Compounds, materials for organic electroluminescence devices, organic electroluminescence devices, and electronic devices

Abstract

A compound represented by the following formula (1).

Description

Technology Field

[0001] The present invention relates to a novel compound, a material for an organic electroluminescence device, an organic electroluminescence device, and an electronic device. Background Technology

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

[0003] Conventional organic EL devices have not yet had sufficient device performance. Although improvements in materials used for organic EL devices are gradually being made to increase device performance, further high performance is required.

[0004] Patent documents 1 and 2 disclose compounds having a specific structure that can be used in an electron transport band installed between the light-emitting layer and the cathode of an organic EL device. Prior art literature

[0005] [Patent Document 1] International Publication No. 2016 / 175292 [Patent Document 2] International Publication No. 2018 / 139662 The problem to be solved

[0006] The objective of the present invention is to provide a compound capable of realizing a higher-performance organic EL device.

[0007] As a result of careful examination by the inventors, it was discovered that by using a compound having a specific structure, it is possible to realize an organic EL device capable of higher performance, particularly higher efficiency or driving at a lower voltage, and thus the present invention was completed. means of solving the problem

[0008] According to the present invention, the following compounds are provided.

[0009] 1. A compound represented by the following formula (1).

[0010]

[0011] [Essence (1),

[0012] R1~R 12 One of them represents a bond with L3.

[0013] R1 to R that do not exhibit binding with L3 12 is, each independently, a hydrogen atom or a substituent. R1 to R that do not exhibit bonding with L3. 12 Groups consisting of two or more adjacent elements do not combine with each other.

[0014] Ar1 and Ar2, each independently,

[0015] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,

[0016] A substituted or unsubstituted ring-forming monovalent complex circulating group having 5 to 50 carbon atoms and not containing a nitrogen atom,

[0017] A univalent complex circulator represented by the following equation (1-21), or

[0018] It is a complex circulator of one value represented by the following equation (1-22).

[0019]

[0020] (Essence (1-21),

[0021] X 21 is, N(R 29 It is ), O, or S.

[0022] R 21 ~R 29 One of them represents a combination with L1 or L2.

[0023] R that does not show binding with L1 or L2 21 ~R 29At least one of the sets consisting of two or more adjacent sets combines to form a substituted or unsubstituted saturated or unsaturated ring, or does not form a substituted or unsubstituted saturated or unsaturated ring.

[0024] R that does not exhibit binding with L1 or L2 and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 21 ~R 29 are, each independently,

[0025] hydrogen atom,

[0026] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0027] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0028] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0029] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0030] -Si(R 911 )(R 912 )(R 913 ),

[0031] -O-(R 914 ),

[0032] -S-(R 915 ),

[0033] -N(R 916 )(R 917 )

[0034] -P(=O)(R 918 )(R 919 )

[0035] (Here, R 911 ~R 919 are, each independently,

[0036] hydrogen atom,

[0037] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0038] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0039] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0040] It is a monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms. R 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of these may be the same or different.),

[0041] Halogen atom, cyano group, nitro group,

[0042] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0043] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0044] It is selected from a group consisting of.)

[0045] Among the formulas (1-22),

[0046] X 31 is, N(R 37 It is ), O, or S.

[0047] R 31 ~R 37 One of them represents a combination with L1 or L2.

[0048] R that does not show binding with L1 or L2 31 ~R 37 At least one of the sets consisting of two or more adjacent sets combines to form a substituted or unsubstituted saturated or unsaturated ring, or does not form a substituted or unsubstituted saturated or unsaturated ring.

[0049] R that does not exhibit binding with L1 or L2 and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 31 ~R 37 Each independently,

[0050] hydrogen atom,

[0051] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0052] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0053] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0054] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0055] -Si(R 911 )(R 912 )(R 913 ),

[0056] -O-(R 914 ),

[0057] -S-(R 915 ),

[0058] -N(R 916 )(R 917 ),

[0059] -P(=O)(R 918 )(R 919 )

[0060] Halogen atom, cyano group, nitro group,

[0061] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0062] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0063] It is selected from a group consisting of.

[0064] R 911 ~R 919 is as defined in the above equation (1-21).

[0065] When there are multiple complex phantoms represented by the above equation (1-21), the multiple complex phantoms represented by the above equation (1-21) may be identical or different.

[0066] When there are multiple complex phantoms represented by the above equation (1-22), the multiple complex phantoms represented by the above equation (1-22) may be identical or different.

[0067] L1 to L3 are each independently a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex circulating group having 5 to 50 atoms.

[0068] n1 is an integer from 0 to 2, and when n1 is 0, (L1) n1 is a single bond. If there are 2 or more L1s, the 2 or more L1s may be the same or different.

[0069] n2 is an integer from 0 to 2, and when n2 is 0, (L2) n2 is a single bond. If there are 2 or more L2s, the 2 or more L2s may be the same or different.

[0070] n3 is an integer from 0 to 3, and when n3 is 0, (L3) n3 is a single bond. If there are 2 or more L3s, the 2 or more L3s may be the same or different.

[0071] R1~R 12 The substituent in the case where is a substituent, R1~R 12 In the case where is a substituent, the substituent in the case of "substituent or non-substituent," and in the case of Ar1 and Ar2, the substituent in the case of "substituent or non-substituent" is,

[0072] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0073] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0074] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0075] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0076] -Si(R911 )(R 912 )(R 913 ),

[0077] -O-(R 914 ),

[0078] -S-(R 915 ),

[0079] -N(R 916 )(R 917 ),

[0080] -P(=O)(R 918 )(R 919 )

[0081] (Here, R 911 ~R 919 are, each independently,

[0082] hydrogen atom,

[0083] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0084] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0085] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0086] It is a monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms. R 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of these may be the same or different.),

[0087] Halogen atom, cyano group, nitro group,

[0088] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0089] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0090] It is selected from a group consisting of.)

[0091] According to the present invention, a compound capable of realizing a higher performance organic EL device can be provided. Brief explanation of the drawing

[0092] FIG. 1 is a diagram showing the schematic configuration of an organic EL device according to one embodiment of the present invention. Specific details for implementing the invention

[0093] [definition]

[0094] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0095] In this specification, in the chemical structural formula, at bondable positions where symbols such as "R" or "D" representing a deuterium atom are not specified, hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms are bonded.

[0096] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, condensed-ring compounds, crosslinked compounds, carbon-ring compounds, and heterocyclic compounds). When the ring is substituted by a substituent, the carbons included in the substituent are not included in the ring-forming carbon number. Regarding the "ring-forming carbon number" described below, unless otherwise noted, they shall be the same. For example, the benzene ring has a ring-forming carbon number of 6, the naphthalene ring has a ring-forming carbon number of 10, the pyridine ring has a ring-forming carbon number of 5, and the furan ring has a ring-forming carbon number of 4. In addition, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25.

[0097] In addition, when a benzene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring of the benzene ring. Therefore, the number of carbon atoms forming the ring of the benzene ring substituted with an alkyl group is 6. In addition, when a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the ring of the naphthalene ring. Therefore, the number of carbon atoms forming the ring of the naphthalene ring substituted with an alkyl group is 10.

[0098] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (e.g., a single ring, a condensed ring, and a ring assembly) (e.g., a single ring compound, a condensed ring compound, a crosslinked compound, a carbon ring compound, and a complex ring compound). Atoms that do not constitute a ring (e.g., a hydrogen atom terminating the bond of an atom constituting a ring) or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. Regarding the "number of ring-forming atoms" described below, they shall be the same unless otherwise noted. For example, the number of ring-forming atoms of a pyridine ring is 6, the number of ring-forming atoms of a quinazolin ring is 10, and the number of ring-forming atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent are not included in the number of ring-forming atoms of a pyridine ring. Therefore, the number of ring-forming atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting substituents are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring bonded to hydrogen atoms or substituents is 10.

[0099] In the present specification, in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms,” “XX to YY carbon atoms” indicates the number of carbon atoms when the ZZ group is unsubstituted and does not include the number of carbon atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer of 1 or more, and “YY” means an integer of 2 or more.

[0100] In the present specification, the “number of atoms XX to YY” in the expression “ZZ group having XX to YY of substituted or unsubstituted atoms” represents the number of atoms when the ZZ group is unsubstituted and does not include the number of atoms of the substituent when it is substituted. Here, “YY” is greater than “XX,” “XX” means an integer greater than or equal to 1, and “YY” means an integer greater than or equal to 2.

[0101] In this specification, the term "unsubstituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group," and the term "substituted ZZ group" indicates the case where the "substituted or unsubstituted ZZ group" is the "substituted ZZ group."

[0102] In this specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not substituted with substituents. The hydrogen atoms in the "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms.

[0103] In addition, in the present specification, "substitution" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are substituted with substituents. Likewise, "substitution" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are substituted with AA groups.

[0104] "Substituents described in this specification"

[0105] The following describes the substituents described in this specification.

