Compound and organic electroluminescent element using same

Abstract

A compound represented by formula (1): # imgabs0 # formula (1) wherein one of R101 to R105 is a single bond to which a group represented by formula (A1) is bonded.

Description

Technical Field

[0001] The present invention relates to a novel compound and an organic electroluminescent device using the same. Background Art

[0002] When voltage is applied to an organic electroluminescent element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to form excitons.

[0003] Conventional organic EL devices have not yet achieved sufficient device performance. While improvements have been made to materials used in organic EL devices to enhance device performance (see Patent Documents 1 to 6), further performance enhancement is still desired.

[0004] Prior art literature

[0005] Patent Literature

[0006] Patent Document 1: U.S. Patent Application Publication No. 2021 / 0083193

[0007] Patent Document 2: European Patent Application Publication No. 3127906

[0008] Patent Document 3: European Patent Application Publication No. 3533784

[0009] Patent Document 4: Chinese Patent Application Publication No. 110183302

[0010] Patent Document 5: Chinese Patent Application Publication No. 111303012

[0011] Patent Document 6: U.S. Patent Application Publication No. 2017 / 0104167 Summary of the Invention

[0012] An object of the present invention is to provide a high-performance organic EL device and a compound capable of realizing the organic EL device.

[0013] According to the present invention, the following compounds and the like are provided.

[0014] 1. A compound represented by the following formula (1),

[0015] [Chemistry 1]

[0016]

[0017] In formula (1),

[0018] R 101 ~R 105One of them is a single bond bonded to the group represented by the following formula (A1);

[0019] [Chemistry 2]

[0020] -(L A1 ) nA1 -Ar A1 (A1)

[0021] In formula (A1),

[0022] L A1 for:

[0023] single bond,

[0024] substituted or unsubstituted phenylene,

[0025] Substituted or unsubstituted biphenyldiyl,

[0026] Substituted or unsubstituted terphenyldiyl,

[0027] substituted or unsubstituted naphthylene,

[0028] substituted or unsubstituted phenanthrene diyl,

[0029] Substituted or unsubstituted triphenylene diyl,

[0030] Substituted or unsubstituted benzanthracenediyl,

[0031] substituted or unsubstituted pyrene diyl,

[0032] Substituted or unsubstituted Two bases,

[0033] Substituted or unsubstituted benzo Two bases,

[0034] Substituted or unsubstituted triphenylenediyl,

[0035] Substituted or unsubstituted benzotriphenylene,

[0036] substituted or unsubstituted fluorenediyl,

[0037] Substituted or unsubstituted benzofluorenediyl,

[0038] Substituted or unsubstituted dibenzofluorenediyl,

[0039] Substituted or unsubstituted naphthofluorenediyl,

[0040] substituted or unsubstituted fluoranthenediyl,

[0041] Substituted or unsubstituted benzofluoranthene diyl,

[0042] Substituted or unsubstituted perylenediyl, or

[0043] a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms; Ar A1 for:

[0044] substituted or unsubstituted phenyl,

[0045] Substituted or unsubstituted biphenyl,

[0046] Substituted or unsubstituted terphenyl,

[0047] substituted or unsubstituted naphthyl,

[0048] Substituted or unsubstituted phenoxy,

[0049] Substituted or unsubstituted triphenylene group,

[0050] Substituted or unsubstituted benzanthryl,

[0051] substituted or unsubstituted pyrenyl,

[0052] Substituted or unsubstituted base,

[0053] Substituted or unsubstituted benzo base,

[0054] Substituted or unsubstituted triphenylene,

[0055] Substituted or unsubstituted benzotriphenylene,

[0056] substituted or unsubstituted fluorenyl,

[0057] substituted or unsubstituted benzofluorenyl,

[0058] Substituted or unsubstituted dibenzofluorenyl,

[0059] Substituted or unsubstituted naphthofluorenyl,

[0060] substituted or unsubstituted fluoranthene group,

[0061] Substituted or unsubstituted benzofluoranthenyl,

[0062] Substituted or unsubstituted perylene, or

[0063] a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms;

[0064] nA1 is an integer from 0 to 3;

[0065] When nA1 is 0, (L A1 ) nA1 is a single bond;

[0066] When nA1 is 2 or 3, multiple L A1connected in series, Ar A1 The farthest L from the dinaphthofuran skeleton A1 Bonding; multiple L A1 Can be the same or different;

[0067] By R 106 ~R 112 , and R which is not a single bond bonded to the group represented by the above formula (A1) 101 ~R 105 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other;

[0068] R not bonded to each other 106 ~R 112 , and R which is not a single bond bonded to the group represented by the above formula (A1) and is not bonded to each other 101 ~R 105 Each independently is:

[0069] hydrogen atoms, or

[0070] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A1);

[0071] The substituents in the case of "substituted or unsubstituted" are:

[0072] an alkyl group having 1 to 50 carbon atoms,

[0073] a halogenated alkyl group having 1 to 50 carbon atoms,

[0074] an alkenyl group having 2 to 50 carbon atoms,

[0075] an alkynyl group having 2 to 50 carbon atoms,

[0076] a cycloalkyl group having 3 to 50 ring carbon atoms,

[0077] an alkylthio group having 1 to 50 carbon atoms,

[0078] an aryloxy group having 6 to 50 ring carbon atoms,

[0079] an arylthio group having 6 to 50 ring carbon atoms,

[0080] Aralkyl having 7 to 50 carbon atoms,

[0081] -Si(R 41 )(R 42 )(R 43 ),

[0082] -C(=O)R 44 、-COOR45 、

[0083] -Ge(R 49 )(R 50 )(R 51 ),

[0084] Hydroxyl,

[0085] cyano,

[0086] Nitro,

[0087] an aryl group having 6 to 50 ring carbon atoms, or

[0088] a monovalent heterocyclic group having 5 to 50 ring atoms;

[0089] R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms;

[0090] R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each may be the same or different.

[0091] 2. A compound represented by the following formula (2),

[0092] [Chemistry 3]

[0093]

[0094] In formula (2),

[0095] R 201 ~R 205 One of them is a single bond bonded to the group represented by the following formula (A2);

[0096] [Chemistry 4]

[0097] -(L A2 ) nA2 -Ar A2 (A2)

[0098] In formula (A2),

[0099] L A2 for:

[0100] single bond,

[0101] a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or

[0102] a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms;

[0103] Ar A2 for:

[0104] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and consisting of 5 or less rings, or

[0105] a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms;

[0106] nA2 is an integer from 0 to 3;

[0107] When nA2 is 0, (L A2 ) nA2 is a single bond;

[0108] When nA2 is 2 or 3, multiple L A2 connected in series, Ar A2 The farthest L from the dinaphthofuran skeleton A2 Bonding; multiple L A2 Can be the same or different;

[0109] By R 206 ~R 212 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A2) 201 ~R 205 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other;

[0110] R not bonded to each other 206 ~R 212 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A2) and is not bonded to each other 201 ~R 205 Each independently is:

[0111] hydrogen atoms, or

[0112] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A2);

[0113] The substituents in the case of "substituted or unsubstituted" are:

[0114] an alkyl group having 1 to 50 carbon atoms,

[0115] a halogenated alkyl group having 1 to 50 carbon atoms,

[0116] an alkenyl group having 2 to 50 carbon atoms,

[0117] an alkynyl group having 2 to 50 carbon atoms,

[0118] a cycloalkyl group having 3 to 50 ring carbon atoms,

[0119] an alkylthio group having 1 to 50 carbon atoms,

[0120] an aryloxy group having 6 to 50 ring carbon atoms,

[0121] an arylthio group having 6 to 50 ring carbon atoms,

[0122] Aralkyl having 7 to 50 carbon atoms,

[0123] -Si(R 41 )(R 42 )(R 43 ),

[0124] -C(=O)R 44 、-COOR 45 、

[0125] -Ge(R 49 )(R 50 )(R 51 ),

[0126] Hydroxyl,

[0127] cyano,

[0128] Nitro,

[0129] an aryl group having 6 to 13 ring carbon atoms, or

[0130] a monovalent heterocyclic group having 5 to 50 ring atoms;

[0131] R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms;

[0132] R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each can be the same or different;

[0133] Among them, L A2 a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, and Ar A2 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in the group are each a group satisfying the following formula (T1),

[0134] T1>1.81eV···(T1)

[0135] In formula (T1), T1 is the triplet energy of the group.

[0136] 3. An organic electroluminescent element comprising:

[0137] cathode,

[0138] Anode, and

[0139] a light-emitting layer disposed between the cathode and the anode;

[0140] The light-emitting layer comprises a first light-emitting layer and a second light-emitting layer;

[0141] The first light-emitting layer comprises a compound represented by the following formula (3):

[0142] [Chemistry 5]

[0143]

[0144] In formula (3),

[0145] R 301 ~R 305 One of them is a single bond bonded to the group represented by the following formula (A3);

[0146] [Chemistry 6]

[0147] -(L A3 ) nA3 -Ar A3 (A3)

[0148] In formula (A3),

[0149] L A3 for:

[0150] single bond,

[0151] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[0152] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;

[0153] ArA3 for:

[0154] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[0155] a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms;

[0156] nA3 is an integer from 0 to 3;

[0157] When nA3 is 0, (L A3 ) nA3 is a single bond;

[0158] When nA3 is 2 or 3, multiple L A3 connected in series, Ar A3 The farthest L from the dinaphthofuran skeleton A3 Bonding; multiple L A3 Can be the same or different;

[0159] By R 306 ~R 312 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A3) 301 ~R 305 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other;

[0160] R not bonded to each other 306 ~R 312 , and R which is not a single bond bonded to the group represented by the above formula (A3) and is not bonded to each other 301 ~R 305 Each independently is:

[0161] hydrogen atoms, or

[0162] A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A3).

[0163] According to the present invention, a high-performance organic EL device and a compound capable of realizing the organic EL device can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0164] Figure 1 : A diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention. DETAILED DESCRIPTION

[0165] [definition]

[0166] In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

[0167] In the present specification, in chemical structural formulas, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded to a position capable of bonding that is not explicitly indicated by symbols such as "R" or "D" representing a deuterium atom.

[0168] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are combined to form a ring structure. When the ring is substituted by a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" recorded below is also the same unless otherwise specified. For example, the number of ring carbon atoms of a benzene ring is 6, the number of ring carbon atoms of a naphthalene ring is 10, the number of ring carbon atoms of a pyridine ring is 5, and the number of ring carbon atoms of a furan ring is 4. In addition, for example, the number of ring carbon atoms of 9,9-diphenylfluorenyl is 13, and the number of ring carbon atoms of 9,9'-spirobifluorenyl is 25.

[0169] When a benzene ring is substituted with a substituent such as an alkyl group, the number of carbon atoms in the alkyl group is not included in the number of carbon atoms in the benzene ring. Therefore, the number of carbon atoms in the benzene ring substituted with an alkyl group is 6. When a naphthalene ring is substituted with a substituent such as an alkyl group, the number of carbon atoms in the alkyl group is not included in the number of carbon atoms in the naphthalene ring. Therefore, the number of carbon atoms in the naphthalene ring substituted with an alkyl group is 10.

[0170] In this specification, the number of ring atoms represents the number of atoms that constitute the ring itself of a compound (such as a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are combined to form a cyclic structure (such as a monocyclic ring, a condensed ring, and a ring set). Atoms that do not constitute a ring (such as a hydrogen atom that terminates the bond of an atom constituting the ring) or atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is also the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent are not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. For example, hydrogen atoms bonded to carbon atoms of the quinoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinoline ring. Therefore, the number of ring atoms of the quinoline ring to which hydrogen atoms or substituents are bonded is 10.

[0171] In this specification, the term "a substituted or unsubstituted ZZ group having XX to YY carbon atoms" refers to the number of carbon atoms in the ZZ group when it is unsubstituted and does not include the number of carbon atoms in the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0172] In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" indicates the number of atoms in the ZZ group when it is unsubstituted and does not include the atomic number of the substituent when it is substituted. Here, "YY" is greater than "XX," "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

[0173] In this specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

[0174] In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.

[0175] In this specification, "substituted" in the context of a "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of a "BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0176] "Substituents described in this specification"

[0177] The substituents described in this specification are described below.

[0178] Unless otherwise specified in the present specification, the “unsubstituted aryl group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0179] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0180] Unless otherwise specified in the present specification, the “unsubstituted alkyl group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0181] Unless otherwise specified in the present specification, the "unsubstituted alkenyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0182] Unless otherwise specified in the present specification, the "unsubstituted alkynyl group" described in the present specification has 2 to 50 carbon atoms, preferably 2 to 20 carbon atoms, and more preferably 2 to 6 carbon atoms.

[0183] Unless otherwise specified in the present specification, the “unsubstituted cycloalkyl group” described in the present specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6.

[0184] Unless otherwise specified in the present specification, the “unsubstituted arylene group” described in the present specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms.

[0185] Unless otherwise specified in the present specification, the number of ring atoms in the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18.

[0186] Unless otherwise specified in the present specification, the “unsubstituted alkylene group” described in the present specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms.

[0187] "Substituted or unsubstituted aryl"

[0188] Specific examples of "substituted or unsubstituted aryl groups" described in this specification (Specific Example Group G1) include the following unsubstituted aryl groups (Specific Example Group G1A) and substituted aryl groups (Specific Example Group G1B). (Herein, "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, the mention of "aryl group" alone includes both "unsubstituted aryl groups" and "substituted aryl groups".

[0189] A "substituted aryl group" means an "unsubstituted aryl group" in which one or more hydrogen atoms are replaced by a substituent. Examples of "substituted aryl groups" include groups in which one or more hydrogen atoms of the "unsubstituted aryl groups" of the following specific example group G1A are replaced by substituents, and examples of substituted aryl groups of the following specific example group G1B are mentioned. It should be noted that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described in this specification also include groups in which a hydrogen atom bonded to a carbon atom of the aryl group itself is further replaced by a substituent, as in the "substituted aryl groups" of the following specific example group G1B, and groups in which a hydrogen atom of a substituent is further replaced by a substituent.

[0190] Unsubstituted aryl (Specific example group G1A):

[0191] Phenyl,

[0192] p-Biphenyl,

[0193] m-Biphenyl,

[0194] o-biphenyl,

[0195] 4-terphenyl-4-yl,

[0196] 4-terphenyl-3-yl,

[0197] 4-terphenyl-2-yl,

[0198] m-terphenyl-4-yl,

[0199] m-terphenyl-3-yl,

[0200] m-terphenyl-2-yl,

[0201] o-terphenyl-4-yl,

[0202] o-terphenyl-3-yl,

[0203] o-terphenyl-2-yl,

[0204] 1-naphthyl,

[0205] 2-naphthyl,

[0206] Anthracene,

[0207] Benzanthryl,

[0208] Fiki,

[0209] Triphenylene,

[0210] Phenalene,

[0211] Pyrene

[0212] base,

[0213] Benzo base,

[0214] triphenylene,

[0215] Benzotriphenylene,

[0216] tetraphenyl,

[0217] Pentaphenyl,

[0218] Fluorenyl,

[0219] 9,9'-spirobifluorenyl,

[0220] Benzofluorenyl,

[0221] Dibenzofluorenyl,

[0222] Fluoranthene group,

[0223] Benzofluoranthene,

[0224] Perylene, and

[0225] A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[0226] [Chemistry 7]

[0227]

[0228] ·Substituted aryl (specific example group G1B): o-tolyl,

[0229] m-Tolyl,

[0230] p-Tolyl,

[0231] p-Xylyl,

[0232] m-xylyl,

[0233] o-xylyl,

[0234] p-Isopropylphenyl,

[0235] m-isopropylphenyl,

[0236] o-isopropylphenyl,

[0237] tert-Butylphenyl,

[0238] m-tert-butylphenyl,

[0239] o-tert-butylphenyl,

[0240] 3,4,5-trimethylphenyl,

[0241] 9,9-dimethylfluorenyl,

[0242] 9,9-Diphenylfluorenyl

[0243] 9,9-bis(4-methylphenyl)fluorenyl,

[0244] 9,9-bis(4-isopropylphenyl)fluorenyl,

[0245] 9,9-bis(4-tert-butylphenyl)fluorenyl,

[0246] Cyanophenyl,

[0247] triphenylsilylphenyl,

[0248] trimethylsilylphenyl,

[0249] Phenyl naphthyl,

[0250] naphthylphenyl, and

[0251] A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the aforementioned general formulae (TEMP-1) to (TEMP-15) are replaced by a substituent.

[0252] "Substituted or unsubstituted heterocyclic group"

[0253] The term "heterocyclic group" as used herein refers to a cyclic group containing at least one heteroatom among the ring atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron atoms.

[0254] The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

[0255] The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

[0256] Specific examples of the "substituted or unsubstituted heterocyclic group" described in this specification (Specific Example Group G2) include the following unsubstituted heterocyclic groups (Specific Example Group G2A) and substituted heterocyclic groups (Specific Example Group G2B). (Herein, an unsubstituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group," and a substituted heterocyclic group refers to a case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group.") In this specification, the term "heterocyclic group" alone includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups."

[0257] A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic groups" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of Specific Example Group G2A below are replaced, and examples of substituted heterocyclic groups of Specific Example Group G2B below. It should be noted that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described in this specification include groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of Specific Example Group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of Specific Example Group G2B are further replaced by substituents.

[0258] 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 represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0259] Specific example group G2B includes, for example, the following substituted heterocyclic groups containing nitrogen atoms (specific example group G2B1), substituted heterocyclic groups containing oxygen atoms (specific example group G2B2), substituted heterocyclic groups containing sulfur atoms (specific example group G2B3), and groups formed by replacing one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) with a substituent (specific example group G2B4).

[0260] Unsubstituted heterocyclic group containing a nitrogen atom (Specific example group G2A1):

[0261] Pyrrolyl,

[0262] Imidazole,

[0263] Pyrazolyl,

[0264] triazole,

[0265] Tetrazolyl,

[0266] Oxazolyl,

[0267] Isoxazolyl,

[0268] Oxadiazolyl,

[0269] Thiazolyl,

[0270] Isothiazolyl,

[0271] Thiadiazole,

[0272] Pyridyl,

[0273] Pyridazinyl,

[0274] Pyrimidine group,

[0275] Pyrazinyl,

[0276] Triazine group,

[0277] Indolyl,

[0278] Isoindolyl,

[0279] Indolizinyl,

[0280] Quinolizinyl,

[0281] Quinolinyl,

[0282] Isoquinolinyl,

[0283] Cinnoline,

[0284] Phthalocyanine,

[0285] Quinazoline,

[0286] Quinoxaline,

[0287] Benzimidazole,

[0288] Indazolyl,

[0289] Phenanthroline,

[0290] Phenanthridinyl,

[0291] Acridinyl,

[0292] Phenoxazine,

[0293] Carbazolyl,

[0294] benzocarbazolyl,

[0295] Morpholino,

[0296] Phenoxazine,

[0297] Phenothiazine,

[0298] azacarbazolyl, and diazacarbazolyl.

