbon atoms as cyclic atoms, and possessing non-aromaticity as a whole. In this specification, a divalent nonaromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[1487] In this specification, a monovalent non-aromatic fused heterocyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) with two or more rings fused together, comprising at least one heteroatom selected from N, O, Si, P, and S in addition to carbon as the cyclic atom, and possessing overall non-aromatic properties. In this specification, a divalent non-aromatic fused heterocyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused heterocyclic group.

[1488] In this specification, "biphenyl" means "phenyl substituted with phenyl". "Biphenyl" belongs to "substituted phenyl" with "aryl group having 6 to 50 carbon atoms in the ring".

[1489] In this specification, "terphenyl" means "a phenyl group substituted with biphenyl". "Terphenyl" belongs to the category of "substituted phenyl groups" whose substituents are "aryl groups with 6 to 50 carbon atoms that are substituted with aryl groups with 6 to 50 carbon atoms in the ring".

[1490] In the compounds represented by the above general formula (21), the chemical bonds that form T1, T2, T3 and T4 are preferably single bonds.

[1491] 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).

[1492] According to one embodiment, in the compound represented by the above general formula (21), the CY1 ring to the CY4 ring can each be independently selected from benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenene, indole, benzoborane heterocyclopentadiene, benzophosphonane heterocyclopentadiene, indene, benzothiophene, benzogermanium heterocyclopentadiene, and benzothiophene. Benzo[selenophene], benzo[furan], carbazole, dibenzoborane, dibenzophosphacyclopentadiene, fluorene, dibenzothiophene, dibenzogermanium, dibenzothiophene, dibenzo[selenophene], dibenzofuran, dibenzothiophene 5-oxide, 9H-fluorene-9-one, dibenzothiophene 5,5-dioxide, azidoindole, azidobenzoborane, azidobenzophosphacyclopentadiene, azidoindene, azidobenzothiophene Azabenzogermanium cyclopentadiene, azabenzothiophene, azabenzoselenene, azabenzofuran, azacarbazole, azadibenzoborone cyclopentadiene, azadibenzophosphazene cyclopentadiene, azafluorene, azadibenzothiophene, azadibenzogermanium cyclopentadiene, azadibenzothiophene, azadibenzoselenene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluorene-9-one, azadi... Benzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, phenanthrene, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiazolid, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiazolid, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[1493] According to one embodiment, at least one of the CY1 ring and CY2 ring in general formula (211), at least one of the CY1 ring to CY3 ring in general formula (212), and at least one of the CY1 ring to CY4 ring in general formula (213) can be a carbene.

[1494] According to one embodiment, Y1 to Y4 in general formulas (211) to (213) can each independently be at least one selected from single bond, double bond, *aO-*b, *aS-*b, *aC(R5)(R6)-*b and *aN(R5)-*b.

[1495] 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) can be an electron-donating group.

[1496] For example, the electron-donating group can be a substituent selected from isopropyl, tert-butyl and the following general formulas (10-1) to (10-61).

[1497]

Chemical Formula 251

[1498]

[1499]

Chemical Formula 252

[1500]

[1501] In the above general formulas (10-1) to (10-61), * represents the bonding position with the adjacent atom.

[1502] In this specification, the deuterium atom is designated as D in the chemical formula, and the protium atom is designated as H or omitted. In this specification, methyl groups are sometimes designated as Me, phenyl groups as Ph, isopropyl groups as i-Pr, and tert-butyl groups as t-Bu.

[1503] According to one embodiment, at least one of R1 and R2 in the above general formula (211) is a non-hydrogen substituent; and / or Y1 is *aN(R5)-*b, and R5 can be a substituted aryl group with 6 to 50 cyclic carbons.

[1504] According to one embodiment, at least one of R1 to R3 in the above general formula (212) is a non-hydrogen substituent; and / or at least one of Y1 and Y2 is *aN(R5)-*b, where R5 can be a substituted aryl group with 6 to 50 cyclic carbons.

[1505] According to one embodiment, at least one of R1 to R4 in the above general formula (213) is a non-hydrogen substituent; and / or at least one of Y1 to Y4 is *aN(R5)-*b, where R5 can be a substituted aryl group with 6 to 50 cyclic carbons.

[1506] In the third embodiment, the compound represented by the above general formula (21) is preferably a compound selected from the compounds represented by the following general formulas (214) and (215).

[1507] [Chemical Formula 253]

[1508]

[1509] [Chemical Formula 254]

[1510]

[1511] (In the above general formulas (214) and (215), M, L2, n1, n2, CY1 ring to CY4 ring, Y1 to Y3, a1 to a3, T1 to T4, R1 to R4 and b1 to b4 have the same meaning as above.)

[1512] According to one embodiment, at least one of the CY1 ring and CY2 ring in general formula (214) and at least one of the CY1 ring to CY4 ring in general formula (215) can be a carbene.

[1513] For example, either the CY1 ring or the CY4 ring in general formula (215) can be a carbene.

[1514] In the third embodiment, it is also preferred that the compound represented by the above general formula (21) is at least one compound selected from the compounds represented by the following general formulas (215A) and (215B).

[1515] [Chemical Formula 255]

[1516]

[1517] [Chemical Formula 256]

[1518]

[1519] (In the above general formulas (215A) and (215B),

[1520] M1 is Pt,

[1521] M2 is selected from the first, second, and third transition metals.

[1522] CY 12 Ring, CY 13 Ring, CY 14 Ring, CY 22 Ring, CY 23 Ring and CY 24 Each ring is independently selected from a carbocyclic group having 5 to 30 carbon atoms and a heterocyclic group having 1 to 30 carbon atoms.

[1523] A 11 A 12 A 21 and A 22 Each is independently either N (nitrogen atom) or P (phosphorus atom).

[1524] X 11 X 12 X 13 X 21 X 22 and X 23 Each can be independently represented by either N (nitrogen atom) or C (carbon atom).

[1525] Y 11 ~Y 13Each group is independently selected from single bonds, double bonds, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic group, divalent heterocyclic groups with 5 to 50 substituted or unsubstituted cyclic atoms, *aO-*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R) 15 (R) 16 )-*b、*aC(R 15 )=C(R 16 )-*b、*aC(R 15 )=*b、*a-Si(R 15 (R) 16 )-*b、*aB(R 15 )-*b、*aN(R 15 )-*b and *aP(R 15 )-*b,

[1526] Y 21 ~Y 23 Each group is independently selected from single bonds, double bonds, substituted or unsubstituted aryl groups with 6 to 50 carbon atoms in the cyclic group, divalent heterocyclic groups with 5 to 50 substituted or unsubstituted cyclic atoms, *aO-*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R) 25 (R) 26 )-*b、*aC(R 25 )=C(R 26 )-*b、*aC(R 25 )=*b、*a-Si(R 25 (R) 26 )-*b、*aB(R 25 )-*b、*aN(R 25 )-*b and *aP(R 25 )-*b,

[1527] a11, a12, and a13 are each independently 1, 2, or 3.

[1528] a21, a22, and a23 are each independently 1, 2, or 3.

[1529] T 11 T 12 T 13 and T 14 Each is independently selected from chemical bonds, *aO-*b, *aS-*b, *aB(R) 17 )-*b、*aN(R 17 )-*b、*aP(R 17 )-*b、*aC(R 17 (R) 18)-*b、*a-Si(R 17 (R) 18 )-*b、*a-Ge(R 17 (R) 18 )-*b, *aC(=O)-*b and *aC(=S)-*b,

[1530] T 21 T 22 T 23 and T 24 They are independently selected from chemical bonds, *aO-*b, *aS-*b, *aB(R) 27 )-*b、*aN(R 27 )-*b、*aP(R 27 )-*b、*aC(R 27 (R) 28 )-*b、*a-Si(R 27 (R) 28 )-*b、*a-Ge(R 27 (R) 28 )-*b, *aC(=O)-*b and *aC(=S)-*b,

[1531] *a and *b are each an independent bonding position with an adjacent atom.

[1532] R 11a R 11b R 11c R 12 ~R 18 R 21a R 21b R 21c and R 22 ~R 28 Each is independently selected from hydrogen atoms, halogen atoms, cyano, nitro, amido, hydrazine, hydrazine, substituted or unsubstituted alkyl with 1 to 50 carbon atoms, substituted or unsubstituted alkenyl with 2 to 50 carbon atoms, substituted or unsubstituted alkynyl with 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 50 carbon atoms, substituted or unsubstituted heterocyclic alkyl with 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl with 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl with 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic with 5 to 50 carbon atoms, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heterocyclic group, -Si(R 251 (R) 252 (R) 253 The group shown is -O-(R) 254 The group shown is -S-(R)255 The group shown is -N(R) 256 (R) 257 The group shown is -C(=O)R 258 The shown groups, -C(=O)(OR) 259 The group shown is -S(=O)2(OR) 260 The group shown is -OP (=O)(OR) 261 (OR) 262 The group shown is -C(R) 263 (R) 264 (R) 265 The group shown is -B(R) 266 (R) 267 The group shown is -P(R) 268 (R) 269 The group shown is -S(=O)(R 270 The group shown is -S(=O)2(R) 271 The group shown is -P(=O)(R 272 (R) 273 The groups shown are -P(=S)(R) 274 (R) 275 The group shown in the figure,

[1533] By R 11a R 11b R 11c and R 12 ~R 18 One or more groups consisting of two or more adjacent elements.

[1534] They bond together to form substituted or unsubstituted monocyclic rings.

[1535] They bond together to form substituted or unsubstituted fused rings, or

[1536] They do not bond with each other.

[1537] By R 21a R 21b R 21c and R 22 ~R 28 One or more groups consisting of two or more adjacent elements.

[1538] They bond together to form substituted or unsubstituted monocyclic rings.

[1539] They bond together to form substituted or unsubstituted fused rings, or

[1540] They do not bond with each other.

[1541] b12, b13, b14, b22, b23, and b24 are each independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[1542] R 251 ~R 275 R in the above general formulas (21), (211), (212), and (213) 251 ~R 275 The meaning is the same.

[1543] According to one implementation, R 251 ~R 275 Each can choose independently.

[1544] hydrogen atom,

[1545] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1546] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1547] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms and

[1548] A group consisting of substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms.

[1549] In R 251 ~R 275 When multiple R exist, multiple R 251 Multiple R 252 Multiple R 253 Multiple R 254 Multiple R 255 Multiple R 256 Multiple R 257 Multiple R 258 Multiple R 259 Multiple R 260 Multiple R 261 Multiple R 262 Multiple R 263 Multiple R 264 Multiple R 265 Multiple R 266 Multiple R 267 Multiple R 268 Multiple R 269 Multiple R 270 Multiple R 271 Multiple R 272 Multiple R 273 Multiple R 274 and multiple R 275 They are either the same as or different from each other.

[1550] According to one embodiment, R in the above general formula (215A) 11b With R 11c The group and R in the above general formula (215B) 21b With R 21c One or more groups in a group can bond together to form a group with at least one R a Substituted or unsubstituted benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, or pyrazine ring, R a R in the above general formula (215A) 11a The meaning is the same in multiple Rs a In the presence of multiple R a They are the same or different.

[1551] According to one embodiment, R in the above general formula (215A) 11a R 11b R 11c and R 14 At least one of them can be an electron-donating group.

[1552] For example, R in the above general formula (215A) 11a and R 14 At least one of them can be an electron-donating group. According to one embodiment, R in general formula (215A) 11a and R 14 At least one of them can be an electron-donating group selected from isopropyl, tert-butyl and the groups shown in the above general formulas (10-1) to (10-61).

[1553] According to one embodiment, R in the above general formula (215B) 22 and R 23 At least one of them is a non-hydrogen substituent; and / or Y 23 For *aN(R) 25 )-*b,R 25 It can be an aryl group with 6 to 50 carbon atoms that are substituted.

[1554] For example, R 22 and R 23At least one of the following is selected from substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted heterocyclic alkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 3 to 50 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -O-(R 254 The groups shown are -S-(R) 255 The group shown in the diagram; and / or Y 23 For *aN(R) 25 )-*b,R 25 It can be an aryl group with 6 to 50 carbon atoms that are substituted.

[1555] For example, R 22 and R 23 At least one of them is selected from alkyl groups having 1 to 50 carbon atoms that are substituted with at least one deuterium, alkenyl groups having 2 to 50 carbon atoms, alkynyl groups having 2 to 50 carbon atoms, cycloalkyl groups having 3 to 50 cyclic carbon atoms, heterocyclic alkyl groups having 3 to 50 cyclic carbon atoms, cycloalkenyl groups having 3 to 50 cyclic carbon atoms, heterocyclic alkenyl groups having 3 to 50 cyclic carbon atoms, aryl groups having 6 to 50 cyclic carbon atoms, heterocyclic groups having 5 to 50 cyclic carbon atoms, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -O-(R 254 The groups shown are -S-(R) 255 The group shown in the diagram; and / or Y 23 For *aN(R) 25 )-*b,R 25 It can be an aryl group with 6 to 50 cyclic carbons that is substituted by at least one deuterium.

[1556] As another example, R 22 and R 23 At least one of them is an electron-donating group selected from isopropyl, tert-butyl, and groups represented by the above general formulas (10-1) to (10-61); and / or Y 23 For *aN(R) 25 )-*b,R 25 It can be an electron-donating group selected from isopropyl, tert-butyl and the groups shown in the above general formulas (10-1) to (10-61).

[1557] According to one embodiment, R in the above general formula (215A) 11a R 11b R 11c and R14 At least one of them is an electron-donating group, and R in the above general formula (215B) is an electron-donating group. 22 and R 23 At least one of them is a non-hydrogen substituent; and / or Y 23 For *aN(R) 25 )-*b,R 25 It can be an aryl group with 6 to 50 carbon atoms that are substituted.

[1558] In the third embodiment, it is also preferred that the compound represented by the above general formula (21) is at least one compound selected from the compounds represented by the following general formulas (215C) and (215D).

[1559] [Chemical Formula 257]

[1560]

[1561] [Chemical Formula 258]

[1562]

[1563] (In the above general formulas (215C) and (215D),

[1564] Z 11 For C(R) 12a ) or N,

[1565] Z 12 For C(R) 12b ) or N,

[1566] Z 13 For C(R) 12c ) or N,

[1567] Z 14 For C(R) 13a ) or N,

[1568] Z 15 For C(R) 13b ) or N,

[1569] Z 16 For C(R) 13c ) or N,

[1570] Z 17 For C(R) 14a ) or N,

[1571] Z 18 For C(R) 14b ) or N,

[1572] Z 19 For C(R) 14c ) or N,

[1573] Z 20 For C(R) 14d ) or N,

[1574] Z 31 For C(R) 15a ) or N,

[1575] Z 32 For C(R) 15b ) or N,

[1576] Z 33 For C(R) 15c ) or N,

[1577] Z 34 For C(R) 15d ) or N,

[1578] R 12a R 12b and R 12 c independently relates to R in the above general formula (215A). 12 Same meaning

[1579] R 13a R 13b and R 13c Each independently relates to R in the above general formula (215A). 13 Same meaning

[1580] R 14a R 14b R 14c and R 14d Each independently relates to R in the above general formula (215A). 14 Same meaning

[1581] R 15a R 15b R 15c and R 15d Each independently relates to R in the above general formula (215A). 15 Same meaning

[1582] M1, A 11 A 12 X 11 ~X 13 Y 11 ~Y 13 a11~a13, T 11 ~T 14 and R 11a ~R 11c respectively with M1 and A in the above general formula (215A) 11 A 12 X11 ~X 13 Y 11 ~Y 13 a11~a13, T 11 ~T 14 and R 11a ~R 11c The meaning is the same.

[1583] According to one implementation, Z in the above general formulas (215C) and (215D) can be... 18 For C(R) 14b ), R 11a ~R 11c and R 14b At least one of them is an electron-donating group. For example, Z in the above general formulas (215C) and (215D) can be an electron-donating group. 18 For C(R) 14b ), R 11a and R 14b At least one of them is an electron-donating group.

[1584] According to one implementation, Z in the above general formulas (215C) and (215D) can be... 18 For C(R) 14b ), R 11a and R 14b At least one of them is an electron-donating group selected from isopropyl, tert-butyl and the groups shown in the above general formulas (10-1) to (10-61).