[0106] The number of ring-forming carbons of the “unsubstituted aryl group” described in this specification is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, more preferably 6 to 18.

[0107] The number of ring-forming atoms of the “unsubstituted complex ring” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0108] The number of carbon atoms of the “unsubstituted alkyl group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.

[0109] The number of carbon atoms of the “unsubstituted alkenyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.

[0110] The number of carbon atoms of the “unsubstituted alkynyl group” described in this specification is 2 to 50 unless otherwise specified in this specification, preferably 2 to 20, more preferably 2 to 6.

[0111] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification.

[0112] The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in this specification is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, more preferably 6 to 18.

[0113] The number of ring-forming atoms of the “unsubstituted divalent complex circulator” described in this specification is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise specified in this specification.

[0114] The number of carbon atoms of the “unsubstituted alkylene group” described in this specification is 1 to 50 unless otherwise specified in this specification, preferably 1 to 20, more preferably 1 to 6.

[0115] · "Substitution or non-substitution aryl"

[0116] Specific examples (Group of Specific Examples G1) of the “substituted or unsubstituted aryl group” described in this specification include the following unsubstituted aryl group (Group of Specific Examples G1A) and substituted aryl group (Group of Specific Examples G1B). (Here, the term “unsubstituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “unsubstituted aryl group,” and the term “substituted aryl group” refers to the case where the “substituted or unsubstituted aryl group” is a “substituted aryl group.”) In this specification, when simply referred to as “aryl group,” it includes both the “unsubstituted aryl group” and the “substituted aryl group.”

[0117] "Substituted aryl group" means a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are substituted with substituents. Examples of "substituted aryl groups" include, for instance, a group in which one or more hydrogen atoms of an "unsubstituted aryl group" of the following specific example group G1A are substituted with substituents, and examples of substituted aryl groups of the following specific example group G1B. Furthermore, the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed herein are merely examples, and the "substituted aryl groups" described in this specification include a group in which a hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" of the following specific example group G1B is further substituted with a substituent.

[0118] ·Muchan's Arilgi (Special Example Group G1A):

[0119] phenyl group,

[0120] p-biphenyl group,

[0121] m-biphenyl group,

[0122] o-biphenyl group,

[0123] p-terphenyl-4-diary,

[0124] p-terphenyl-3-diary,

[0125] p-terphenyl-2-diary,

[0126] m-terphenyl-4-diary,

[0127] m-terphenyl-3-diary,

[0128] m-terphenyl-2-diary,

[0129] o-terphenyl-4-diary,

[0130] o-terphenyl-3-diary,

[0131] o-terphenyl-2-diyl,

[0132] 1-Naphthyl group,

[0133] 2-Naphthyl group,

[0134] Anthrill,

[0135] Benzoanthryl group,

[0136] phenanthril group,

[0137] Benzophenanthrile group,

[0138] Penalenyl group,

[0139] Pyreneyl group,

[0140] Crysenyl group,

[0141] benzocrysenyl group,

[0142] triphenylenyl group,

[0143] benzotriphenylenyl group,

[0144] tetracenyl group,

[0145] Pentacenyl group,

[0146] Fluorenyl group,

[0147] 9,9'-spirobifluorenyl group,

[0148] benzofluorenyl group,

[0149] dibenzofluorenyl group,

[0150] Fluoranthenyl group,

[0151] benzofluranthenyl group,

[0152] perylenyl group, and

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

[0154]

[0155]

[0156] · Substitution Aryl group (Specific example group G1B):

[0157] o-tollil group,

[0158] m-tolyl group,

[0159] p-tolyl group,

[0160] Para-xyl group,

[0161] meta-xylyl group,

[0162] Ortho-xyl group,

[0163] para-isopropylphenyl group,

[0164] meta-isopropylphenyl group,

[0165] Ortho-isopropylphenyl group,

[0166] para-t-butylphenyl group,

[0167] meta-t-butylphenyl group,

[0168] Ortho-t-butylphenyl group,

[0169] 3,4,5-trimethylphenyl group,

[0170] 9,9-dimethylfluorenyl group,

[0171] 9,9-diphenylfluorenyl group,

[0172] 9,9-bis(4-methylphenyl)fluorenyl group,

[0173] 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0174] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0175] cyanophenyl group,

[0176] triphenylsilylphenyl group,

[0177] trimethylsilylphenyl group,

[0178] phenylnaphthyl group,

[0179] Naphthylphenyl group, and

[0180] A group in which one or more hydrogen atoms of a monovalent group derived from a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are substituted with substituents.

[0181] · "Substitutional or Non-substitutional Complex Recall"

[0182] The “complex circulating group” described in this specification is a ring-forming group comprising at least one heteroatom in the ring-forming atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.

[0183] The “complex ring” described in this specification is a simple ring or a condensed ring.

[0184] The “complex generator” described in this specification is an aromatic complex generator or a non-aromatic complex generator.

[0185] Examples of specific examples (group of specific examples G2) of the “complex circulator with or without permutation” described in this specification include the following complex circulators with or without permutation (group of specific examples G2A) and complex circulators with permutation (group of specific examples G2B). (Here, a complex circulator with or without permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with or without permutation,” and a complex circulator with permutation refers to the case where the “complex circulator with or without permutation” is a “complex circulator with permutation.”) In this specification, when simply referred to as a “complex circulator,” it includes both a “complex circulator with or without permutation” and a “complex circulator with permutation.”

[0186] "Substituted complex sphere" refers to a group in which one or more hydrogen atoms of a "non-substituted complex sphere" are substituted with substituents. Specific examples of a "substituted complex sphere" include a group in which a hydrogen atom of a "non-substituted complex sphere" of the following group of examples G2A is substituted, and an example of a substituted complex sphere of the following group of examples G2B. Furthermore, the examples of "non-substituted complex spheres" and "substituted complex spheres" listed herein are merely examples, and the "substituted complex sphere" described in this specification includes a group in which a hydrogen atom bonded to the ring-forming atom of the complex sphere itself in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted complex sphere" of the following group of examples G2B is further substituted with a substituent.

[0187] Specific example group G2A includes, for example, an unsubstituted complex group containing a nitrogen atom (Specific example group G2A1), an unsubstituted complex group containing an oxygen atom (Specific example group G2A2), an unsubstituted complex group containing a sulfur atom (Specific example group G2A3), and a monovalent complex group (Specific example group G2A4) derived by excluding one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).

[0188] Specific example group G2B includes, for example, a substituent complex group containing a nitrogen atom (Specific example group G2B1), a substituent complex group containing an oxygen atom (Specific example group G2B2), a substituent complex group containing a sulfur atom (Specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent complex group derived from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are substituted with a substituent (Specific example group G2B4).

[0189] · Unsubstituted complex saturators containing nitrogen atoms (Specific example group G2A1):

[0190] pyrrolyl group,

[0191] Imidajorilgi,

[0192] pyrazolyl group,

[0193] triazolyl group,

[0194] tetrazolyl group,

[0195] Oxazoligi,

[0196] Isooxazolilgi,

[0197] Oxadiazolyl group,

[0198] Thiazolyl group,

[0199] isothiazolyl group,

[0200] Thiadiazolylgi,

[0201] Piridilgi,

[0202] Piridajinilgi,

[0203] pyrimidinyl group,

[0204] Pyrazinyl group,

[0205] triazinyl group,

[0206] Indolil,

[0207] Isoindolilgi,

[0208] Indolezinyl group,

[0209] Quinolidinyl group,

[0210] Quinolyl group,

[0211] isoquinolyl group,

[0212] Sinnolilgi,

[0213] Phthalaginyl group,

[0214] Quinazolinyl group,

[0215] Quinoxalinyl group,

[0216] benzimidazolyl group,

[0217] Indazolillgi,

[0218] phenanthrolinyl group,

[0219] phenanthridinyl group,

[0220] Acridinyl group,

[0221] phenazinyl group,

[0222] Carbazolyl group,

[0223] benzocarbazolyl group,

[0224] Morpolinogi,

[0225] phenoxazinyl group,

[0226] Phenothiazinyl group,

[0227] Azacarbazolyl group, and diazcarbazolyl group.

[0228] · Unsubstituted complex mutators containing oxygen atoms (Specific example group G2A2):

[0229] Purilgi,

[0230] Oxazoligi,

[0231] Isooxazolilgi,

[0232] Oxadiazolyl group,

[0233] xanthenyl group,

[0234] benzofuranyl group,

[0235] isobenzofuranyl group,

[0236] dibenzofuranyl group,

[0237] Naphthobenzofuranyl group,

[0238] Benzooxazolyl group,

[0239] Benzoisoxazolyl group,

[0240] phenoxazinyl group,

[0241] Morpolinogi,

[0242] dinaphthofranyl group,

[0243] Azadibenzofuranyl group,

[0244] Diazadibenzofuranyl group,

[0245] Azanaptobenzofuranyl group, and

[0246] Diazanaptobenzofuranyl group.