[0299] Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2): furyl,

[0300] Oxazolyl,

[0301] Isoxazolyl,

[0302] Oxadiazolyl,

[0303] Xanthoxylum,

[0304] Benzofuranyl,

[0305] Isobenzofuranyl,

[0306] dibenzofuranyl,

[0307] naphthobenzofuranyl,

[0308] Benzoxazolyl,

[0309] Benzisoxazolyl,

[0310] Phenoxazine,

[0311] Morpholino,

[0312] dinaphthofuranyl,

[0313] Azadibenzofuranyl,

[0314] Diazadibenzofuranyl,

[0315] azanaphthobenzofuranyl, and

[0316] naphthyridinylbenzofuranyl.

[0317] Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3): thienyl,

[0318] Thiazolyl,

[0319] Isothiazolyl,

[0320] Thiadiazole,

[0321] benzothienyl,

[0322] Isobenzothienyl,

[0323] dibenzothienyl,

[0324] naphthobenzothienyl, benzothiazolyl,

[0325] Benzisothiazolyl,

[0326] Phenothiazine,

[0327] dinaphthothiophenyl,

[0328] azadibenzothienyl,

[0329] diazadibenzothienyl,

[0330] azanaphthobenzothienyl, and

[0331] diazanaphthobenzothienyl.

[0332] A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0333] [Chemistry 9]

[0334]

[0335] [Chemistry 10]

[0336]

[0337] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each independently represents an oxygen atom, a sulfur atom, NH or CH2. A and Y A At least one of them is an oxygen atom, a sulfur atom or NH.

[0338] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A When at least one of is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above-mentioned general formula (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0339] Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

[0340] (9-phenyl)carbazolyl,

[0341] (9-biphenyl)carbazolyl,

[0342] (9-phenyl)phenylcarbazolyl,

[0343] (9-naphthyl)carbazolyl,

[0344] Diphenylcarbazol-9-yl,

[0345] phenylcarbazol-9-yl,

[0346] Methylbenzimidazole,

[0347] Ethylbenzimidazolyl,

[0348] Phenyltriazine,

[0349] Biphenyl triazine group,

[0350] Diphenyltriazine,

[0351] Phenylquinazolinyl, and

[0352] Biphenylquinazolinyl.

[0353] Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

[0354] Phenyldibenzofuranyl,

[0355] Methyldibenzofuranyl,

[0356] tert-Butyldibenzofuranyl, and

[0357] The monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0358] -Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

[0359] Phenyldibenzothiophene,

[0360] Methyldibenzothiophene,

[0361] tert-Butyldibenzothienyl, and

[0362] The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0363] Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the aforementioned general formulae (TEMP-16) to (TEMP-33) are replaced by a substituent (Specific Example Group G2B4):

[0364] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to carbon atoms forming a ring of the monovalent heterocyclic group, X A and Y A When at least one of the is NH, the hydrogen atom bonded to the nitrogen atom, and X A and Y A When one of the hydrogen atoms of the methylene group is CH2, one or more hydrogen atoms are present.

[0365] "Substituted or unsubstituted alkyl"

[0366] Specific examples of "substituted or unsubstituted alkyl groups" described in this specification (Specific Example Group G3) include the following unsubstituted alkyl groups (Specific Example Group G3A) and substituted alkyl groups (Specific Example Group G3B). (Herein, "unsubstituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group.") Hereinafter, when "alkyl" is mentioned alone, both "unsubstituted alkyl groups" and "substituted alkyl groups" are included.

[0367] "Substituted alkyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In this specification, the alkyl group in "unsubstituted alkyl" means a chain alkyl group. Therefore, "unsubstituted alkyl" includes a straight-chain "unsubstituted alkyl" and a branched "unsubstituted alkyl". It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in this specification also includes a group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl" of the specific example group G3B is further replaced by a substituent.

[0368] Unsubstituted alkyl (Specific example group G3A):

[0369] methyl,

[0370] Ethyl,

[0371] n-propyl,

[0372] Isopropyl,

[0373] n-Butyl,

[0374] Isobutyl,

[0375] sec-butyl, and

[0376] tert-butyl.

[0377] Substituted alkyl (Specific example group G3B):

[0378] Heptafluoropropyl (including isomers),

[0379] Pentafluoroethyl,

[0380] 2,2,2-trifluoroethyl,

[0381] trifluoromethyl.

[0382] "Substituted or unsubstituted alkenyl"

[0383] Specific examples of the "substituted or unsubstituted alkenyl group" described in this specification (Specific Example Group G4) include the following unsubstituted alkenyl groups (Specific Example Group G4A) and substituted alkenyl groups (Specific Example Group G4B). (Here, "unsubstituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group", and "substituted alkenyl group" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when "alkenyl group" is mentioned alone, both "unsubstituted alkenyl group" and "substituted alkenyl group" are included.

[0384] "Substituted alkenyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups having substituents, and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" described in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituents in the "substituted alkenyl" of the specific example group G4B are further replaced by substituents.

[0385] Unsubstituted alkenyl (Specific example Group G4A):

[0386] Vinyl,

[0387] Allyl,

[0388] 1-butenyl,

[0389] 2-Butenyl, and

[0390] 3-Butenyl.

[0391] Substituted alkenyl (Specific example group G4B):

[0392] 1,3-Butadienyl,

[0393] 1-Methylvinyl,

[0394] 1-methylallyl,

[0395] 1,1-dimethylallyl,

[0396] 2-methylallyl, and

[0397] 1,2-Dimethylallyl.

[0398] "Substituted or unsubstituted alkynyl"

[0399] Specific examples of "substituted or unsubstituted alkynyl groups" described in this specification (Specific Example Group G5) include the following unsubstituted alkynyl groups (Specific Example Group G5A). (Here, unsubstituted alkynyl groups refer to "substituted or unsubstituted alkynyl groups" as "unsubstituted alkynyl groups.") Hereinafter, when "alkynyl" is mentioned alone, both "unsubstituted alkynyl groups" and "substituted alkynyl groups" are included.

[0400] "Substituted alkynyl" means a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (Specific Example Group G5A) are replaced by a substituent.

[0401] Unsubstituted alkynyl (Specific example group G5A):

[0402] ethynyl

[0403] "Substituted or unsubstituted cycloalkyl"

[0404] Specific examples of the "substituted or unsubstituted cycloalkyl group" described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl groups (Specific Example Group G6A) and substituted cycloalkyl groups (Specific Example Group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group," and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" alone includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups."

[0405] "Substituted cycloalkyl" means a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B) can be cited. It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" described in this specification also includes groups in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and groups in which the hydrogen atoms of the substituents in the "substituted cycloalkyl" of the specific example group G6B are further replaced by substituents.

[0406] Unsubstituted cycloalkyl (Specific example group G6A):

[0407] Cyclopropyl,

[0408] Cyclobutyl,

[0409] Cyclopentyl,

[0410] Cyclohexyl,

[0411] 1-adamantyl,

[0412] 2-adamantyl,

[0413] 1-norbornyl, and

[0414] 2-Norbornyl.

[0415] Substituted cycloalkyl (specific example group G6B):

[0416] 4-Methylcyclohexyl.

[0417] ·“-Si(R 901 )(R 902 )(R 903 )”

[0418] As described in this specification, -Si(R 901 )(R 902 )(R 903 Specific examples of the group represented by (specific example group G7) include:

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

[0420] -Si(G1)(G2)(G2),

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

[0422] -Si(G2)(G2)(G2),

[0423] -Si(G3)(G3)(G3), and

[0424] -Si(G6)(G6)(G6).

[0425] here,

[0426] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0427] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0428] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0429] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0430] A plurality of G1s in -Si(G1)(G1)(G1) are the same as or different from each other.

[0431] A plurality of G2s in -Si(G1)(G2)(G2) are the same as or different from each other.

[0432] A plurality of G1s in -Si(G1)(G1)(G2) are the same as or different from each other.

[0433] Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

[0434] Multiple G3s in -Si(G3)(G3)(G3) are the same as or different from each other.

[0435] A plurality of G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

[0436] ·“-O-(R 904 )”

[0437] As described in this specification, -O-(R 904 Specific examples of the group represented by (specific example group G8) include:

[0438] -O(G1),

[0439] -O(G2),

[0440] -O(G3), and

[0441] -O(G6).

[0442] here,

[0443] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0444] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0445] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0446] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0447] ·“-S-(R 905 )”

[0448] As -S-(R 905 Specific examples of the group represented by (specific example group G9) include:

[0449] -S(G1),

[0450] -S(G2),

[0451] -S(G3), and

[0452] -S(G6).

[0453] here,

[0454] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0455] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0456] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0457] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0458] ·“-N(R 906 )(R 907 )”

[0459] As described in this specification, -N(R 906 )(R 907 Specific examples of the group represented by (specific example group G10) include:

[0460] -N(G1)(G1),

[0461] -N(G2)(G2),

[0462] -N(G1)(G2),

[0463] -N(G3)(G3), and

[0464] -N(G6)(G6).

[0465] here,

[0466] G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[0467] G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[0468] G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

[0469] G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

[0470] - A plurality of G1s in N(G1)(G1) are the same as or different from each other.

[0471] - A plurality of G2s in N(G2)(G2) are the same as or different from each other.

[0472] - A plurality of G3's in N(G3)(G3) are the same as or different from each other.

[0473] A plurality of G6's in -N(G6)(G6) are the same as or different from each other.

[0474] "Halogen atoms"

[0475] Specific examples of the "halogen atom" described in this specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0476] "Substituted or unsubstituted fluoroalkyl"

[0477] The “substituted or unsubstituted fluoroalkyl group” described in this specification means a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a “substituted or unsubstituted alkyl group” is replaced by a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a “substituted or unsubstituted alkyl group” are replaced by fluorine atoms (perfluoro group). Unless otherwise stated 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. A “substituted fluoroalkyl group” means a group in which one or more hydrogen atoms of a “fluoroalkyl group” are replaced by a substituent. It should be noted that the “substituted fluoroalkyl group” described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a “substituted fluoroalkyl group” are further replaced by a substituent, and a group in which one or more hydrogen atoms of a substituent in a “substituted fluoroalkyl group” are further replaced by a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0478] "Substituted or unsubstituted haloalkyl"

[0479] As used herein, a "substituted or unsubstituted haloalkyl group" refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. Unless otherwise specified herein, an "unsubstituted haloalkyl group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms in a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the aforementioned "alkyl" (specific example group G3) are replaced by halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

[0480] "Substituted or unsubstituted alkoxy"

[0481] A specific example of a "substituted or unsubstituted alkoxy group" described in this specification is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Unless otherwise specified in this specification, an "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0482] "Substituted or unsubstituted alkylthio"

[0483] A specific example of a "substituted or unsubstituted alkylthio group" described herein is a group represented by -S(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Unless otherwise specified herein, an "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30, and more preferably 1 to 18 carbon atoms.

[0484] "Substituted or unsubstituted aryloxy group"

[0485] Specific examples of "substituted or unsubstituted aryloxy groups" described herein include groups represented by -O(G1), where G1 represents a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified herein, "unsubstituted aryloxy groups" have 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0486] "Substituted or unsubstituted arylthio"

[0487] Specific examples of "substituted or unsubstituted arylthio groups" described herein include -S(G1), where G1 represents a "substituted or unsubstituted aryl group" described in Specific Example Group G1. Unless otherwise specified herein, an "unsubstituted arylthio group" has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18.

[0488] "Substituted or unsubstituted trialkylsilyl"

[0489] Specific examples of "trialkylsilyl groups" described in this specification are groups represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in Specific Example Group G3. Multiple G3s in -Si(G3)(G3)(G3) are the same or different. Unless otherwise specified in this specification, each alkyl group in a "trialkylsilyl group" has 1 to 50 carbon atoms, preferably 1 to 20, and more preferably 1 to 6.

[0490] "Substituted or unsubstituted aralkyl"

[0491] Specific examples of "substituted or unsubstituted aralkyl groups" described in this specification are groups represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3, and G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1. Therefore, an "aralkyl group" is a group in which a hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group." The number of carbon atoms in an "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0492] Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, and 2-β-naphthylisopropyl.

[0493] Unless otherwise specified in the present specification, the substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl, etc.

[0494] The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, (9-phenyl)carbazolyl ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl, or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazolyl, (9-phenyl)phenylcarbazolyl, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazinyl, biphenyltriazinyl, diphenyltriazinyl, phenyldibenzofuranyl, and phenyldibenzothiophenyl, etc.

[0495] In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0496] [Chemistry 11]

[0497]

[0498] In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

[0499] [Chemistry 12]

[0500]

[0501] In the aforementioned general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding site.

[0502] In the present specification, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups unless otherwise specified in the present specification.

[0503] [Chemistry 13]

[0504]

[0505] In the aforementioned general formulas (TEMP-34) to (TEMP-41), * represents a bonding site.

[0506] Unless otherwise specified in the present specification, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like.

[0507] "Substituted or unsubstituted arylene group"

[0508] Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom from the aromatic ring. Specific examples of the "substituted or unsubstituted arylene group" (Specific Example Group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in Specific Example Group G1 by removing one hydrogen atom from the aromatic ring.

[0509] "Substituted or unsubstituted divalent heterocyclic group"

[0510] Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom from the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (Specific Example Group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2 by removing one hydrogen atom from the heterocyclic ring.

[0511] "Substituted or unsubstituted alkylene"

[0512] Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom from the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (Specific Example Group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in Specific Example Group G3 by removing one hydrogen atom from the alkyl chain.

[0513] Unless otherwise specified in the present specification, the substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68).

[0514] [Chemistry 14]

[0515]

[0516] [Chemistry 15]

[0517]

[0518] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10are each independently a hydrogen atom or a substituent.

[0519] In the aforementioned general formulas (TEMP-42) to (TEMP-52), * represents a bonding site.

[0520] [Chemistry 16]

[0521]

[0522] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 are each independently a hydrogen atom or a substituent.

[0523] Formula Q9 and Q 10 They may be bonded to each other via a single bond to form a ring.

[0524] In the aforementioned general formulas (TEMP-53) to (TEMP-62), * represents a bonding site.

[0525] [Chemistry 17]

[0526]

[0527] In the aforementioned general formulae (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0528] In the aforementioned general formulas (TEMP-63) to (TEMP-68), * represents a bonding site.

[0529] Unless otherwise described in the present specification, the substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102).

[0530] [Chemistry 18]

[0531]

[0532] [Chemistry 19]

[0533]

[0534] [Chemistry 20]

[0535]

[0536] In the aforementioned general formulae (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0537] [Chemistry 21]

[0538]

[0539] [Chemistry 22]

[0540]

[0541] [Chemistry 23]

[0542]

[0543] [Chemistry 24]

[0544]

[0545] In the aforementioned general formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0546] The above is the description of the “substituents described in the present specification”.

[0547] "When bonds form a ring"

[0548] In this specification, the situation where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other” means the situation where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring”, the situation where “one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring”, and the situation where “one or more groups consisting of two or more adjacent groups are not bonded to each other”.

[0549] The following describes the case where "one or more adjacent groups of two or more groups are bonded to form a substituted or unsubstituted monocyclic ring" and the case where "one or more adjacent groups of two or more groups are bonded to form a substituted or unsubstituted fused ring" (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring"). This description is based on the case of an anthracene compound represented by the following general formula (TEMP-103) in which the parent skeleton is an anthracene ring.

[0550] [Chemistry 25]

[0551]

[0552] For example, R 921 ~R 930 In the case of "one or more groups consisting of two or more adjacent groups are bonded to each other to form a ring", the group consisting of two adjacent groups as one group is R 921 With R 922 Group, R 922 With R 923 Group, R 923 With R 924Group, R 924 With R 930 Group, R 930 With R 925 Group, R 925 With R 926 Group, R 926 With R 927 Group, R 927 With R 928 Group, R 928 With R 929 The group, and R 929 With R 921 group.

[0553] The above “one or more groups” means that two or more adjacent groups can form a ring at the same time. 921 With R 922 Bonded to each other to form ring Q A And at the same time R 925 With R 926 Bonded to each other to form ring Q B In the case of, the anthracene compound represented by the aforementioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0554] [Chemistry 26]

[0555]

[0556] The case where "a group consisting of two or more adjacent members" forms a ring includes not only the case where adjacent "two" members are bonded as in the above example, but also the case where adjacent "three or more" members are bonded. For example, if R 921 With R 922 Bonded to each other to form ring Q A , and R 922 With R 923 Bonded to each other to form ring Q C , consisting of three adjacent (R 921 、R 922 and R 923 ) are bonded to each other to form a ring and fused to form an anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and Ring Q C Total R 922 .

[0557] [Chemistry 27]

[0558]

[0559] The "monocyclic ring" or "condensed ring" formed as a structure of a single ring may be a saturated ring or an unsaturated ring. Even when "one group consisting of two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" may 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 a "monocyclic ring" or a "condensed ring". In addition, the ring Q formed in the above general formula (TEMP-105) A and Ring Q C The ring Q of the above general formula (TEMP-105) is A With Ring Q C Through Ring Q A With Ring Q C The ring Q of the aforementioned general formula (TMEP-104) A If it is a benzene ring, then ring Q A The ring Q of the aforementioned general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a fused ring.

[0560] "Unsaturated rings" include, in addition to aromatic hydrocarbon rings and aromatic heterocycles, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double bonds and / or triple bonds in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazoline, quinolizine, indoline, isoindoline, etc.). "Saturated rings" include aliphatic hydrocarbon rings without unsaturated bonds and non-aromatic heterocycles without unsaturated bonds.

[0561] Specific examples of the aromatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

[0562] Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups listed as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

[0563] Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

[0564] "Forming a ring" means forming a ring only by multiple atoms of the parent skeleton, or by multiple atoms of the parent skeleton and one or more arbitrary atoms. For example, R 921 With R 922 Ring Q formed by mutual bonding A Meaning by R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922As a specific example, in the case where R 921 With R 922 Formation of ring Q A In the case of R 921 The carbon atom of the anthracene skeleton to which it is bonded, R 922 When the carbon atom of the anthracene skeleton is bonded to form a monocyclic unsaturated ring with four carbon atoms, R 921 With R 922 The ring formed is a benzene ring.

[0565] Here, "any atom" is preferably at least one atom selected from a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise specified in this specification. For any atom (e.g., a carbon atom or a nitrogen atom), bonds that do not form a ring may be terminated with hydrogen atoms or the like, or may be substituted with "any substituents" described below. When any atom other than a carbon atom is included, the resulting ring is a heterocycle.

[0566] Unless otherwise specified in the present specification, the number of "one or more arbitrary atoms" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

[0567] Unless otherwise specified in the present specification, "monocyclic ring" is preferred over "monocyclic ring" and "condensed ring".

[0568] In the present specification, unless otherwise specified, "unsaturated ring" is preferred over "saturated ring" and "unsaturated ring".