[1585] In the third embodiment, it is also preferred that the compound represented by the above general formula (21) is the compound represented by the following general formula (215E).

[1586] [Chemical Formula 259]

[1587]

[1588] (In the above general formula (215E),

[1589] Z 21 For C(R) 22a ) or N, Z 22 For C(R) 22b ) or N, Z 23 For C(R) 22c ) or N, Z 24 For C(R) 23a ) or N, Z 25 For C(R) 23b ) or N, Z 27 For C(R) 24a ) or N, Z 28 For C(R) 24b) or N, Z 29 For C(R) 24c ) or N, Z 30 For C(R) 24d ) or N, Z 41 For C(R) 25a ) or N, Z 42 For C(R) 25b ) or N, Z 43 For C(R) 25c ) or N, Z 44 For C(R) 25d ) or N,

[1590] R 22a R 22b and R 22c Each independently relates to R in the above general formula (215B). 22 Same meaning

[1591] R 23a and R 23b Each independently relates to R in the above general formula (215B). 23 Same meaning

[1592] R 24a R 24b R 24c and R 24d Each independently relates to R in the above general formula (215B). 24 Same meaning

[1593] R 25a R 25b R 25c and R 25d Each independently relates to R in the above general formula (215B). 25 Same meaning

[1594] M2, A 21 A 22 X 21 ~X 23 Y 21 Y 22 a21, a22, T 21 ~T 24 and R 21a ~R 21c respectively with M2 and A in the above general formula (215B) 21 A 22 X 21 ~X 23 Y 21 Y 22 a21, a22, T 21 ~T 24 and R 21a~R 21c The meaning is the same.

[1595] According to one implementation, in the above general formula (215E), M2 can be Pt.

[1596] According to one embodiment, in the above general formula (215E), Z 22 For C(R) 22b Z 42 For C(R) 25b ), R 22b and R 25b At least one of them can be a substituent that is not hydrogen. For example, R 22b and R 25b At least one of them may be selected from substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted heterocyclic alkyl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 3 to 50 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 3 to 50 carbon atoms, substituted or unsubstituted aryl groups having 6 to 50 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 50 carbon atoms, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -O-(R 254 The groups shown are -S-(R) 255 The group shown is ).

[1597] According to one embodiment, in the above general formula (215E), Z 22 For C(R) 22b Z 42 For C(R) 25b ), R 22b and R 25b At least one of them may be selected from alkyl groups having 1 to 50 carbon atoms that are substituted with at least one deuterium, alkenyl groups having 2 to 50 carbon atoms, alkynyl groups having 2 to 50 carbon atoms, cycloalkyl groups having 3 to 50 cyclic carbon atoms, heterocyclic alkyl groups having 3 to 50 cyclic carbon atoms, cycloalkenyl groups having 3 to 50 cyclic carbon atoms, heterocyclic alkenyl groups having 3 to 50 cyclic carbon atoms, aryl groups having 6 to 50 cyclic carbon atoms, heterocyclic groups having 5 to 50 cyclic carbon atoms, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -O-(R 254 The groups shown are -S-(R) 255 The group shown is ).

[1598] According to one embodiment, in the above general formula (215E), Z 22 For C(R) 22b Z 42 For C(R)25b ), R 22b and R 25b At least one of them can be an electron-donating group selected from isopropyl, tert-butyl and the groups shown in the above general formulas (10-1) to (10-61).

[1599] In the compounds represented by the above general formula (21), as T 11 T 12 T 13 T 14 T 21 T 22 T 23 and T 24 The chemical bonds are preferably single bonds.

[1600] (Specific examples of phosphorescent metal complexes)

[1601] Specific examples of phosphorescent metal complexes as a third embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

[1602] [Chemical Formula 260]

[1603]

[1604]

Chemical Formula 261

[1605]

[1606]

Chemical Formula 262

[1607]

[1608] [Chemical Formula 263]

[1609]

[1610] [Chemical Formula 264]

[1611]

[1612] [Chemical Formula 265]

[1613]

[1614] (Delayed fluorescence compounds)

[1615] In this embodiment, the delayed fluorescence compound is not a phosphorescent metal complex. Preferably, the delayed fluorescence compound is not a metal complex.

[1616] In this embodiment, the delayed fluorescence compound is preferably a compound represented by the following general formula (H1).

[1617]

Chemical Formula 266

[1618]

[1619] (In the above general formula (H1),

[1620] A H A group having at least one local structure selected from the general formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8) below.

[1621] D H The group is represented by the following general formula (221), (222) or (223).

[1622] L H for

[1623] single bond,

[1624] Substituted or unsubstituted aromatic rings with 6 to 50 carbon atoms, or

[1625] Heterocycles with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1626] m is 1, 2, 3, 4, or 5, and there are multiple A's. H They are the same or different.

[1627] n is 1, 2, 3, 4, or 5, and there are multiple Ds. H (They may be the same or different.)

[1628] [Chemical Formula 267]

[1629]

[1630] (In the above general formulas (a-1) to (a-8), * independently represents the bonding position with other atoms in the molecule of the above delayed fluorescence compound.)

[1631] [Chemical Formula 268]

[1632]

[1633] [Chemical Formula 269]

[1634]

[1635] [Chemical Formula 270]

[1636]

[1637] (in the above general formula (221) R) 21 ~R 28 One or more groups consisting of two or more adjacent elements.

[1638] They bond together to form substituted or unsubstituted monocyclic rings.

[1639] They bond together to form substituted or unsubstituted fused rings, or

[1640] They do not bond with each other.

[1641] In the above general formula (222), R 221 ~R 228 One or more groups consisting of two or more adjacent elements.

[1642] They bond together to form substituted or unsubstituted monocyclic rings.

[1643] They bond together to form substituted or unsubstituted fused rings, or

[1644] They do not bond with each other.

[1645] In the above general formula (223), R 231 ~R 238 One or more groups consisting of two or more adjacent elements.

[1646] They bond together to form substituted or unsubstituted monocyclic rings.

[1647] They bond together to form substituted or unsubstituted fused rings, or

[1648] They do not bond with each other.

[1649] In the above general formula (221), R does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 21 ~R 28 R in the above general formula (222) is a monocyclic ring that does not form a substituted or unsubstituted ring and a fused ring that does not form a substituted or unsubstituted ring. 221 ~R 228 And R in the above general formula (223) that does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted fused ring. 231 ~R 238 Each independently

[1650] hydrogen atom,

[1651] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1652] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1653] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1654] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1655] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1656] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1657] -O-(R 904 The groups shown in the figure,

[1658] -S-(R 905 The groups shown in the figure,

[1659] -N(R 906 (R) 907 The groups shown in the figure,

[1660] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1661] -C(=O)R 908 The groups shown

[1662] -COOR 909 The groups shown

[1663] Halogen atoms,

[1664] cyano,

[1665] Nitro,

[1666] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[1667] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[1668] -B(R 936 (R) 937 The groups shown in the figure,

[1669] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1670] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1671] In the above general formulas (222) and (223),

[1672] Ring A, ring B, and ring C are each independently a ring structure selected from any one of the ring structures shown in general formulas (224) and (225) below.

[1673] Rings A, B, and C can merge with adjacent rings at any position.

[1674] p, px, and py are each independently 1, 2, 3, or 4.

[1675] When p is 2, 3, or 4, multiple rings A may be identical or different.

[1676] When px is 2, 3, or 4, multiple rings B may be identical or different.

[1677] When py is 2, 3, or 4, multiple rings C may be identical or different.

[1678] In the above general formulas (221) to (223), * indicates the relationship with L. H (The bonding location.)

[1679]

Chemical Formula 271

[1680]

[1681] (In the above general formula (224),

[1682] r is 0, 2, or 4.

[1683] Composed of multiple R 29 Groups

[1684] They bond together to form substituted or unsubstituted monocyclic rings.

[1685] They bond together to form substituted or unsubstituted fused rings, or

[1686] They do not bond with each other.

[1687] In the above general formula (225), X A It consists of sulfur atoms, oxygen atoms, or C(R) atoms. 291 (R) 292 ),

[1688] By R 291 and R 292 Groups

[1689] They bond together to form substituted or unsubstituted monocyclic rings.

[1690] They bond together to form substituted or unsubstituted fused rings, or

[1691] They do not bond with each other.

[1692] R does not form substituted or unsubstituted monocyclic rings and does not form substituted or unsubstituted fused rings. 29 R 291 and R 292 Each independently

[1693] hydrogen atom,

[1694] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1695] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1696] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1697] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1698] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1699] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1700] -O-(R 904 The groups shown in the figure,

[1701] -S-(R 905 The groups shown in the figure,

[1702] -N(R 906 (R) 907 The groups shown in the figure,

[1703] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1704] -C(=O)R 908 The groups shown

[1705] -COOR 909 The groups shown

[1706] Halogen atoms,

[1707] cyano,

[1708] Nitro,

[1709] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[1710] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[1711] -B(R936 (R) 937 The groups shown in the figure,

[1712] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1713] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1714] Multiple R 29 They are the same or different.

[1715] Multiple R 291 They are the same or different.

[1716] Multiple R 292 They are the same or different.

[1717] Multiple X A (They may be the same or different.)

[1718] (In the above delayed fluorescence compounds, R) 901 R 902 R 903 R 904 R 905 R 906 R 907 R 908 R 909 R 931 R 932 R 933 R 934 R 935 R 936 and R 937 Each independently

[1719] hydrogen atom,

[1720] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1721] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1722] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1723] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1724] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[1725] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[1726] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[1727] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[1728] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[1729] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[1730] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[1731] In R 908 In the case of multiple Rs, multiple Rs 908 They are the same or different.

[1732] In R 909 In the case of multiple Rs, multiple Rs 909 They are the same or different.

[1733] In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different.

[1734] In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different.

[1735] In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different.

[1736] In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different.

[1737] In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different.

[1738] In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different.

[1739] In R 937 In the case of multiple Rs, multiple Rs 937(They may be the same or different.)

[1740] In this embodiment, the delayed fluorescence compound is preferably a compound represented by the following general formula (H10).

[1741]

Chemical Formula 272

[1742]

[1743] (In the above general formula (H10),

[1744] CN stands for cyano group.

[1745] L H For substituted or unsubstituted aromatic hydrocarbon rings with 6 to 30 carbon atoms,

[1746] D 11 and D 12 Each is independently a group represented by the general formula (221), (222), or (223) above.

[1747] m is 1, 2, 3, 4, or 5.

[1748] nx is 0, 1, 2, 3, 4, or 5.

[1749] ny is 0, 1, 2, 3, 4, or 5.

[1750] nx + ny is 1, 2, 3, 4 or 5.

[1751] D 11 and D 12 They are the same or different.

[1752] Multiple D 11 They are the same or different.

[1753] Multiple D 12 (They may be the same or different.)

[1754] In this embodiment, the delayed fluorescence compound is preferably a compound represented by the following general formula (H100).

[1755] [Chemical Formula 273]

[1756]

[1757] (In the above general formula (H100), L) H D 11 D 12 m, nx, and ny are respectively related to L in the above general formula (H10) H D 11 D 12 m, nx, and ny have the same meaning.

[1758] R is independent of each

[1759] hydrogen atom,

[1760] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1761] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1762] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1763] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1764] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1765] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1766] -O-(R 904 The groups shown in the figure,

[1767] -S-(R 905 The groups shown in the figure,

[1768] -N(R 906 (R) 907 The groups shown in the figure,

[1769] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1770] -C(=O)R 908 The groups shown

[1771] -COOR 909 The groups shown

[1772] cyano,

[1773] Nitro,

[1774] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[1775] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[1776] -B(R 936 (R) 937 The groups shown in the figure,

[1777] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1778] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1779] In this compound, at least one R is a substituent, and at least one R acting as a substituent is bonded to the L of the compound represented by the above general formula (H100) via a carbon-carbon bond. H bonding,

[1780] k is an integer greater than or equal to 1

[1781] Multiple R values ​​may be the same or different.

[1782] In this embodiment, the delayed fluorescence compound is preferably a compound represented by the following general formula (H101).

[1783] [Chemical Formula 274]

[1784]

[1785] (In the above general formula (H101),

[1786] D 11 and D 12 Each of the above general formulas (H10) contains D. 11 and D 12 Same meaning

[1787] Each R has the same meaning as R in the above general formula (H100).

[1788] m is 1, 2, 3, or 4.

[1789] nx is 0, 1, 2, 3 or 4.

[1790] ny is 0, 1, 2, 3, or 4.

[1791] k is 1, 2, 3, or 4.

[1792] nx + ny is 1, 2, 3, or 4.

[1793] (m + nx + ny + k = 6)

[1794] In this embodiment, the delayed fluorescence compound is preferably a compound represented by the following general formula (H110), (H120) or (H130).

[1795] [Chemical Formula 275]

[1796]

[1797] (In the above general formulas (H110), (H120) and (H130),

[1798] D 11 and D12 Each of the above general formulas (H10) contains D. 11 and D 12 Same meaning

[1799] Each R has the same meaning as R in the above general formula (H100).

[1800] nx is 0, 1, 2, or 3.

[1801] ny is 0, 1, 2 or 3.

[1802] k is 1, 2, or 3.

[1803] nx + ny is 1, 2, or 3.

[1804] (nx + ny + k = 4.)

[1805] In this embodiment, the group represented by the above general formula (222) in the delayed fluorescence compound is preferably selected from any one of the groups represented by the following general formulas (22A), (22B), (22C), (22D), (22E) and (22F).

[1806] [Chemical Formula 276]

[1807]

[1808] [Chemical Formula 277]

[1809]

[1810] [Chemical Formula 278]

[1811]

[1812] [Chemical Formula 279]

[1813]

[1814] [Chemical Formula 280]

[1815]

[1816]

Chemical Formula 281

[1817]

[1818] (In the above general formulas (22A), (22B), (22C), (22D), (22E) and (22F),

[1819] R 221 ~R 228 R in the above general formula (222) respectively 221 ~R228 Same meaning

[1820] R 229 and R 230 Each independently relates to R in the above general formula (224). 29 Same meaning

[1821] X A X in the above general formula (225) A Same meaning

[1822] In the above general formulas (22A), (22B), (22C), (22D), (22E), and (22F), the asterisk (*) indicates the bonding position.

[1823] In the organic EL element of this embodiment, when the delayed fluorescence compound is a compound represented by general formula (H101), the * in general formulas (22A), (22B), (22C), (22D), (22E) and (22F) is bonded to the benzene ring explicitly depicted in general formula (H101).

[1824] In the delayed fluorescence compound of this embodiment, X is also preferred. A It consists of either a sulfur atom or an oxygen atom.

[1825] In the delayed fluorescence compound of this embodiment, at X A For C(R) 291 (R) 292 In the case of R, it is preferable to have R. 291 and R 292 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 cyclic carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 cyclic atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 cyclic carbon atoms.

[1826] In the delayed fluorescence compound of this embodiment, it is also preferred that it is composed of R 21 ~R 28 The groups consisting of two or more adjacent elements are not bonded to each other.

[1827] In the delayed fluorescence compound of this embodiment, it is also preferred that it is composed of R 221 ~R 228 The groups consisting of two or more adjacent elements are not bonded to each other.

[1828] In the delayed fluorescence compound of this embodiment, it is also preferred that it is composed of R 231 ~R238 The groups consisting of two or more adjacent elements are not bonded to each other.

[1829] In this embodiment, each of the R atoms in the delayed fluorescence compound is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

[1830] In this embodiment, each of the R atoms in the delayed fluorescence compound is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 cyclic atoms.

[1831] R in the delayed fluorescence compound of this embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

[1832] R in the delayed fluorescence compound of this embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238、 and R 29 Each of the following is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 cyclic atoms.

[1833] Preferably, in the delayed fluorescence compound of this embodiment, each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 cyclic atoms.

[1834] R in the delayed fluorescence compound of this embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 30 carbon atoms, or a substituted or unsubstituted cyclic group having 5 to 30 heterocyclic atoms.

[1835] Preferably, in the delayed fluorescence compound of this embodiment, each R is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 cyclic carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 cyclic atoms.