[0247] · Unsubstitutable complex circulators containing sulfur atoms (Specific example group G2A3):

[0248] thienyl group,

[0249] Thiazolyl group,

[0250] isothiazolyl group,

[0251] Thiadiazolylgi,

[0252] benzothiophenyl group (benzothienyl group),

[0253] isobenzothiophenyl group (isobenzothienyl group),

[0254] dibenzothiophenyl group (dibenzothienyl group),

[0255] Naphthobenzothiophenyl group (naphthobenzothienyl group),

[0256] benzothiazolyl group,

[0257] Benzoisothiazolyl group,

[0258] Phenothiazinyl group,

[0259] dinaphthothiophenyl group (dinaphthienyl group),

[0260] Azadibenzothiophenyl group (azadibenzothienyl group),

[0261] Diazadibenzothiophenyl group (diazadibenzothienyl group),

[0262] Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and

[0263] Diazanaptobenzothiophenyl group (diazanaptobenzothienyl group).

[0264] · A monovalent complex circulator derived by excluding one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific example group G2A4):

[0265]

[0266]

[0267] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH.

[0268] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A In the case where at least one of them is NH or CH2, the monovalent complex cyclic groups derived from the ring structures represented by the general formulas (TEMP-16) to (TEMP-33) include a monovalent group obtained by excluding one hydrogen atom from these NH or CH2.

[0269] · Substitutional complex vacancies containing nitrogen atoms (Specific example group G2B1):

[0270] (9-phenyl)carbazolyl group,

[0271] (9-biphenylyl)carbazolyl group,

[0272] (9-phenyl)phenylcarbazolyl group,

[0273] (9-naphthyl)carbazolyl group,

[0274] Diphenylcarbazole-9-diary,

[0275] Phenylcarbazole-9-diary,

[0276] methylbenzimidazolyl group,

[0277] Ethylbenzimidazolyl group,

[0278] phenyltriazinyl group,

[0279] biphenyltriazinyl group,

[0280] diphenyltriazinyl group,

[0281] Phenylquinazolinyl group, and

[0282] Biphenylquinazolinyl group.

[0283] · Substitutional complex mutators containing oxygen atoms (Specific example group G2B2):

[0284] Phenyldibenzofuranyl group,

[0285] methyldibenzofuranyl group,

[0286] t-butyldibenzofuranyl group, and

[0287] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0288] · Complex substitutions containing sulfur atoms (Specific example group G2B3):

[0289] Phenyldibenzothiophenyl group,

[0290] methyldibenzothiophenyl group,

[0291] t-butyldibenzothiophenyl group, and

[0292] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0293] · A group in which one or more hydrogen atoms of a monovalent complex cyclic group derived from the above general formulas (TEMP-16) to (TEMP-33) are substituted with substituents (Specific Example Group G2B4):

[0294] The above “one or more hydrogen atoms of a monovalent complex group” means one or more hydrogen atoms selected from a hydrogen atom bonded to a ring-forming carbon atom of the monovalent complex group, a hydrogen atom bonded to a nitrogen atom when at least one of XA and YA is NH, and a hydrogen atom of a methylene group when one of XA and YA is CH2.

[0295] · Substituted or unsubstituted alkyl group

[0296] Examples of specific examples (Group of Specific Examples G3) of the “substituted or unsubstituted alkyl group” described in this specification include the following unsubstituted alkyl group (Group of Specific Examples G3A) and substituted alkyl group (Group of Specific Examples G3B). (Here, the term “unsubstituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group,” and the term “substituted alkyl group” refers to the case where the “substituted or unsubstituted alkyl group” is a “substituted alkyl group.”) Hereinafter, when simply referred to as “alkyl group,” both the “unsubstituted alkyl group” and the “substituted alkyl group” are included.

[0297] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include the group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (Specific Example Group G3A) are substituted with substituents, and examples of a substituted alkyl group (Specific Example Group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a chain-type alkyl group. Accordingly, "unsubstituted alkyl group" includes straight-chain "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups." In addition, the examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed herein are merely examples, and the "substituted alkyl groups" described in this specification include groups in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent, and groups in which the hydrogen atom of the substituent in the "substituted alkyl group" of Specific Example Group G3B is further substituted with a substituent.

[0298] · Unsubstituted alkyl group (Specific Example Group G3A):

[0299] methyl group,

[0300] ethyl group,

[0301] n-Profilter,

[0302] isopropyl group,

[0303] n-butyl group,

[0304] isobutyl group,

[0305] s-butyl group, and

[0306] t-butyl group.

[0307] · Substituted alkyl group (Specific Example Group G3B):

[0308] heptafluoropropyl group (including isomers),

[0309] pentafluoroethyl group,

[0310] 2,2,2-trifluoroethyl group, and

[0311] Trifluoromethyl group.

[0312] · "Substituted or unsubstituted alkenyl group"

[0313] Examples of specific examples (Group of Specific Examples G4) of the “substituted or unsubstituted alkenyl group” described in this specification include the following unsubstituted alkenyl group (Group of Specific Examples G4A) and substituted alkenyl group (Group of Specific Examples G4B). (Here, “unsubstituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “unsubstituted alkenyl group,” and “substituted alkenyl group” refers to the case where the “substituted or unsubstituted alkenyl group” is the “substituted alkenyl group.”) In this specification, when simply referred to as “alkenyl group,” it includes both the “unsubstituted alkenyl group” and the “substituted alkenyl group.”

[0314] "Substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are substituted with substituents. Specific examples of "substituted alkenyl groups" include the following "unsubstituted alkenyl groups" (Group of Specific Examples G4A) having substituents and examples of substituted alkenyl groups (Group of Specific Examples G4B). Furthermore, the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed herein are merely examples, and the "substituted alkenyl groups" described in this specification include a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" of Group of Specific Examples G4B is further substituted with a substituent.

[0315] · Non-substitutional alkenyl group (Special Example Group G4A):

[0316] vinyl,

[0317] Alilgi,

[0318] 1-butenyl group,

[0319] 2-butenyl group, and

[0320] 3-butenyl group.

[0321] · Substitutional alkenyl group (Specific example group G4B):

[0322] 1,3-butanedienyl group,

[0323] 1-methylvinyl group,

[0324] 1-methylallyl group,

[0325] 1,1-dimethylallyl group,

[0326] 2-methylallyl group, and

[0327] 1,2-dimethylallyl group.

[0328] · "Substituted or unsubstituted alkynyl group"

[0329] Examples of specific examples (Group of Examples G5) of the “substituted or unsubstituted alkynyl group” described in this specification include the following unsubstituted alkynyl group (Group of Examples G5A). (Here, the term “unsubstituted alkynyl group” refers to the case where the “substituted or unsubstituted alkynyl group” is the “unsubstituted alkynyl group.”) Hereinafter, when simply referred to as “alkynyl group,” both the “unsubstituted alkynyl group” and the “substituted alkynyl group” are included.

[0330] "Substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are substituted with substituents. Specific examples of "substituted alkynyl group" include the group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" (Specific Example Group G5A) below are substituted with substituents.

[0331] · Unsubstituted alkynyl group (Specific example group G5A):

[0332] Ethinyl group

[0333] · "Substituted or unsubstituted cycloalkyl group"

[0334] Specific examples (Group of Specific Examples G6) of the “substituted or unsubstituted cycloalkyl group” described in this specification include the following unsubstituted cycloalkyl group (Group of Specific Examples G6A) and substituted cycloalkyl group (Group of Specific Examples G6B). (Here, “unsubstituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group,” and “substituted cycloalkyl group” refers to the case where the “substituted or unsubstituted cycloalkyl group” is a “substituted cycloalkyl group.”) In this specification, when simply referred to as “cycloalkyl group,” it includes both “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”

[0335] "Substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are substituted with substituents. Specific examples of "substituted cycloalkyl groups" include a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (Specific Example Group G6A) are substituted with substituents, and examples of a substituted cycloalkyl group (Specific Example Group G6B). Furthermore, the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed herein are merely examples, and the "substituted cycloalkyl groups" described in this specification include a group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl group itself in the "substituted cycloalkyl group" of Specific Example Group G6B are substituted with substituents, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" of Specific Example Group G6B is further substituted with a substituent.

[0336] · Unsubstituted cycloalkyl group (Specific Example Group G6A):

[0337] cyclopropyl group,

[0338] cyclobutyl group,

[0339] Cyclopentyl group,

[0340] cyclohexyl group,

[0341] 1-adamantyl group,

[0342] 2-adamantyl group,

[0343] 1-norbornyl group, and

[0344] 2-Norbornilgi.

[0345] · Substituted cycloalkyl group (Specific Example Group G6B):

[0346] 4-methylcyclohexyl group.