[0569] Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

[0570] Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

[0571] In the case where "one or more groups consisting of two or more adjacent groups" are "bonded to each other to form a substituted or unsubstituted monocyclic ring", or in the case where "they are bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise specified in this specification, it is preferred that one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and one to fifteen atoms of at least one type selected from carbon atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

[0572] When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "Substituents described in the present specification."

[0573] When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "Substituents described in the present specification."

[0574] The above is an explanation of the case where "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more groups consisting of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring" ("case where they are bonded to form a ring").

[0575] Substituents in the case of "substituted or unsubstituted"

[0576] In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, a group selected from the following:

[0577] unsubstituted alkyl group having 1 to 50 carbon atoms,

[0578] unsubstituted alkenyl having 2 to 50 carbon atoms,

[0579] unsubstituted alkynyl group having 2 to 50 carbon atoms,

[0580] unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0581] -Si(R 901 )(R 902 )(R 903 ),

[0582] -O-(R 904 ),

[0583] -S-(R 905 ),

[0584] -N(R 906 )(R 907 ),

[0585] Halogen atoms, cyano, nitro,

[0586] an unsubstituted aryl group having 6 to 50 ring carbon atoms, and

[0587] an unsubstituted heterocyclic group having 5 to 50 ring atoms;

[0588] Here, R 901 ~R 907 Each independently is:

[0589] hydrogen atoms,

[0590] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[0591] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[0592] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[0593] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[0594] R 901 When there are two or more, two or more R 901 Same or different from each other,

[0595] R 902 When there are two or more, two or more R 902 Same or different from each other,

[0596] R 903 When there are two or more, two or more R 903 Same or different from each other,

[0597] R 904 When there are two or more, two or more R 904 Same or different from each other,

[0598] R 905 When there are two or more, two or more R 905 Same or different from each other,

[0599] R 906 When there are two or more, two or more R 906 Same or different from each other,

[0600] R 907 When there are two or more, two or more R 907 Same as or different from each other.

[0601] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0602] an alkyl group having 1 to 50 carbon atoms,

[0603] an aryl group having 6 to 50 ring carbon atoms, and

[0604] A heterocyclic group having 5 to 50 ring atoms.

[0605] In one embodiment, the substituent in the aforementioned "substituted or unsubstituted" case is selected from the following groups:

[0606] an alkyl group having 1 to 18 carbon atoms,

[0607] an aryl group having 6 to 18 ring carbon atoms, and

[0608] A heterocyclic group having 5 to 18 ring atoms.

[0609] Specific examples of each of the above-mentioned optional substituents are the same as the specific examples of the substituents described in the above section "Substituents described in the present specification".

[0610] Unless otherwise stated in this specification, any adjacent substituents may form a "saturated ring" or an "unsaturated ring" with each other, preferably forming a substituted or unsubstituted saturated 5-membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably forming a benzene ring.

[0611] Unless otherwise specified in the present specification, an arbitrary substituent may further have a substituent. The substituent further possessed by an arbitrary substituent is the same as the arbitrary substituent described above.

[0612] In this specification, the numerical range using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit and the numerical value BB described after "AA to BB" as the upper limit.

[0613] [New compound]

[0614] The compound according to one embodiment of the present invention is a compound represented by formula (1) or formula (2) described below.

[0615] The compound of one embodiment of the present invention can improve device performance when used in an organic EL device. In particular, device performance can be improved by using the compound in one light-emitting layer of a stacked light-emitting layer.

[0616] [Compound represented by formula (1)]

[0617] The compound of one embodiment of the present invention is represented by the following formula (1):

[0618] [Chemistry 28]

[0619]

[0620] In formula (1),

[0621] R 101 ~R 105 One of them is a single bond bonded to the group represented by the following formula (A1);

[0622] [Chemistry 29]

[0623] -(L A1 )nA1 -Ar A1 (Al)

[0624] In formula (A1),

[0625] L A1 for:

[0626] single bond,

[0627] substituted or unsubstituted phenylene,

[0628] Substituted or unsubstituted biphenyldiyl,

[0629] Substituted or unsubstituted terphenyldiyl,

[0630] substituted or unsubstituted naphthylene,

[0631] substituted or unsubstituted phenanthrene diyl,

[0632] Substituted or unsubstituted triphenylene diyl,

[0633] Substituted or unsubstituted benzanthracenediyl,

[0634] substituted or unsubstituted pyrene diyl,

[0635] Substituted or unsubstituted Two bases,

[0636] Substituted or unsubstituted benzo Two bases,

[0637] Substituted or unsubstituted triphenylenediyl,

[0638] Substituted or unsubstituted benzotriphenylene,

[0639] substituted or unsubstituted fluorenediyl,

[0640] Substituted or unsubstituted benzofluorenediyl,

[0641] Substituted or unsubstituted dibenzofluorenediyl,

[0642] Substituted or unsubstituted naphthofluorenediyl,

[0643] substituted or unsubstituted fluoranthenediyl,

[0644] Substituted or unsubstituted benzofluoranthene diyl,

[0645] Substituted or unsubstituted perylenediyl, or

[0646] a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms;

[0647] Ar A1 for:

[0648] substituted or unsubstituted phenyl,

[0649] Substituted or unsubstituted biphenyl,

[0650] Substituted or unsubstituted terphenyl,

[0651] substituted or unsubstituted naphthyl,

[0652] Substituted or unsubstituted phenoxy,

[0653] Substituted or unsubstituted triphenylene group,

[0654] Substituted or unsubstituted benzanthryl,

[0655] substituted or unsubstituted pyrenyl,

[0656] Substituted or unsubstituted base,

[0657] Substituted or unsubstituted benzo base,

[0658] Substituted or unsubstituted triphenylene,

[0659] Substituted or unsubstituted benzotriphenylene,

[0660] substituted or unsubstituted fluorenyl,

[0661] Substituted or unsubstituted benzofluorenyl,

[0662] Substituted or unsubstituted dibenzofluorenyl,

[0663] Substituted or unsubstituted naphthofluorenyl,

[0664] substituted or unsubstituted fluoranthene group,

[0665] Substituted or unsubstituted benzofluoranthenyl,

[0666] Substituted or unsubstituted perylene, or

[0667] a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms;

[0668] nA1 is an integer from 0 to 3;

[0669] When nA1 is 0, (L A1 ) nA1 is a single bond;

[0670] When nA1 is 2 or 3, multiple L A1 connected in series, Ar A1 The farthest L from the dinaphthofuran skeleton A1 Bonding; multiple L A1 Can be the same or different;

[0671] By R 106 ~R 112 , and R which is not a single bond bonded to the group represented by the above formula (A1) 101 ~R 105 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other;

[0672] R not bonded to each other 106 ~R 112 , and R which is not a single bond bonded to the group represented by the above formula (A1) and is not bonded to each other 101 ~R 105 Each independently is:

[0673] hydrogen atoms, or

[0674] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A1);

[0675] The substituents in the case of "substituted or unsubstituted" are:

[0676] an alkyl group having 1 to 50 carbon atoms,

[0677] a halogenated alkyl group having 1 to 50 carbon atoms,

[0678] an alkenyl group having 2 to 50 carbon atoms,

[0679] an alkynyl group having 2 to 50 carbon atoms,

[0680] a cycloalkyl group having 3 to 50 ring carbon atoms,

[0681] an alkylthio group having 1 to 50 carbon atoms,

[0682] an aryloxy group having 6 to 50 ring carbon atoms,

[0683] an arylthio group having 6 to 50 ring carbon atoms,

[0684] Aralkyl having 7 to 50 carbon atoms,

[0685] -Si(R 41 )(R 42 )(R 43 ),

[0686] -C(=O)R 44 、-COOR 45 、

[0687] -Ge(R 49 )(R 50 )(R51 ),

[0688] Hydroxyl,

[0689] cyano,

[0690] Nitro,

[0691] an aryl group having 6 to 50 ring carbon atoms, or

[0692] a monovalent heterocyclic group having 5 to 50 ring atoms;

[0693] R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms;

[0694] R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each may be the same or different.

[0695] In formula (1), when nA1 is 2 or 3, multiple L A1 connected in series, Ar A1 The farthest L from the dinaphthofuran skeleton A1 Bonding" for description.

[0696] It is obvious from the definition that when nA1 is 2 or 3, multiple L A1 In the dinaphthofuran skeleton and Ar A1 They are connected in series without branches.

[0697] For example, R 105 is a single bond bonded to the group represented by formula (A1). When nA1 is 3, the compound represented by formula (1) has a structure represented by the following formula (E1).

[0698] [Chemistry 30]

[0699]

[0700] In formula (1), L in formula (A1) A1 When Ar is a single bond, A1 Directly bonded to the dinaphthofuran skeleton.

[0701] The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the above formula (A1)" will be described.

[0702] The case where the "group represented by the aforementioned formula (A1)" is different from the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" includes cases where the chemical formulas (skeletons) are different, and cases where the chemical formulas (skeletons) are the same but contain different isotopes. Isotopes refer to atoms with the same atomic number but different neutron numbers. For example, benzene (C6H6) and deuterated benzene (C6D6) are different.

[0703] In addition, when the "group represented by the aforementioned formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" have substituents with the same skeleton, and the substitution positions of the substituents are different, the "group represented by the aforementioned formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are not the same.

[0704] For example, the following compound is not included in formula (1) because both the "group represented by the above formula (A1)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are phenanthren-9-yl groups.

[0705] [Chemistry 31]

[0706]

[0707] In one embodiment, R 102 ~R 105 One of them is a single bond bonded to the group represented by the above formula (A1).

[0708] In one embodiment, R 102 、R 103 and R 105 One of them is a single bond bonding to the group represented by the above formula (A1).

[0709] In one embodiment, R 103 and R 105 One of them is a single bond bonding to the group represented by the above formula (A1).

[0710] In one embodiment, R 102 It is a single bond bonding to the group represented by the above formula (A1).

[0711] In one embodiment, R 103 It is a single bond bonding to the group represented by the above formula (A1).

[0712] In one embodiment, R 105 It is a single bond bonding to the group represented by the above formula (A1).

[0713] In one embodiment, L A1 for:

[0714] single bond,

[0715] substituted or unsubstituted phenylene,

[0716] substituted or unsubstituted naphthylene,

[0717] Substituted or unsubstituted benzanthracenediyl,

[0718] substituted or unsubstituted pyrene diyl,

[0719] Substituted or unsubstituted benzofluorenediyl, or

[0720] Substituted or unsubstituted dibenzofluorenediyl.

[0721] In one embodiment, L A1 for:

[0722] Single key, or

[0723] a substituted or unsubstituted phenylene group.

[0724] In one embodiment, Ar A1 for:

[0725] substituted or unsubstituted phenyl,

[0726] substituted or unsubstituted naphthyl,

[0727] Substituted or unsubstituted benzanthryl

[0728] substituted or unsubstituted pyrenyl,

[0729] substituted or unsubstituted benzofluorenyl,

[0730] Substituted or unsubstituted dibenzofluorenyl,

[0731] Substituted or unsubstituted naphthobenzofuranyl, or

[0732] a substituted or unsubstituted benzoxanthenyl group.

[0733] In one embodiment, Ar A1 for:

[0734] substituted or unsubstituted phenyl,

[0735] substituted or unsubstituted naphthyl,

[0736] Substituted or unsubstituted benzanthryl

[0737] substituted or unsubstituted pyrenyl,

[0738] Substituted or unsubstituted benzofluorenyl, or

[0739] a substituted or unsubstituted dibenzofluorenyl group.

[0740] In one embodiment, the group represented by the above formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7).

[0741] [Chemistry 32]

[0742]

[0743] [Chemistry 33]

[0744]

[0745] In formula (A1-1) to formula (A1-7), nA1 and L A1 As defined in the above formula (A1).

[0746] R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 , and R A91 ~R A99 Each independently is:

[0747] hydrogen atoms,

[0748] an alkyl group having 1 to 50 carbon atoms,

[0749] an aryl group having 6 to 50 ring carbon atoms, or

[0750] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0751] In one embodiment, the group represented by the above formula (A1) is a group represented by any one of the above formulas (A1-1) to (A1-5).

[0752] In one embodiment, the compound represented by the above formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3).

[0753] [Chemistry 34]

[0754]

[0755] [Chemistry 35]

[0756]

[0757] In formula (1-1) to formula (1-3), nA1, L A1 、Ar A1 、R 101 ~R 112 As defined in the above formula (1).

[0758] In one embodiment, the compound represented by the aforementioned formula (1) is a compound represented by the aforementioned formula (1-1) or formula (1-2).

[0759] In one embodiment, the compound represented by the above formula (1) is a compound represented by any one of the following formulas (1-11) to (1-19).

[0760] [Chemistry 36]

[0761]

[0762] [Chemistry 37]

[0763]

[0764] [Chemistry 38]

[0765]

[0766] [Chemistry 39]

[0767]

[0768] [Chemistry 40]

[0769]

[0770] In formula (1-11) to formula (1-19), nA1, L A1 、R 101 ~R 112 As defined in formula (1);

[0771] R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 , and R A91 ~R A99 Each independently is:

[0772] hydrogen atoms,

[0773] an alkyl group having 1 to 50 carbon atoms,

[0774] an aryl group having 6 to 50 ring carbon atoms, or

[0775] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0776] In one embodiment, the compound represented by the above formula (1) is a compound represented by any one of the above formulas (1-11) to (1-14).

[0777] In one embodiment, R which is not a single bond 101 ~R 112 A hydrogen atom.

[0778] In one embodiment, R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 and R A91 ~R A99 Each independently is:

[0779] hydrogen atoms,

[0780] methyl,

[0781] Phenyl, or

[0782] Naphthyl.

[0783] In one embodiment, R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 and R A91 ~R A99 Each is independently a hydrogen atom, a methyl group or a phenyl group.

[0784] In one embodiment, R A11 ~R A14 and R A16 ~R A19 is a hydrogen atom, R A15 It is a phenyl group.

[0785] In one embodiment, R A11 ~R A19 A hydrogen atom.

[0786] In one embodiment, RA21 ~R A26 and R A28 ~R A32 A hydrogen atom.

[0787] In one embodiment, R A21 ~R A26 and R A28 ~R A31 is a hydrogen atom, R A27 It is a phenyl group.

[0788] In one embodiment, R A41 ~R A49 and R A61 ~R A71 is a hydrogen atom, R A50 ~R A51 and R A72 ~R A73 It is a methyl group.

[0789] In one embodiment, R A81 ~R A89 A hydrogen atom.

[0790] In one embodiment, R A91 ~R A99 A hydrogen atom.

[0791] In one embodiment, R as a hydrogen atom A81 ~R A89 At least one of them is a deuterium atom.

[0792] In one embodiment, R as a hydrogen atom A91 ~R A99 At least one of them is a deuterium atom.

[0793] In this specification, "deuterium atoms" in hydrogen atoms means that the ratio of deuterium atoms relative to the total of protium and deuterium atoms in the hydrogen atoms is greater than that found in nature. The ratio of deuterium atoms relative to the total of protium and deuterium atoms relative to the total of protium and deuterium atoms can be confirmed by nuclear magnetic resonance (NMR) equipment.

[0794] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (1) are selected from:

[0795] an alkyl group having 1 to 50 carbon atoms,

[0796] an aryl group having 6 to 50 ring carbon atoms, and

[0797] A monovalent heterocyclic group having 5 to 50 ring atoms.

[0798] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (1) are selected from:

[0799] an alkyl group having 1 to 18 carbon atoms,

[0800] an aryl group having 6 to 18 ring carbon atoms, and

[0801] A monovalent heterocyclic group having 5 to 18 ring atoms.

[0802] The compound represented by formula (1) can be synthesized according to the Examples by using known substitution reactions and starting materials corresponding to the target compound.

[0803] Although specific examples of the compound represented by formula (1) are described below, these are merely illustrative and the compound represented by formula (1) is not limited to the following specific examples.

[0804] [Chemistry 41]

[0805]

[0806] [Chemistry 42]

[0807]

[0808] [Chemistry 43]

[0809]

[0810] [Chemistry 44]

[0811]

[0812] [Chemistry 45]

[0813]

[0814] [Chemistry 46]

[0815]

[0816] [Chemistry 47]

[0817]

[0818] [Chemistry 48]

[0819]

[0820] [Chemistry 49]

[0821]

[0822] [Chemistry 50]

[0823]

[0824] [Chemistry 51]

[0825]

[0826] [Chemistry 52]

[0827]

[0828] [Chemistry 53]

[0829]

[0830] [Chemistry 54]

[0831]

[0832] [Chemistry 55]

[0833]

[0834] [Chemistry 56]

[0835]

[0836] [Chemistry 57]

[0837]

[0838] [Chemistry 58]

[0839]

[0840] [Chemistry 59]

[0841]

[0842] [Chemistry 60]

[0843]

[0844] [Chemistry 61]

[0845]

[0846] [Chemistry 62]

[0847]

[0848] [Chemistry 63]

[0849]

[0850] [Chemistry 64]

[0851]

[0852] [Chemistry 65]

[0853]

[0854] [Chemistry 66]

[0855]

[0856] [Chemistry 67]

[0857]

[0858] [Chemistry 68]

[0859]

[0860] [Chemistry 69]

[0861]

[0862] [Chemistry 70]

[0863]

[0864] [Chemistry 71]

[0865]

[0866] [Chemistry 72]

[0867]

[0868] [Chemistry 73]

[0869]

[0870] [Chemistry 74]

[0871]

[0872] [Chemistry 75]

[0873]

[0874] [Chemistry 76]

[0875]

[0876] [Chemistry 77]

[0877]

[0878] [Chemistry 78]

[0879]

[0880] [Chemistry 79]

[0881]

[0882] [Chemistry 80]

[0883]

[0884] [Chemistry 81]

[0885]

[0886] [Chemistry 82]

[0887]

[0888] [Chemistry 83]

[0889]

[0890] [Chemistry 84]

[0891]

[0892] [Chemistry 85]

[0893]

[0894] [Chemistry 86]

[0895]

[0896] [Chemistry 87]

[0897]

[0898] [Chemistry 88]

[0899]

[0900] [Chemistry 89]

[0901]

[0902] [Chemistry 90]

[0903]

[0904] [Chemistry 91]

[0905]

[0906] [Chemistry 92]

[0907]

[0908] [Chemistry 93]

[0909]

[0910] [Chemistry 94]

[0911]

[0912] [Chemistry 95]

[0913]

[0914] [Chemistry 96]

[0915]

[0916] [Chemistry 97]

[0917]

[0918] [Chemistry 98]

[0919]

[0920] [Chemistry 99]

[0921]

[0922] [Chemistry 100]

[0923]

[0924] [Chemistry 101]

[0925]

[0926] [Chemistry 102]

[0927]

[0928] [Chemistry 103]

[0929]

[0930] [Chemistry 104]

[0931]

[0932] [Chemistry 105]

[0933]

[0934] [Chemistry 106]

[0935]

[0936] [Chemistry 107]

[0937]

[0938] [Chemistry 108]

[0939]

[0940] [Chemistry 109]

[0941]

[0942] [Chemistry 110]

[0943]

[0944] [Chemistry 111]

[0945]

[0946] [Chemistry 112]

[0947]

[0948] [Chemistry 113]

[0949]

[0950] [Chemistry 114]

[0951]

[0952] [Chemistry 115]

[0953]

[0954] [Chemistry 116]

[0955]

[0956] [Chemistry 117]

[0957]

[0958] [Chemistry 118]

[0959]

[0960] [Chemistry 119]

[0961]

[0962] [Chemistry 120]

[0963]

[0964] [Chemistry 121]

[0965]

[0966] [Chemistry 122]

[0967]

[0968] [Chemistry 123]

[0969]

[0970] [Chemistry 124]

[0971]

[0972] [Chemistry 125]

[0973]

[0974] [Chemistry 126]

[0975]

[0976] [Chemistry 127]

[0977]

[0978] [Chemistry 128]

[0979]

[0980] [Chemistry 129]

[0981]

[0982] [Chemistry 130]

[0983]

[0984] [Chemistry 131]

[0985]

[0986] [Chemistry 132]

[0987]

[0988] [Chemistry 133]

[0989]

[0990] [Chemistry 134]

[0991]

[0992] [Chemistry 135]

[0993]

[0994] [Chemistry 136]

[0995]

[0996] [Chemistry 137]

[0997]

[0998] [Chemistry 138]

[0999]

[1000] [Chemistry 139]

[1001]

[1002] [Chemistry 140]

[1003]

[1004] [Compound represented by formula (2)]

[1005] The compound according to one embodiment of the present invention is represented by the following formula (2).