[1836] R in the delayed fluorescence compound of this embodiment 21 ~R 28 R 221 ~R 228 R 231 ~R 238 and R 29 Each of the following is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cyclic group having 6 to 18 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 cyclic atoms.

[1837] In the compounds involved in this embodiment, it is preferred that the substituents, when described as "substituted or unsubstituted", are...

[1838] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[1839] Unsubstituted alkenyl groups with 2 to 25 carbon atoms

[1840] Unsubstituted acetylinyl groups with 2 to 25 carbon atoms

[1841] Unsubstituted cycloalkyl groups with 3 to 25 carbon atoms

[1842] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1843] -O-(R 904 The groups shown in the figure,

[1844] -S-(R 905 The groups shown in the figure,

[1845] -N(R 906 (R) 907 The groups shown in the figure,

[1846] Unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1847] -C(=O)R 908 The groups shown

[1848] -COOR 909 The groups shown

[1849] -P(=O)(R 931 (R) 932 The groups shown in the figure,

[1850] -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure,

[1851] -B(R 936 (R) 937 The groups shown in the figure,

[1852] -S(=O)2R 938 The groups shown

[1853] Halogen atoms,

[1854] cyano,

[1855] Nitro,

[1856] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[1857] Unsubstituted heterocyclic groups with 5–25 cyclic atoms,

[1858] R 901 ~R 909 and R 931 ~R 938 Each independently

[1859] hydrogen atom,

[1860] Unsubstituted alkyl groups having 1 to 25 carbon atoms

[1861] Unsubstituted aryl groups with 6 to 25 carbon atoms, or

[1862] Unsubstituted heterocyclic groups with 5 to 25 cyclic atoms.

[1863] In the compounds involved in this embodiment, it is preferred that the substituents described as "substituted or unsubstituted" are halogen atoms, unsubstituted alkyl groups having 1 to 25 carbon atoms, unsubstituted aryl groups having 6 to 25 cyclic carbon atoms, or unsubstituted heterocyclic groups having 5 to 25 cyclic atoms.

[1864] In the compounds involved in this embodiment, it is preferred that the substituents described as "substituted or unsubstituted" are unsubstituted alkyl groups having 1 to 10 carbon atoms, unsubstituted aryl groups having 6 to 12 cyclic carbon atoms, or unsubstituted heterocyclic groups having 5 to 12 cyclic atoms.

[1865] In the compounds involved in this embodiment, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups.

[1866] In this specification, -O-(R 904 The group shown in R 904 In the case of hydrogen atoms, it is a hydroxyl group.

[1867] In this specification, -S-(R 905 The group shown in R 905 In the case of hydrogen atoms, it is a thiol group.

[1868] In this specification, -P(=O)(R 931 (R) 932 The group shown in R 931 and R 932 In the case of a substituent, it is a substituted phosphine oxide group.

[1869] In this specification, -Ge(R) 933 (R) 934 (R) 935 The group shown in R 933 R 934 and R 935 In the case of a substituent, it is a substituted germanium group.

[1870] In this specification, -B(R) 936 (R) 937 The group shown in R 936 and R 937 In the case of a substituent, it is a substituted methylborane.

[1871] (Thermally activated delayed fluorescence)

[1872] In this specification, thermally activated delayed fluorescence is sometimes referred to as delayed fluorescence.

[1873] Regarding delayed fluorescence, it is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). This document explains that if the energy difference ΔE between the excited singlet and excited triplet states of a fluorescent luminescent material can be reduced... 13In such cases, the reverse energy transfer from the excited triplet state to the excited singlet state, which typically has a low transition probability, occurs with high efficiency, exhibiting thermally activated delayed fluorescence (TADF). Furthermore, the generation mechanism of delayed fluorescence is explained in Figure 10.38 of this literature. The TADF mechanism utilizes the phenomenon of reverse intersystem crossing from the triplet exciton to the singlet exciton under thermal influence when using materials with a small energy difference (ΔST) between the singlet and triplet energy levels. Compounds exhibiting thermally activated delayed fluorescence (TADF property) (hereinafter also referred to as TADF-type compounds) are known to have intramolecularly bonded donor and acceptor sites.

[1874] Generally, delayed fluorescence can be confirmed by transient photoluminescence (PL) measurement.

[1875] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement refers to the method of exciting a sample by irradiating it with a pulsed laser and measuring the decay behavior (transient characteristics) of PL emission after irradiation stops. PL emission in TADF compounds is classified into emission components originating from singlet excitons generated by the initial PL excitation and emission components originating from singlet excitons generated via triplet excitons. The lifetime of the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission originating from these singlet excitons decays rapidly after irradiation with a pulsed laser.

[1876] On the other hand, delayed fluorescence, originating from the emission of singlet excitons generated via long-lived triplet excitons, decays slowly. Thus, there is a significant temporal difference between the emission of singlet excitons generated from the initial PL excitation and the emission of singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[1877] Figure 2 A schematic diagram of an exemplary apparatus for measuring transient pulse-force (PL) is shown. For the use of... Figure 2 The method for measuring transient PL and an example of delayed fluorescence behavior analysis are explained.

[1878] Figure 2 The transient pulse pulsation (PL) measuring device 100 includes: a pulsed laser unit 101 capable of irradiating light of a specified wavelength, a sample chamber 102 for containing the sample to be measured, a beam splitter 103 for splitting the light emitted from the sample to be measured, a streak camera 104 for imaging 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 2 The recording device.

[1879] The sample contained in the sample chamber 102 can be obtained by forming a thin film on a quartz substrate by doping a matrix material with a doping material at a concentration of 12% by mass.

[1880] For the thin film sample contained in the sample chamber 102, a pulsed laser is irradiated from the pulsed laser unit 101 to excite the doped material. The emitted light is extracted along a direction 90 degrees relative to the irradiation direction of the excitation light, and the extracted light is split using a beam splitter 103 to image a two-dimensional image within a streak camera 104. As a result, a two-dimensional image is obtained with the vertical axis corresponding to time, the horizontal axis corresponding to wavelength, and the bright spots corresponding to emission intensity. If this two-dimensional image is divided along a predetermined time axis, an emission spectrum with emission intensity as the vertical axis and wavelength as the horizontal axis can be obtained. Furthermore, if this two-dimensional image is divided along a wavelength axis, a decay curve (transient PL) with the logarithm of emission intensity as the vertical axis and time as the horizontal axis can be obtained.

[1881] For example, thin film sample A was prepared by using compound HX1 as the matrix material and compound DX1 as the dopant material, and transient PL was measured.

[1882]

Chemical Formula 282

[1883]

[1884] Here, the decay curves were analyzed using the aforementioned thin film sample A and thin film sample B. For thin film sample B, the thin film sample was prepared using the aforementioned compound HX2 as the matrix material and the aforementioned compound DX1 as the dopant material, as described above.

[1885] Figure 3 The decay curves obtained from the transient PL measured on thin film sample A and thin film sample B are shown.

[1886] [Chemical Formula 283]

[1887]

[1888] As described above, by transient photoluminescence (PL) measurement, a luminescence decay curve can be obtained with the vertical axis representing luminescence intensity and the horizontal axis representing time. Based on this luminescence decay curve, the ratio of fluorescence intensity emitted by a singlet excited state generated through photoexcitation to delayed fluorescence emitted by a singlet excited state generated via reverse energy transfer from a triplet excited state can be estimated. In materials with delayed fluorescence, the intensity of slowly decaying delayed fluorescence is relatively large compared to the intensity of rapidly decaying fluorescence.

[1889] Specifically, luminescence from delayed-fluorescence materials can be categorized into prompt luminescence and delayed luminescence. Prompt luminescence refers to luminescence observed immediately from the excited state after being excited by a pulse of light (light irradiated by a pulsed laser) of a wavelength absorbed by the delayed-fluorescence material. Delay luminescence refers to luminescence that is not observed immediately after excitation by the same pulse of light but is observed later.

[1890] The amounts and ratios of Prompt and Delay luminescence can be determined using the same method described in "Nature 492, 234-238, 2012" (Reference 1). It should be noted that the apparatus used for calculating the amounts of Prompt and Delay luminescence is not limited to the apparatus described in Reference 1 above, or... Figure 2 The recording device.

[1891] Furthermore, the determination of the delayed fluorescence property of the delayed fluorescence compound according to this embodiment uses a sample prepared by the method described below. For example, the delayed fluorescence compound according to this embodiment is dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength is prepared to remove the contribution of self-absorption. In addition, to prevent extinction due to oxygen, the sample solution is degassed by freezing and then sealed in a covered cuvette under an argon atmosphere, thereby preparing an argon-saturated oxygen-free sample solution.

[1892] The fluorescence spectra of the above sample solutions were measured using a spectrophotometer FP-8600 (manufactured by Nippon Spectrophotometer Co., Ltd.). Additionally, the fluorescence spectrum of 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, according to equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[1893] In this embodiment, the amount of Prompt luminescence (instantaneous luminescence) of the target compound is set as X. P Set the amount of delayed emission (delayed emission) to X. D At that time, X D / X P The value is preferably 0.05 or higher.

[1894] The determination of the amount and ratio of Prompt and Delay luminescence for compounds other than delayed fluorescent compounds in this specification is the same as the determination of the amount and ratio of Prompt and Delay luminescence for delayed fluorescent compounds involved in this embodiment.

[1895] (ΔST)

[1896] In this embodiment, the minimum excited singlet energy S1 is compared with the bandgap T at 77 [K]. 77K The difference (S1-T) 77K ) is defined as ΔST.

[1897] In this embodiment, the lowest excitation singlet energy S1(GT2) of the delayed fluorescence compound and the band gap T at 77 [K] of the delayed fluorescence compound are... 77K The difference ΔST(GT2) is preferably less than 0.5 eV, more preferably less than 0.3 eV, further preferably less than 0.2 eV, even more preferably less than 0.1 eV, and still more preferably less than 0.01 eV. That is, preferably, ΔST(GT2) satisfies the following mathematical formula (Mathematical Formula 2), (Mathematical Formula 2A), (Mathematical Formula 2B), (Mathematical Formula 2C), or (Mathematical Formula 2D).

[1898] ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.5 eV …(Mathematical Formula 2)

[1899] ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.3 eV …(Mathematical expression 2A)

[1900] ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.2 eV …(Mathematical expression 2B)

[1901] ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.1 eV …(Mathematical expression 2C)

[1902] ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.01 eV …(Mathematical expression 2D)

[1903] (Relationship between triplet energy and band gap at 77 K)

[1904] Here, the relationship between the triplet energy and the band gap at 77 [K] is explained. In this embodiment, the band gap at 77 [K] has a point that differs from the normally defined triplet energy.

[1905] The triplet energy is determined as follows. First, the compound to be measured is dissolved in a suitable solvent to obtain a solution, which is then sealed in a quartz glass tube to prepare a sample. For this sample, the phosphorescence spectrum (with the vertical axis set as phosphorescence intensity and the horizontal axis as wavelength) is measured at a low temperature (77 K). The rising tangent on the short wavelength side of the phosphorescence spectrum is used as the tangent, and the triplet energy is calculated using a prescribed conversion formula based on the wavelength value of the intersection of the tangent and the horizontal axis.

[1906] Here, the compounds with thermally activated delayed fluorescence (ΔST) involved in this embodiment are preferably compounds with small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are more likely to occur even at low temperatures (77 [K]), and excited singlet and excited triplet states coexist. As a result, the spectrum obtained by measuring in the same manner as above includes the emission from both excited singlet and excited triplet states. Although it is difficult to distinguish which state emitted the light, it is considered that the triplet energy value is basically dominant.

[1907] Therefore, although the measurement method is the same as that for the usual triplet energy T in this embodiment, in order to distinguish the difference in a strict sense, the following measured value is referred to as the band gap T. 77K The compound to be tested was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)) to obtain a concentration of 10 μmol / L, and this solution was added to a quartz cuvette as the test sample. For this test sample, the phosphorescence spectrum was measured at a low temperature (77 K) (the vertical axis was set as phosphorescence intensity and the horizontal axis as wavelength). For the rising tangent on the short wavelength side of the phosphorescence spectrum, the wavelength value λ based on the intersection of the tangent and the horizontal axis was determined. edge [nm], the energy calculated by the following conversion formula (F1) is set as the band gap T when the energy is 77 [K]. 77K .

[1908] Conversion formula (F1): T 77K [eV] = 1239.85 / λ edge

[1909] The tangent for the rise on the short-wavelength side of the phosphorescence spectrum is derived as follows. Consider the tangent at each point on the spectral curve, moving from the short-wavelength side of the phosphorescence spectrum up to the shortest wavelength maximum among the spectral maxima, towards the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope reaches its maximum (i.e., the tangent at the inflection point) is taken as the tangent for the rise on the short-wavelength side of the phosphorescence spectrum.

[1910] It should be noted that the maximum point of peak intensity with less than 15% of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above. The tangent line drawn at the point where the slope value is the maximum value closest to the maximum value on the shortest wavelength side is taken as the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.

[1911] Phosphorescence can be measured using the main body of the F-4500 spectrophotometer manufactured by Hitachi High Tech Co., Ltd. It should be noted that the measuring apparatus is not limited to this; measurements can be performed by combining a cooling device, a cryogenic container, an excitation source, and a light-receiving device.

[1912] (Lowest Excited Singlet Energy S1)

[1913] The following methods can be cited as methods for determining the lowest excited singlet energy S1 using a solution (sometimes called the solution method).

[1914] A 10 μmol / L toluene solution of the compound to be measured was prepared and added to a quartz cuvette. The absorption spectrum of the sample was measured at room temperature (300 K) (vertical axis is set as absorption intensity, horizontal axis is set as wavelength). For the downward tangent on the longer wavelength side of the absorption spectrum, the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis was substituted into the conversion formula (F2) shown later to calculate the lowest excited singlet energy.

[1915] Conversion formula (F2): S1[eV]=1239.85 / λedge

[1916] As an absorption spectroscopy measuring device, examples include, but are not limited to, the Hitachi spectrophotometer (device name: U3310).

[1917] The tangent for the downward sag on the longer wavelength side of the absorption spectrum is derived as follows. Consider the tangent at various points on the spectral curve as the longest wavelength maximum is moved along the longer wavelength direction. This tangent exhibits a slope that repeatedly decreases and then increases as the curve declines (i.e., as the value on the vertical axis decreases). The tangent drawn at the point where the slope is minimized on the longest wavelength side (excluding cases where absorbance is below 0.1) is taken as the tangent for the downward sag on the longer wavelength side of the absorption spectrum.

[1918] It should be noted that the maximum absorbance values ​​below 0.2 are not included in the maximum values ​​on the longest wavelength side mentioned above.

[1919] (Method for manufacturing delayed-fluorescence compounds)

[1920] Delayed fluorescence compounds can be manufactured using known methods. Alternatively, delayed fluorescence compounds can also be manufactured by mimicking known methods, using known alternative reactions and starting materials corresponding to the target substance.

[1921] (Specific examples of delayed fluorescence compounds)

[1922] Specific examples of delayed fluorescence compounds include the following compounds. However, the present invention is not limited to these specific examples.

[1923] [Chemical Formula 284]

[1924]

[1925] [Chemical Formula 285]

[1926]

[1927] [Chemical Formula 286]

[1928]

[1929] [Chemical Formula 287]

[1930]

[1931] [Chemical Formula 288]

[1932]

[1933] [Chemical Formula 289]

[1934]

[1935] [First Main Material]

[1936] In one embodiment of the third method, the first host material is a compound comprising one or more local structures selected from the group consisting of local structures represented by the following general formulas (301) to (318) in a single molecule. In this specification, the compound used as the first host material is sometimes referred to as the third compound.

[1937] [Chemical Formula 290]

[1938]

[1939]

Chemical Formula 291

[1940]

[1941] (In the above general formula (301),

[1942] A31 ~A 36 Each independently consists of a nitrogen atom and CR. 31 Or carbon atoms bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[1943] Among them, A 31 ~A 36 At least one of them is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[1944] In R 31 In the case of multiple Rs, multiple Rs 31 They may be identical or different, consisting of multiple Rs 31 One or more groups consisting of two or more adjacent elements.

[1945] They bond together to form substituted or unsubstituted monocyclic rings.