[0347] ·「-Si(R 901 )(R 902 )(R 903 The device indicated by )

[0348] -Si(R as described in this specification) 901 )(R 902 )(R 903 As for a specific example of the device indicated by ) (specific example group G7),

[0349] -Si(G1)(G1)(G1),

[0350] -Si(G1)(G2)(G2),

[0351] -Si(G1)(G1)(G2),

[0352] -Si(G2)(G2)(G2),

[0353] -Si(G3)(G3)(G3), and

[0354] -Si(G6)(G6)(G6)

[0355] ...can be cited. Here,

[0356] G1 is the “substituted or non-substituted aryl group” described in Specific Example Group G1.

[0357] G2 is the "substitutional or non-substitutional complex circulator" described in specific example group G2.

[0358] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0359] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0360] In -Si(G1)(G1)(G1), multiple G1s are identical or different from each other.

[0361] In -Si(G1)(G2)(G2), multiple G2s are identical or different from each other.

[0362] In -Si(G1)(G1)(G2), multiple G1s are identical or different from each other.

[0363] In -Si(G2)(G2)(G2), the multiple G2s are identical or different from each other.

[0364] In Si(G3)(G3)(G3), the multiple G3s are identical or different from each other.

[0365] In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from each other.

[0366] ·「-O-(R 904 The unit indicated by )

[0367] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),

[0368] -O(G1),

[0369] -O(G2),

[0370] -O(G3), and

[0371] -O(G6)

[0372] ...can be cited.

[0373] Here,

[0374] G1 is the “substituted or non-substituted aryl group” described in Specific Example Group G1.

[0375] G2 is the "substitutional or non-substitutional complex circulator" described in specific example group G2.

[0376] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0377] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0378] ·「-S-(R 905 The unit indicated by )

[0379] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),

[0380] -S(G1),

[0381] -S(G2),

[0382] -S(G3), and

[0383] -S(G6)

[0384] ...can be cited.

[0385] Here,

[0386] G1 is the “substituted or non-substituted aryl group” described in Specific Example Group G1.

[0387] G2 is the "substitutional or non-substitutional complex circulator" described in specific example group G2.

[0388] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0389] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0390] ·「-N(R 906 )(R 907 The unit indicated by )

[0391] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),

[0392] -N(G1)(G1),

[0393] -N(G2)(G2),

[0394] -N(G1)(G2),

[0395] -N(G3)(G3), and

[0396] -N(G6)(G6)

[0397] ...can be cited.

[0398] Here,

[0399] G1 is the “substituted or non-substituted aryl group” described in Specific Example Group G1.

[0400] G2 is the "substitutional or non-substitutional complex circulator" described in specific example group G2.

[0401] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0402] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0403] In -N(G1)(G1), multiple G1s are identical or different from each other.

[0404] In -N(G2)(G2), multiple G2s are identical or different from each other.

[0405] In -N(G3)(G3), multiple G3s are identical or different from each other.

[0406] In -N(G6)(G6), multiple G6s are identical or different from each other.

[0407] · "Halogen atom"

[0408] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0409] · "Substituted or unsubstituted fluoroalkyl group"

[0410] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group of the "substituted or unsubstituted alkyl group" is substituted with a fluorine atom, and also includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group of the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of the "fluoroalkyl group" are substituted with a substituent. In addition, the “substituted fluoroalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted fluoroalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted fluoroalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted fluoroalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a fluorine atom.

[0411] · "Substituted or unsubstituted haloalkyl group"

[0412] The "substituted or unsubstituted haloalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group of the "substituted or unsubstituted alkyl group" is substituted with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group of the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of the "haloalkyl group" are substituted with a substituent. In addition, the “substituted haloalkyl group” described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain in the “substituted haloalkyl group” are further substituted with a substituent, and a group in which one or more hydrogen atoms of the substituent in the “substituted haloalkyl group” are further substituted with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group in which one or more hydrogen atoms in the “alkyl group” (specific example group G3) are substituted with a halogen atom. A haloalkyl group may be referred to as an alkyl halide group.

[0413] · "Substitutional or non-substitutional alkoxyl group"

[0414] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0415] · "Substituted or unsubstituted alkylthio groups"

[0416] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. Unless otherwise specified in this specification, the number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18.

[0417] · "Substituted or unsubstituted aryloxy group"

[0418] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted aryloxy group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0419] · "Substitution or non-substitution arylthioge"

[0420] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), wherein G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. The number of ring-forming carbons of the “unsubstituted arylthio group” is 6 to 50 unless otherwise specified in this specification, preferably 6 to 30, and more preferably 6 to 18.

[0421] · Substituted or unsubstituted trialkylsilyl group

[0422] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), wherein G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. In -Si(G3)(G3)(G3), the plurality of G3s may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0423] · "Aralkilgi of Substitution or Non-Substitution"

[0424] A specific example of the “substituted or unsubstituted aralkyl group” described in this specification is a group represented by -(G3)-(G1), wherein G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3, and G1 is the “substituted or unsubstituted aryl group” described in the group of specific examples G1. Accordingly, the “aralkyl group” is a group in which a hydrogen atom of the “alkyl group” is substituted with an “aryl group” as a substituent, and is one embodiment of the “substituted alkyl group.” The “unsubstituted aralkyl group” is the “unsubstituted alkyl group” substituted with the “unsubstituted aryl group,” and the number of carbon atoms of the “unsubstituted aralkyl group” is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified in this specification.

[0425] Specific examples of “substituted or unsubstituted aralkyl groups” include benzyl groups, 1-phenylethyl groups, 2-phenylethyl groups, 1-phenylisopropyl groups, 2-phenylisopropyl groups, phenyl-t-butyl groups, α-naphthylmethyl groups, 1-α-naphthylethyl groups, 2-α-naphthylethyl groups, 1-α-naphthylisopropyl groups, 2-α-naphthylisopropyl groups, β-naphthylmethyl groups, 1-β-naphthylethyl groups, 2-β-naphthylethyl groups, 1-β-naphthylisopropyl groups, and 2-β-naphthylisopropyl groups.

[0426] The substituted or unsubstituted aryl groups described in this specification are, unless otherwise specified in this specification, preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-4-yl groups, p-terphenyl-3-yl groups, p-terphenyl-2-yl groups, m-terphenyl-4-yl groups, m-terphenyl-3-yl groups, m-terphenyl-2-yl groups, o-terphenyl-4-yl groups, o-terphenyl-3-yl groups, o-terphenyl-2-yl groups, 1-naphthyl groups, 2-naphthyl groups, anthryl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, triphenylenyl groups, fluorenyl groups, 9,9'-spirobifluorenyl groups, 9,9-dimethylfluorenyl groups, and 9,9-diphenylfluorenyl groups, etc.

[0427] The substituted or unsubstituted complex groups described in this specification, unless otherwise specified in this specification, are preferably pyridyl groups, pyrimidinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, quinazolinyl groups, benzimidazolyl groups, phenanthrolinyl groups, carbazolyl groups (1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups or 9-carbazolyl groups), benzocarbazolyl groups, azacarbazolyl groups, diazacarbazolyl groups, dibenzofuranyl groups, naphthobenzofuranyl groups, azadibenzofuranyl groups, diazadibenzofuranyl groups, dibenzothiophenyl groups, naphthobenzothiophenyl groups, azadibenzothiophenyl groups, diazadibenzothiophenyl groups, (9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group or (9-phenyl)carbazol-4-yl group), (9-biphenyllil)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylliltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0428] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.

[0429]

[0430] In this specification, the (9-phenyl)carbazolyl group is, specifically, any one of the following groups, unless otherwise specified in this specification.

[0431]

[0432] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates a bonding site.

[0433] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following groups, unless otherwise specified in this specification.

[0434]

[0435] In the above general formulas (TEMP-34) to (TEMP-41), * indicates a bonding site.

[0436] The substituted or unsubstituted alkyl groups described in this specification are, unless otherwise specified in this specification, preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-butyl groups, etc.

[0437] · "Substitutional or non-substitutional arylene groups"

[0438] The “substituted or unsubstituted arylene group” described in this specification is a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” unless otherwise noted. Specific examples of the “substituted or unsubstituted arylene group” (Specific Example Group G12) include a divalent group derived by removing one hydrogen atom from the aryl ring from the “substituted or unsubstituted aryl group” described in Specific Example Group G1.

[0439] · "Divination of Substitution or Non-Substitution of a Bivalent Complex Call"

[0440] The “substituted or unsubstituted divalent complex ring” described in this specification is, unless otherwise noted, a divalent ring derived by excluding one hydrogen atom from the “substituted or unsubstituted complex ring”. Specific examples of the “substituted or unsubstituted divalent complex ring” (Specific Example Group G13) include a divalent ring derived by excluding one hydrogen atom from the “substituted or unsubstituted complex ring” described in Specific Example Group G2.

[0441] · "Substituted or unsubstituted alkylene group"

[0442] The “substituted or unsubstituted alkylene group” described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” unless otherwise specified. Specific examples of the “substituted or unsubstituted alkylene group” (Specific Example Group G14) include a divalent group derived by removing one hydrogen atom on the alkyl chain from the “substituted or unsubstituted alkyl group” described in Specific Example Group G3.