[1006] [Chemistry 141]

[1007]

[1008] In formula (2),

[1009] R 201 ~R 205 One of them is a single bond bonded to the group represented by the following formula (A2);

[1010] [Chemistry 142]

[1011] -(L A2 ) nA2 -Ar A2 (A2)

[1012] In formula (A2),

[1013] L A2 for:

[1014] single bond,

[1015] a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or

[1016] A substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.

[1017] Ar A2 for:

[1018] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and consisting of 5 or less rings, or

[1019] A substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms.

[1020] nA2 is an integer from 0 to 3.

[1021] When nA2 is 0, (L A2 ) nA2 For a single bond.

[1022] When nA2 is 2 or 3, multiple L A2 connected in series, Ar A2 The farthest L from the dinaphthofuran skeleton A2 Bonding. Multiple L A2 Can be the same or different.

[1023] By R 206 ~R 212 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A2) 201 ~R 205 One or more adjacent groups of two or more of the rings may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1024] R not bonded to each other 206 ~R 212 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A2) and is not bonded to each other 201 ~R 205 Each independently is:

[1025] hydrogen atoms, or

[1026] A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A2).

[1027] The substituents in the case of "substituted or unsubstituted" are:

[1028] an alkyl group having 1 to 50 carbon atoms,

[1029] a halogenated alkyl group having 1 to 50 carbon atoms,

[1030] an alkenyl group having 2 to 50 carbon atoms,

[1031] an alkynyl group having 2 to 50 carbon atoms,

[1032] a cycloalkyl group having 3 to 50 ring carbon atoms,

[1033] an alkylthio group having 1 to 50 carbon atoms,

[1034] an aryloxy group having 6 to 50 ring carbon atoms,

[1035] an arylthio group having 6 to 50 ring carbon atoms,

[1036] Aralkyl having 7 to 50 carbon atoms,

[1037] -Si(R 41 )(R 42 )(R 43 ),

[1038] -C(=O)R 44 、-COOR 45 、

[1039] -Ge(R 49 )(R 50 )(R 51 ),

[1040] Hydroxyl,

[1041] cyano,

[1042] Nitro,

[1043] an aryl group having 6 to 13 ring carbon atoms, or

[1044] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1045] R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.

[1046] R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each may be the same or different.

[1047] Among them, L A2 a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, and Ar A2 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in the group are each a group satisfying the following formula (T1),

[1048] T1>1.81eV···(T1)

[1049] In formula (T1), T1 is the triplet energy of the group.

[1050] In formula (2), when nA1 is 2 or 3, multiple L A2 connected in series, Ar A2 The farthest L from the dinaphthofuran skeleton A2 Bonding" for description.

[1051] It is obvious from the definition that when nA1 is 2 or 3, multiple L A2 In the dinaphthofuran skeleton and Ar A2 They are connected in series without branches.

[1052] For example, R 205 is a single bond bonded to the group represented by formula (A2). When nA1 is 3, the compound represented by formula (2) has a structure represented by the following formula (E2).

[1053] [Chemistry 143]

[1054]

[1055] In formula (2), L in formula (A2) A2 When Ar is a single bond, A2 Directly bonded to the dinaphthofuran skeleton.

[1056] The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the above formula (A2)" will be described.

[1057] The case where the "group represented by the aforementioned formula (A2)" is different from the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" includes cases where the chemical formulas (skeletons) are different, and cases where the chemical formulas (skeletons) are the same but contain different isotopes. Isotopes refer to atoms with the same atomic number but different neutron numbers. For example, benzene (C6H6) and deuterated benzene (C6D6) are different.

[1058] In addition, when the "group represented by the aforementioned formula (A2)" and the "substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms" have substituents with the same skeleton, and the substitution positions of the substituents are different, the "group represented by the aforementioned formula (A2)" and the "substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms" are not the same.

[1059] For example, the following compound is not included in formula (2) because both the "group represented by the above formula (A2)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are phenanthren-9-yl groups.

[1060] [Chemistry 144]

[1061]

[1062] In formula (2), the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and composed of 5 or less rings" will be described.

[1063] "Consisting of one ring" means a single ring.

[1064] For example, a phenyl group consists of one ring.

[1065] “Composed of X rings (X is an integer of 2 or greater)” means a polycyclic ring in which X rings are fused or spiro-bonded.

[1066] In the case of "substituted or unsubstituted", when substituents are bonded to each other to form a ring, and when they are fused or spiro-bonded to a ring having the substituent, the ring formed by the substituents being bonded to each other is also included in the "X rings".

[1067] For example, the following naphthyl group is composed of two rings. This naphthyl group may have a substituent.

[1068] [Chemistry 145]

[1069]

[1070] For example, the following benzofluorenyl group is composed of four rings. This benzofluorenyl group may have a substituent.

[1071] [Chemistry 146]

[1072]

[1073] For example, the following spirobifluorenyl group is composed of 6 rings.

[1074] [Chemistry 147]

[1075]

[1076] That is, "composed of 5 or less rings" means a monocyclic ring, or a polycyclic ring in which 2, 3, 4 or 5 rings are fused or spiro-bonded.

[1077] In formula (2), for “L A2 a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, and Ar A2 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms each satisfying the following formula (T1) is described.

[1078] T1>1.81eV···(T1)

[1079] In formula (T1), T1 is the triplet energy of the group.

[1080] In formula (2), L A2 When it is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, the group satisfies the above formula (T1).

[1081] In other words, it is not a single bond L A2 The above formula (T1) is satisfied.

[1082] L is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms A2 When there are two or more of them, L is a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms. A2 Each satisfies the above formula (T1).

[1083] In other words, it is not a single bond L A2 When there are multiple L, it is not a single bond A2 Each satisfies the above formula (T1).

[1084] In formula (2), Ar A2 The above formula (T1) is satisfied.

[1085] In one embodiment, L A2 a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, and Ar A2 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, each of which is a group satisfying the following formula (T2), or each of which is a group satisfying the following formula (T3), or each of which is a group satisfying the following formula (T4), or each of which is a group satisfying the following formula (T5).

[1086] T1>1.82eV···(T2)

[1087] T1>1.83eV···(T3)

[1088] T1>1.84eV···(T4)

[1089] T1>1.85eV···(T5)

[1090] Where T1 is the triplet energy of the group.

[1091] The upper limit of T1 is not particularly limited, and is, for example, 2.20 eV, 2.60 eV, 3.00 eV, or 3.40 eV.

[1092] T1 in formulas (T1) to (T5) is calculated by the method described in Examples.

[1093] In one embodiment, R 202 ~R 205 One of them is a single bond bonded to the group represented by the above formula (A2).

[1094] In one embodiment, R 202 、R 203 and R 205 One of them is a single bond bonded to the group represented by the above formula (A2).

[1095] In one embodiment, R 203 and R 205 One of them is a single bond bonded to the group represented by the above formula (A2).

[1096] In one embodiment, L A2 for:

[1097] single bond,

[1098] substituted or unsubstituted phenylene,

[1099] substituted or unsubstituted naphthylene,

[1100] Substituted or unsubstituted benzanthracenediyl,

[1101] substituted or unsubstituted pyrene diyl,

[1102] Substituted or unsubstituted benzofluorenediyl, or

[1103] Substituted or unsubstituted dibenzofluorenediyl.

[1104] In one embodiment, L A2 for:

[1105] Single key, or

[1106] a substituted or unsubstituted phenylene group.

[1107] In one embodiment, Ar A2 for:

[1108] substituted or unsubstituted phenyl,

[1109] substituted or unsubstituted naphthyl,

[1110] Substituted or unsubstituted benzanthryl,

[1111] substituted or unsubstituted pyrenyl,

[1112] substituted or unsubstituted benzofluorenyl,

[1113] Substituted or unsubstituted dibenzofluorenyl,

[1114] Substituted or unsubstituted naphthobenzofuranyl, or

[1115] a substituted or unsubstituted benzoxanthenyl group.

[1116] In one embodiment, Ar A2 for:

[1117] substituted or unsubstituted phenyl,

[1118] substituted or unsubstituted naphthyl,

[1119] Substituted or unsubstituted benzanthryl,

[1120] substituted or unsubstituted pyrenyl,

[1121] Substituted or unsubstituted benzofluorenyl, or

[1122] a substituted or unsubstituted dibenzofluorenyl group.

[1123] In one embodiment, the group represented by the above formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7).

[1124] [Chemistry 148]

[1125]

[1126] [Chemistry 149]

[1127]

[1128] In formula (A2-1) to formula (A2-7), nA2 and L A2 As defined in the above formula (A2).

[1129] R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is:

[1130] hydrogen atoms,

[1131] an alkyl group having 1 to 50 carbon atoms,

[1132] an aryl group having 6 to 13 ring carbon atoms, or

[1133] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1134] In one embodiment, the compound represented by the aforementioned formula (2) is a compound represented by any one of the following formulas (2-1) to (2-3).

[1135] [Chemistry 150]

[1136]

[1137] [Chemistry 151]

[1138]

[1139] In formula (2-1) to formula (2-3), nA2, L A2 、Ar A2 、R 201 ~R 212 As defined in formula (2) above.

[1140] In one embodiment, the compound represented by the aforementioned formula (2) is a compound represented by the aforementioned formula (2-1) or formula (2-2).

[1141] In one embodiment, the compound represented by the above formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19).

[1142] [Chemistry 152]

[1143]

[1144] [Chemistry 153]

[1145]

[1146] [Chemistry 154]

[1147]

[1148] [Chemistry 155]

[1149]

[1150] [Chemistry 156]

[1151]

[1152] In formula (2-11) to formula (2-19), nA2, L A2 、R 201 ~R 212 As defined in formula (2) above.

[1153] R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is:

[1154] hydrogen atoms,

[1155] an alkyl group having 1 to 50 carbon atoms,

[1156] an aryl group having 6 to 13 ring carbon atoms, or

[1157] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1158] In one embodiment, the compound represented by the above formula (2) is a compound represented by any one of the above formulas (2-11) to (2-14).

[1159] In one embodiment, R which is not a single bond 201 ~R 212 A hydrogen atom.

[1160] In one embodiment, R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is:

[1161] hydrogen atoms,

[1162] methyl,

[1163] Phenyl, or

[1164] Naphthyl.

[1165] In one embodiment, R A111 ~R A119 、R A121~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each is independently a hydrogen atom, a methyl group or a phenyl group.

[1166] In one embodiment, R A111 ~R A114 and R A116 ~R A119 is a hydrogen atom, R A115 It is a phenyl group.

[1167] In one embodiment, R A111 ~R A119 A hydrogen atom.

[1168] In one embodiment, R A121 ~R A126 and R A128 ~R A132 A hydrogen atom.

[1169] In one embodiment, R A121 ~R A126 and R A128 ~R A131 is a hydrogen atom, R A127 It is a phenyl group.

[1170] In one embodiment, R A141 ~R A149 and R A161 ~R A171 is a hydrogen atom, R A150 ~R A151 and R A172 ~R A173 It is a methyl group.

[1171] In one embodiment, R A181 ~R A189 A hydrogen atom.

[1172] In one embodiment, R A191 ~R A199 A hydrogen atom.

[1173] In one embodiment, R as a hydrogen atom A181 ~R A189 At least one of them is a deuterium atom.

[1174] In one embodiment, R as a hydrogen atom A191 ~R A199At least one of them is a deuterium atom.

[1175] In this specification, "deuterium atoms" in hydrogen atoms means that the ratio of deuterium atoms relative to the total of protium and deuterium atoms in the hydrogen atoms is greater than that found in nature. The ratio of deuterium atoms relative to the total of protium and deuterium atoms relative to the total of protium and deuterium atoms can be confirmed by nuclear magnetic resonance (NMR) equipment.

[1176] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (2) are selected from:

[1177] an alkyl group having 1 to 50 carbon atoms,

[1178] an aryl group having 6 to 13 ring carbon atoms, and

[1179] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1180] In one embodiment, the substituents in the case of "substituted or unsubstituted" in formula (2) are selected from:

[1181] an alkyl group having 1 to 18 carbon atoms,

[1182] an aryl group having 6 to 13 ring carbon atoms, and

[1183] A monovalent heterocyclic group having 5 to 18 ring atoms.

[1184] The compound represented by formula (2) can be synthesized according to the Examples by using known substitution reactions and starting materials corresponding to the target compound.

[1185] Specific examples of the compound represented by formula (2) include the following compounds in addition to the specific examples of the compound represented by formula (1). These are merely examples, and the compound represented by formula (2) is not limited to the following specific examples.

[1186] [Chemistry 157]

[1187]

[1188] [Chemistry 158]

[1189]

[1190] [Chemistry 159]

[1191]

[1192] [Materials for organic electroluminescent devices]

[1193] The compound of one embodiment of the present invention is useful as a material for an organic EL device, and can be used as a material used in a light-emitting layer of an organic EL device, for example.

[1194] [Organic EL element]

[1195] An organic EL device according to one embodiment of the present invention will be described.

[1196] An organic EL element according to one embodiment of the present invention comprises a cathode, an anode, and a light-emitting layer disposed between the cathode and the anode; the light-emitting layer comprises a first light-emitting layer and a second light-emitting layer, and the first light-emitting layer comprises a compound represented by formula (3) described below.

[1197] The organic EL element according to one embodiment of the present invention can improve performance by having the above-mentioned configuration.

[1198] Reference Figure 1 A schematic configuration of an organic EL element according to one embodiment of the present invention will be described.

[1199] An organic EL element 1 according to one embodiment of the present invention includes a substrate 2 , an anode 3 , a light-emitting layer 5 , a cathode 10 , a hole-transporting region 4 between the anode 3 and the light-emitting layer 5 , and an electron-transporting region 6 between the light-emitting layer 5 and the cathode 10 .

[1200] The light-emitting layer 5 has a stacked structure including at least a first light-emitting layer and a second light-emitting layer.

[1201] Typical element structures of the organic EL element of the present invention include:

[1202] (1) Anode / light-emitting layer / cathode

[1203] (2) Anode / Hole Injection Layer / Light Emitting Layer / Cathode

[1204] (3) Anode / light-emitting layer / electron injection and transport layer / cathode

[1205] (4) Anode / Hole Injection Layer / Light Emitting Layer / Electron Injection / Transport Layer / Cathode

[1206] (5) Anode / organic semiconductor layer / light-emitting layer / cathode

[1207] (6) Anode / organic semiconductor layer / electron barrier layer / light-emitting layer / cathode

[1208] (7) Anode / Organic semiconductor layer / Light-emitting layer / Adhesion-improving layer / Cathode

[1209] (8) Anode / Hole Injection / Transport Layer / Light Emitting Layer / Electron Injection / Transport Layer / Cathode

[1210] (9) Anode / insulating layer / luminescent layer / insulating layer / cathode

[1211] (10) Anode / inorganic semiconductor layer / insulating layer / luminescent layer / insulating layer / cathode

[1212] (11) Anode / organic semiconductor layer / insulating layer / luminescent layer / insulating layer / cathode

[1213] (12) Anode / Insulating layer / Hole injection and transport layer / Light-emitting layer / Insulating layer / Cathode

[1214] (13) Anode / Insulating layer / Hole injection / Transport layer / Light-emitting layer / Electron injection / Transport layer / Cathode

[1215] etc. structures.

[1216] Among the above, the configuration (8) is preferably used, but is not limited thereto.

[1217] In the light-emitting layer, the formation positions of the first light-emitting layer and the second light-emitting layer are not limited. In one embodiment, the light-emitting layer includes the first light-emitting layer and the second light-emitting layer in this order from the anode side.

[1218] In one embodiment, the first light-emitting layer and the second light-emitting layer are directly adjacent to each other.

[1219] In this specification, “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”.

[1220] In one embodiment, the organic EL device according to one embodiment of the present invention includes a hole transport layer between the anode and the light-emitting layer.

[1221] In one embodiment, the organic EL device according to one embodiment of the present invention includes an electron transport layer between the cathode and the light-emitting layer.

[1222] Hereinafter, members that can be used in the organic EL element of one embodiment of the present invention, materials constituting each layer, and the like will be described.

[1223] (First light-emitting layer)

[1224] The first light-emitting layer contains a compound represented by the following formula (3).

[1225] [Chemistry 160]

[1226]

[1227] In formula (3),

[1228] R 301 ~R 305 One of them is a single bond bonded to the group represented by the following formula (A3).

[1229] [Chemistry 161]

[1230] -(L A3 ) nA3 -Ar A3 (A3)

[1231] In formula (A3),

[1232] L A3 for:

[1233] single bond,

[1234] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1235] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1236] Ar A3 for:

[1237] a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or

[1238] A substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms.

[1239] nA3 is an integer from 0 to 3;

[1240] When nA3 is 0, (L A3 ) nA3 For a single bond.

[1241] When nA3 is 2 or 3, multiple L A3 connected in series, Ar A3 The farthest L from the dinaphthofuran skeleton A3 Bonding. Multiple L A3 Can be the same or different.

[1242] By R 306 ~R 312 , and R which is not a single bond bonded to the group represented by the aforementioned formula (A3) 301 ~R 305 One or more adjacent groups of two or more of the rings may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1243] R not bonded to each other 306 ~R 312 , and R which is not a single bond bonded to the group represented by the above formula (A3) and is not bonded to each other 301 ~R 305 Each independently is:

[1244] hydrogen atoms, or

[1245] A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the aforementioned formula (A3).