[1946] They bond together to form substituted or unsubstituted fused rings, or

[1947] They do not bond with each other.

[1948] In the above general formula (302),

[1949] A1 to A4 are each independently nitrogen atoms, CR 32 Or carbon atoms bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[1950] R 32 Each is independently a hydrogen atom or a substituent, or an adjacent R 32 One or more groups from each other's groups bond together to form a loop.

[1951] In R 32 In the case of multiple Rs, multiple Rs 32 They may be identical or different, consisting of multiple Rs 32 One or more groups consisting of two or more adjacent elements.

[1952] They bond together to form substituted or unsubstituted monocyclic rings.

[1953] They bond together to form substituted or unsubstituted fused rings, or

[1954] They do not bond with each other.

[1955] X 30 For NR 33 C(R) 34 (R) 35 ), Si(R) 36 (R) 37), oxygen atom, sulfur atom, nitrogen atom bonded to other atoms or other structures in the molecule of the third compound mentioned above, and R 38 Carbon atoms that are bonded to other atoms or other structures in the molecule of the third compound mentioned above, or to R 39 Silicon atoms bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[1956] Among them, carbon atoms in A1 to A4, X 30 nitrogen atoms, X 30 carbon atoms and X 30 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound.

[1957] By R 34 and R 35 Groups

[1958] They bond together to form substituted or unsubstituted monocyclic rings.

[1959] They bond together to form substituted or unsubstituted fused rings, or

[1960] They do not bond with each other.

[1961] By R 36 and R 37 Groups

[1962] They bond together to form substituted or unsubstituted monocyclic rings.

[1963] They bond together to form substituted or unsubstituted fused rings, or

[1964] They do not bond with each other.

[1965] In the above general formula (303),

[1966] By R 315 and R 316 Groups

[1967] They bond together to form substituted or unsubstituted monocyclic rings.

[1968] They bond together to form substituted or unsubstituted fused rings, or

[1969] They do not bond with each other.

[1970] In the above general formulas (301) to (304),

[1971] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 31 R 32 R 34 R 35R 36 R 37 R 315 and R 316 and R 33 R 38 R 39 and R 317 Each independently

[1972] hydrogen atom

[1973] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[1974] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[1975] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[1976] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[1977] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[1978] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[1979] -O-(R 904 The groups shown in the figure,

[1980] -S-(R 905 The groups shown in the figure,

[1981] -N(R 906 (R) 907 The groups shown in the figure,

[1982] -C(=O)R 908 The groups shown

[1983] -COOR 909 The groups shown

[1984] -P(=O)(R 910 (R) 911 The groups shown in the figure,

[1985] -P(=O)(OR 912 (OR) 913 The groups shown in the figure,

[1986] -Ge(R 914 (R) 915 (R) 916 The groups shown in the figure,

[1987] -B(R 917 (R)918 The groups shown in the figure,

[1988] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[1989] Halogen atoms,

[1990] cyano,

[1991] Nitro,

[1992] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[1993] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[1994] In the above general formulas (303) to (318),

[1995] * indicates the bonding site with other atoms or other structures in the molecule of the third compound mentioned above.

[1996] When the local structures shown in the above general formulas (301) to (304) are each present in multiples in the above third compound,

[1997] The local structures shown in the above general formula (301) may be the same or different from each other.

[1998] The local structures shown in the above general formula (302) may be the same or different from each other.

[1999] The local structures shown in multiple general formulas (303) above may be the same as or different from each other.

[2000] The local structures shown in multiple general formulas (304) above may be identical or different from each other.

[2001] (In the third compound mentioned above, R) 901 ~R 918 Each independently

[2002] hydrogen atom,

[2003] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2004] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2005] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2006] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2007] In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different.

[2008] In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different.

[2009] In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different.

[2010] In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different.

[2011] In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different.

[2012] In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different.

[2013] In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different.

[2014] In R 908 In the case of multiple Rs, multiple Rs 908 They are the same or different.

[2015] In R 909 In the case of multiple Rs, multiple Rs 909 They are the same or different.

[2016] In R 910 In the case of multiple Rs, multiple Rs 910 They are the same or different.

[2017] In R 911 In the case of multiple Rs, multiple Rs 911 They are the same or different.

[2018] In R 912 In the case of multiple Rs, multiple Rs 912 They are the same or different.

[2019] In R 913 In the case of multiple Rs, multiple Rs 913 They are the same or different.

[2020] In R 914 In the case of multiple Rs, multiple Rs 914 They are the same or different.

[2021] In R 915In the case of multiple Rs, multiple Rs 915 They are the same or different.

[2022] In R 916 In the case of multiple Rs, multiple Rs 916 They are the same or different.

[2023] In R 917 In the case of multiple Rs, multiple Rs 917 They are the same or different.

[2024] In R 918 In the case of multiple Rs, multiple Rs 918 (They may be the same or different.)

[2025] In the above general formula (302), in X 30 In the case of “nitrogen atoms bonded to other atoms or other structures in the molecule of a third compound”, the above general formula (302) is represented by the following general formula (302-1).

[2026] In the above general formula (302), in X 30 For "with R" 38 In the case of "carbon atoms bonded to other atoms or other structures in the molecule of the third compound", the above general formula (302) is represented by the following general formula (302-2).

[2027] In the above general formula (302), in X 30 For "with R" 39 In the case of silicon atoms bonded to other atoms or other structures in the molecule of the third compound, the above general formula (302) is represented by the following general formula (302-3).

[2028] In general formulas (302-1) to (302-3), A1 to A4 each have the same meaning as A1 to A4 in the above general formula (302), R 38 and R 39 Each independently relates to R in the above general formula (302) 32 The meanings are the same, with * indicating the bonding site with other atoms or other structures in the molecule of the third compound.

[2029]

Chemical Formula 292

[2030]

[2031] In one embodiment, the first body material has at least one local structure as shown in the above general formula (301).

[2032] In one embodiment, the local structure shown in the above general formula (301) is at least one selected from the group consisting of the local structures shown in the following general formulas (A31) to (A39).

[2033] [Chemical Formula 293]

[2034]

[2035] [Chemical Formula 294]

[2036]

[2037] [Chemical Formula 295]

[2038]

[2039] (In the above general formulas (A31) to (A36), A) 32 ~A 36 Each is independently a nitrogen atom or CR 31 R 31 R in the above general formula (301) 31 The meaning is the same; * indicates a bonding site with other atoms or other structures in the molecule of the third compound mentioned above.

[2040] In the above general formulas (A37) and (A38), A 31 ~A 42 Each is independently a nitrogen atom or CR 31 Or, R is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above. 31 Each independently relates to R in the above general formula (301) 31 The meanings are the same, A 31 ~A 42 At least one of them is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[2041] In the above general formula (A39), A 31 ~A 38 Each is independently a nitrogen atom or CR 31 Or, R is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above. 31 Each independently relates to R in the above general formula (301) 31 Same meaning, X 31 and X 32 Each independently relates to X in the above general formula (302). 30 The meanings are the same, and A 31 ~A 38 carbon atoms, X 31 and X32 nitrogen atoms, X 31 and X 32 carbon atoms and X 31 and X 32 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound.

[2042] In one embodiment, the first body material has at least one local structure as shown in the above general formula (302).

[2043] In one embodiment, the local structure shown in the above general formula (302) is at least one selected from the group consisting of the local structures shown in the following general formulas (B31) to (B44).

[2044] [Chemical Formula 296]

[2045]

[2046] In the above general formulas (B31) to (B36), Ax1 to Ax4 are each independently a nitrogen atom or a CR atom. 32 R 32 Each independently relates to R in the above general formula (302) 32 Same meaning, X 30 X in the above general formula (302) 30 The meaning is the same; * indicates a bonding site with other atoms or other structures in the molecule of the third compound mentioned above.

[2047] In the above general formula (B37), Ax1, Ax2, and Ay1 to Ay4 are each independently nitrogen atoms or CR atoms. 32 Or, R is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above. 32 Each independently relates to R in the above general formula (302) 32 Same meaning, X 30 X in the above general formula (302) 30 The meanings are the same, among which the carbon atoms and X in Ax1, Ax2 and Ay1~Ay4 are... 30 nitrogen atoms, X 30 carbon atoms and X 30 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound.

[2048] In the above general formula (B38), Ay1 to Ay8 are each independently a nitrogen atom or a CR atom. 32 Or, R is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above. 32Each independently relates to R in the above general formula (302) 32 Same meaning, X 30 X in the above general formula (302) 30 The meanings are the same; carbon atoms and X in Ay1 to Ay8 are... 30 nitrogen atoms, X 30 carbon atoms and X 30 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound.

[2049] [Chemical Formula 297]

[2050]

[2051] [Chemical Formula 298]

[2052]

[2053]

Chemical Formula 299

[2054]

[2055] (In the above general formulas (B39) to (B44), Ay1 to Ay8 and Ay9 to Ay8 are...) 12 Each is independently a nitrogen atom or CR 32 Or, R is a carbon atom bonded to other atoms or other structures in the molecule of the third compound mentioned above. 32 Each independently relates to R in the above general formula (302) 32 Same meaning, X 39 and X 30 Each independently relates to X in the above general formula (302). 30 Same meaning

[2056] Ay1~Ay8 and Ay9~Ay 12 carbon atoms, X 39 and X 30 nitrogen atoms, X 39 and X 30 carbon atoms and X 39 and X 30 At least one of the silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound.

[2057] In the third compound of this embodiment, R 31 R 32 and R 315 ~R 317Each of the following is preferably a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group with 6 to 30 carbon atoms in a cyclic ring, an unsubstituted heterocyclic group with 5 to 30 carbon atoms in a cyclic ring, an unsubstituted alkyl group with 1 to 30 carbon atoms in a cyclic ring, an unsubstituted haloalkyl group with 1 to 30 carbon atoms in a cyclic ring, an unsubstituted alkylsilyl group with 3 to 30 carbon atoms in a cyclic ring, an unsubstituted arylphosphoryl group with 6 to 60 carbon atoms in a cyclic ring, an unsubstituted alkoxy group with 1 to 30 carbon atoms in a cyclic ring, an unsubstituted aryloxy group with 6 to 30 carbon atoms in a cyclic ring, an amino group, an unsubstituted alkylamino group with 2 to 30 carbon atoms in a cyclic ring, an unsubstituted arylamino group with 6 to 60 carbon atoms in a cyclic ring, a mercapto group, an unsubstituted alkylthio group with 1 to 30 carbon atoms in a cyclic ring, or an unsubstituted arylthio group with 6 to 30 carbon atoms in a cyclic ring.

[2058] In the third compound of this embodiment, R 31 R 32 and R 315 ~R 317 More preferably, each of the following is independent of the following: hydrogen atom, halogen atom, cyano group, unsubstituted aryl group with 6 to 14 cyclic carbons, unsubstituted heterocyclic group with 5 to 14 cyclic carbons, unsubstituted alkyl group with 1 to 6 carbons, unsubstituted haloalkyl group with 1 to 6 carbons, unsubstituted alkylsilyl group with 3 to 6 carbons, unsubstituted arylsilyl group with 6 to 60 cyclic carbons, unsubstituted arylphosphoryl group with 6 to 60 cyclic carbons, unsubstituted alkoxy group with 1 to 6 carbons, unsubstituted aryloxy group with 6 to 14 cyclic carbons, amino group, unsubstituted alkylamino group with 2 to 12 carbons, unsubstituted arylamino group with 6 to 60 cyclic carbons, mercapto group, unsubstituted alkylthio group with 1 to 6 carbons, or unsubstituted arylthio group with 6 to 14 cyclic carbons.

[2059] In the third compound of this embodiment, R 31 R 32 and R 315 ~R 317 The preferred atom is hydrogen.

[2060] In the third compound of this embodiment, X 30 R in 33 ~R 39 and X 39 R in 33 ~R 39 (with X) 30 R in 33 ~R 39 (with the same meaning) Each is preferably a hydrogen atom, an unsubstituted aryl group with 6 to 30 carbon atoms, an unsubstituted heterocyclic group with 5 to 30 carbon atoms, an unsubstituted alkyl group with 1 to 30 carbon atoms, or an unsubstituted haloalkyl group with 1 to 30 carbon atoms.

[2061] In the third compound of this embodiment, X30 R in 33 ~R 39 and X 39 R in 33 ~R 39 More preferably, each of the following is a hydrogen atom, an unsubstituted aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted haloalkyl group having 1 to 6 carbon atoms.

[2062] In the third compound of this embodiment, X 30 R in 33 ~R 39 and X 39 R in 33 ~R 39 Each of the components is further preferably an unsubstituted aryl group having 6 to 14 carbon atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[2063] As a local structure represented by any of the above general formulas (301) to (318), for example, the local structures represented by the following general formulas (A301) to (A321) and (B301) to (B325) can be cited.

[2064] Preferably, the third compound contains at least one of the local structures shown in the following general formulas (A301) to (A321) and (B301) to (B325) in one molecule.

[2065]

Chemical Formula 300

[2066]

[2067]

Chemical Formula 301

[2068]

[2069] In the above general formulas (A301) to (A307), R 301 ~R 306 Each independently relates to R in the above general formula (301) 31 The meaning is the same, R 301 ~R 306 At least one of them is a single bond that is bonded to other atoms or other structures in the molecule of the third compound.

[2070] In the above general formulas (A301) to (A307), adjacent R 301 and R 302 group, R 302 and R 303 group, R 303 and R 304 group, R304 and R 305 group, R 305 and R 306 The group and R 306 and R 301 One or more groups of the group are 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.

[2071]

Chemical Formula 302

[2072]

[2073] In the above general formulas (A308) to (A309), R 310 Each independently relates to R in the above general formula (301) 31 The meaning is the same, R 310 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound mentioned above, and multiple R 310 They may be identical or different, and consist of multiple R 310 One or more of the two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, a substituted or unsubstituted fused ring, or not bonded to each other.

[2074]

Chemical Formula 303

[2075]

[2076] Chemical formula 304

[2077]

[2078] In the above general formulas (A310) to (A314), R 310 and R 312 ~R 314 Each independently relates to R in the above general formula (301) 31 Same meaning, X 310 Each independently relates to X in the above general formula (302). 30 The meanings are the same, where R 310 and R 312 ~R 314 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound, or X 310 At least one of the nitrogen, carbon, and silicon atoms in the compound is bonded to other atoms or other structures in the molecule of the third compound, and multiple R atoms are bonded to each other. 310 They are the same or different.

[2079] In the above general formulas (A310) to (A314), multiple R 310 A group consisting of two or more adjacent elements, R 312 and R 313 The group and X 310 R in 34 and R 35 The group (with X) 30 R in 34 and R 35 (The meanings of the groups are the same) X 310 R in 36 and R 37 The group (with X) 30 R in 36 and R 37 (The meaning of the group is the same) One or more groups are 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.

[2080]

Chemical Formula 305

[2081]

[2082] In the above general formulas (A315) to (A319), R 310 and R 312 ~R 314 Each independently relates to R in the above general formula (301) 31 The meanings are the same, where R 310 and R 312 ~R 314 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound mentioned above, and multiple R 310 They are the same or different.

[2083] In the above general formulas (A315) to (A319), multiple R 310 Groups consisting of two or more adjacent elements and R 312 and R 313 One or more groups of the group are 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.

[2084]

Chemical Formula 306

[2085]

[2086] In the above general formulas (A320) to (A321), R 310 Each independently relates to R in the above general formula (301) 31 The meanings are the same, where R 310At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound mentioned above, and multiple R 310 They are the same or different.

[2087] In the above general formulas (A320) to (A321), multiple R 310 One or more of the two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, a substituted or unsubstituted fused ring, or not bonded to each other.

[2088]

Chemical Formula 307

[2089]

[2090]

Chemical Formula 308

[2091]

[2092]

Chemical Formula 309

[2093]

[2094] In the above general formulas (B301) to (B309), R 314 and R 321 ~R 331 Each independently relates to R in the above general formula (302) 32 The meanings are the same, where R 314 and R 321 ~R 331 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound.

[2095] In the above general formulas (B301) to (B302), R 322 and R 323 group, R 323 and R 314 The group and R 314 and R 321 One or more groups of the group are 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.