[0443] The substituted or unsubstituted arylene groups described in this specification are, unless otherwise specified in this specification, preferably any one of the following general formulas (TEMP-42) to (TEMP-68).

[0444]

[0445]

[0446] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0447] In the above general formulas (TEMP-42) to (TEMP-52), * indicates a bonding site.

[0448]

[0449] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0450] Formula Q9 and Q 10 They may also join together through single bonds to form a ring.

[0451] In the above general formulas (TEMP-53) to (TEMP-62), * indicates a bonding site.

[0452]

[0453] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0454] In the above general formulas (TEMP-63) to (TEMP-68), * indicates a bonding site.

[0455] The bivalent complex ring with or without substitution described in this specification is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

[0456]

[0457]

[0458]

[0459] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.

[0460]

[0461]

[0462]

[0463]

[0464] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0465] The above is an explanation of the “substituents described in this specification.”

[0466] · "When combined to form a ring"

[0467] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or non-substituted single ring, combine to form a substituted or non-substituted condensed ring, or do not combine to each other” means the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted single ring,” the case where “one or more of two or more adjacent groups combine to form a substituted or non-substituted condensed ring,” and the case where “one or more of two or more adjacent groups do not combine to each other.”

[0468] In this specification, the following describes cases in which "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted single ring" and "one or more groups of two or more adjacent groups combine to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "combined to form a ring"). The description is given by way of example an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is ​​an anthracene ring.

[0469]

[0470] For example, R 921 ~R 930 In the case where "one or more sets of two or more adjacent groups combine to form a ring," the two adjacent groups forming one set refer to R 921 and R 922 of, R 922 and R 923 of, R 923 and R 924 of, R 924 and R 930 of, R 930 and R 925 of, R 925 and R 926 of, R926 and R 927 of, R 927 and R 928 of, R 928 and R 929 of the group and R 929 and R 921 It is the group of.

[0471] The above "one or more sets" means that two or more sets of the above-mentioned two or more adjacent sets may simultaneously form a ring. For example, R 921 and R 922 They combine with each other to form the ring Q A Forms, and simultaneously R 925 and R 926 These combine with each other to form the ring Q B In the case where it is formed, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0472]

[0473] The phrase “cases where a group consisting of two or more adjacent units” forms a ring includes not only cases where a group consisting of “two” adjacent units combines as in the example above, but also cases where a group consisting of “three or more” adjacent units combines. For example, R 921 and R 922 They combine with each other to form the ring Q A It forms and also R 922 and R 923 These combine with each other to form the ring Q C Forms, and 3 adjacent (R 921 , R 922 and R 923 This refers to the case where groups consisting of ) combine with each other to form a ring and condense onto the anthracene matrix, and in this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C is R922 Share.

[0474]

[0475] The formed "single ring" or "condensed ring" is a structure consisting solely of the formed ring, and may be a saturated ring or an unsaturated ring. Even if "a set of two adjacent rings" forms a "single ring" or a "condensed ring," the "single 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 are respectively a "single ring" or a "condensed ring." In addition, the ring Q formed in the above general formula (TEMP-105) A and ring Q C is a "condensed ring". The ring Q of the above general formula (TEMP-105) A and ring Q C is, ring Q A and ring Q C It becomes a condensed ring through condensation. The ring Q of the above general formula (TMEP-104) A If it is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A is a condensed ring.

[0476] “Unsaturated ring” includes, in addition to aromatic hydrocarbon rings and aromatic heterocyclic rings, aliphatic hydrocarbon rings having unsaturated bonds, i.e., double and / or triple bonds, in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.) and non-aromatic heterocyclic rings having unsaturated bonds (e.g., dihydropyran, imidazoline, pyrazolin, quinolizine, indoline, isoindoline, etc.). “Saturated ring” includes aliphatic hydrocarbon rings that do not have unsaturated bonds or non-aromatic heterocyclic rings that do not have unsaturated bonds.

[0477] As a specific example of an aromatic hydrocarbon ring, a structure in which the group cited as a specific example in specific example group G1 is terminated by a hydrogen atom can be cited.

[0478] As a specific example of an aromatic complex ring, a structure in which the aromatic complex ring group cited as a specific example in specific example group G2 is terminated by a hydrogen atom can be cited.

[0479] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group of specific examples in group G6 is terminated by a hydrogen atom can be cited.

[0480] "Forming a ring" means forming a ring with only multiple atoms of the matrix, or with multiple atoms of the matrix and one or more arbitrary atoms. For example, R represented in the above general formula (TEMP-104). 921 and R 922 A ring Q formed by the combination of each other A is, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 It refers to a ring formed by a carbon atom of the anthracene skeleton to which it bonds, and one or more arbitrary atoms. As a specific example, R 921 and R 922 Lo ring Q A In the case where it forms, R 921 The carbon atom of the anthracene skeleton that bonds with this, and R 922 In the case where it forms a monocyclic unsaturated ring with four carbon atoms and a carbon atom of the anthracene skeleton to which it bonds, R 921 and R 922 The ring formed by is a benzene ring.

[0481] Here, "any atom" is preferably at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, unless otherwise specified in this specification. In any atom (e.g., carbon atoms or nitrogen atoms), bonds that do not form a ring may be terminated by hydrogen atoms, etc., or substituted by "any substituent" described below. When any atom other than a carbon atom is included, the ring formed is a complex ring.

[0482] Unless otherwise specified in this specification, “one or more atoms” constituting a single ring or a condensed ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5.

[0483] Unless otherwise specified in this specification, among "single ring" and "condensed ring," it is preferably "single ring".

[0484] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring."

[0485] Unless otherwise stated in this specification, "single ring" is preferably a benzene ring.

[0486] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0487] In the case where “one or more sets of two or more adjacent groups” combine with each other to form a substituted or unsubstituted single ring or “combine with each other to form a substituted or unsubstituted condensed ring,” unless otherwise specified in this specification, preferably, one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted “unsaturated ring” consisting of a plurality of atoms of the matrix and at least one atom selected from the group consisting of 1 to 15 carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0488] In the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in this specification."

[0489] In the case where the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "optional substituent" described below. Specific examples of substituents in the case where the above-mentioned "mono-ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned section "Substituents described in this specification."

[0490] The above is an explanation regarding the case where “one or more of two or more adjacent groups combine to form a single ring with or without substitution” and the case where “one or more of two or more adjacent groups combine to form a condensed ring with or without substitution” (the case where they combine to form a ring).

[0491] · Substituents in the case of "substituent or non-substituent"

[0492] In one embodiment of this specification, the substituent in the case of "substituent or non-substituent" (which may be referred to as "optional substituent" in this specification) is, for example

[0493] Unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0494] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0495] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0496] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0497] -Si(R 901 )(R 902 )(R 903 ),

[0498] -O-(R 904 ),

[0499] -S-(R 905 ),

[0500] -N(R 906 )(R 907 ),

[0501] Halogen atom, cyano group, nitro group,

[0502] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0503] Unsubstituted complex circulators with 5 to 50 ring-forming atoms

[0504] It is a group selected from the group consisting of, and

[0505] Here, R 901 ~R 907 Each independently

[0506] hydrogen atom,

[0507] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0508] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0509] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0510] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0511] R 901 If there are 2 or more of these, 2 or more R 901 They are identical or different from each other,

[0512] R 902 If there are 2 or more, 2 or more R 902 are identical or different from each other,

[0513] R 903 If there are 2 or more of these, 2 or more R 903 They are identical or different from each other,

[0514] R 904 If there are 2 or more, 2 or more R 904are identical or different from each other,

[0515] R 905 If there are 2 or more, 2 or more R 905 are identical or different from each other,

[0516] R 906 If there are 2 or more of these, 2 or more R 906 They are identical or different from each other,

[0517] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.

[0518] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0519] alkyl group having 1 to 50 carbon atoms,

[0520] A ring-forming aryl group having 6 to 50 carbon atoms, and

[0521] Complex circulators with 5 to 50 ring-forming atoms

[0522] It is a group selected from a group consisting of

[0523] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0524] alkyl group having 1 to 18 carbon atoms,

[0525] A ring-forming aryl group having 6 to 18 carbon atoms, and

[0526] Complex circulators with 5 to 18 ring-forming atoms

[0527] It is a group selected from a group consisting of

[0528] Specific examples of each of the above-mentioned arbitrary substituents are specific examples of substituents described in the above-mentioned section "Substituents described in this specification".

[0529] Unless otherwise specified in this specification, any adjacent substituents may form a “saturated ring” or an “unsaturated ring,” preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring.

[0530] Unless otherwise stated in this specification, any substituent may have additional substituents. Any additional substituents of any substituent are the same as said arbitrary substituent.

[0531] In the present specification, the numerical range indicated using “AA to BB” means a range that includes the numerical value AA listed before “AA to BB” as a lower limit value and the numerical value BB listed after “AA to BB” as an upper limit value.

[0532] [Novel Compound]

[0533] A compound according to one embodiment of the present invention is represented by the following formula (1).