[1246] In formula (3), when nA1 is 2 or 3, multiple L A3 connected in series, Ar A3 The farthest L from the dinaphthofuran skeleton A3 Bonding" for description.

[1247] It is obvious from the definition that when nA1 is 2 or 3, multiple L A3 In the dinaphthofuran skeleton and Ar A3 They are connected in series without branches.

[1248] For example, R 305 It is a single bond bonded to the group represented by formula (A3). When nA1 is 3, the compound represented by formula (3) has a structure represented by the following formula (E3).

[1249] [Chemistry 162]

[1250]

[1251] In formula (3), L in formula (A3) A3 When Ar is a single bond, A3 Directly bonded to the dinaphthofuran skeleton.

[1252] The "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the above formula (A3)" will be described.

[1253] The "group represented by the aforementioned formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" may differ from each other in terms of chemical structural formulas (skeletons) or in terms of the same chemical structural formula (skeleton) but containing different isotopes. Isotopes are atoms with the same atomic number but different neutron numbers. For example, benzene (C6H6) and deuterated benzene (C6D6) are different.

[1254] In addition, when the "group represented by the aforementioned formula (A3)" and the "substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms" have substituents with the same skeleton, and the substitution positions of the substituents are different, the "group represented by the aforementioned formula (A3)" and the "substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms" are not the same.

[1255] For example, the following compound is not included in formula (3) because both the "group represented by the aforementioned formula (A3)" and the "substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms" are phenanthren-9-yl groups.

[1256] [Chemistry 163]

[1257]

[1258] In one embodiment, R 302 ~R 305 One of them is a single bond bonding to the group represented by the above formula (A3).

[1259] In one embodiment, R 302 、R 303 and R 305 One of them is a single bond bonding to the group represented by the above formula (A3).

[1260] In one embodiment, R 303 and R 305 One of them is a single bond bonding to the group represented by the above formula (A3).

[1261] In one embodiment, L A3 for:

[1262] single bond,

[1263] substituted or unsubstituted phenylene,

[1264] substituted or unsubstituted naphthylene,

[1265] Substituted or unsubstituted benzanthracenediyl,

[1266] substituted or unsubstituted pyrene diyl,

[1267] Substituted or unsubstituted benzofluorenediyl, or

[1268] Substituted or unsubstituted dibenzofluorenediyl.

[1269] In one embodiment, L A3 for:

[1270] Single key, or

[1271] a substituted or unsubstituted phenylene group.

[1272] In one embodiment, Ar A3 for:

[1273] substituted or unsubstituted phenyl,

[1274] substituted or unsubstituted naphthyl,

[1275] Substituted or unsubstituted benzanthryl,

[1276] substituted or unsubstituted pyrenyl,

[1277] substituted or unsubstituted benzofluorenyl,

[1278] Substituted or unsubstituted dibenzofluorenyl,

[1279] Substituted or unsubstituted naphthobenzofuranyl, or

[1280] a substituted or unsubstituted benzoxanthenyl group.

[1281] In one embodiment, Ar A3 for:

[1282] substituted or unsubstituted phenyl,

[1283] substituted or unsubstituted naphthyl,

[1284] Substituted or unsubstituted benzanthryl,

[1285] substituted or unsubstituted pyrenyl,

[1286] Substituted or unsubstituted benzofluorenyl, or

[1287] a substituted or unsubstituted dibenzofluorenyl group.

[1288] In one embodiment, the group represented by the above formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7).

[1289] [Chemistry 164]

[1290]

[1291] In formula (A3-1) to formula (A3-7), nA3 and L A3 As defined in the above formula (A3).

[1292] R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is:

[1293] hydrogen atoms,

[1294] an alkyl group having 1 to 50 carbon atoms,

[1295] a halogenated alkyl group having 1 to 50 carbon atoms,

[1296] an alkenyl group having 2 to 50 carbon atoms,

[1297] an alkynyl group having 2 to 50 carbon atoms,

[1298] a cycloalkyl group having 3 to 50 ring carbon atoms,

[1299] an alkoxy group having 1 to 50 carbon atoms,

[1300] an alkylthio group having 1 to 50 carbon atoms,

[1301] an aryloxy group having 6 to 50 ring carbon atoms,

[1302] an arylthio group having 6 to 50 ring carbon atoms,

[1303] Aralkyl having 7 to 50 carbon atoms,

[1304] -Si(R 941 )(R 942 )(R 943 ),

[1305] -C(=O)R 944 、-COOR 945 、

[1306] -S(=O)2R 946 、

[1307] -P(=O)(R 947 )(R 948 ),

[1308] -Ge(R 949 )(R 950 )(R 951 ),

[1309] -N(R 952 )(R 953 ),

[1310] Hydroxyl,

[1311] Halogen atoms,

[1312] cyano,

[1313] Nitro,

[1314] an aryl group having 6 to 50 ring carbon atoms, or

[1315] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1316] R 941 ~R 953 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.

[1317] R 941 ~R 953 When there are two or more, two or more R 941~R 953 Each may be the same or different.

[1318] In one embodiment, the group represented by the above formula (A3) is a group represented by any one of the above formulas (A3-1) to (A3-5).

[1319] In one embodiment, the compound represented by the above formula (3) is a compound represented by any one of the following formulas (3-1) to (3-3).

[1320] [Chemistry 166]

[1321]

[1322] [Chemistry 167]

[1323]

[1324] In formula (3-1) to formula (3-3), nA3, L A3 、Ar A3 and R 301 ~R 312 As defined in the above formula (1).

[1325] In one embodiment, the compound represented by the aforementioned formula (3) is a compound represented by the aforementioned formula (3-1) or formula (3-2).

[1326] In one embodiment, the compound represented by the above formula (3) is a compound represented by any one of the following formulas (3-11) to (3-19).

[1327] [Chemistry 168]

[1328]

[1329] [Chemistry 169]

[1330]

[1331] [Chemistry 170]

[1332]

[1333] [Chemistry 171]

[1334]

[1335] In formula (3-11) to formula (3-19), nA3, L A3 、R 301 ~R 312 As defined in formula (3) above.

[1336] R A211~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is:

[1337] hydrogen atoms,

[1338] an alkyl group having 1 to 50 carbon atoms,

[1339] a halogenated alkyl group having 1 to 50 carbon atoms,

[1340] an alkenyl group having 2 to 50 carbon atoms,

[1341] an alkynyl group having 2 to 50 carbon atoms,

[1342] a cycloalkyl group having 3 to 50 ring carbon atoms,

[1343] an alkoxy group having 1 to 50 carbon atoms,

[1344] an alkylthio group having 1 to 50 carbon atoms,

[1345] an aryloxy group having 6 to 50 ring carbon atoms,

[1346] an arylthio group having 6 to 50 ring carbon atoms,

[1347] Aralkyl having 7 to 50 carbon atoms,

[1348] -Si(R 941 )(R 942 )(R 943 ),

[1349] -C(=O)R 944 、-COOR 945 、

[1350] -S(=O)2R 946 、

[1351] -P(=O)(R 947 )(R 948 ),

[1352] -Ge(R 949 )(R 950 )(R 951 ),

[1353] -N(R 952 )(R 953 ),

[1354] Hydroxyl,

[1355] Halogen atoms,

[1356] cyano,

[1357] Nitro,

[1358] an aryl group having 6 to 50 ring carbon atoms, or

[1359] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1360] R 941 ~R 953 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.

[1361] R 941 ~R 953 When there are two or more, two or more R 941 ~R 953 Each may be the same or different.

[1362] In one embodiment, the compound represented by the above formula (3) is a compound represented by any one of the above formulas (3-11) to (3-14).

[1363] In one embodiment, R which is not a single bond 301 ~R 312 A hydrogen atom.

[1364] In one embodiment, R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 and R A261 ~R A273 Each independently is:

[1365] hydrogen atoms,

[1366] an alkyl group having 1 to 50 carbon atoms,

[1367] an aryl group having 6 to 50 ring carbon atoms, or

[1368] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1369] In one embodiment, R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 and RA261 ~R A273 Each independently is:

[1370] hydrogen atoms,

[1371] an alkyl group having 1 to 18 carbon atoms,

[1372] an aryl group having 6 to 18 ring carbon atoms, or

[1373] A monovalent heterocyclic group having 5 to 18 ring atoms.

[1374] In one embodiment, R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is:

[1375] hydrogen atoms,

[1376] methyl,

[1377] Phenyl, or

[1378] Naphthyl.

[1379] In one embodiment, R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each is independently a hydrogen atom, a methyl group or a phenyl group.

[1380] In one embodiment, R A211 ~R A214 and R A216 ~R A219 is a hydrogen atom, R A215 It is a phenyl group.

[1381] In one embodiment, R A211 ~R A219 A hydrogen atom.

[1382] In one embodiment, R A221 ~R A226 and RA228 ~R A232 A hydrogen atom.

[1383] In one embodiment, R A221 ~R A226 and R A228 ~R A231 is a hydrogen atom, R A227 It is a phenyl group.

[1384] In one embodiment, R A241 ~R A249 and R A261 ~R A271 is a hydrogen atom, R A250 ~R A251 and R A272 ~R A273 It is a methyl group.

[1385] In one embodiment, R A281 ~R A289 A hydrogen atom.

[1386] In one embodiment, R A291 ~R A299 A hydrogen atom.

[1387] In one embodiment, R as a hydrogen atom A281 ~R A289 At least one of them is a deuterium atom.

[1388] In one embodiment, R as a hydrogen atom A291 ~R A299 At least one of them is a deuterium atom.

[1389] In this specification, "deuterium atoms" in hydrogen atoms means that the ratio of deuterium atoms relative to the total of protium and deuterium atoms in the hydrogen atoms is greater than that found in nature. The ratio of deuterium atoms relative to the total of protium and deuterium atoms relative to the total of protium and deuterium atoms can be confirmed by nuclear magnetic resonance (NMR) equipment.

[1390] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the aforementioned formula (3) is selected from:

[1391] an alkyl group having 1 to 50 carbon atoms,

[1392] a halogenated alkyl group having 1 to 50 carbon atoms,

[1393] an alkenyl group having 2 to 50 carbon atoms,

[1394] an alkynyl group having 2 to 50 carbon atoms,

[1395] a cycloalkyl group having 3 to 50 ring carbon atoms,

[1396] an alkoxy group having 1 to 50 carbon atoms,

[1397] an alkylthio group having 1 to 50 carbon atoms,

[1398] an aryloxy group having 6 to 50 ring carbon atoms,

[1399] an arylthio group having 6 to 50 ring carbon atoms,

[1400] Aralkyl having 7 to 50 carbon atoms,

[1401] -Si(R 41 )(R 42 )(R 43 ),

[1402] -C(=O)R 44 、-COOR 45 、

[1403] -S(=O)2R 46 、

[1404] -P(=O)(R 47 )(R 48 ),

[1405] -Ge(R 49 )(R 50 )(R 51 ),

[1406] -N(R 52 )(R 53 ),

[1407] Hydroxyl,

[1408] Halogen atoms,

[1409] cyano,

[1410] Nitro,

[1411] an aryl group having 6 to 50 ring carbon atoms, and

[1412] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1413] R 41 ~R 53 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms.

[1414] R 41 ~R 53 When there are two or more, two or more R 41 ~R 53 Each may be the same or different.

[1415] In one embodiment, the substituent in the case of "substituted or unsubstituted" in the aforementioned formula (3) is selected from:

[1416] an alkyl group having 1 to 50 carbon atoms,

[1417] an aryl group having 6 to 50 ring carbon atoms, and

[1418] A monovalent heterocyclic group having 5 to 50 ring atoms.

[1419] In one embodiment, the compound represented by the aforementioned formula (3) is the compound represented by the aforementioned formula (1).

[1420] In one embodiment, the compound represented by the aforementioned formula (3) is the compound represented by the aforementioned formula (2).

[1421] The compound represented by formula (3) can be synthesized according to the Examples by using known substitution reactions and starting materials corresponding to the target compound.

[1422] Specific examples of the compound represented by formula (3) include the specific examples of the compound represented by formula (1) or formula (2). These are merely examples, and the compound represented by formula (3) is not limited to the specific examples of the compound represented by formula (1) or formula (2).

[1423] Specific examples of the compound represented by formula (3) include the following compounds in addition to the specific examples of the compound represented by formula (1) or formula (2). These are merely examples, and the compound represented by formula (3) is not limited to the following specific examples.

[1424] [Chemistry 172]

[1425]

[1426] [Chemistry 173]

[1427]

[1428] [Chemistry 174]

[1429]

[1430] [Chemistry 175]

[1431]

[1432] [Chemistry 176]

[1433]

[1434] [Chemistry 177]

[1435]

[1436] [Chemistry 178]

[1437]

[1438] [Chemistry 179]

[1439]

[1440] [Chemistry 180]

[1441]

[1442] [Chemistry 181]

[1443]

[1444] [Chemistry 182]

[1445]

[1446] [Chemistry 183]

[1447]

[1448] [Chemistry 184]

[1449]

[1450] [Chemistry 185]

[1451]

[1452] [Chemistry 186]

[1453]

[1454] [Chemistry 187]

[1455]

[1456] [Chemistry 188]

[1457]

[1458] [Chemistry 189]

[1459]

[1460] [Chemistry 190]

[1461]

[1462] [Chemistry 191]

[1463]

[1464] [Chemistry 192]

[1465]

[1466] In one embodiment, the first light-emitting layer contains the compound represented by the above formula (3) and the second compound.

[1467] The compound represented by the above formula (3) and the second compound are different from each other.

[1468] (Second compound)

[1469] In one embodiment, the second compound is a light-emitting material.

[1470] In one embodiment, the second compound is a fluorescent compound.

[1471] In one embodiment, the second compound is a compound that emits light with a maximum peak wavelength of fluorescence of 430 nm to 480 nm. In this specification, the maximum peak wavelength of fluorescence may be referred to as the maximum peak wavelength of fluorescence.

[1472] In this specification, the maximum peak wavelength of fluorescence refers to the wavelength of the compound to be measured at 10 -6 mol / L or above, 10 -5 The maximum peak wavelength of the fluorescence spectrum at which the luminescence intensity is maximum is measured in a toluene solution dissolved at a concentration of mol / L or less. A fluorescence spectrometer (FP-8300, manufactured by JASCO Corporation) can be used as the measuring apparatus. It should be noted that the fluorescence spectrometer is not limited to the apparatus exemplified here.

[1473] Examples of the second compound include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylamino Derivatives, aryl substitution Derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthenefluoranthene derivatives, boron atom-containing compounds, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives and tetracene derivatives, etc.

[1474] Examples of the second compound include one or more compounds selected from the group consisting of a compound represented by the following formula (D1), a compound represented by the following formula (D2), a compound represented by the following formula (D3), and a compound represented by the following formula (D4).

[1475] (Compound represented by formula (D1))

[1476] The compound represented by formula (D1) will be described.

[1477] [Chemistry 193]

[1478]

[1479] In formula (D1),

[1480] Z is independently CRa or a nitrogen atom.

[1481] Ring A1 and Ring A2 are each independently:

[1482] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1483] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1484] When there are plural Ra's, one or more groups consisting of two or more adjacent Ra's may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1485] n21 and n22 are each independently 0, 1, 2, 3 or 4.

[1486] When there are multiple Rb, one or more groups consisting of two or more adjacent Rb may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1487] When there are multiple Rc's, one or more groups consisting of two or more adjacent Rc's may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1488] Ra, Rb and Rc which are not bonded to each other are each independently:

[1489] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1490] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1491] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1492] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1493] -Si(R 901 )(R 902 )(R 903 ),

[1494] -O-(R 904 ),

[1495] -S-(R 905 ),

[1496] -N(R 906 )(R 907 ),

[1497] Halogen atoms, cyano, nitro,

[1498] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1499] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1500] R 901 ~R 907 Each independently is:

[1501] hydrogen atoms,

[1502] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1503] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1504] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1505] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1506] R 901 ~R 907 When there are two or more, two or more R 901 ~R 907 Each may be the same or different.

[1507] Examples of the "aromatic hydrocarbon ring" of the A1 ring and the A2 ring include the same structures as those of the compounds obtained by introducing hydrogen atoms into the above-mentioned "aryl group having 6 to 50 ring carbon atoms".

[1508] The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms in the central condensed bicyclic structure of the aforementioned formula (D1) as ring-constituting atoms.

[1509] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom is introduced into the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[1510] Examples of the "heterocycle" for the A1 ring and the A2 ring include the same structures as those of the compounds obtained by introducing hydrogen atoms into the above-mentioned "heterocyclic group having 5 to 50 ring atoms".

[1511] The "heterocycle" of the A1 ring and the A2 ring contains two carbon atoms in the central fused bicyclic structure of the aforementioned formula (D1) as ring-constituting atoms.

[1512] Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom is introduced into the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[1513] Rb is bonded to any carbon atom forming the aromatic hydrocarbon ring as the A1 ring, or is bonded to any atom forming the heterocyclic ring as the A1 ring.

[1514] Rc is bonded to any carbon atom forming the aromatic hydrocarbon ring as the A2 ring, or is bonded to any atom forming the heterocyclic ring as the A2 ring.

[1515] In one embodiment, at least one of Ra, Rb, and Rc is a group represented by the following formula (D1a).

[1516] In one embodiment, at least two of Ra, Rb, and Rc are groups represented by the following formula (D1a).

[1517] [Chemistry 194]

[1518] -L D101 -Ar D101 (Dla)

[1519] In formula (D1a),

[1520] L D101 for:

[1521] single bond,

[1522] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1523] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1524] Ar D101 for:

[1525] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1526] a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or

[1527] A group represented by the following formula (D1b).

[1528] [Chemistry 195]

[1529]

[1530] In formula (D1b),

[1531] L D102 and L D103 Each independently is:

[1532] single bond,

[1533] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

[1534] A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1535] By Ar D102 and Ar D103 The constituent groups may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1536] Ar not bonded to each other D102 and Ar D103 Each independently is:

[1537] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1538] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1539] In one embodiment, R 901 ~R 907 Each independently is:

[1540] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1541] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1542] The compound represented by formula (D1) can be synthesized by using existing reactions and raw materials corresponding to the target product.

[1543] Specific examples of the compound represented by formula (D1) include the following compounds. These are merely examples, and the compound represented by formula (D1) is not limited to the following specific examples.

[1544] [Chemistry 196]

[1545]

[1546] (Compound represented by formula (D2))

[1547] The compound represented by formula (D2) will be described.