[2096] In the above general formulas (B305) to (B306), R 324 and R 325 group, R 325 and R 326 group, R 326 and R 327 group, R 327 and R 328 The group and R 328 and R329 One or more groups of the group are 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.

[2097] In the above general formula (B307), R 324 and R 325 group, R 325 and R 326 group, R 326 and R 327 group, R 327 and R 328 group, R 328 and R 329 group, R 329 and R 314 The group and R 314 and R 324 One or more groups of the group are 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.

[2098] In the above general formulas (B308) to (B309), R 324 and R 325 group, R 325 and R 326 group, R 330 and R 331 The group and R 331 and R 329 One or more groups of the group are 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.

[2099]

Chemical Formula 310

[2100]

[2101]

Chemical Formula 311

[2102]

[2103]

Chemical Formula 312

[2104]

[2105] In the above general formulas (B310) to (B317), R 310 and R 332 ~R 335 Each independently relates to R in the above general formula (302) 32 The meanings are the same, where R 310 and R 332 ~R 335At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound mentioned above, and multiple R 310 They are the same or different.

[2106] In the above general formulas (B310) to (B317), multiple R 310 Groups consisting of two or more adjacent elements and R 332 and R 333 One or more groups of the group are 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.

[2107]

Chemical Formula 313

[2108]

[2109]

Chemical Formula 314

[2110]

[2111]

Chemical Formula 315

[2112]

[2113] In the above general formulas (B318) to (B323), R 310 Each independently relates to R in the above general formula (302) 32 With the same meaning, Xa and Xb are each independently related to X in the above general formula (302). 30 The meanings are the same, where R 310 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa and Xb is bonded to other atoms or other structures in the molecule of the third compound, and multiple R 310 They are the same or different.

[2114] In the above general formulas (B318) to (B323), multiple R 310 A group consisting of two or more adjacent elements, and R in Xa 34 and R 35 The group and R in Xb 34 and R 35 The group (with X) 30 R in 34 and R 35 (The meanings of the groups are the same) and R in Xa 36 and R 37 The group and R in Xb 36 and R 37 The group (with X) 30R in 36 and R 37 (The meaning of the group is the same) One or more groups are 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.

[2115]

Chemical Formula 316

[2116]

[2117] In the above general formulas (B324) to (B325), R 310 Each independently relates to R in the above general formula (302) 32 With the same meaning, Xa, Xb, and Xc are each independently related to X in the above general formula (302). 30 The meanings are the same, where R 310 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa, Xb, and Xc is bonded to other atoms or other structures in the molecule of the third compound, and multiple R 310 They are the same or different.

[2118] In the above general formulas (B324) to (B325), multiple R 310 R in groups of two or more adjacent elements, Xa, Xb, and Xc 34 and R 35 The group (with X) 30 R in 34 and R 35 (The meanings of the groups are the same) and R in Xa, Xb and Xc 36 and R 37 The group (with X) 30 R in 36 and R 37 (The meaning of the group is the same) One or more groups are 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.

[2119] In the above general formulas (A301)~(A321) and (B301)~(B325), R 310 R 301 ~R 306 R 312 ~R 314 R 321 ~R 331 and R 332 ~R 335Each of the following is preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 carbon atoms in a cyclic ring, an unsubstituted heterocyclic group having 5 to 30 carbon atoms in a cyclic ring, an unsubstituted alkyl group having 1 to 30 carbon atoms in a cyclic ring, or an unsubstituted haloalkyl group having 1 to 30 carbon atoms in a cyclic ring; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, an unsubstituted heterocyclic group having 5 to 14 carbon atoms in a cyclic ring, an unsubstituted alkyl group having 1 to 6 carbon atoms in a cyclic ring, or an unsubstituted haloalkyl group having 1 to 6 carbon atoms in a cyclic ring; and even more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 carbon atoms in a cyclic ring, or an unsubstituted alkyl group having 1 to 6 carbon atoms in a cyclic ring.

[2120] In the above general formulas (A301)~(A321) and (B301)~(B325), Xa, Xb, Xc and X 310 R in 33 ~R 39 (with X) 30 R in 33 ~R 39 (With the same meaning) Each is preferably a hydrogen atom, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted haloalkyl group having 1 to 30 carbon atoms; more preferably a hydrogen atom, an unsubstituted aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted haloalkyl group having 1 to 6 carbon atoms; even more preferably an unsubstituted aryl group having 6 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[2121] In this embodiment, preferably, the third compound (I) has at least one cyano, amino, substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, and substituted or unsubstituted cyclic arylamino group having 6 to 60 carbon atoms, or (II) has at least one monovalent 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 silazine, 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.

[2122] In this embodiment, more preferably, the third compound (III) has at least one cyano group, or (IV) has at least one monovalent 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 silazine, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[2123] In this embodiment, it is further preferred that the third compound has at least one monovalent 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.

[2124] In this embodiment, it is preferred that the third compound has at least one monovalent residue derived from substituted or unsubstituted carbazole.

[2125] In this embodiment, it is preferred that the third compound has at least one local structure represented by the following general formula (35).

[2126]

Chemical Formula 317

[2127]

[2128] (In the above general formula (35), R) 350 ~R 358 At least one of them is a single bond bonded to other atoms or other structures in the molecule of the third compound mentioned above.

[2129] R is not a single bond 350 ~R 358 Each independently

[2130] hydrogen atom

[2131] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2132] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2133] Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms

[2134] Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms

[2135] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2136] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2137] -O-(R 904 The groups shown in the figure,

[2138] -S-(R 905 The groups shown in the figure,

[2139] -N(R 906 (R) 907 The groups shown in the figure,

[2140] -C(=O)R 908 The groups shown

[2141] -COOR 909 The groups shown

[2142] -P(=O)(R 910 (R) 911 The groups shown in the figure,

[2143] -Ge(R 912 (R) 913 (R) 914 The groups shown in the figure,

[2144] -B(R 915 (R) 916 The groups shown in the figure,

[2145] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2146] Halogen atoms,

[2147] cyano,

[2148] Nitro,

[2149] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2150] (Substituted or unsubstituted heterocyclic groups with 5 to 50 cyclic atoms)

[2151] In the above general formula (35), R 350 Preferably, it is an aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted, a heterocyclic group with 5 to 30 carbon atoms that has been substituted or unsubstituted, an alkyl group with 1 to 30 carbon atoms that has been substituted or unsubstituted, or a haloalkyl group with 1 to 30 carbon atoms that has been substituted or unsubstituted, more preferably an aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted, or an alkyl group with 1 to 30 carbon atoms that has been substituted or unsubstituted, and even more preferably an aryl group with 6 to 30 carbon atoms that has been substituted or unsubstituted.

[2152] (The third compound represented by general formula (361) or (362))

[2153] In this embodiment, it is also preferred that the third compound is a compound represented by the following general formula (361) or the following general formula (362).

[2154]

Chemical Formula 318

[2155]

[2156] (In the above general formula (361), Ar) 361 for

[2157] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 30 carbon atoms, or

[2158] Heterocycles with 5 to 30 cyclic atoms, substituted or unsubstituted.

[2159] m1 is 1, 2, 3, 4, 5, or 6.

[2160] R 361 As an electron-donating group, R 361 Each and constitute Ar 361 Element bonding,

[2161] When m1 is 2 or higher, multiple R 361 They are the same or different.

[2162] Among them, Ar 361 Non-electron-withdrawing aromatic hydrocarbon rings and heterocycles, in Ar 361 When a substituent is present, the substituent is not an electron-withdrawing group.

[2163] In the above general formula (362), Ar 362 for

[2164] Substituted or unsubstituted aromatic hydrocarbon rings with 6 to 30 carbon atoms, or

[2165] Heterocycles with 5 to 30 cyclic atoms, substituted or unsubstituted.

[2166] n1 is 1, 2, 3, 4, 5, or 6.

[2167] R 362 R is an electron-withdrawing group. 362 Each and constitute Ar 362 Element bonding,

[2168] When n1 is 2 or more, multiple R 362 They are the same or different.

[2169] Among them, Ar 362 Non-electron-donating aromatic hydrocarbon rings and heterocycles, in Ar 362 (When a substituent is present, the substituent is not an electron-donating group.)

[2170] In the above general formulas (361) and (362), it is preferred that Ar 361 and Ar 362 Each of the above residues is independently derived from any of the compounds represented by the following general formulas (A61) and (A62).

[2171]

Chemical Formula 319

[2172]

[2173] In this embodiment, it is preferred that R in the above general formula (361) is... 361 Each is independently a monovalent or more residue derived from any of the compounds represented by the following general formulas (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following general formula (DN7).

[2174]

Chemical Formula 320

[2175]

[2176]

Chemical Formula 321

[2177]

[2178]

Chemical Formula 322

[2179]

[2180] (In the above general formula (DN7), * each represents and constitutes Ar) 361 (The bonded parts of the element.)

[2181] In this embodiment, it is preferred that R in the above general formula (362) is... 362 Each of the following is a monovalent or more residue derived independently from any of the compounds shown in the general formulas (AC4) to (AC18) and (AC22) to (AC23), or any of the groups shown in the general formulas (AC1) to (AC3), (AC19) to (AC21) and (AC24).

[2182]

Chemical Formula 323

[2183]

[2184] [Chemical Formula 324]

[2185]

[2186] (In the above general formula (AC1), n) AIt can be 1, 2, or 3.

[2187] In the above general formulas (AC22) to (AC23), X1 to X8 are each independently CR. 363 Alternatively, it may be a carbon atom bonded to other atoms or other structures in the molecule of the aforementioned third compound, wherein at least one of the carbon atoms in X1 to X8 is bonded to Ar. 362 Element bonding,

[2188] In the above general formula (AC24), X1 to X8 are each independently a nitrogen atom or a CR atom. 363 Or, to constitute Ar 362 Carbon atoms bonded by elements,

[2189] In the above general formulas (AC22) to (AC24), in R 363 In the case of multiple Rs, multiple Rs 363 They may be identical or different, consisting of multiple Rs 363 One or more groups consisting of two or more adjacent elements.

[2190] They bond together to form substituted or unsubstituted monocyclic rings.

[2191] They bond together to form substituted or unsubstituted fused rings, or

[2192] They do not bond with each other.

[2193] R does not form the aforementioned substituted or unsubstituted monocyclic rings and does not form the aforementioned substituted or unsubstituted fused rings. 363 Each independently relates to R in the above general formula (302) 32 Same meaning

[2194] In the above general formulas (AC1)~(AC3), (AC19)~(AC21) and (AC24), * respectively represent and constitute Ar 362 (The bonded parts of the element.)

[2195] In this embodiment, it is also preferred that the third compound is a compound represented by the following general formula (33).

[2196] [Chemical Formula 325]

[2197]

[2198] (In the above general formula (33),

[2199] X 33 It is an oxygen atom, a sulfur atom, or a group represented by N-Rb.

[2200] Z1~Z 12Each is independently a nitrogen atom or a group represented by C-Rc.

[2201] Ar 34 and Ar 35 Each independently

[2202] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2203] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2204] L 34 and L 35 Each independently

[2205] single bond,

[2206] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2207] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2208] Rb and Rc are each independent of each other.

[2209] hydrogen atom,

[2210] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2211] Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms

[2212] Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms

[2213] Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms

[2214] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2215] -C(=O)R 908 The groups shown

[2216] -COOR 909 The groups shown

[2217] -P(=O)(R 910 (R) 911 The groups shown in the figure,

[2218] -Ge(R 912 (R) 913 (R) 914 The groups shown in the figure,

[2219] cyano,

[2220] Nitro,

[2221] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2222] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2223] When multiple Rc exist, these Rcs may be identical or different from each other.

[2224] In the compounds represented by the above general formula (33), in -L 34 -Ar 34 The group shown is related to -L 35 -Ar 35 When the groups shown are the same substituents, it is also preferred that Z1 and Z2 are the same substituents. 12 Z2 and Z 11 , Z3 and Z 10 The groups Z4 and Z9, Z5 and Z8, and Z6 and Z7 are not all identical groups. In this case, in the above general formula (33), the group containing X... 33 The right-side fusion structure of the pentagon and the inclusion of X 33 The structure of the left side of the five-membered ring is different, and the compound shown in the above general formula (33) is a compound with an asymmetric structure.

[2225] In the compounds represented by the above general formula (33), it is preferred that -L 34 -Ar 34 The group shown is related to -L 35 -Ar 35 The groups shown are different from each other. In this case, as in the above, the compound shown by the above general formula (33) is a compound with an asymmetric structure.

[2226] In this embodiment, it is also preferred that the third compound is a compound represented by the following general formula (32).

[2227]

Chemical Formula 326

[2228]

[2229] (In the above general formula (32),

[2230] Ar 31 and Ar 32 Each independently

[2231] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2232] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2233] L 31 and L 32 Each independently

[2234] single bond,

[2235] Substituted or unsubstituted arylene groups with 6 to 50 carbon atoms, or

[2236] Divalent heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2237] L 33 for

[2238] Substituted or unsubstituted monocyclic hydrocarbon groups with 6 or fewer carbon atoms, or

[2239] Monocyclic heterocyclic groups with 6 or fewer cyclic atoms, whether substituted or unsubstituted.

[2240] m is 0, 1, 2, or 3, and multiple L 33 They are the same or different.

[2241] X1~X8 and Y1~Y8 are each independently N or CRf.

[2242] Among them, one of X5 to X8 and one of Y1 to Y4 are connected via L. 33 The bonded carbon atoms may be directly bonded carbon atoms.

[2243] Rf is independent of each

[2244] hydrogen atom,

[2245] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms

[2246] -Si(R 901 (R) 902 (R) 903 The groups shown in the figure,

[2247] Halogen atoms,

[2248] Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or

[2249] Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted.

[2250] When multiple Rf exist, these Rf may be the same or different from each other.

[2251] The compounds represented by the above general formula (32) satisfy one or both of the following (i) and (ii).

[2252] (i)Ar 31 and Ar 32At least one of them is an aryl group with 6 to 50 cyclic carbons substituted by a cyano group, or a heterocyclic group with 5 to 50 cyclic atoms substituted by a cyano group.

[2253] (ii) At least one of X1 to X4 and Y5 to Y8 is a CRf, and at least one of the Rf groups of X1 to X4 and Y5 to Y8 is an aryl group with 6 to 50 cyclic carbons substituted with a cyano group, or a heterocyclic group with 5 to 50 cyclic atoms substituted with a cyano group.

[2254] In the compounds shown in the above general formula (32), the aromatic hydrocarbon group with 6 to 50 cyclic carbons substituted with cyano and the heterocyclic group with 5 to 50 cyclic atoms substituted with cyano may further have substituents other than cyano.

[2255] In the compound represented by the above general formula (32), m is preferably 0, 1 or 2, more preferably 0 or 1. In the compound represented by the above general formula (32), when m is 0, one of X5 to X8 is directly bonded to one of Y1 to Y4 via a single bond.

[2256] In the compounds represented by the above general formula (32), it is preferred that any one of the groups selected from X6 and Y3, X6 and Y2, and X7 and Y3 is via L 33 Bonded carbon atoms, or directly bonded carbon atoms.

[2257] The group of X6 and Y3 is connected via L 33 In the case of bonded carbon atoms, or directly bonded carbon atoms, the compound represented by the above general formula (32) is represented by the following general formula (321).

[2258] [Chemical Formula 327]

[2259]

[2260] (In the above general formula (321), Ar) 31 Ar 32 L 31 L 32 L 33 m, X1~X5, X7~X8, Y1~Y2 and Y4~Y8 are respectively related to Ar in the above general formula (32). 31 Ar 32 L 31 L 32 L 33 The terms m, X1~X5, X7~X8, Y1~Y2, and Y4~Y8 have the same meaning, and the compound represented by the above general formula (321) satisfies at least one of the conditions in (i) and (ii) above.

[2261] In the compounds represented by the above general formula (32), -Ar is preferred. 31 -L 31 The group shown is related to -Ar 32 -L 32 The groups shown are different from each other.

[2262] As L 33 The monocyclic hydrocarbon group having 6 or fewer carbon atoms is preferably at least one group selected from the group consisting of phenylene, cyclopentenylene, cyclopentadienylene, cyclohexylene, and cyclopentenylene, and more preferably phenylene.