[0534]

[0535] [Essence (1),

[0536] R1~R 12 One of them represents a bond with L3.

[0537] R1 to R that do not exhibit binding with L3 12 is, each independently, a hydrogen atom or a substituent. R1 to R that do not exhibit bonding with L3. 12 Groups consisting of two or more adjacent elements do not combine with each other.

[0538] Ar1 and Ar2, each independently,

[0539] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,

[0540] A substituted or unsubstituted ring-forming monovalent complex circulating group having 5 to 50 carbon atoms and not containing a nitrogen atom,

[0541] A univalent complex circulator represented by the following equation (1-21), or

[0542] It is a complex circulator of one value represented by the following equation (1-22).

[0543]

[0544] (Essence (1-21),

[0545] X 21 is, N(R 29 It is ), O, or S.

[0546] R 21 ~R 29 One of them represents a combination with L1 or L2.

[0547] R that does not show binding with L1 or L2 21 ~R 29 At least one of the sets consisting of two or more adjacent sets combines to form a substituted or unsubstituted saturated or unsaturated ring, or does not form a substituted or unsubstituted saturated or unsaturated ring.

[0548] R that does not exhibit binding with L1 or L2 and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 21 ~R 29 are, each independently,

[0549] hydrogen atom,

[0550] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0551] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0552] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0553] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0554] -Si(R 911 )(R912 )(R 913 ),

[0555] -O-(R 914 ),

[0556] -S-(R 915 ),

[0557] -N(R 916 )(R 917 )

[0558] -P(=O)(R 918 )(R 919 )

[0559] (Here, R 911 ~R 919 are, each independently,

[0560] hydrogen atom,

[0561] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0562] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0563] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0564] It is a monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms. R 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of these may be the same or different.),

[0565] Halogen atom, cyano group, nitro group,

[0566] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0567] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0568] It is selected from a group consisting of.

[0569] Among the formulas (1-22),

[0570] X31 is, N(R 37 It is ), O, or S.

[0571] R 31 ~R 37 One of them represents a combination with L1 or L2.

[0572] R that does not show binding with L1 or L2 31 ~R 37 At least one of the sets consisting of two or more adjacent sets combines to form a substituted or unsubstituted saturated or unsaturated ring, or does not form a substituted or unsubstituted saturated or unsaturated ring.

[0573] R that does not exhibit binding with L1 or L2 and does not form the aforementioned substituted or unsubstituted saturated or unsaturated ring 31 ~R 37 Each independently,

[0574] hydrogen atom,

[0575] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0576] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0577] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0578] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0579] -Si(R 911 )(R 912 )(R 913 ),

[0580] -O-(R 914 ),

[0581] -S-(R 915 ),

[0582] -N(R 916 )(R 917 )

[0583] -P(=O)(R 918 )(R 919 )

[0584] Halogen atom, cyano group, nitro group,

[0585] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0586] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0587] It is selected from a group consisting of.

[0588] R 911 ~R 919 is as defined in the above equation (1-21).

[0589] When there are multiple complex phantoms represented by the above equation (1-21), the multiple complex phantoms represented by the above equation (1-21) may be identical or different.

[0590] When there are multiple complex phantoms represented by the above equation (1-22), the multiple complex phantoms represented by the above equation (1-22) may be identical or different.

[0591] L1 to L3 are each independently a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming divalent complex circulating group having 5 to 50 atoms.

[0592] n1 is an integer from 0 to 2, and when n1 is 0, (L1) n1 is a single bond. If there are 2 or more L1s, the 2 or more L1s may be the same or different.

[0593] n2 is an integer from 0 to 2, and when n2 is 0, (L2) n2 is a single bond. If there are 2 or more L2s, the 2 or more L2s may be the same or different.

[0594] n3 is an integer from 0 to 3, and when n3 is 0, (L3) n3is a single bond. If there are 2 or more L3s, the 2 or more L3s may be the same or different.

[0595] R1~R 12 The substituent in the case where is a substituent, R1~R 12 In the case where is a substituent, the substituent in the case of "substituent or non-substituent," and in the case of Ar1 and Ar2, the substituent in the case of "substituent or non-substituent" is,

[0596] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0597] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0598] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0599] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0600] -Si(R 911 )(R 912 )(R 913 ),

[0601] -O-(R 914 ),

[0602] -S-(R 915 ),

[0603] -N(R 916 )(R 917 ),

[0604] -P(=O)(R 918 )(R 919 )

[0605] (Here, R 911 ~R 919 are, each independently,

[0606] hydrogen atom,

[0607] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0608] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0609] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0610] It is a monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms. R 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of these may be the same or different.),

[0611] Halogen atom, cyano group, nitro group,

[0612] A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0613] A monovalent complex circulating group that does not contain nitrogen atoms, having 5 to 50 substituted or unsubstituted ring-forming atoms.

[0614] It is selected from a group consisting of.)

[0615] A compound according to one embodiment of the present invention has the above-described structure, and when used in an organic EL device, the device performance can be improved. Specifically, an organic EL device capable of higher efficiency or driving at a lower voltage can be realized.

[0616] R1~R 12 One of them indicates a bond with L3. "Indicates a bond" means that L3, R1~R 12 It means directly bonding to any one of the carbon atoms on the benzanthracene ring. If n3 is 0, (L3) n3 The carbon atoms in the six-membered ring that bond with this, and R1~R 12 The carbon atoms on the benzanthracene ring that bond are directly bonded by single bonds.

[0617] In one embodiment, R7 and R 12 One of them indicates a bond with L3.

[0618] In one embodiment, R7 represents a bond with L3. In this case, R 12 is a hydrogen atom or a substituent, and in one embodiment, R 12 is a hydrogen atom.

[0619] In one embodiment, R 12 represents a bond with L3. In this case, R7 is a hydrogen atom or a substituent, and in one embodiment, R7 is a substituent.

[0620] In one embodiment, n3 is 1.

[0621] In one embodiment, n3 is 0.

[0622] In one embodiment, L3 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming 5 to 50 atoms, a divalent complex circulating group that does not contain nitrogen atoms.

[0623] Regarding the “divalent complex mutator not containing nitrogen atoms, having 5 to 50 ring-forming atoms, either substituent or unsubstituent,” the divalent complex mutator not containing nitrogen atoms is a cyclic divalent group comprising one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms as heteroatoms. The above complex mutator is identical to the “substituent or unsubstituent divalent complex mutator” in the [definition] except that it does not contain nitrogen atoms.

[0624] In one embodiment, L3 is a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms.

[0625] In one embodiment, L3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzocrisenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzoflurenyl group, a substituted or unsubstituted dibenzoflurenyl group, a substituted or unsubstituted It is a divalent group derived by removing one hydrogen atom from an aromatic hydrocarbon ring from a fluoranthenyl group, a substituted or unsubstituted benzofluranthenyl group, or a substituted or unsubstituted perylenyl group.

[0626] In one embodiment, L3 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0627] Ar1 and Ar2 are each independently a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming 5 to 50 monovalent complex valence group that does not contain nitrogen atoms, a monovalent complex valence group represented by the following formula (1-21), or a monovalent complex valence group represented by the following formula (1-22).

[0628] Regarding the “monovalent complex mutator not containing nitrogen atoms, having 5 to 50 ring-forming atoms, either substituent or unsubstituent,” the monovalent complex mutator not containing nitrogen atoms is a cyclic monovalent group comprising one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms as heteroatoms. The above complex mutator is identical to the “substituent or unsubstituent complex mutator” in the [definition] except that it does not contain nitrogen atoms.

[0629] In one embodiment, Ar1 and Ar2 are each independently,

[0630] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,

[0631] A complex circulator of 1 value represented by the above equation (1-21), or

[0632] It is a complex generator of 1 value represented by the above equation (1-22).

[0633] In one embodiment, Ar1 and Ar2 are each independently substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms.

[0634] In one embodiment, Ar1 and Ar2 are each independently,

[0635] Substituted or unsubstituted phenyl group,

[0636] Substituted or unsubstituted biphenyl group,

[0637] Substituted or unsubstituted terphenyl diary,

[0638] Substituted or unsubstituted phenanthryl group,

[0639] Substituted or unsubstituted benzophenanthryl group,

[0640] Substituted or unsubstituted phenalenyl group,

[0641] Substituted or unsubstituted pyrenyl group,

[0642] Substituted or unsubstituted crisenyl group,

[0643] Substituted or unsubstituted benzocrysenyl group,

[0644] Substituted or unsubstituted triphenylenyl group,

[0645] Substituted or unsubstituted benzotriphenylenyl group,

[0646] Substituted or unsubstituted tetracenyl group,

[0647] Substituted or unsubstituted pentaxenyl group,

[0648] Substituted or unsubstituted fluorenyl group,

[0649] Substituted or unsubstituted 9,9'-spirobifluorenyl group,

[0650] Substituted or unsubstituted benzofluorenyl group,

[0651] Substituted or unsubstituted dibenzofluorenyl group,

[0652] Substituted or unsubstituted fluoranthenyl group,

[0653] A substituted or unsubstituted benzofluranthenyl group, and

[0654] Substituted or unsubstituted perylenyl group

[0655] It is a single unit selected from a group consisting of

[0656] Ar1 and Ar2 may be the same or different. Also, -(L1) n1 -Ar1 and -(L2) n2 -Ar2 may be the same or different.