[1548] [Chemistry 197]

[1549]

[1550] In formula (D2),

[1551] By R D201 ~R D207 and R D211 ~R D217 One or more adjacent groups of two or more of them may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1552] R not bonded to each other D201 ~R D207 and R D211 ~R D217 Each independently is:

[1553] hydrogen atoms,

[1554] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1555] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1556] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1557] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1558] -Si(R 901 )(R 902 )(R 903 )

[1559] -O-(R 904 ),

[1560] -S-(R 905 ),

[1561] -N(R 906 )(R 907 ),

[1562] Halogen atoms, cyano, nitro,

[1563] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1564] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1565] R D221 and R D222 Each independently is:

[1566] hydrogen atoms,

[1567] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1568] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1569] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1570] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1571] -Si(R 901 )(R 902 )(R 903 ),

[1572] -O-(R 904 ),

[1573] -S-(R 905 ),

[1574] -N(R 906 )(R 907 ),

[1575] Halogen atoms, cyano, nitro,

[1576] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1577] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1578] R 901 ~R 907 As defined in the above formula (D1).

[1579] “By R D201 ~R D207 and R D211 ~R D217 A group of two or more adjacent groups is "a group" such as R D201 With R D202 The group composed of R D202 With R D203 The group composed of R D203 With R D204 The group composed of R D205 With R D206 The group composed of R D206 With R D207 The group composed of R D201 With R D202 With R D203 Composition of groups etc.

[1580] In one embodiment, R D201 ~R D207 and R D211 ~R D217 At least one of them is -N(R 906 )(R 907 ).

[1581] In one embodiment, R D201 ~R D207 and R D211 ~R D217 At least two of them are -N(R 906 )(R 907 ).

[1582] In one embodiment, R D201 ~R D207 At least one of them is -N(R 906 )(R 907 ).

[1583] In one embodiment, R D211 ~R D217 At least one of them is -N(R 906 )(R 907 ).

[1584] In one embodiment, R D201 ~R D207 At least one of the R D211 ~R D217 At least one of each of which is independently -N(R 906 )(R 907 ).

[1585] In one embodiment, instead of -N(R 906 )(R 907 ) of R D201 ~R D207 and R D211 ~R D217 Each independently is:

[1586] hydrogen atoms,

[1587] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1588] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1589] The compound represented by formula (D2) can be synthesized by using existing reactions and raw materials corresponding to the target product.

[1590] Specific examples of the compound represented by formula (D2) include the following compounds. These are merely examples, and the compound represented by formula (D2) is not limited to the following specific examples.

[1591] [Chemistry 198]

[1592]

[1593] [Chemistry 199]

[1594]

[1595] (Compound represented by formula (D3))

[1596] The compound represented by formula (D3) is described.

[1597] [Chemistry 200]

[1598]

[1599] In formula (D3),

[1600] Ring a, ring b and ring c are each independently:

[1601] a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

[1602] A substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

[1603] R D301 and R D302 Each independently bonds to the aforementioned a ring, b ring, or c ring to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.

[1604] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring D301 and R D302 Each independently is:

[1605] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1606] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1607] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1608] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1609] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1610] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1611] The a ring, the b ring, and the c ring are fused to the central fused bicyclic structure of the aforementioned formula (D3) consisting of a boron atom, two nitrogen atoms, and seven carbon atoms.

[1612] The "aromatic hydrocarbon rings" of ring a, ring b, and ring c have the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group having 6 to 50 ring carbon atoms."

[1613] The "aromatic hydrocarbon ring" of ring a contains three carbon atoms in the central fused bicyclic structure of the aforementioned formula (D3) as ring-constituting atoms.

[1614] The "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms in the central fused bicyclic structure of the aforementioned formula (D3) as ring-constituting atoms.

[1615] Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds in which a hydrogen atom is introduced into the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

[1616] Examples of the "heterocycle" of ring a, ring b and ring c include the same structures as those of compounds obtained by introducing hydrogen atoms into the above-mentioned "heterocyclic group having 5 to 50 ring atoms".

[1617] The "heterocycle" of ring a comprises three carbon atoms in the central fused bicyclic structure of the aforementioned formula (D3) as ring atoms. The "heterocycle" of ring b and ring c comprises two carbon atoms in the central fused bicyclic structure of the aforementioned formula (D3) as ring atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom is introduced into the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

[1618] R D301 and R D302 Each independently bonds to the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case includes the nitrogen atom on the central fused bicyclic structure of the aforementioned formula (D3). The heterocyclic ring in this case may also contain heteroatoms other than nitrogen atoms. R D301 or R D302 Specifically, the atoms constituting the a ring, the b ring or the c ring are bonded to the atoms constituting the R D301 or R D302 For example, R D301 Can be bonded to a ring to form a D301 A nitrogen-containing heterocyclic ring having a ring fused with a ring of a, ...

[1619] R D301 When bonded to the b ring, R D302 When bonded to the a ring, and R D302 The case of bonding to the C ring is the same as above.

[1620] In one embodiment, the ring a, ring b, and ring c in the formula (D3) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

[1621] In one embodiment, the ring a, ring b, and ring c in the formula (D3) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

[1622] In one embodiment, R in the aforementioned formula (D3) D301 and R D302 Each independently is:

[1623] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1624] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1625] In one embodiment, R in the aforementioned formula (D3) D301 and R D302 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1626] In one embodiment, the compound represented by the aforementioned formula (D3) is a compound represented by the following formula (D32).

[1627] [Chemistry 201]

[1628]

[1629] In formula (D32),

[1630] R D301A and selected from R D311 and R D321 One or more of them may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1631] R D302A and selected from R D313 and R D314 One or more of them may be bonded to form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1632] R which does not form the aforementioned substituted or unsubstituted heterocyclic ring D301A and R D302A Each independently is:

[1633] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1634] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1635] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1636] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1637] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1638] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1639] By R D311 ~R D321的 One or more adjacent groups of two or more of the rings may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1640] R does not form the aforementioned substituted or unsubstituted heterocyclic ring, does not form the aforementioned monocyclic ring, and does not form the aforementioned condensed ring D311 ~R D321 Each independently is:

[1641] hydrogen atoms,

[1642] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1643] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1644] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1645] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1646] -Si(R 901 )(R 902 )(R 903 ),

[1647] -O-(R 904 ),

[1648] -S-(R 905 ),

[1649] -N(R 906 )(R 907 ),

[1650] Halogen atoms, cyano, nitro,

[1651] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1652] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1653] R 901 ~R 907 As defined in the above formula (D1).

[1654] R in the above formula (D32) D301A and R D302A Respectively with R of the above formula (D3) D301 and R D302 correspond.

[1655] For example, R D301A With R D311 These rings may be bonded to form a 2-ring fused, 3-ring fused, 4-ring fused, or 5-ring or more fused nitrogen-containing heterocyclic ring in which the ring containing these rings is fused to the benzene ring corresponding to the a ring. Specific examples of such nitrogen-containing heterocyclic rings include compounds corresponding to the nitrogen-containing 2-ring or more fused heterocyclic groups in Specific Example Group G2. D301A With R D321 Bonding situation, R D302A With R D313 Bonding situation, and R D302A With R D314 The bonding situation is the same as above.

[1656] In one embodiment, R D311 ~R D321 One or more groups of two or more adjacent

[1657] bonded to each other to form a substituted or unsubstituted monocyclic ring, or

[1658] They are bonded to each other to form a substituted or unsubstituted fused ring.

[1659] For example, R D311 With R D312 The six-membered ring to which these rings are bonded may be fused to a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring. The fused rings formed are naphthalene, carbazole, indole, benzofuran, dibenzofuran, or dibenzothiophene rings.

[1660] In one embodiment, R D311 ~R D321 Each independently is:

[1661] hydrogen atoms,

[1662] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1663] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1664] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1665] In one embodiment, R D311 ~R D321 Each independently is:

[1666] hydrogen atoms,

[1667] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1668] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1669] In one embodiment, R D311 ~R D321 Each independently is:

[1670] hydrogen atoms, or

[1671] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1672] In one embodiment, R D311 ~R D321 Each independently is:

[1673] hydrogen atoms, or

[1674] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1675] R D311 ~R D321 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1676] In one embodiment, the compound represented by the aforementioned formula (D32) is a compound represented by the following formula (D33).

[1677] [Chemistry 202]

[1678]

[1679] In formula (D33),

[1680] R D331 With R D346 The bonds may form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1681] R D333 With R D347The bonds may form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1682] R D334 With R D351 The bonds may form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1683] R D341 With R D342 The bonds may form a substituted or unsubstituted heterocyclic ring, or may not form a substituted or unsubstituted heterocyclic ring.

[1684] By R D331 ~R D321的 One or more adjacent groups of two or more of the rings may be bonded to each other to form a substituted or unsubstituted monocyclic ring, or may be bonded to each other to form a substituted or unsubstituted condensed ring, or may not be bonded to each other.

[1685] R not bonded to each other D331 ~R D351 Each independently is:

[1686] hydrogen atoms,

[1687] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1688] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1689] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1690] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1691] -Si(R 901 )(R 902 )(R 903 ),

[1692] -O-(R 904 ),

[1693] -S-(R 905 ),

[1694] -N(R 906 )(R 907 ),

[1695] Halogen atoms, cyano, nitro,

[1696] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1697] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1698] R 901 ~R907 As defined in the above formula (D1).

[1699] R D331 Can be used with R D346 bonded to form a substituted or unsubstituted heterocyclic ring. For example, R D331 With R D346 Can bond to form R D346 A nitrogen-containing heterocyclic ring having three or more rings fused together by condensing a benzene ring, a ring containing N, and a benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the nitrogen-containing heterocyclic group having three or more rings fused together in Specific Example Group G2. D333 With R D347 Bonding situation, R D334 With R D351 Bonding situation, and R D341 With R D342 The bonding situation is the same as above.

[1700] In one embodiment, R D331 ~R D351 Each independently is:

[1701] hydrogen atoms,

[1702] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1703] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1704] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1705] In one embodiment, R D331 ~R D351 Each independently is:

[1706] hydrogen atoms,

[1707] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1708] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1709] In one embodiment, R D331 ~R D351 Each independently is:

[1710] hydrogen atoms, or

[1711] A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1712] In one embodiment, RD331 ~R D351 Each independently is:

[1713] hydrogen atoms, or

[1714] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1715] R D331 ~R D351 At least one of them is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1716] In one embodiment, the compound represented by the aforementioned formula (D33) is a compound represented by the following formula (D33A).

[1717] [Chemistry 203]

[1718]

[1719] In formula (D33A),

[1720] R D361 for:

[1721] hydrogen atoms,

[1722] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1723] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1724] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1725] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1726] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1727] R D362 ~R D365 Each independently is:

[1728] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1729] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1730] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1731] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1732] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1733] In one embodiment, RD361 ~R D365 Each independently is:

[1734] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1735] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1736] In one embodiment, R D361 ~R D365 Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[1737] In one embodiment, the compound represented by the aforementioned formula (D33) is a compound represented by the following formula (D33B).

[1738] [Chemistry 204]

[1739]

[1740] In formula (D33B),

[1741] R D371 and R D372 Each independently is:

[1742] hydrogen atoms,

[1743] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1744] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1745] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1746] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1747] -N(R 906 )(R 907 ),or

[1748] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1749] R D373 ~R D375 Each independently is:

[1750] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1751] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1752] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1753] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1754] -N(R 906 )(R 907 ),or

[1755] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1756] R 906 and R 907 As defined in the above formula (D1).

[1757] In one embodiment, the compound represented by the aforementioned formula (D33) is a compound represented by the following formula (D33B′).

[1758] [Chemistry 205]

[1759]

[1760] In formula (D33B'), R D372 ~R D375 As defined above in formula (D33B).

[1761] In one embodiment, R D371 ~R D375 At least one of the following is:

[1762] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1763] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1764] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1765] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1766] -N(R 906 )(R 907 ),or

[1767] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1768] In one embodiment, R D372 for:

[1769] hydrogen atoms,

[1770] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1771] -N(R 906 )(R 907 ),or

[1772] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

[1773] R D371 and R D373 ~R D375 Each independently is:

[1774] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1775] -N(R 906 )(R 907 ),or

[1776] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1777] In one embodiment, the compound represented by the aforementioned formula (D33) is a compound represented by the following formula (D33C).

[1778] [Chemistry 206]

[1779]

[1780] In formula (D33C),

[1781] R D381 and R D382 Each independently is:

[1782] hydrogen atoms,

[1783] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1784] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1785] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1786] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1787] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1788] R D383 ~R D386 Each independently is:

[1789] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1790] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1791] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1792] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

[1793] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1794] In one embodiment, the compound represented by the aforementioned formula (D33) is a compound represented by the following formula (D33C′).

[1795] [Chemistry 207]

[1796]

[1797] In formula (D33C'), R D383 ~R D386 As defined above in formula (D33C).

[1798] In one embodiment, R D381 ~R D386 Each independently is:

[1799] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

[1800] A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1801] In one embodiment, R D381 ~R D386 Each is independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

[1802] The compound represented by the above formula (D3) can be prepared by first connecting the ring a, ring b and ring c with a first linking group (containing NR D301 Groups and groups containing NR D302 The intermediate is produced by bonding the rings a, b, and c via a second linker (a group containing a boron atom) to produce the final product (the second reaction). Amination reactions such as the Buchwald–Hartwig reaction can be used in the first reaction. Tandem Hetero-Friedel-Crafts reactions can be used in the second reaction.

[1803] The compound represented by formula (D3) can be synthesized by using existing reactions and raw materials corresponding to the target product.

[1804] Specific examples of the compound represented by formula (D3) include the following compounds. These are merely examples, and the compound represented by formula (D3) is not limited to the following specific examples.

[1805] [Chemistry 208]

[1806]

[1807] [Chemistry 209]

[1808]

[1809] [Chemistry 210]

[1810]

[1811] [Chemistry 211]

[1812]

[1813] [Chemistry 212]

[1814]

[1815] [Chemistry 213]

[1816]

[1817] [Chemistry 214]

[1818]

[1819] [Chemistry 215]

[1820]

[1821] [Chemistry 216]

[1822]

[1823] [Chemistry 217]

[1824]

[1825] [Chemistry 218]

[1826]

[1827] [Chemistry 219]

[1828]

[1829] [Chemistry 220]

[1830]

[1831] (Compound represented by formula (D4))

[1832] The compound represented by formula (D4) will be described.

[1833] [Chemistry 221]

[1834]

[1835] In formula (D4),

[1836] R D401 With R D402 Group, R D402 With R D403 Group, and R D403 With R D404 At least one of the groups is bonded to each other to form a divalent group represented by the following formula (D42).

[1837] R D405 With R D406 Group, R D406 With R D407 The group, and R D407 With R D408 At least one of the groups is bonded to each other to form a divalent group represented by the following formula (D43).

[1838] [Chemistry 222]

[1839]

[1840] R that does not form a divalent group represented by the above formula (D42) D401 ~R D404 and R D411 ~R D414 At least one of them is a monovalent group represented by the following formula (D44).

[1841] R does not form a divalent group represented by the above formula (D43) D405 ~R D408 and R D421 ~R D424 At least one of them is a monovalent group represented by the following formula (D44).

[1842] X D4 is an oxygen atom, a sulfur atom or NR D409 .

[1843] R does not form a divalent group represented by the above formula (D42) and formula (D43) and is not a monovalent group represented by the above formula (D44) D401 ~R D408 、 R is not a monovalent group represented by the above formula (D44) D411 ~R D414 and R D421 ~R D424 , and R D409 Each independently is:

[1844] hydrogen atoms,

[1845] a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

[1846] a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

[1847] a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

[1848] a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

[1849] -Si(R 901 )(R 902 )(R 903 ),

[1850] -O-(R 904 ),

[1851] -S-(R 905 ),

[1852] -N(R 906 )(R 907 ),

[1853] Halogen atoms, cyano, nitro,

[1854] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1855] A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

[1856] [Chemistry 223]

[1857]

[1858] In formula (D44),

[1859] Ar D401 and Ar D402 Each independently is:

[1860] a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

[1861] A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

[1862] L D401 ~L D403 Each independently is:

[1863] single bond,

[1864] a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

[1865] a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

[1866] A divalent linking group formed by bonding 2 to 4 groups selected from a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.

[1867] L D401 It bonds to the ring structure represented by the aforementioned formula (D4), the group represented by the formula (D42), or the group represented by the formula (D43).

[1868] In the aforementioned formula (D4), the positions at which the divalent group represented by the aforementioned formula (D42) and the divalent group represented by the aforementioned formula (D43) are formed are not particularly limited, and may be D401 ~R D408 The possible positions to form the group.

[1869] The compound represented by formula (D4) can be synthesized by using existing reactions and raw materials corresponding to the target product.

[1870] As the compound represented by the above formula (D4), in addition to the compounds described in International Publication No. 2014 / 104144, the following compounds can be given as specific examples. These are merely examples, and the compound represented by the formula (D4) is not limited to the following specific examples.

[1871] [Chemistry 224]

[1872]

[1873] In addition to the compounds represented by the above formula (D1), formula (D2), formula (D3), and formula (D4), for example, the following compounds can be used as the second compound.

[1874] [Chemistry 225]

[1875]

[1876] [Chemistry 226]

[1877]

[1878] [Chemistry 227]

[1879]

[1880] [Chemistry 228]

[1881]

[1882] In one embodiment, the first light-emitting layer contains the compound represented by the above formula (3) as a host material (also sometimes referred to as a matrix material).

[1883] In one embodiment, the first light-emitting layer further contains a dopant material.

[1884] In one embodiment, the first light-emitting layer contains the second compound as a dopant material (also sometimes referred to as a guest material, emitter, or light-emitting material).

[1885] In one embodiment, the first light-emitting layer contains the dopant material in an amount greater than 1.1 mass % and 1.2 mass % or greater, or 1.5 mass % or greater, based on the total mass of the first light-emitting layer.

[1886] In one embodiment, the first light-emitting layer contains a dopant material in an amount of 10 mass % or less, 7 mass % or less, or 5 mass % or less of the total mass of the first light-emitting layer.

[1887] In one embodiment, the first emitting layer contains 60 mass% or more, 70 mass% or more, 80 mass% or more, 90 mass% or more, or 95 mass% or more of the host material based on the total mass of the first emitting layer.

[1888] In one embodiment, the first light-emitting layer contains a host material in an amount of 99 mass % or less based on the total mass of the first light-emitting layer.

[1889] The first light-emitting layer may contain materials other than the host material and the dopant material.

[1890] The first light-emitting layer may contain only one host material or two or more host materials. The first light-emitting layer may contain only one dopant material or two or more host materials.

[1891] (Second light-emitting layer)

[1892] The second light-emitting layer contains at least one compound different from the first light-emitting layer. In one embodiment, the second light-emitting layer contains a host material. As the host material, in addition to the compound represented by the above formula (3), for example, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex, 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative, 3) a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or 4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[1893] In one embodiment, the second host material is a compound different from the first host material contained in the first light-emitting layer.

[1894] In one embodiment, the second light-emitting layer further comprises a dopant material. As the dopant material, for example, the second compound described above can be used. Alternatively, a known phosphorescent material can be used as the dopant material.