[2263] As L 33 The monocyclic heterocyclic group having 6 or fewer cyclic atoms is preferably at least one group selected from the group consisting of pyrrolyl, pyrazinyl, pyridinyl, furylene, and thiophenylene.

[2264] In one embodiment, the light-emitting layer may contain two or more third compounds with different molecular structures. By mixing compounds with different charge transport properties, the charge balance within the light-emitting layer is improved, and an increase in luminous efficiency is expected. Furthermore, by forming an excitocomplex with two or more third compounds (the first host material), the excitation energy decreases, allowing for driving at a lower voltage compared to the case where the light-emitting layer contains only one third compound.

[2265] (Method for manufacturing the third compound)

[2266] The third compound can be manufactured using known methods. Alternatively, the third compound can also be manufactured by following known methods, using known alternative reactions and starting materials corresponding to the target substance.

[2267] (Specific examples of the third compound)

[2268] Specific examples of the third compound as a third embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

[2269] [Chemical Formula 328]

[2270]

[2271]

Chemical Formula 329

[2272]

[2273]

Chemical Formula 330

[2274]

[2275]

Chemical Formula 331

[2276]

[2277]

Chemical Formula 332

[2278]

[2279]

Chemical Formula 333

[2280]

[2281]

Chemical Formula 334

[2282]

[2283]

Chemical Formula 335

[2284]

[2285]

Chemical Formula 336

[2286]

[2287]

Chemical Formula 337

[2288]

[2289]

Chemical Formula 338

[2290]

[2291] [Chemical Formula 339]

[2292]

[2293] [Chemical Formula 340]

[2294]

[2295]

Chemical Formula 341

[2296]

[2297]

Chemical Formula 342

[2298]

[2299]

Chemical Formula 343

[2300]

[2301]

Chemical Formula 344

[2302]

[2303] [Chemical Formula 345]

[2304]

[2305]

Chemical Formula 346

[2306]

[2307] [Chemical Formula 347]

[2308]

[2309] [Chemical Formula 348]

[2310]

[2311] [Chemical Formula 349]

[2312]

[2313] [Chemical Formula 350]

[2314]

[2315]

Chemical Formula 351

[2316]

[2317]

Chemical Formula 352

[2318]

[2319]

Chemical Formula 353

[2320]

[2321] [Chemical Formula 354]

[2322]

[2323]

Chemical Formula 355

[2324]

[2325] [Chemical Formula 356]

[2326]

[2327] [Chemical Formula 357]

[2328]

[2329] [Chemical Formula 358]

[2330]

[2331] [Chemical Formula 359]

[2332]

[2333]

Chemical Formula 360

[2334]

[2335]

Chemical Formula 361

[2336]

[2337]

Chemical Formula 362

[2338]

[2339]

Chemical Formula 363

[2340]

[2341]

Chemical Formula 364

[2342]

[2343]

Chemical Formula 365

[2344]

[2345]

Chemical Formula 366

[2346]

[2347]

Chemical Formula 367

[2348]

[2349]

Chemical Formula 368

[2350]

[2351] [Chemical Formula 369]

[2352]

[2353] [Chemical Formula 370]

[2354]

[2355]

Chemical Formula 371

[2356]

[2357]

Chemical Formula 372

[2358]

[2359]

Chemical Formula 373

[2360]

[2361] [Chemical Formula 374]

[2362]

[2363] [Chemical Formula 375]

[2364]

[2365] [Chemical Formula 376]

[2366]

[2367]

Chemical Formula 377

[2368]

[2369] [Chemical Formula 378]

[2370]

[2371] [Chemical Formula 379]

[2372]

[2373]

Chemical Formula 380

[2374]

[2375]

Chemical Formula 381

[2376]

[2377]

Chemical Formula 382

[2378]

[2379]

Chemical Formula 383

[2380]

[2381]

Chemical Formula 384

[2382]

[2383]

Chemical Formula 385

[2384]

[2385] [Chemical Formula 386]

[2386]

[2387] [Chemical Formula 387]

[2388]

[2389]

Chemical Formula 388

[2390]

[2391] [Chemical Formula 389]

[2392]

[2393] [Chemical Formula 390]

[2394]

[2395]

Chemical Formula 391

[2396]

[2397] [Chemical Formula 392]

[2398]

[2399]

Chemical Formula 393

[2400]

[2401] (The relationship between the first host material, the sensitizing material, and the fluorescent luminescent material in the luminescent layer)

[2402] In one embodiment, the sensitizing material is a phosphorescent metal complex. In another embodiment, the luminescent layer may contain a phosphorescent metal complex as the sensitizing material but not a delayed fluorescence compound.

[2403] Figure 4 This diagram illustrates an example of the energy level relationship between the first host material (third compound), the phosphorescent metal complex (second compound) serving as a sensitizer, and the fluorescent material (first compound) in the luminescent layer. Figure 4In this context, S0 represents the ground state. S1(M3) represents the lowest excited singlet state of the first host material, and T1(M3) represents the lowest excited triplet state of the first host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M1) represents the lowest excited singlet state of the fluorescent material, and T1(M1) represents the lowest excited triplet state of the fluorescent material. Figure 4 The dashed arrow pointing from T1(M2) to S1(M1) represents the dipole energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material.

[2404] like Figure 4 As shown, if a phosphorescent metal complex is used as the sensitizing material, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can undergo intersystem crossing to the lowest excited triplet state T1(M2) due to spin-orbit interactions and heavy atom effects. Then, a dipole energy transfer occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent material, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of the fluorescent material can be observed. It is believed that, theoretically, the internal quantum efficiency can be increased to 100% using this mechanism.

[2405] In one embodiment, it is also preferred that the band gap T at 77 [K] of the phosphorescent metal complex is... 77K (GP2) and the lowest excitation singlet energy S1(D) of the fluorescent luminescent material satisfy the following mathematical expression (Mathematical Expression 3).

[2406] T 77K (GP2)>S1(D) …(Mathematical Expression 3)

[2407] In one embodiment, it is also preferred that the bandgap T at 77 [K] of the first host material and the phosphorescent metal complex is... 77K The following mathematical expression (Mathematical Expression 3A) satisfies the relationship.

[2408] T 77K (H1)>T 77K (GP2) …(Mathematical expression 3A)

[2409] In one embodiment, it is also preferred that the bandgap T at 77 [K] of the first host material and the phosphorescent metal complex is... 77K The lowest excitation singlet energy S1(D) of the fluorescent luminescent material satisfies the following mathematical expression (Mathematical Expression 3B).

[2410] T 77K (H1)>T 77K (GP2)>S1(D) …(Mathematical expression 3B)

[2411] The lowest excitation singlet energy S1(D) of the fluorescent luminescent material and the band gap T at 77 [K] of the fluorescent luminescent material 77K (D) usually satisfies the following mathematical expression (mathematical expression 3C).

[2412] S1(D)>T 77K (D) …(Mathematical expression 3C)

[2413] In one embodiment, it is also preferred that the lowest excitation singlet energy S1(H1) of the first host material and the lowest excitation singlet energy S1(GP2) of the phosphorescent metal complex satisfy the following mathematical expression (Mathematical Expression 5).

[2414] S1(H1)>S1(GP2) …(Mathematical Expression 5)

[2415] In one embodiment, it is also preferred that the lowest excitation singlet energy S1(GP2) of the phosphorescent metal complex and the lowest excitation singlet energy S1(D) of the fluorescent material satisfy the following mathematical formula (Formula 5A).

[2416] S1(GP2)>S1(D) …(Mathematical expression 5A)

[2417] In one embodiment, it is also preferred that the lowest excitation singlet energy S1 of the first host material, the phosphorescent metal complex, and the fluorescent material satisfies the following mathematical formula (Formula 5B).

[2418] S1(H1)>S1(GP2)>S1(D) …(Mathematical expression 5B)

[2419] In one embodiment of the third embodiment, the sensitizing material is a delayed-fluorescence compound. In another embodiment of the third embodiment, the luminescent layer contains a delayed-fluorescence compound as the sensitizing material and may not contain a phosphorescent metal complex.

[2420] Figure 5 This is a diagram illustrating an example of the energy level relationship between the first host material (third compound), the delayed-fluorescence compound (second compound) acting as a sensitizer, and the fluorescent luminescent material (first compound) in the luminescent layer. Figure 5In this context, S0 represents the ground state. S1(M3) represents the lowest excited singlet state of the first host material, and T1(M3) represents the lowest excited triplet state of the first 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(M1) represents the lowest excited singlet state of the fluorescent luminescent material, and T1(M1) represents the lowest excited triplet state of the fluorescent luminescent material. Figure 5 The dashed arrow pointing from S1(M2) to S1(M1) represents a Forster-type energy transfer from the lowest excited singlet state of a delayed fluorescent compound to the lowest excited singlet state of a fluorescent material.

[2421] like Figure 5 As shown, if a compound with a small ΔST(M2) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo a reverse intersystem crossing to the lowest excited singlet state S1(M2) using thermal energy. Then, a 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(M1). As a result, fluorescence luminescence originating from the lowest excited singlet state S1(M1) of the fluorescent material can be observed. It is believed that, theoretically, the internal quantum efficiency can be increased to 100% by utilizing delayed fluorescence based on this TADF mechanism.

[2422] In one embodiment, it is also preferred that the lowest excitation singlet energy S1(GT2) of the delayed fluorescence compound and the lowest excitation singlet energy S1(D) of the fluorescent material satisfy the following mathematical formula (Formula 4).

[2423] S1(GT2)>S1(D) …(Mathematical Expression 4)

[2424] In one embodiment, it is also preferred that the lowest excitation singlet energy S1(H1) of the first host material and the lowest excitation singlet energy S1(GT2) of the delayed fluorescence compound satisfy the following mathematical formula (Formula 4A).

[2425] S1(H1)>S1(GT2) …(Mathematical expression 4A)

[2426] In one embodiment, it is also preferred that the lowest excitation singlet energy S1 of the first host material, the delayed fluorescence compound, and the fluorescent luminescent material satisfies the following mathematical formula (Formula 4B).

[2427] S1(H1)>S1(GT2)>S1(D) …(Mathematical expression 4B)

[2428] In one embodiment, it is also preferred that the bandgap T at 77 [K] of the first host material and the delayed fluorescence compound is... 77K The following mathematical expression (Mathematical Expression 6) is satisfied.

[2429] T 77K (H1)>T 77K (GT2) …(Mathematical Expression 6)

[2430] In one embodiment, it is also preferred that the band gap T at 77 [K] of the delayed fluorescent compound is [not specified]. 77K (GT2) and the band gap T at 77 [K] of the fluorescent material 77K (D) satisfies the following mathematical expression (Mathematical Expression 6A).

[2431] T 77K (GT2)>T 77K (D) …(Mathematical expression 6A)

[2432] In one embodiment, it is also preferred that the band gap T at 77 [K] for the first host material, the delayed fluorescence compound, and the fluorescent luminescent material is [value missing]. 77K The following mathematical expression (Mathematical Expression 6B) is satisfied.

[2433] T 77K (H1)>T 77K (GT2)>T 77K (D) …(Mathematical expression 6B)

[2434] When the organic EL element of the third embodiment emits light, the light-emitting layer is preferably emitted mainly by a fluorescent compound.

[2435] The maximum peak wavelength of light emitted by the organic EL element was determined as follows.

[2436] Applying a voltage to an organic EL element to achieve a current density of 10 mA / cm² 2 The spectroradiance spectrum at that time was measured using a CS-2000 spectroradiometer (manufactured by Konica Minolta Co., Ltd.).

[2437] In the obtained spectroradiance spectrum, the peak wavelength of the emission spectrum where the luminous intensity reaches its maximum is determined and taken as the maximum peak wavelength (unit: nm).

[2438] (The content of compounds in the luminescent layer)

[2439] The content of the first host material (third compound), the sensitizing material (second compound), and the fluorescent luminescent material (first compound) contained in the luminescent layer is preferably within the following range, for example.

[2440] The content of the first host material (third compound) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more.

[2441] The content of the first host material (third compound) in the light-emitting layer is preferably 95% by mass or less, more preferably 90% by mass or less.

[2442] When the sensitizing material (second compound) is a delayed fluorescence compound, the content of the delayed fluorescence compound in the luminescent layer is preferably 5% by mass or more, and more preferably 10% by mass or more.

[2443] The content of delayed fluorescence compound in the luminescent layer is preferably 50% by mass or less, more preferably 30% by mass or less.

[2444] When the sensitizing material (second compound) is a phosphorescent metal complex, the content of the phosphorescent metal complex in the luminescent layer is preferably 5% by mass or more, and more preferably 10% by mass or more.

[2445] The content of phosphorescent metal complex in the light-emitting layer is preferably 50% by mass or less, more preferably 30% by mass or less.

[2446] The content of the fluorescent luminescent material (first compound) in the luminescent layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more.

[2447] The content of the fluorescent luminescent material (first compound) in the luminescent layer is preferably 10% by mass or less, more preferably 5% by mass or less.

[2448] The maximum allowed content of the first host material (third compound), sensitizing material (second compound), and fluorescent luminescent material (first compound) in the luminescent layer is 100% by mass. It should be noted that this embodiment does not exclude the inclusion of materials other than the first host material, sensitizing material, and fluorescent luminescent material in the luminescent layer. In the third embodiment, the luminescent layer may contain only one type of the first host material, sensitizing material, and fluorescent luminescent material, or it may contain two or more types.

[2449] (Thickness of the light-emitting layer)

[2450] The thickness of the light-emitting layer in the organic EL element of the third embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less.

[2451] The structure of organic EL elements will be further explained.

[2452] (Substrate)

[2453] The substrate is used as a support for the organic electroluminescent (EL) element. Examples of substrates that can be used include glass, quartz, and plastic. Flexible substrates can also be used. A flexible substrate is a substrate that can be bent (flexible). Examples of flexible substrates include plastic substrates. Materials used to form the plastic substrate include, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Inorganic vapor-deposited films can also be used.

[2454] (anode)

[2455] The anode formed on the substrate is preferably a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically 4.0 eV or higher). Examples of such anodes include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[2456] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% zinc oxide relative to indium oxide. Alternatively, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% tungsten oxide and 0.1% to 1% zinc oxide relative to indium oxide. Furthermore, these materials can also be fabricated using vacuum evaporation, coating, inkjet printing, spin coating, and other similar methods.

[2457] In the EL layer formed on the anode, the hole injection layer formed with the anode in contact with the ground is formed using a composite material that is easy to inject holes with, which is independent of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[2458] Elements belonging to Group 1 or Group 2 of the periodic table that have low work functions can also be used, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and their alloys to form the anode, vacuum evaporation or sputtering methods can be used. Furthermore, when using silver paste, coating or inkjet printing methods can be used.

[2459] When the organic EL element is a bottom-emitting type, the anode is preferably formed of a metallic material that has light transmittance or semi-transmittance properties, allowing light from the light-emitting layer to pass through. In this specification, light transmittance or semi-transmittance refers to the property of transmitting 50% or more (preferably 80% or more) of the light emitted by the light-emitting layer. The metallic material having light transmittance or semi-transmittance properties can be appropriately selected from the materials listed in the section on the anode.

[2460] In the case of a top-emitting organic EL element, the anode is a reflective electrode with a reflective layer. The reflective layer is preferably formed of a metallic material with light reflectivity. In this specification, light reflectivity refers to the property of reflecting 50% or more (preferably 80% or more) of the light emitted by the light-emitting layer. The metallic material with light reflectivity can be appropriately selected from the materials listed in the section on the anode.

[2461] The anode can consist of only a reflective layer, or it can be a multilayer structure having a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has both a reflective layer and a conductive layer, it is preferable to place the conductive layer between the reflective layer and the hole transport region. The conductive layer can be appropriately selected from the materials listed in the section on anodes described above.

[2462] (cathode)

[2463] The cathode preferably uses metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically, below 3.8 eV). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[2464] It should be noted that when using alkali metals, alkaline earth metals, or alloys containing them to form the cathode, vacuum evaporation or sputtering methods can be used. Additionally, when using silver paste, coating or inkjet printing methods can be used.