[0657] In one embodiment, Ar1 is a group selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.

[0658] In one embodiment, Ar1 is a group selected from the group consisting of a substituted or unsubstituted phenyl group and a substituted or unsubstituted biphenyl group.

[0659] In one embodiment, Ar1 is an unsubstituted group or a group having a cyano group as a substituent.

[0660] In one embodiment, Ar2 is a group selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group.

[0661] In one embodiment, Ar2 is a group selected from the group consisting of a substituted or unsubstituted phenyl group and a substituted or unsubstituted biphenyl group.

[0662] In one embodiment, Ar2 is an unsubstituted group or a group having a cyano group as a substituent.

[0663] In one embodiment, in the case of "substituted or non-substituted" in Ar1 and Ar2, the substituent is a non-substituted group, and R is the substituent in the above formula (1-21). 21 ~R 29 is an unsubstituent group, and R is a substituent in the above formula (1-22). 31 ~R 37 This is the unit of substitution.

[0664] In the case of "substituted or unsubstituted" in Ar1 and Ar2, the substituent being an unsubstituted group means that the groups exemplified as "substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms" in the case of "substituted or unsubstituted" in Ar1 and Ar2 all do not have substituents, that is, they are "unsubstituted alkyl groups having 1 to 50 carbon atoms," etc.

[0665] R, the substituent in the above formula (1-21). 21 ~R 29 What is called a non-substitutable group is, R 21 ~R 29This means that the groups exemplified as “substituted or unsubstituted C1-50 alkyl groups” all do not have substituents, that is, they are “unsubstituted C1-50 alkyl groups”, etc.

[0666] R, a substituent in the above formula (1-22). 31 ~R 37 This unsubstituted group is, R 31 ~R 37 This means that the groups exemplified as “substituted or unsubstituted C1-50 alkyl groups” all do not have substituents, that is, they are “unsubstituted C1-50 alkyl groups”, etc.

[0667] In one embodiment, R in the above formula (1-21) 21 ~R 24 Two adjacent atoms combine to form a substituted or unsubstituted benzene ring, and R 21 ~R 24 The other two do not form substituted or unsubstituted saturated or unsaturated rings, and also, R 25 ~R 28 A group consisting of two or more adjacent rings does not form a substituted or unsubstituted saturated or unsaturated ring.

[0668] In one embodiment, R in the above formula (1-21) 21 ~R 28 A group consisting of two or more adjacent rings does not form a substituted or unsubstituted saturated or unsaturated ring.

[0669] In one embodiment, R in the above formula (1-22) 31 ~R 36 A group consisting of two or more adjacent rings does not form a substituted or unsubstituted saturated or unsaturated ring.

[0670] In one embodiment, L1 and L2 are each independently a substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming 5 to 50 non-nitrogenous complex cyclic group.

[0671] In one embodiment, L1 and L2 are each independently substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms.

[0672] In one embodiment, L1 and L2 are each independently a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzocrisenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzoflurenyl group, a substituted or unsubstituted dibenzoflurenyl group, a substituted or unsubstituted It is a divalent group derived by removing one hydrogen atom from an aromatic hydrocarbon ring from a fluoranthenyl group, a substituted or unsubstituted benzofluranthenyl group, or a substituted or unsubstituted perylenyl group.

[0673] In one embodiment, n1 is 0.

[0674] In one embodiment, n2 is 0.

[0675] In one embodiment, the compound represented by the above formula (1) does not contain an anthracene structure.

[0676] The statement that it does not contain an anthracene structure means that the compound represented by Formula (1) does not contain, in part, a monovalent or divalent or higher group derived from anthracene. Here, an anthracene structure refers to a structure in which only three benzene rings are condensed, and does not refer to a condensed ring structure derived from anthracene such as benzanthracene.

[0677] In addition, in one embodiment, the compound represented by formula (1) does not include a condensed ring structure containing anthracene as a partial structure, in addition to the benzanthracene structure represented by parentheses in formula (1).

[0678] The statement that it does not contain a condensed ring structure containing anthracene as a partial structure means that the compound represented by Formula (1) does not contain, in part, a monovalent or divalent or higher group derived from a condensed ring structure containing anthracene as a partial structure, other than the benzanthracene structure represented by the parentheses in Formula (1). Here, a condensed ring structure containing anthracene as a partial structure refers to a structure in which a substituted or unsubstituted saturated or unsaturated ring is condensed in one or more sets of two or more adjacent bonding sites among the 10 bonding sites on the anthracene structure, and examples include benzanthracene, naphthacene, benzopyrene, etc.

[0679] In one embodiment, the compound represented by the above formula (1) does not include a nitrogen-containing six-membered ring structure or a condensation structure containing a nitrogen-containing six-membered ring structure as a partial structure, in addition to the pyrimidine backbone to which L1, L2, and L3 are bonded.

[0680] The statement that it does not contain a nitrogen-containing six-membered ring structure other than the pyrimidine backbone to which L1, L2, and L3 are bound means that the compound represented by Formula (1) does not contain, in part, a monovalent or divalent or higher group derived from a nitrogen-containing six-membered ring (e.g., pyridine, pyrimidine, triazine, etc.) other than the pyrimidine backbone to which L1, L2, and L3 are bound.

[0681] The statement that it does not contain a condensation structure containing a nitrogen-containing six-membered ring skeleton as a partial structure means that the compound represented by Formula (1) does not contain, in part, a monovalent or divalent or higher group derived from a condensation ring (e.g., benzopyridine, quinazoline, etc.) containing a nitrogen-containing six-membered ring skeleton as a partial structure.

[0682] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (11).

[0683]

[0684] (In Equation (11), Ar1, Ar2, L3, R1 to R6, and R8 to R 11 is as defined in the above equation (1).

[0685] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (21).

[0686]

[0687] (In Equation (21), Ar1, Ar2, R1 to R6, and R8 to R 11 is as defined in the above equation (1).

[0688] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (31).

[0689]

[0690] (Equation (31), Ar1, Ar2, L2, L3, R1 to R6, and R8 to R 11 is as defined in the above equation (1).

[0691] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (41).

[0692]

[0693] (Equation (41), Ar1, Ar2, L3, R1~R 11 is as defined in the above equation (1).

[0694] In one embodiment, R4 is a hydrogen atom.

[0695] In one embodiment, R1 to R6 and R8 to R 11 It is a hydrogen atom.

[0696] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (12).

[0697]

[0698] (In Equation (12), Ar1 and Ar2 are as defined in Equation (1) above.)

[0699] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (13).

[0700]

[0701] (In Equation (13), Ar1 and Ar2 are as defined in Equation (1) above.)

[0702] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (14).

[0703]

[0704] (In Equation (14), L2, Ar1 and Ar2 are as defined in Equation (1) above.)

[0705] In one embodiment, the compound represented by the above formula (1) is a compound represented by the following formula (15).

[0706]

[0707] (In Equation (15), Ar1 and Ar2 are as defined in Equation (1) above.)

[0708] As stated in [Definition], the "hydrogen atom" used in this specification includes light hydrogen atoms, deuterium atoms, and tritium atoms. Accordingly, the compound of the invention may include naturally occurring deuterium atoms.

[0709] In addition, deuterium atoms may be intentionally introduced into the inventive compound by using a compound that has been deuterinized in part or all of the raw material compound. Accordingly, in one embodiment of the present invention, the compound represented by Formula (1) contains at least one deuterium atom. That is, the compound of the present embodiment may be a compound represented by Formula (1), wherein at least one of the hydrogen atoms included in the compound is a deuterium atom.

[0710] In the compound represented by formula (1), at least one hydrogen atom selected from the hydrogen atom of the benzanthracene structure; the hydrogen atom of L3; the hydrogen atom of the pyrimidine skeleton to which L1, L2, and L3 are bonded; the hydrogen atom of L1; the hydrogen atom of L2; the hydrogen atom of Ar1; and the hydrogen atom of Ar2 may be a deuterium atom.

[0711] The deuterium content of a compound depends on the deuterium content of the raw material compound used. Even if a raw material with a specified deuterium content is used, a certain proportion of naturally occurring light hydrogen isotopes may be included. Therefore, the aspect of deuterium content includes a ratio that accounts for trace amounts of naturally occurring isotopes, in addition to the ratio obtained by simply counting the number of deuterium atoms represented by the chemical formula.

[0712] In one embodiment, the deuterium content of the compound is, for example, 1% or more, 3% or more, 5% or more, 10% or more, or 50% or more.

[0713] Specific examples of the compound represented by Formula (1) are described below, but these are merely examples and the compound represented by Formula (1) is not limited to the following specific examples.