[1895] In one embodiment, the dopant material of the second light-emitting layer is a compound different from the dopant material of the first light-emitting layer.

[1896] In one embodiment, the dopant material of the second light-emitting layer is the same compound as the dopant material of the first light-emitting layer.

[1897] In one embodiment, the second light-emitting layer contains the dopant material in an amount greater than 1.1 mass % and 1.2 mass % or greater, or 1.5 mass % or greater, based on the total mass of the second light-emitting layer.

[1898] In one embodiment, the second light-emitting layer contains a dopant material in an amount of 10 mass % or less, 7 mass % or less, or 5 mass % or less of the total mass of the second light-emitting layer.

[1899] In one embodiment, the second emitting layer contains 60 mass % or more, 70 mass % or more, 80 mass % or more, 90 mass % or more, or 95 mass % or more of the host material based on the total mass of the second emitting layer.

[1900] In one embodiment, the second light-emitting layer contains a host material in an amount of 99 mass % or less based on the total mass of the second light-emitting layer.

[1901] The second light-emitting layer may contain materials other than the host material and the dopant material.

[1902] The second light-emitting layer may contain only one host material or two or more host materials. The second light-emitting layer may contain only one dopant material or two or more host materials.

[1903] The second light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer.

[1904] In one embodiment, the second light-emitting layer is a fluorescent light-emitting layer.

[1905] In the organic EL device of one embodiment of the present invention, the first emitting layer may contain, in addition to the compound represented by formula (3), any conventionally known materials and device configurations as long as the effects of the present invention are not impaired.

[1906] (Substrate)

[1907] The substrate serves as a support for the light-emitting element. Examples of substrates include glass, quartz, and plastic. Flexible substrates can also be used. Flexible substrates are bendable (flexible) substrates, such as plastic substrates made of polycarbonate or polyvinyl chloride.

[1908] (anode)

[1909] The anode formed on the substrate is preferably made of a metal, alloy, conductive compound, or mixture thereof with a high work function (specifically, 4.0 eV or greater). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), or metal nitrides (e.g., titanium nitride).

[1910] (Hole Injection Layer)

[1911] The hole injection layer is a layer containing a substance with high hole injection properties. As substances with high hole injection properties, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, aromatic amine compounds, or polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used.

[1912] (Hole Transport Layer)

[1913] The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used in the hole transport layer. Polymer compounds such as poly (N-vinyl carbazole) (abbreviated as: PVK) and poly (4-vinyl triphenylamine) (abbreviated as: PVTPA) can also be used. Among them, as long as the hole transport property is higher than the electron transport property, substances other than the above can be used. It should be noted that the layer containing a substance with high hole transport properties can be not only a single layer, but also a layer formed by stacking two or more layers containing the above substances.

[1914] (Guest (dopant) material of the light-emitting layer)

[1915] The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used. For example, as a highly luminescent substance, in addition to the compound represented by formula (D1), the compound represented by formula (D2), the compound represented by formula (D3), and the compound represented by formula (D4), a fluorescent compound that emits fluorescence and a phosphorescent compound that emits phosphorescence can also be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.

[1916] As the blue fluorescent material that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. As green fluorescent luminescent materials that can be used in the luminescent layer, aromatic amine derivatives, etc. can be used. As red fluorescent luminescent materials that can be used in the luminescent layer, butane derivatives, diamine derivatives, etc. can be used.

[1917] As blue-based phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used. As green-based phosphorescent materials that can be used in the light-emitting layer, iridium complexes are used. As red-based phosphorescent materials that can be used in the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used.

[1918] (Host material of light-emitting layer)

[1919] The light-emitting layer may be a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As a substance for dispersing the highly luminescent substance, various substances can be used in addition to the materials used in the present invention described above (the compound represented by formula (1), the compound represented by formula (2), and the compound represented by formula (3)). It is preferred to use a substance having a higher lowest unoccupied molecular orbital energy level (LUMO energy level) and a lower highest occupied molecular orbital energy level (HOMO energy level) than the highly luminescent substance.

[1920] As the material for dispersing the highly luminescent substance (host material), 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) a heterocyclic compound such as an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; 3) a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or 4) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

[1921] Furthermore, as a host material, a compound having delayed fluorescence (thermally activated delayed fluorescence) can also be used. The light-emitting layer preferably contains the material used in the present invention described above and a delayed fluorescence host compound.

[1922] The light-emitting layer may or may not contain other substances besides the materials used in the present invention described above.

[1923] (Electron Transport Layer)

[1924] The electron transport layer is a layer containing a substance with high electron transport properties. Examples of the electron transport layer include: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, oxazine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds.

[1925] (Electron Injection Layer)

[1926] The electron injection layer is a layer containing a substance with high electron injection properties. Metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinoline-lithium (Liq), lithium oxide (LiO) and the like can be used in the electron injection layer. x ) and other alkali metals, alkaline earth metals, or compounds thereof.

[1927] (cathode)

[1928] The cathode is preferably a metal, alloy, conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

[1929] The cathode is usually formed by vacuum deposition or sputtering. When silver paste is used, coating or inkjet methods can be used.

[1930] When an electron injection layer is provided, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function.

[1931] (Electron blocking layer, hole blocking layer, exciton blocking layer)

[1932] An electron blocking layer, a hole blocking layer, an exciton (triplet) blocking layer, or the like may be provided adjacent to the light-emitting layer.

[1933] An electron-blocking layer blocks electrons from leaking from the light-emitting layer to the hole-transporting layer. A hole-blocking layer blocks holes from leaking from the light-emitting layer to the electron-transporting layer. An exciton-blocking layer blocks excitons generated in the light-emitting layer from diffusing to adjacent layers, thereby confining the excitons within the light-emitting layer.

[1934] In the organic EL device of one embodiment of the present invention, the thickness of each layer is not particularly limited, but is generally preferably in the range of several nm to 1 μm in order to suppress defects such as pinholes, keep the applied voltage low, and improve luminous efficiency.

[1935] In the organic EL element of one embodiment of the present invention, the method for forming each layer is not particularly limited. Conventionally known formation methods such as vacuum evaporation and spin coating can be used. Each layer, such as the light-emitting layer, can be formed by a known coating method such as vacuum evaporation, molecular beam evaporation (MBE), or dipping a solution dissolved in a solvent, spin coating, casting, rod coating, or roller coating.

[1936] [Electronic equipment]

[1937] An electronic device according to one embodiment of the present invention is characterized by including the organic EL element according to one embodiment of the present invention.

[1938] Specific examples of electronic devices include display components such as organic EL panel modules; display devices such as televisions, mobile phones, and personal computers; and light-emitting devices such as lighting and vehicle lamps.

[1939] Example

[1940] Compounds

[1941] The compounds represented by formula (1), formula (2) or formula (3) used in the production of the organic EL devices of the examples are shown below.

[1942] [Chemistry 229]

[1943]

[1944] [Chemistry 230]

[1945]

[1946] [Chemistry 231]

[1947]

[1948] The compounds used in the production of the organic EL device of the comparative example are shown below.

[1949] [Chemistry 232]

[1950]

[1951] The structures of other compounds used in the production of the organic EL devices of Examples and Comparative Examples are shown below.

[1952] [Chemistry 233]

[1953]

[1954] [Chemistry 234]

[1955]

[1956] (Evaluation of Group T1)

[1957] For the groups shown in Table 1, the triplet excited state energy (T1) was calculated by the time-dependent density functional method (TD-B3LYP / 6-31G(d)) for the most stable structure calculated using B3LYP / 6-31G(d). The following software, functionals, and basis functions were used.

[1958] Software: Gaussian 16, Revision B.01

[1959] Functional: B3LYP

[1960] Basis function: 6-31G(d)

[1961] The evaluation results are shown in Table 1.

[1962] [Table 1]

[1963]

[1964] (Evaluation of Compounds)

[1965] The singlet energy (S1) and triplet energy (T1) of the compounds used as host materials or dopant materials in the production of the organic EL devices of Examples and Comparative Examples were measured as follows.

[1966] Singlet energy S1

[1967] Prepare a 10 μmol / L toluene solution of the compound to be measured, add it to a quartz cell, and measure the absorption spectrum of the sample at room temperature (300K) (vertical axis: absorption intensity, horizontal axis: wavelength). Draw a tangent to the falling edge on the long wavelength side of the absorption spectrum, and take the wavelength value λ at the intersection of the tangent and the horizontal axis. edge Substitute [nm] into the following conversion formula (F2) to calculate the singlet energy.

[1968] Conversion formula (F2): S1 [eV] = 1239.85 / λ edge

[1969] As an absorption spectrum measuring apparatus, a spectrophotometer manufactured by Hitachi, Ltd. (apparatus name: U3310) was used.

[1970] A tangent line is drawn to the falling edge of the absorption spectrum on the long-wavelength side as follows. Consider the tangent line at each point on the absorption spectrum's maximum value, as you move along the spectrum curve from the maximum value on the longest wavelength side toward the long wavelength. This tangent line repeats as the curve descends (i.e., as the value on the vertical axis decreases), the slope decreases, then increases, and so on. The tangent line drawn at the point where the slope reaches its minimum on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is defined as the tangent line to the falling edge of the absorption spectrum on the long-wavelength side.

[1971] In addition, the maximum point where the absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

[1972] Triplet energy T1

[1973] The compound to be measured was 10 -5 mol / L or above 10 -4 mol / L or less was dissolved in EPA (diethyl ether: isopentane: ethanol = 5:5:2 (volume ratio)), and this solution was added to a quartz cell as a measurement sample. The phosphorescence spectrum of this measurement sample was measured at a low temperature (77 [K]) (vertical axis: phosphorescence intensity, horizontal axis: wavelength). A tangent line was drawn to the rising edge of the short-wavelength side of the phosphorescence spectrum, and the wavelength value λ at the intersection of this tangent line and the horizontal axis was used as the reference. edge [nm], and the energy calculated by the following conversion formula (F1) is referred to as triplet energy T1.

[1974] Conversion formula (F1): T1 [eV] = 1239.85 / λ edge

[1975] As described below, a tangent line is drawn along the rising edge of the phosphorescence spectrum on the short-wavelength side. As the spectrum curve moves from the short-wavelength side of the phosphorescence spectrum to the shortest-wavelength maximum among the spectral maxima, a tangent line is drawn toward each point on the long-wavelength side of the curve. The slope of this tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where this slope reaches its maximum (i.e., the tangent line at the inflection point) is defined as the tangent line to the rising edge of the phosphorescence spectrum on the short-wavelength side.

[1976] It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent line drawn at the point where the slope value closest to the maximum value on the shortest wavelength side is taken as the tangent line of the rising edge on the short wavelength side of the phosphorescence spectrum.

[1977] Phosphorescence was measured using a spectrofluorometer model F-7100 manufactured by Hitachi High-Tech Co., Ltd.

[1978] [Table 2]

[1979] Compound <![CDATA[S1(eV)]]> <![CDATA[T1(eV)]]> BH1-1 3.10 2.07 BH1-2 3.22 2.07 BH1-3 3.09 2.34 BH1-4 3.13 2.34 BH1-5 3.08 2.07 BH1-6 3.15 2.08 BH1-7 3.14 2.08 BH1-8 3.17 2.21 BH1-9 3.30 2.35 BH1-10 3.04 2.05 BH1-11 3.10 2.08 BH1-12 3.08 2.07 BH1-13 3.14 2.08 BH1-Ref1 3.08 2.05 BH2-1 3.01 1.87 BD1 2.80 2.45

[1980] Example 1

[1981] Production of organic EL devices

[1982] An organic EL device was produced as follows.

[1983] A 25 mm x 75 mm x 1.1 mm thick glass substrate (manufactured by GEOMATEC) with an ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes to obtain an ITO film thickness of 130 nm.

[1984] The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum evaporation apparatus. Compound HI1 was first deposited on the surface with the transparent electrode to cover the transparent electrode, forming a first hole transport layer with a thickness of 5 nm.

[1985] Compound HT1 was evaporated on the first hole transport layer to form a second hole transport layer having a thickness of 80 nm.

[1986] Compound EBL1 was vapor-deposited on the second hole transport layer to form a third hole transport layer having a thickness of 10 nm.

[1987] On the third hole transport layer, compound BH1-1 (host material) and compound BD1 (dopant material) were co-evaporated so that the ratio of compound BD1 was 2 mass %, thereby forming a first light-emitting layer with a thickness of 5 nm.

[1988] On the first emitting layer, compound BH2-1 (host material) and compound BD1 (dopant material) were co-evaporated so that the ratio of compound BD1 was 2 mass %, thereby forming a second emitting layer having a thickness of 20 nm.

[1989] Compound HBL1 was evaporated on the second light-emitting layer to form a first electron transport layer with a thickness of 10 nm.

[1990] Compound ET1 was evaporated on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.

[1991] LiF was evaporated on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

[1992] Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

[1993] The device structure of the organic EL device of Example 1 is briefly shown below.

[1994] ITO(130) / HI1(5) / HT1(80) / EBL1(10) / BH1-1:BD1(5:2%) / BH2-1:BD1(20:2%) / HBL1(10) / ET1(15) / LiF(1) / Al(80)

[1995] The numbers in parentheses represent the film thickness (unit: nm).

[1996] In addition, the numbers expressed as percentages in parentheses represent the ratio (mass %) of the latter compound in the layer.

[1997] <Evaluation of Organic EL Devices>

[1998] The following evaluations were performed on the produced organic EL devices. The results are shown in Table 3.

[1999] Driving voltage

[2000] The organic EL devices prepared in Examples and Comparative Examples were measured at a current density of 10 mA / cm 2 The voltage (unit: V) when voltage is applied to the organic EL element in this manner.

[2001] Maximum peak wavelength λ p

[2002] The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) at a current density of 10 mA / cm 2 The maximum peak wavelength λ is obtained from the obtained spectral radiation brightness spectrum when voltage is applied to the element. p (Unit: nm).

[2003] CIE1931 chromaticity

[2004] The luminance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Co., Ltd.) at a current density of 10 mA / cm 2 The CIE1931 chromaticity coordinates (x, y) when voltage is applied to the organic EL element in a manner.

[2005] Examples 2 to 13, Comparative Example 1

[2006] The results are shown in Table 3.

[2007] [Table 3]

[2008]

[2009] As shown in Table 3, the organic EL elements of Examples 1 to 13 using the first compound having the structure represented by formula (1) as the first host material achieve lower device voltage and suppress chromaticity degradation compared to the organic EL element of Comparative Example 1 using BH1-Ref1.

[2010] <Synthesis of Compounds>

[2011] (Synthesis Example 1) Synthesis of BH1-1

[2012] BH1-1 was synthesized by the following synthetic route.

[2013] [Chemistry 235]

[2014]

[2015] Intermediate 1 (2.67 g), intermediate 2 (2.30 g), Pd2 (dba) 3 (0.12 g), SPhos (0.21 g) and cesium carbonate (4.20 g) were added to a beaker, and after replacing the beaker with nitrogen, 1,4-dioxane (28 mL) and water (4.6 mL) were added, and heated and stirred under reflux for 6 hours. After the reaction solution was cooled, methanol was added, the precipitated solid was filtered out, and washed with methanol and water. The crude product was purified by silica gel column chromatography to obtain BH1-1 as a light yellow solid (2.53 g, yield 72%).

[2016] The results of mass spectrometry analysis showed that the product had a molecular weight of 544.65 and m / e=545, and was identified as the target product.

[2017] (Synthesis Example 2) Synthesis of BH1-2

[2018] BH1-2 was synthesized by the following synthetic route.

[2019] [Chemistry 236]

[2020]

[2021] BH1-2 was obtained as a pale yellow solid (1.81 g, yield 52%) by the same method as that of BH1-1, except that Intermediate 3 was used instead of Intermediate 1.

[2022] The results of mass spectrometry analysis showed that the product had a molecular weight of 544.65 and m / e=545, and was identified as the target product.

[2023] (Synthesis Example 3) Synthesis of BH1-3

[2024] BH1-3 were synthesized by the following synthetic route.

[2025] [Chemistry 237]

[2026]

[2027] Intermediate 1 (5.04 g), intermediate 4 (4.00 g), Pd2(dba)3 (0.22 g), and SPhos (0.40 g) were added to a beaker. After the beaker was purged with nitrogen, 1,4-dioxane (122 mL) and a 2M aqueous sodium carbonate solution (15.2 mL) were added, and the mixture was heated and stirred under reflux for 6 hours. The solvent was distilled off, and the resulting crude product was purified by silica gel column chromatography and washed with toluene and dimethoxyethane to obtain BH1-3 as a white solid (4.02 g, yield 59%).

[2028] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 560.69 and m / e=561.

[2029] (Synthesis Example 4) Synthesis of BH1-4

[2030] BH1-4 were synthesized by the following synthetic route.

[2031] [Chemistry 238]

[2032]

[2033] BH1-4 was obtained as a white solid (3.19 g, yield 49%) by the same method as that of BH1-3 except that Intermediate 5 was used instead of Intermediate 4.

[2034] The results of mass spectrometry analysis showed that the product had a molecular weight of 510.63 and m / e=511, and was identified as the target product.

[2035] (Synthesis Example 5) Synthesis of BH1-5

[2036] BH1-5 was synthesized by the following synthetic route.

[2037] [Chemistry 239]

[2038]

[2039] BH1-5 was obtained as a white solid (1.43 g, yield 40%) by the same method as that of BH1-1 except that Intermediate 6 was used instead of Intermediate 2.

[2040] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 468.55 and m / e of 469.

[2041] (Synthesis Example 6) Synthesis of BH1-6

[2042] BH1-6 was synthesized by the following synthetic route.

[2043] [Chemistry 240]

[2044]

[2045] BH1-6 was obtained as a white solid (1.19 g, yield 33%) by the same method as that of BH1-1, except that Intermediate 3 was used instead of Intermediate 1 and Intermediate 6 was used instead of Intermediate 2.

[2046] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 468.55 and m / e of 469.

[2047] (Synthesis Example 7) Synthesis of BH1-7

[2048] BH1-7 was synthesized by the following synthetic route.

[2049] [Chemistry 241]

[2050]

[2051] BH1-7 was obtained as a white solid (1.78 g, yield 71%) by the same method as that of BH1-3 except that Intermediate 7 was used instead of Intermediate 4.

[2052] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 494.59 and m / e=495.

[2053] (Synthesis Example 8) Synthesis of BH1-8

[2054] BH1-8 was synthesized by the following synthetic route.

[2055] [Chemistry 242]

[2056]

[2057] BH1-8 was obtained as a white solid (1.32 g, yield 54%) by the same method as that of BH1-3 except that Intermediate 8 was used instead of Intermediate 4.

[2058] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 484.55 and m / e=485.

[2059] (Synthesis Example 9) Synthesis of BH1-9

[2060] BH1-9 was synthesized by the following synthetic route.