[2465] It should be noted that by setting an electron injection layer, various conductive materials such as Al, Ag, ITO, graphene, and indium tin oxide containing silicon or silicon oxide can be used to form cathodes regardless of the work function. These conductive materials can be deposited using sputtering, inkjet printing, spin coating, and other methods.

[2466] 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 metallic material. The light-reflective metallic material can be appropriately selected from the materials listed in the section on the cathode described above.

[2467] In the case of a top-emitting organic EL element, the cathode is preferably formed of a transparent or semi-transparent metallic material that transmits light from the light-emitting layer. The transparent or semi-transparent metallic material can be appropriately selected from the materials listed in the section on cathodes described above.

[2468] The organic EL element involved in the third embodiment can be a bottom-emitting organic EL element. Alternatively, the organic EL element involved in this embodiment can be a top-emitting organic EL element.

[2469] When the organic EL element is a bottom-emitting type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode.

[2470] When the organic EL element is a top-emitting type, it is preferable that the anode is a light-reflective electrode with light reflectivity and the cathode is a light-transmitting electrode with light transmittance.

[2471] (Capping layer)

[2472] In the case of top-emitting organic EL elements, the organic EL elements usually have a capping layer on the top of the cathode.

[2473] The capping layer may contain, for example, at least one compound selected from polymers, metal oxides, metal fluorides, metal borides, silicon nitrides, and silicon compounds (silicon oxides, etc.).

[2474] In addition, the capping layer may contain, for example, at least one compound selected from aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives.

[2475] In addition, laminates containing layers of these substances can also be used as capping layers.

[2476] (hole injection layer)

[2477] A hole injection layer is a layer containing a material with high hole injection capability. Materials with high hole injection capability can 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.

[2478] In addition, examples of substances with high hole injection potential include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB), and 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as TDATA). Aromatic amine compounds such as DNTPD, 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) are among the examples.

[2479] In addition, high-molecular-weight compounds (oligomers, dendritic polymers, polymers, etc.) can also be used as substances with high hole injection capabilities. Examples include poly(N-vinylcarbazole) (PVK), poly(4-vinyltriphenylamine) (PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (Poly-TPD). Furthermore, acid-containing polymers such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can also be used.

[2480] (Hole transport layer)

[2481] The hole transport layer is a layer containing substances with high hole transport capacity. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N- Aromatic amine compounds such as [phenylamino]biphenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) are mentioned. The substances described herein mainly possess 10 -6 cm 2 Substances with a hole mobility of / Vs or higher.

[2482] Carbazole derivatives such as CBP, CzPA, and PCzPA, as well as 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) (PVK) and poly(4-vinyltriphenylamine) (PVTPA) can also be used.

[2483] It should be noted that any substance whose hole transport capacity is higher than that of an electron can also use these other substances. It should also be noted that the layer containing the substance with high hole transport capacity can be not only a single layer, but also a layer composed of two or more layers formed by stacking the aforementioned substances.

[2484] (Electron transport layer)

[2485] The electron transport layer is a layer containing substances with high electron transport capacity. The electron transport layer can utilize 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) high molecular weight compounds. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium (BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to metal complexes, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as p-EtTAZ), phenanthroline (abbreviated as BPhen), copper hydroxide (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)zirconia (abbreviated as BzOs) can also be used. The substances described herein mainly possess 10 -6 cm 2 Materials with an electron mobility of / Vs or higher. It should be noted that any material whose electron transport capability is higher than its hole transport capability can also be used as an electron transport layer, regardless of the specific materials mentioned above. Furthermore, the electron transport layer can be a single layer or a layer composed of two or more layers of the aforementioned materials stacked together.

[2486] Alternatively, polymeric compounds can be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[2487] (Electron injection layer)

[2488] The electron injection layer is a layer containing a material with high electron-injection properties. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used in the electron injection layer. Alternatively, materials containing alkali metals, alkaline earth metals, or their compounds can be used; specifically, materials containing magnesium (Mg) in Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently in this case.

[2489] Alternatively, a composite material consisting of an organic compound and an electron donor can be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because it generates electrons within the organic compound through the electron donor. In this case, the organic compound is preferably a material with excellent electron transport properties; specifically, substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) described above can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides and alkaline earth metal oxides are preferred, such as lithium oxides, calcium oxides, and barium oxides. Furthermore, Lewis bases such as magnesium oxide can also be used. Additionally, organic compounds such as tetrathiofulvalene (TTF) can also be used.

[2490] (Layer Formation Method)

[2491] The method for forming each layer of the organic EL element involved in any of the embodiments described above is not limited except as specifically mentioned above. Known methods such as vacuum evaporation, sputtering, plasma deposition, ion plating and other dry film formation methods, spin coating, immersion coating, flow coating and inkjet coating and other wet film formation methods can be used.

[2492] (film thickness)

[2493] The thickness of each organic layer in 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 easily generated; if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of a few nm to 1 μm.

[2494] The organic EL element according to the third embodiment can improve the luminous efficiency of the organic EL element. The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[2495] [Fourth Implementation Method]

[2496] The structure of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same symbols, names, etc., are given to the same constituent elements as in the third embodiment, and the description is omitted or simplified. In addition, in the fourth embodiment, the same materials and compounds as those described in the third embodiment may be used for materials and compounds not specifically mentioned.

[2497] (Emitting layer)

[2498] In the organic EL element according to the fourth embodiment, the light-emitting layer contains a first host material (third compound) and a fluorescent luminescent material (first compound). The first host material and the fluorescent luminescent material are different materials. In the fourth embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex.

[2499] In the fourth embodiment, a single layer contains a first host material and a fluorescent luminescent material. For example, when an organic EL element has one luminescent layer, the single luminescent layer contains the first host material and the fluorescent luminescent material; when multiple luminescent layers are present, any single luminescent layer among the multiple luminescent layers contains the first host material and the fluorescent luminescent material.

[2500] [Fluorescent materials]

[2501] In the fourth embodiment, the fluorescent luminescent material is the compound involved in the first embodiment (the first compound).

[2502] [First Main Material]

[2503] In the fourth embodiment, the first host material may be the third compound described in the third embodiment.

[2504] (The relationship between the first host material and the fluorescent luminescent material in the luminescent layer)

[2505] Figure 6 This is a diagram illustrating an example of the energy level relationship between the first host material and the fluorescent luminescent material when the luminescent layer contains a first host material (third compound) and a fluorescent luminescent material (first compound).

[2506] exist Figure 6 In this context, S0 represents the ground state. S1(M3) represents the lowest excited singlet state of the first host material, and T1(M3) represents the lowest excited triplet state of the first host material. S1(M1) represents the lowest excited singlet state of the fluorescent luminescent material, and T1(M1) represents the lowest excited triplet state of the fluorescent luminescent material. Figure 6The dashed arrow pointing from S1(M3) to S1(M1) indicates a Forster-type energy transfer from the lowest excited singlet state of the first host material to the lowest excited singlet state of the fluorescent material, generating the lowest excited singlet state S1(M1). As a result, fluorescence luminescence originating from the lowest excited singlet state S1(M1) can be observed in the fluorescent material. It is believed that, theoretically, the internal quantum efficiency could be increased to 100% using this mechanism.

[2507] exist Figure 6 Preferably, the lowest excitation singlet state energy S1(D) of the fluorescent luminescent material is similar to the band gap T at 77 [K] of the fluorescent luminescent material. 77K (D) satisfies the relationship of the above mathematical expression (mathematical expression 3C).

[2508] exist Figure 6 In this context, it is also preferred that the bandgap T at 77 [K] of the first host material and the fluorescent luminescent material is [value missing]. 77K The following mathematical expression (Mathematical Expression 6C) is satisfied.

[2509] T 77K (H1)>T 77K (D) …(Mathematical expression 6C)

[2510] exist Figure 6 Preferably, the lowest excitation singlet energy S1 of the first host material and the fluorescent luminescent material satisfies the following mathematical formula (formula 4C).

[2511] S1(H1)>S1(D) …(Mathematical expression 4C)

[2512] (The content of compounds in the luminescent layer)

[2513] In the fourth embodiment, the content of the first host material (third compound) and the fluorescent luminescent material (first compound) contained in the luminescent layer is preferably within the following range, for example.

[2514] The content of the first main material 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. Alternatively, the content of the first main material 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.

[2515] The content of the fluorescent luminescent material is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less.

[2516] It should be noted that the third embodiment does not exclude the inclusion of materials other than the first host material and the fluorescent luminescent material in the light-emitting layer.

[2517] The luminescent layer may contain only one type of primary host material, or it may contain two or more types of primary host materials. The luminescent layer may contain only one type of fluorescent luminescent material, or it may contain two or more types of fluorescent luminescent materials.

[2518] The organic EL element according to the fourth embodiment can improve the luminous efficiency of the organic EL element. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[2519] [Fifth Implementation Method]

[2520] The structure of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third and fourth embodiments are given the same symbols, names, etc., and are omitted or simplified in description. In addition, in the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third and fourth embodiments can be used.

[2521] (Emitting layer)

[2522] In the organic EL element according to the fifth embodiment, the light-emitting layer contains a delayed fluorescence compound and a fluorescent luminescent material (first compound). The delayed fluorescence compound and the fluorescent luminescent material are different materials. In the fifth embodiment, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex.

[2523] In the fifth embodiment, the single layer contains a delayed fluorescence compound and a fluorescent luminescent material. For example, when the organic EL element has one luminescent layer, the single luminescent layer contains a delayed fluorescence compound and a fluorescent luminescent material; when it has multiple luminescent layers, any single luminescent layer among the multiple luminescent layers contains a delayed fluorescence compound and a fluorescent luminescent material.

[2524] [Fluorescent materials]

[2525] In the fifth embodiment, the fluorescent luminescent material is the compound involved in the first embodiment (the first compound).

[2526] [Delayed fluorescence compounds]

[2527] In the fifth embodiment, a second compound, which is a sensitizing material described in the third embodiment and is also a delayed fluorescence compound, can be used as the delayed fluorescence compound.

[2528] Figure 7 This is a diagram illustrating an example of the energy level relationship between the delayed-fluorescence compound (second compound) and the fluorescent luminescent material (first compound) in a case where the luminescent layer contains both a delayed-fluorescence compound (second compound) and a fluorescent luminescent material (first compound). Figure 7 In this context, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of a delayed fluorescent compound, and T1(M2) represents the lowest excited triplet state of a delayed fluorescent compound. S1(M1) represents the lowest excited singlet state of a fluorescent luminescent material, and T1(M1) represents the lowest excited triplet state of a fluorescent luminescent material. Figure 7 The dashed arrow pointing from S1(M2) to S1(M1) represents a Forster-type energy transfer from the lowest excited singlet state of a delayed fluorescent compound to the lowest excited singlet state of a fluorescent material.

[2529] like Figure 7 As shown, if a compound with a small ΔST(M2) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo a reverse intersystem crossing to the lowest excited singlet state S1(M2) under the influence of thermal energy. Then, a 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(M1). As a result, fluorescence luminescence originating from the lowest excited singlet state S1(M1) of the fluorescent material can be observed. It is believed that, theoretically, the internal quantum efficiency can be increased to 100% by utilizing delayed fluorescence based on this TADF mechanism.

[2530] exist Figure 7 Preferably, the lowest excitation singlet state energy S1(D) of the fluorescent luminescent material is similar to the band gap T at 77 [K] of the fluorescent luminescent material. 77K (D) satisfies the relationship of the above mathematical expression (mathematical expression 3C).

[2531] exist Figure 7 Preferably, the lowest excitation singlet energy S1(GT2) of the delayed fluorescence compound and the lowest excitation singlet energy S1(D) of the fluorescent luminescent material satisfy the following mathematical formula (Formula 4).

[2532] S1(GT2)>S1(D) …(Mathematical Expression 4)

[2533] exist Figure 7 In this context, it is also preferred that the band gap T at 77 [K] of the delayed fluorescent compound is [specifically, a value that is not explicitly stated in the original text].77K (GT2) and the band gap T at 77 [K] of the fluorescent material 77K (D) satisfies the following mathematical expression (Mathematical Expression 6A).

[2534] T 77K (GT2)>T 77K (D) …(Mathematical expression 6A)

[2535] (The content of compounds in the luminescent layer)

[2536] In the fifth embodiment, the content of the delayed fluorescence compound (second compound) and the fluorescent luminescent material (first compound) contained in the luminescent layer is preferably within the following range, for example.

[2537] The content of the delayed fluorescence 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. Alternatively, the content of the delayed fluorescence 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.

[2538] The content of the fluorescent luminescent material is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less.

[2539] It should be noted that the third embodiment does not exclude the inclusion of materials other than delayed fluorescence compounds and fluorescent luminescent materials in the luminescent layer.

[2540] The luminescent layer may contain only one delayed-fluorescence compound or two or more delayed-fluorescence compounds. The luminescent layer may contain only one fluorescent material or two or more fluorescent materials.

[2541] The organic EL element according to the fifth embodiment can improve the luminous efficiency of the organic EL element. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[2542] [Sixth Implementation Method]

[2543] The structure of the organic EL element according to the sixth embodiment will be described. In the description of the sixth embodiment, the same symbols, names, etc. as those in the third to fifth embodiments are given and the description is omitted or simplified. In addition, in the sixth embodiment, the same materials and compounds as those described in the third to fifth embodiments may be used for materials and compounds not specifically mentioned.

[2544] (Emitting layer)

[2545] In the organic EL element according to the sixth embodiment, the light-emitting layer contains a first host material, a fourth compound as a second host material, a sensitizing material, and a fluorescent luminescent material. The first host material (third compound) and the second host material (fourth compound) are different from each other. Other aspects are the same as those of the organic EL element according to the third embodiment. In the sixth embodiment, the first host material, the second host material, the sensitizing material, and the fluorescent luminescent material are different materials.

[2546] In one embodiment of the sixth method, the light-emitting layer comprises a first host material, a second host material, a phosphorescent metal complex serving as a sensitizing material, and a fluorescent light-emitting material.

[2547] In one embodiment of the sixth embodiment, the luminescent layer comprises a first host material, a second host material, a delayed-fluorescence compound serving as a sensitizing material, and a fluorescent luminescent material. In this embodiment, it is preferable that the luminescent layer does not contain a phosphorescent metal complex.

[2548] In the sixth embodiment, a single layer contains a first host material, a second host material, a sensitizing material, and a fluorescent luminescent material. For example, when an organic EL element has one luminescent layer, the single luminescent layer contains the first host material, the second host material, the sensitizing material, and the fluorescent luminescent material; when multiple luminescent layers are present, any single luminescent layer among the multiple luminescent layers contains the first host material, the second host material, the sensitizing material, and the fluorescent luminescent material.

[2549] [Fluorescent materials]

[2550] In the sixth embodiment, the fluorescent luminescent material is the compound involved in the first embodiment (the first compound).

[2551] [Sensitized Materials]

[2552] In the sixth embodiment, the second compound (phosphorescent metal complex or delayed fluorescence compound) described in the third embodiment can be used as the sensitizing material.

[2553] [First Main Material and Second Main Material]

[2554] In the sixth embodiment, the first main material (third compound) described in the third embodiment can be used independently as both the first main material and the second main material.

[2555] (The relationship between the first host material, the second host material, the sensitizing material, and the fluorescent luminescent material in the luminescent layer)

[2556] In one embodiment of the sixth embodiment, the sensitizing material is a phosphorescent metal complex. In another embodiment of the sixth embodiment, the luminescent layer contains a phosphorescent metal complex as the sensitizing material and may not contain a delayed fluorescence compound.

[2557] In one embodiment of the sixth method, the light-emitting layer comprises a first host material (third compound), a second host material (fourth compound), a phosphorescent metal complex (second compound) serving as a sensitizing material, and a fluorescent material (first compound).