[2061] [Chemistry 243]

[2062]

[2063] BH1-9 was obtained as a white solid (1.66 g, yield 63%) by the same method as that of BH1-3 except that Intermediate 9 was used instead of Intermediate 4.

[2064] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 484.55 and m / e=485.

[2065] (Synthesis Example 10) Synthesis of BH1-10

[2066] BH1-10 was synthesized by the following synthetic route.

[2067] [Chemistry 244]

[2068]

[2069] BH1-10 was obtained as a white solid (1.25 g, yield 32%) by the same method as that of BH1-1 except that Intermediate 10 was used instead of Intermediate 2.

[2070] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 570.69 and m / e of 571.

[2071] (Synthesis Example 11) Synthesis of BH1-11

[2072] BH1-11 was synthesized by the following synthetic route.

[2073] [Chemistry 245]

[2074]

[2075] Intermediate 11 (5.0 g) was added to dichloromethane (300 mL), and pyridine (2.78 g) was further added, followed by ice cooling and stirring. Subsequently, trifluoromethanesulfonic anhydride (5.95 g) was added dropwise, and the mixture was stirred at room temperature for 3 hours after the addition was completed. After adding water and taking the organic phase, the solvent was distilled off, and the crude product was purified by silica gel column chromatography to obtain intermediate 12 (4.5 g, yield 61%). Using this intermediate 12, synthesis was carried out in the same manner as in the synthesis of BH1-1 to obtain BH1-11 as a white solid (3.9 g, yield 77%).

[2076] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 468.55 and m / e of 469.

[2077] (Synthesis Example 12) Synthesis of BH1-12

[2078] BH1-12 was synthesized by the following synthetic route.

[2079] [Chemistry 246]

[2080]

[2081] BH1-12 was obtained as a white solid (1.38 g, yield 43%) by the same method as that of BH1-1 except that Intermediate 13 was used instead of Intermediate 2.

[2082] As a result of mass spectrometry analysis, the product was identified as the target product with a molecular weight of 477.61 and m / e=478.

[2083] (Synthesis Example 13) Synthesis of BH1-13

[2084] BH1-13 was synthesized by the following synthetic route.

[2085] [Chemistry 247]

[2086]

[2087] BH1-13 was obtained as a white solid (1.61 g, yield 47%) by the same method as that of BH1-1 except that Intermediate 14 was used instead of Intermediate 2.

[2088] The results of mass spectrometry analysis showed that the product had a molecular weight of 505.66 and m / e=506, and was identified as the target product.

[2089] While several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art may readily make numerous modifications to these illustrative embodiments and / or examples without materially departing from the novel teachings and effects of the present invention. Therefore, these numerous modifications are intended to be within the scope of the present invention.

[2090] The contents of the documents described in this specification and the applications on which the Paris Convention priority claim of the present application is based are incorporated herein by reference in their entirety.

Claims

1. A compound represented by the following formula (1), [Chemistry 248] In formula (1), R 101 ~R 105 One of them is a single bond bonded to the group represented by the following formula (A1); [Chemistry 249] -(L A1 ) nA1 -With A1 (A1) In formula (A1), L A1 for: single bond, substituted or unsubstituted phenylene, Substituted or unsubstituted biphenyldiyl, Substituted or unsubstituted terphenyldiyl, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrene diyl, Substituted or unsubstituted triphenylene diyl, Substituted or unsubstituted benzanthracenediyl, substituted or unsubstituted pyrene diyl, Substituted or unsubstituted Two bases, Substituted or unsubstituted benzo Two bases, Substituted or unsubstituted triphenylenediyl, Substituted or unsubstituted benzotriphenylene, substituted or unsubstituted fluorenediyl, Substituted or unsubstituted benzofluorenediyl, Substituted or unsubstituted dibenzofluorenediyl, Substituted or unsubstituted naphthofluorenediyl, substituted or unsubstituted fluoranthenediyl, Substituted or unsubstituted benzofluoranthene diyl, Substituted or unsubstituted perylenediyl, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms; Ar A1 for: substituted or unsubstituted phenyl, Substituted or unsubstituted biphenyl, Substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted phenoxy, Substituted or unsubstituted triphenylene group, Substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, Substituted or unsubstituted base, Substituted or unsubstituted benzo base, Substituted or unsubstituted triphenylene, Substituted or unsubstituted benzotriphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted naphthofluorenyl, substituted or unsubstituted fluoranthene group, Substituted or unsubstituted benzofluoranthenyl, Substituted or unsubstituted perylene, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms; nA1 is an integer from 0 to 3; When nA1 is 0, (L A1 ) nA1 is a single bond; When nA1 is 2 or 3, multiple L A1 connected in series, Ar A1 The farthest L from the dinaphthofuran skeleton A1 Bonding; multiple L A1 Can be the same or different; By R 106 ~R 112 , and R which is not a single bond bonded to the group represented by the formula (A1) 101 ~R 105 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other; R not bonded to each other 106 ~R 112 , and R which is not a single bond bonded to the group represented by the formula (A1) and is not bonded to each other 101 ~R 105 Each independently is: hydrogen atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by formula (A1); The substituents in the case of "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, Aralkyl having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 )、 -C(=O)R 44 -COOR 45 、 -Ge(R 49 )(R 50 )(R 51 )、 Hydroxyl, cyano, Nitro, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each may be the same or different.

2. The compound according to claim 1, wherein R 102 ~R 105 One of them is a single bond bonding to the group represented by the above formula (A1).

3. The compound according to claim 1 or 2, wherein R 102 、R 103 and R 105 One of them is a single bond bonding to the group represented by the above formula (A1).

4. The compound according to any one of claims 1 to 3, wherein L A1 for: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, Substituted or unsubstituted benzanthracenediyl, substituted or unsubstituted pyrene diyl, Substituted or unsubstituted benzofluorenediyl, or Substituted or unsubstituted dibenzofluorenediyl.

5. The compound according to any one of claims 1 to 4, wherein L A1 for: Single key, or a substituted or unsubstituted phenylene group.

6. The compound according to any one of claims 1 to 5, wherein Ar A1 for: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted benzanthryl substituted or unsubstituted pyrenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted benzoxanthenyl group.

7. The compound according to any one of claims 1 to 6, wherein The group represented by the formula (A1) is a group represented by any one of the following formulas (A1-1) to (A1-7), [Chemistry 250] [Chemistry 251] In formula (A1-1) to formula (A1-7), nA1 and L A1 As defined in formula (A1); R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 and R A91 ~R A99 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring atoms.

8. The compound according to any one of claims 1 to 7, wherein The compound represented by the formula (1) is a compound represented by any one of the following formulas (1-1) to (1-3), [Chemistry 252] [Chemistry 253] In formula (1-1) to formula (1-3), nA1, L A1 、Ar A1 、R 101 ~R 112 As defined in formula (1).

9. The compound according to any one of claims 1 to 8, wherein The compound represented by the formula (1) is a compound represented by any one of the following formulas (1-11) to (1-19), [Chemistry 254] [Chemistry 255] [Chemistry 256] [Chemistry 257] [Chemistry 258] In formula (1-11) to formula (1-19), nA1, L A1 、R 101 ~R 112 As defined in formula (1); R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 and R A91 ~R A99 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring atoms.

10. The compound according to any one of claims 1 to 9, wherein R is not a single bond 101 ~R 112 A hydrogen atom.

11. The compound according to any one of claims 7 to 10, wherein R A11 ~R A19 、R A21 ~R A32 、R A41 ~R A51 、R A61 ~R A73 、R A81 ~R A89 and R A91 ~R A99 Each independently is: hydrogen atoms, methyl, Phenyl, or Naphthyl.

12. A compound represented by the following formula (2), [Chemistry 259] In formula (2), R 201 ~R 205 One of them is a single bond bonded to the group represented by the following formula (A2); [Chemistry 260] <h2 style=";text-align:left;direction:ltr">-(L<h2 style=";text-align:left;direction:ltr"> A2 <h2 style=";text-align:left;direction:ltr"> )<h2 style=";text-align:left;direction:ltr"> nA2 <h2 style=";text-align:left;direction:ltr"> -Ar<h2 style=";text-align:left;direction:ltr"> A2 <h2 style=";text-align:left;direction:ltr"> (A2) In formula (A2), L A2 for: single bond, a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms, or a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms; Ar A2 for: a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and consisting of 5 or less rings, or a substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms; nA2 is an integer from 0 to 3; When nA2 is 0, (L A2 ) nA2 is a single bond; When nA2 is 2 or 3, multiple L A2 connected in series, Ar A2 The farthest L from the dinaphthofuran skeleton A2 Bonding; multiple L A2 Can be the same or different; By R 206 ~R 212 , and R which is not a single bond bonded to the group represented by the formula (A2) 201 ~R 205 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other; R not bonded to each other 206 ~R 212 , and R which is not a single bond bonded to the group represented by the formula (A2) and is not bonded to each other 201 ~R 205 Each independently is: hydrogen atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by formula (A2); The substituents in the case of "substituted or unsubstituted" are: an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, Aralkyl having 7 to 50 carbon atoms, -Si(R 41 )(R 42 )(R 43 )、 -C(=O)R 44 -COOR 45 、 -Ge(R 49 )(R 50 )(R 51 )、 Hydroxyl, cyano, Nitro, an aryl group having 6 to 13 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 41 ~R 45 and R 49 ~R 51 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 41 ~R 45 and R 49 ~R 51 When there are two or more, two or more R 41 ~R 45 and R 49 ~R 51 Each can be the same or different; in, L A2 a substituted or unsubstituted arylene group having 6 to 21 ring carbon atoms and a substituted or unsubstituted divalent oxygen-containing heterocyclic group having 5 to 30 ring atoms, and Ar A2 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms and the substituted or unsubstituted monovalent oxygen-containing heterocyclic group having 5 to 30 ring atoms in the group are each a group satisfying the following formula (T1), T1>1.81eV···(T1) In formula (T1), T1 is the triplet energy of the group.

13. The compound according to claim 12, wherein R 202 ~R 205 One of them is a single bond bonding to the group represented by the above formula (A2).

14. The compound according to claim 12 or 13, wherein R 202 、R 203 and R 205 One of them is a single bond bonding to the group represented by the above formula (A2).

15. The compound according to any one of claims 12 to 14, wherein L A2 for: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, Substituted or unsubstituted benzanthracenediyl, substituted or unsubstituted pyrene diyl, Substituted or unsubstituted benzofluorenediyl, or Substituted or unsubstituted dibenzofluorenediyl.

16. The compound according to any one of claims 12 to 15, wherein L A2 for: Single key, or a substituted or unsubstituted phenylene group.

17. The compound according to any one of claims 12 to 16, wherein Ar A2 for: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, Substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted benzoxanthenyl group.

18. The compound according to any one of claims 12 to 17, wherein The group represented by the formula (A2) is a group represented by any one of the following formulas (A2-1) to (A2-7), [Chemistry 261] [Chemistry 262] In formula (A2-1) to formula (A2-7), nA2 and L A2 As defined in formula (A2); R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 13 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring atoms.

19. The compound according to any one of claims 12 to 18, wherein The compound represented by the formula (2) is a compound represented by any one of the following formulas (2-1) to (2-3), [Chemistry 263] [Chemistry 264] In formula (2-1) to formula (2-3), nA2, L A2 、Ar A2 、R 201 ~R 212 As defined in formula (2).

20. The compound according to any one of claims 12 to 19, wherein The compound represented by the formula (2) is a compound represented by any one of the following formulas (2-11) to (2-19), [Chemistry 265] [Chemistry 266] [Chemistry 267] [Chemistry 268] [Chemistry 269] In formula (2-11) to formula (2-19), nA2, L A2 、R 201 ~R 212 As defined in formula (2); R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 13 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring atoms.

21. The compound according to any one of claims 12 to 20, wherein R is not a single bond 201 ~R 212 A hydrogen atom.

22. The compound according to any one of claims 18 to 21, wherein R A111 ~R A119 、R A121 ~R A132 、R A141 ~R A151 、R A161 ~R A173 、R A181 ~R A189 and R A191 ~R A199 Each independently is: hydrogen atoms, methyl, Phenyl, or Naphthyl. 23 . The compound according to claim 1 , which is a material for an organic electroluminescent device.

24. An organic electroluminescent element comprising: cathode, Anode, and a light-emitting layer disposed between the cathode and the anode; The light-emitting layer comprises a first light-emitting layer and a second light-emitting layer; The first light-emitting layer comprises a compound represented by the following formula (3); [Chemistry 270] In formula (3), R 301 ~R 305 One of them is a single bond bonded to the group represented by the following formula (A3); [Chemistry 271] <h2 style=";text-align:left;direction:ltr">-(L<h2 style=";text-align:left;direction:ltr"> A3 <h2 style=";text-align:left;direction:ltr"> )<h2 style=";text-align:left;direction:ltr"> nA3 <h2 style=";text-align:left;direction:ltr"> -Ar<h2 style=";text-align:left;direction:ltr"> A3 <h2 style=";text-align:left;direction:ltr"> (A3) In formula (A3), L A3 for: single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; Ar A3 for: a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 30 ring atoms; nA3 is an integer from 0 to 3; When nA3 is 0, (L A3 ) nA3 is a single bond; When nA3 is 2 or 3, multiple L A3 connected in series, Ar A3 The farthest L from the dinaphthofuran skeleton A3 Bonding; multiple L A3 Can be the same or different; By R 306 ~R 312 , and R which is not a single bond bonded to the group represented by the formula (A3) 301 ~R 305 One or more adjacent groups of two or more of the substituted or unsubstituted monocyclic rings are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other; R not bonded to each other 306 ~R 312 , and R which is not a single bond bonded to the group represented by the formula (A3) and is not bonded to each other 301 ~R 305 Each independently is: hydrogen atoms, or A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, which is different from the group represented by the above formula (A3).

25. The organic electroluminescent element according to claim 24, wherein R 302 ~R 305 One of them is a single bond bonding to the group represented by the above formula (A3).

26. The organic electroluminescent element according to claim 24 or 25, wherein R 302 、R 303 and R 305 One of them is a single bond bonding to the group represented by the above formula (A3).

27. The organic electroluminescent element according to any one of claims 24 to 26, wherein L A3 for: single bond, substituted or unsubstituted phenylene, substituted or unsubstituted naphthylene, Substituted or unsubstituted benzanthracenediyl, substituted or unsubstituted pyrene diyl, Substituted or unsubstituted benzofluorenediyl, or Substituted or unsubstituted dibenzofluorenediyl.

28. The organic electroluminescent element according to any one of claims 24 to 27, wherein L A3 for: Single key, or a substituted or unsubstituted phenylene group.

29. The organic electroluminescent element according to any one of claims 24 to 28, wherein Ar A3 for: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted benzanthryl, substituted or unsubstituted pyrenyl, substituted or unsubstituted benzofluorenyl, Substituted or unsubstituted dibenzofluorenyl, Substituted or unsubstituted naphthobenzofuranyl, or a substituted or unsubstituted benzoxanthenyl group.

30. The organic electroluminescent element according to any one of claims 24 to 29, wherein The group represented by the formula (A3) is a group represented by any one of the following formulas (A3-1) to (A3-7), [Chemistry 272] [Chemistry 273] In formula (A3-1) to formula (A3-7), nA3 and L A3 As defined in formula (A3); R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, Aralkyl having 7 to 50 carbon atoms, -Si(R 941 )(R 942 )(R 943 )、 -C(=O)R 944 -COOR 945 、 -S(=O)2R 946 、 -P(=O)(R 947 )(R 948 )、 -Ge(R 949 )(R 950 )(R 951 )、 -N(R 952 )(R 953 )、 Hydroxyl, Halogen atoms, cyano, Nitro, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 941 ~R 953 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 941 ~R 953 When there are two or more, two or more R 941 ~R 953 Each may be the same or different.

31. The organic electroluminescent element according to any one of claims 24 to 30, wherein The compound represented by the formula (3) is a compound represented by any one of the following formulas (3-1) to (3-3), [Chemistry 274] [Chemistry 275] In formula (3-1) to formula (3-3), nA3, L A3 、Ar A3 and R 301 ~R 312 As defined in formula (1).

32. The organic electroluminescent element according to any one of claims 24 to 31, wherein The compound represented by the formula (3) is a compound represented by any one of the following formulas (3-11) to (3-19), [Chemistry 276] [Chemistry 277] [Chemistry 278] [Chemistry 279] In formula (3-11) to formula (3-19), nA3, L A3 、R 301 ~R 312 As defined in formula (3); R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, a halogenated alkyl group having 1 to 50 carbon atoms, an alkenyl group having 2 to 50 carbon atoms, an alkynyl group having 2 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an alkoxy group having 1 to 50 carbon atoms, an alkylthio group having 1 to 50 carbon atoms, an aryloxy group having 6 to 50 ring carbon atoms, an arylthio group having 6 to 50 ring carbon atoms, Aralkyl having 7 to 50 carbon atoms, -Si(R 941 )(R 942 )(R 943 )、 -C(=O)R 944 -COOR 945 、 -S(=O)2R 946 、 -P(=O)(R 947 )(R 948 )、 -Ge(R 949 )(R 950 )(R 951 )、 -N(R 952 )(R 953 )、 Hydroxyl, Halogen atoms, cyano, Nitro, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 941 ~R 953 Each is independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or a monovalent heterocyclic group having 5 to 50 ring atoms; R 941 ~R 953 When there are two or more, two or more R 941 ~R 953 Each may be the same or different.

33. The organic electroluminescent element according to any one of claims 24 to 32, wherein R is not a single bond 301 ~R 312 A hydrogen atom.

34. The organic electroluminescent element according to any one of claims 30 to 33, wherein R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 、R A261 ~R A273 、R A281 ~R A289 and R A291 ~R A299 Each independently is: hydrogen atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, or A monovalent heterocyclic group having 5 to 50 ring atoms.

35. The organic electroluminescent element according to any one of claims 30 to 34, wherein R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 and R A261 ~R A273 Each independently is: hydrogen atoms, an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, or A monovalent heterocyclic group having 5 to 18 ring atoms.

36. The organic electroluminescent element according to any one of claims 30 to 35, wherein R A211 ~R A219 、R A221 ~R A232 、R A241 ~R A251 and R A261 ~R A273 Each independently is: hydrogen atoms, methyl, Phenyl, or Naphthyl.

37. The organic electroluminescent element according to any one of claims 24 to 36, wherein The light-emitting layer includes the first light-emitting layer and the second light-emitting layer in this order from the anode side.

38. The organic electroluminescent element according to any one of claims 24 to 37, wherein The first light-emitting layer and the second light-emitting layer are directly adjacent to each other.

39. The organic electroluminescent element according to any one of claims 24 to 38, wherein A hole transport layer is provided between the anode and the light-emitting layer.

40. The organic electroluminescent element according to any one of claims 24 to 39, wherein An electron transport layer is provided between the cathode and the light-emitting layer.

41. An electronic device comprising the organic electroluminescent element according to any one of claims 24 to 40.

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