[2558] Figure 8 This is a diagram illustrating an example of the energy level relationships among the first host material (third compound), the second host material (fourth compound), the phosphorescent metal complex (second compound) serving as a sensitizer, and the fluorescent material (first compound) in the luminescent layer. Figure 8 In this diagram, S0 represents the ground state. S1(M3) represents the lowest excited singlet state of the first host material, and T1(M3) represents the lowest excited triplet state of the first host material. S1(M4) represents the lowest excited singlet state of the second host material, and T1(M4) represents the lowest excited triplet state of the second host material. S1(M2) represents the lowest excited singlet state of the phosphorescent metal complex, and T1(M2) represents the lowest excited triplet state of the phosphorescent metal complex. S1(M1) represents the lowest excited singlet state of the fluorescent material, and T1(M1) represents the lowest excited triplet state of the fluorescent material. Figure 8 The dashed arrow pointing from T1(M2) to S1(M1) represents the dipole energy transfer from the lowest excited triplet state of the phosphorescent metal complex to the lowest excited singlet state of the fluorescent material.

[2559] like Figure 8As shown, if a phosphorescent metal complex is used as the sensitizing material, the lowest excited singlet state S1(M2) of the phosphorescent metal complex can undergo intersystem crossing to the lowest excited triplet state T1(M2) under the influence of spin-orbit interactions and heavy atom effects. Then, a dipole energy transfer occurs from the lowest excited triplet state T1(M2) of the phosphorescent metal complex to the fluorescent luminescent material, generating the lowest excited singlet state S1(M1). As a result, fluorescence luminescence originating from the lowest excited singlet state S1(M1) of the fluorescent luminescent material can be observed. It is believed that, theoretically, the internal quantum efficiency can be increased to 100% using this mechanism.

[2560] It should be noted that the energy level relationship between S1(M3) and S1(M4), and the energy level relationship between T1(M3) and T1(M4) are not limited to... Figure 8 .

[2561] In one embodiment of the sixth embodiment, it is preferred that the light-emitting layer satisfies at least one of the above mathematical formulas (mathematical formula 3), (mathematical formula 3A), (mathematical formula 3B), (mathematical formula 3C), (mathematical formula 5), ​​(mathematical formula 5A), and (mathematical formula 5B).

[2562] In one embodiment, when the sensitizing material is a phosphorescent metal complex, the bandgap T of the second host material at 77 [K] is... 77K The band gap T at 77 [K] for (H2) and its phosphorescent metal complex 77K (GP2) is represented by the following mathematical expression (Mathematical Expression 31A).

[2563] T 77K (H2)>T 77K (GP2) …(Mathematical expression 31A)

[2564] In one embodiment, preferably, the band gap T at 77 [K] of the second host material and the phosphorescent metal complex is... 77K The lowest excitation singlet energy S1(D) of the fluorescent luminescent material satisfies the following mathematical expression (Mathematical Expression 31B).

[2565] T 77K (H2)>T 77K (GP2)>S1(D) …(Mathematical expression 31B)

[2566] In one embodiment, it is also preferred that the lowest excitation singlet energy S1(H2) of the second host material and the lowest excitation singlet energy S1(GP2) of the phosphorescent metal complex satisfy the following mathematical formula (Mathematical Formula 51).

[2567] S1(H2)>S1(GP2) …(Mathematical Expression 51)

[2568] In one embodiment, it is also preferred that the lowest excitation singlet energy S1 of the second host material, the phosphorescent metal complex, and the fluorescent material satisfies the following mathematical formula (Formula 51B).

[2569] S1(H2)>S1(GP2)>S1(D) …(Mathematical expression 51B)

[2570] In one embodiment of the sixth embodiment, the sensitizing material is a delayed-fluorescence compound. In another embodiment of the sixth embodiment, the luminescent layer contains a delayed-fluorescence compound as the sensitizing material. In yet another embodiment of the sixth embodiment, the luminescent layer does not contain a phosphorescent metal complex.

[2571] In one embodiment of the sixth method, the luminescent layer comprises a first host material (third compound), a second host material (fourth compound), a delayed fluorescence compound (second compound) serving as a sensitizing material, and a fluorescent luminescent material (first compound).

[2572] In one embodiment of the sixth embodiment, it is preferred that the light-emitting layer satisfies at least one of the mathematical formulas (mathematical formula 4), (mathematical formula 4A), (mathematical formula 4B), (mathematical formula 6), (mathematical formula 6A), and (mathematical formula 6B) described in the third embodiment.

[2573] In one embodiment, preferably, the lowest excitation singlet energy S1(H2) of the second host material and the lowest excitation singlet energy S1(GT2) of the delayed fluorescence compound satisfy the relationship of the above mathematical formula (Mathematical Formula 41A).

[2574] S1(H2)>S1(GT2) …(Mathematical expression 41A)

[2575] In one embodiment, preferably, the lowest excitation singlet energy S1 of the second host material, the delayed fluorescence compound, and the fluorescent luminescent material satisfies the relationship of the above mathematical formula (Mathematical Formula 41B). ...

Claims

1. The compound represented by the following formula (1), In equations (1) and (12), Ry is an aryl group, either substituted or unsubstituted, with 6 to 50 carbon atoms in a cyclic structure. At least one of the groups selected from R1 to R3 is the group represented by formula (12). R1 to R3 of the groups not shown in formula (12) are each independently... hydrogen atom, or Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, m1 + m2 = 4, m1 is 0, 1, 2, 3, or 4. n1 + n2 = 4, n1 is 0, 1, 2, 3 or 4. in, m1 + n1 is 1, 2, 3, 4, 5, 6, 7, or 8. HAr is a heterocyclic group with 5 to 50 substituted or unsubstituted cyclic atoms. R 11 ~R 15 R 18 R 19 R 21 ~R 23 R A and R B Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -C(=O)(OR 802 The groups shown in the figure, Halogen atoms, cyano, Nitro, -P(=O)(R 931 (R) 932 The groups shown in the figure, -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure, -B(R 936 (R) 937 The groups shown in the figure, -B(OR 938 (OR) 939 The groups shown in the figure, -OS(=O)2(R 940 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. Among them, R A and R B It cannot be both hydrogen atoms at the same time. When there are multiple groups represented by formula (12), the multiple groups represented by formula (12) may be the same as or different from each other. When multiple HArs exist, they may be identical or different from each other. In R 18 In the case of multiple Rs, multiple Rs 18 They are the same or different. In R 19 In the case of multiple Rs, multiple Rs 19 They are the same or different. In equation (12), * represents the bonding position. In the compound represented by formula (1), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. In R 901 In the case of multiple Rs, multiple Rs 901 They are the same or different. In R 902 In the case of multiple Rs, multiple Rs 902 They are the same or different. In R 903 In the case of multiple Rs, multiple Rs 903 They are the same or different. In R 904 In the case of multiple Rs, multiple Rs 904 They are the same or different. In R 905 In the case of multiple Rs, multiple Rs 905 They are the same or different. In R 906 In the case of multiple Rs, multiple Rs 906 They are the same or different. In R 907 In the case of multiple Rs, multiple Rs 907 They are the same or different. In R 801 In the case of multiple Rs, multiple Rs 801 They are the same or different. In R 802 In the case of multiple Rs, multiple Rs 802 They are the same or different. In R 931 In the case of multiple Rs, multiple Rs 931 They are the same or different. In R 932 In the case of multiple Rs, multiple Rs 932 They are the same or different. In R 933 In the case of multiple Rs, multiple Rs 933 They are the same or different. In R 934 In the case of multiple Rs, multiple Rs 934 They are the same or different. In R 935 In the case of multiple Rs, multiple Rs 935 They are the same or different. In R 936 In the case of multiple Rs, multiple Rs 936 They are the same or different. In R 937 In the case of multiple Rs, multiple Rs 937 They are the same or different. In R 938 In the case of multiple Rs, multiple Rs 938 They are the same or different. In R 939 In the case of multiple Rs, multiple Rs 939 They are the same or different. In R 940 In the case of multiple Rs, multiple Rs 940 They are the same or different.

2. The compound according to claim 1, wherein, At least one of the groups consisting of R1 and R3 is selected as the group shown in formula (12).

3. The compound according to claim 1, wherein, The compound represented by formula (1) is the compound represented by formula (10) below. In the above formula (10), R1~R3, R 11 ~R 15 R 18 R 19 The meanings of HAr, m1, m2, n1, and n2 are respectively the same as R1~R3, R in the above formula (1). 11 ~R 15 R 18 R 19 HAr, m1, m2, n1, and n2 have the same meaning. R4 to R6 are each independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or The group represented by formula (12), R 16 and R 17 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -C(=O)(OR 802 The groups shown in the figure, Halogen atoms, cyano, Nitro, -P(=O)(R 931 (R) 932 The groups shown in the figure, -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure, -B(R 936 (R) 937 The groups shown in the figure, -B(OR 938 (OR) 939 The groups shown in the figure, -OS(=O)2(R 940 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. When there are multiple groups represented by formula (12), the multiple groups represented by formula (12) may be the same as or different from each other. In equation (10), R 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 The meanings of each are independently related to R in equation (1). 901 R 902 R 903 R 904 R 905 R 906 R 907 R 801 R 802 R 931 R 932 R 933 R 934 R 935 R 936 R 937 R 938 R 939 and R 940 The meanings are the same.

4. The compound according to claim 3, wherein, One of the groups consisting of R1 to R3 is selected as the group represented by formula (12), and one of the groups consisting of R4 to R6 is selected as the group represented by formula (12).

5. The compound according to claim 3 or 4, wherein, The compound represented by formula (10) is a compound represented by formula (112) or (113) below. In equations (112) and (113), R1~R3, R 11 ~R 15 R 18 R 19 The meanings of HAr, m1, m2, n1, and n2 are respectively the same as R1~R3, R in the above formula (1). 11 ~R 15 R 18 R 19 HAr, m1, m2, n1, and n2 have the same meaning. R4~R6 and R 16 ~R 17 The meanings are respectively related to R4~R6 and R in the above formula (10). 16 ~R 17 The meaning is the same. R 21 ~R 23 R A and R B The meanings are respectively related to R in equation (12). 21 ~R 23 R A and R B The meanings are the same, multiple R 21 Multiple Rs that are the same or different 22 Multiple Rs that are the same or different 23 Multiple Rs that are the same or different A Multiple Rs that are the same or different B They are the same or different.

6. The compound according to any one of claims 1 to 5, wherein, R 11 ~R 15 R 18 R 19 and R 21 ~R 23 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

7. The compound according to claim 3 or 4, wherein, The compound represented by formula (10) is a compound represented by formula (110) or (111) below. In equations (110) and (111), R1~R6, R 11 ~R 17 The meanings of HAr are respectively related to R1~R6 and R in the above formula (10). 11 ~R 17 The meaning of HAr is the same as that of HAr; multiple HArs may be the same or different from each other. R 181 R 183 R 184 R 191 R 192 R 193 and R 194 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -C(=O)(OR 802 The groups shown in the figure, Halogen atoms, cyano, Nitro, -P(=O)(R 931 (R) 932 The groups shown in the figure, -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure, -B(R 936 (R) 937 The groups shown in the figure, -B(OR 938 (OR) 939 The groups shown in the figure, -OS(=O)2(R 940 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively related to R in equation (1). 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

8. The compound according to any one of claims 1 to 7, wherein, R A and R B One of them is Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Aryl groups, substituted or unsubstituted, with 6 to 50 carbon atoms. R A and R B The other party is hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

9. The compound according to any one of claims 1 to 8, wherein, R A and R B Each independently Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, or Aryl groups with 6 to 50 carbon atoms, either substituted or unsubstituted.

10. The compound according to any one of claims 1 to 9, wherein, HAr is a monovalent group derived from the ring structure shown in formula (13) below. In the above equation (13), X3 represents oxygen atoms, sulfur atoms, and N(R) atoms. 39 ) or Si(R 39A (R) 39B ), By R 351 and R 352 Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. By R 39A and R 39B Groups They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. By R 31 ~R 34 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R 39 R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 31 ~R 34 R 39A R 39B R 351 and R 352 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -C(=O)(OR 802 The groups shown in the figure, Halogen atoms, cyano, Nitro, -P(=O)(R 931 (R) 932 The groups shown in the figure, -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure, -B(R 936 (R) 937 The groups shown in the figure, -B(OR 938 (OR) 939 The groups shown in the figure, -OS(=O)2(R 940 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively related to R in equation (1). 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

11. The compound according to claim 10, wherein, The monovalent group derived from the ring structure shown in formula (13) is a monovalent group derived from the ring structure shown in formulas (13A), (13B), (13C), (13D), (13E), or (13F). In equations (13A), (13B), and (13C), R 31 ~R 34 R 39 R 351 and R 352 The meanings are respectively related to R in equation (13). 31 ~R 34 R 39 R 351 and R 352 The meaning is the same. In the given equations (13D), (13E), and (13F), R 31 ~R 34 and R 39 The meanings are respectively related to R in equation (13). 31 ~R 34 and R 39 The meaning is the same. By R 35 ~R 38 One or more groups consisting of two or more adjacent elements. They bond together to form substituted or unsubstituted monocyclic rings. They bond together to form substituted or unsubstituted fused rings, or They do not bond with each other. R does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted fused ring. 35 ~R 38 Each independently hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms Substituted or unsubstituted alkyl halides with 1 to 50 carbon atoms Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms Substituted or unsubstituted cycloalkyl groups with 3 to 50 carbon atoms -Si(R 901 (R) 902 (R) 903 The groups shown in the figure, -O-(R 904 The groups shown in the figure, -S-(R 905 The groups shown in the figure, -N(R 906 (R) 907 The groups shown in the figure, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms -C(=O)R 801 The groups shown -C(=O)(OR 802 The groups shown in the figure, Halogen atoms, cyano, Nitro, -P(=O)(R 931 (R) 932 The groups shown in the figure, -Ge(R 933 (R) 934 (R) 935 The groups shown in the figure, -B(R 936 (R) 937 The groups shown in the figure, -B(OR 938 (OR) 939 The groups shown in the figure, -OS(=O)2(R 940 The groups shown in the figure, Substituted or unsubstituted aryl groups with 6 to 50 carbon atoms, or Heterocyclic groups with 5 to 50 cyclic atoms, substituted or unsubstituted. R 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are respectively related to R in equation (1). 901 ~R 907 R 801 ~R 802 and R 931 ~R 940 The meanings are the same.

12. The compound according to claim 10 or 11, wherein, By R 351 and R 352 The groups formed are not mutually bonded. By R 31 ~R 34 Two or more adjacent groups are not bonded to each other. By R 35 ~R 38 Two or more adjacent groups are not bonded to each other.

13. The compound according to claim 11 or 12, wherein, The monovalent group derived from the ring structure shown in formula (13) is a monovalent group derived from the ring structure shown in formula (13D).

14. The compound according to any one of claims 11 to 13, wherein, The R in (13D) 39 A single bond that bonds with the formula (1).

15. The compound according to any one of claims 1 to 14, wherein, R 21 ~R 23 It is a hydrogen atom.

16. A material for an organic electroluminescent element comprising any one of claims 1 to 15.

17. An organic electroluminescent element having cathode, anode, and An organic layer disposed between the cathode and the anode, The organic layer comprises the compound of any one of claims 1 to 15 as the first compound.

18. The organic electroluminescent element according to claim 17, wherein, The organic layer has at least one light-emitting layer. At least one of the at least one light-emitting layers contains the first compound.

19. The organic electroluminescent element according to claim 18, wherein, At least one of the at least one light-emitting layers contains the first compound as a fluorescent light-emitting material.

20. The organic electroluminescent element according to claim 19, wherein, At least one of the at least one light-emitting layers contains the fluorescent light-emitting material, the sensitizing material, and the host material.

21. The organic electroluminescent element according to claim 20, wherein, The sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed fluorescence compounds.

22. The organic electroluminescent element according to claim 20 or 21, wherein, The sensitizing material is a phosphorescent metal complex.

23. The organic electroluminescent element according to claim 19, wherein, At least one of the at least one light-emitting layers contains the fluorescent light-emitting material and the host material.

24. The organic electroluminescent element according to any one of claims 18 to 23, wherein, A hole transport layer is included between the anode and the light-emitting layer closest to the anode among the at least one light-emitting layers.

25. The organic electroluminescent element according to any one of claims 18 to 24, wherein, An electron transport layer is included between the cathode and the light-emitting layer closest to the cathode among the at least one light-emitting layers.

26. An electronic device comprising the organic electroluminescent element according to any one of claims 17 to 25.

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