[0714]

[0715]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722]

[0723]

[0724]

[0725]

[0726]

[0727]

[0728]

[0729]

[0730]

[0731]

[0732]

[0733]

[0734]

[0735]

[0736]

[0737]

[0738]

[0739]

[0740]

[0741]

[0742]

[0743]

[0744]

[0745]

[0746]

[0747]

[0748]

[0749]

[0750]

[0751]

[0752]

[0753]

[0754]

[0755]

[0756]

[0757]

[0758]

[0759]

[0760]

[0761]

[0762]

[0763]

[0764]

[0765]

[0766]

[0767]

[0768]

[0769]

[0770]

[0771]

[0772]

[0773]

[0774]

[0775]

[0776]

[0777]

[0778]

[0779]

[0780]

[0781]

[0782]

[0783]

[0784]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795]

[0796]

[0797]

[0798]

[0799]

[0800]

[0801]

[0802]

[0803]

[0804]

[0805]

[0806]

[0807]

[0808]

[0809]

[0810]

[0811]

[0812]

[0813]

[0814]

[0815]

[0816]

[0817]

[0818]

[0819]

[0820]

[0821]

[0822]

[0823]

[0824]

[0825]

[0826]

[0827]

[0828]

[0829]

[0830]

[0831]

[0832]

[0833]

[0834] [Materials for Organic Electroluminescence Devices]

[0835] A compound according to one embodiment of the present invention is useful as a material for organic EL devices, for example, as a material used in the electron transport band of an organic EL device.

[0836] [Organic EL Device]

[0837] An organic EL device according to one embodiment of the present invention will be described.

[0838] An organic EL device according to one embodiment of the present invention has a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers comprises a compound according to one embodiment of the present invention.

[0839] An organic EL device according to one embodiment of the present invention preferably comprises an anode, a light-emitting layer, an electron transport band, and a cathode in this order, and the electron transport band comprises a compound according to one embodiment of the present invention.

[0840] As a representative device configuration of the above organic EL device, a structure in which the following structures (1) to (4) are stacked on a substrate is exemplified.

[0841] (1) Anode / Luminous layer / Cathode

[0842] (2) Anode / Hole transport band / Emitting layer / Cathode

[0843] (3) Anode / emissive layer / electron transport band / cathode

[0844] (4) Anode / Hole transport band / Emitting layer / Electron transport band / Cathode

[0845] (「 / 」 indicates that each layer is stacked adjacently.)

[0846] The electron transport band is typically composed of one or more layers selected from the electron injection layer and the electron transport layer. The hole transport band is typically composed of one or more layers selected from the hole injection layer and the hole transport layer.

[0847] A schematic configuration of an organic EL device of one embodiment of the present invention will be described with reference to FIG. 1.

[0848] An organic EL element (1) according to one embodiment of the present invention has a substrate (2), an anode (3), a light-emitting layer (5), a cathode (10), a hole transport band (4) between the anode (3) and the light-emitting layer (5), and an electron transport band (6) between the light-emitting layer (5) and the cathode (10).

[0849] Hereinafter, a component that can be used in an organic EL device according to one embodiment of the present invention, and a material other than the compound constituting each layer, will be described.

[0850] (Circuit board)

[0851] A substrate is used as a support for a light-emitting element. For example, glass, quartz, plastic, etc. may be used as the substrate. In addition, a flexible substrate may be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include polycarbonate, plastic substrates containing polyvinyl chloride, etc.

[0852] (anode)

[0853] For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a large work function (specifically 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), or nitrides of metallic materials (e.g., titanium nitride) may be used.

[0854] (Hole injection layer)

[0855] The hole injection layer is a layer containing a material with high hole injection properties. Materials with high hole injection properties may include 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.).

[0856] (Pure transport layer)

[0857] The hole transport layer is a layer containing a material with high hole transportability. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., may be used for the hole transport layer. Polymeric compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) or poly(4-vinyltriphenylamine) (abbreviated: PVTPA) may also be used. However, if the material has higher hole transportability than electron transportability, materials other than these may be used. Furthermore, the layer containing a material with high hole transportability may not only be a single layer, but may also be a layer made of the above material stacked in two or more layers.

[0858] (Guest (dopant) material of the emissive layer)

[0859] The emissive layer is a layer containing a material with high luminescence, and various materials can be used. For example, as the material with high luminescence, fluorescent compounds that emit fluorescence or phosphorescent compounds that emit phosphorescence can be used. Fluorescent compounds are compounds capable of emitting light from a singlet excited state, and phosphorescent compounds are compounds capable of emitting light from a triplet excited state.

[0860] As blue fluorescent light-emitting materials that can be used in the light-emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc., can be used. As green fluorescent light-emitting materials that can be used in the light-emitting layer, aromatic amine derivatives, etc., can be used. As red fluorescent light-emitting materials that can be used in the light-emitting layer, tetracene derivatives, diamine derivatives, etc., can be used.

[0861] Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the emissive layer. Iridium complexes are used as green phosphorescent materials that can be used in the emissive layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the emissive layer.

[0862] (Host material of the light-emitting layer)

[0863] As for the emissive layer, it may be configured such that the aforementioned highly luminescent material (guest material) is dispersed in another material (host material). Various materials may be used as the material for dispersing the highly luminescent material, and it is preferable to use a material that has a lower luminosone level (LUMO level) and a lower hominosone level than the highly luminescent material.

[0864] As a material (host material) for dispersing a highly luminescent substance, 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 condensed aromatic compound such as a carbazole derivative, anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative, 4) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

[0865] (Electron transport layer)

[0866] The electron transport layer is a layer containing a material with high electron transportability. In the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) complex aromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds may be used.

[0867] In one embodiment, the electron transport layer may include, or may not include, other materials as described above in addition to the compound represented by formula (1).

[0868] In one embodiment, the electron transport layer comprises, in addition to the compound represented by formula (1), one or more compounds selected from the group consisting of compounds containing alkali metals and compounds containing metals belonging to Group 13 of the periodic table. Examples of such compounds include lithium fluoride, lithium oxide, 8-hydroxyquinolinolato-lithium (Liq), cesium fluoride, tris(8-quinolinolato)aluminum (Alq3), tris(4-methyl-8-quinolinolato)aluminum (Almq3), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum (BAlq), etc.

[0869] The ratio (mass ratio) of the compound represented by formula (1), the compound containing an alkali metal, and the compound containing a metal belonging to Group 13 of the periodic table is not particularly limited, but is, for example, 10:90 to 90:10.

[0870] An organic EL device according to one embodiment of the present invention has an electron transport band having a first layer (also referred to as a "first electron transport layer" or "hole barrier layer") and a second layer (also referred to as a "second electron transport layer") in that order from the light-emitting layer side, and the second layer comprises a compound represented by formula (1). In this case, the above-mentioned first layer may, for example, be configured with the aforementioned electron transport layer. In an organic EL device according to another embodiment of the present invention, the first layer comprises a compound represented by formula (1). In this case, the above-mentioned second layer may, for example, be configured with the aforementioned electron transport layer.

[0871] (Electron injection layer)

[0872] The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, metal complex compounds such as lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), 8-hydroxyquinolinolato-lithium (Liq), alkali metals such as lithium oxide (LiOx), alkaline earth metals, or compounds thereof may be used.

[0873] (cathode)

[0874] For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof that have 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, namely alkali metals such as lithium (Li) or cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0875] The cathode is typically formed by vacuum deposition or sputtering. In addition, when using silver paste, coating or inkjet methods may be used.

[0876] In addition, when an electron injection layer is installed, a cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, silicon, or indium-tin oxide containing silicon oxide, regardless of the magnitude of the work function.

[0877] In an organic EL device according to one embodiment of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes and to suppress the applied voltage to a low level and improve luminous efficiency, a range of several nm to 1 μm is preferred.

[0878] In an organic EL device according to one embodiment of the present invention, the method of forming each layer is not particularly limited. Conventionally known formation methods such as vacuum deposition and spin coating may be used. Each layer, such as a light-emitting layer, may be formed by known methods such as vacuum deposition, molecular beam deposition (MBE), or dipping of a solution dissolved in a solvent, spin coating, casting, bar coating, or roll coating.

[0879] [Electronic devices]

[0880] An electronic device according to one embodiment of the present invention is characterized by having an organic EL element according to one embodiment of the present invention.

[0881] Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, or personal computers, and light-emitting devices such as lighting or vehicle lighting fixtures.

[0882] Examples

[0883] <Compounds>

[0884] The compound represented by formula (1) used in the manufacture of the organic EL device of the example is shown below.

[0885]

[0886]

[0887] The structure of the compound used to manufacture the organic EL device of the comparative example is shown below.

[0888]

[0889] The structures of other compounds used in the manufacture of the organic EL devices of the examples and comparative examples are shown below.

[0890]

[0891]

[0892] Example 1

[0893] Fabrication of Organic EL Devices

[0894] An organic EL device was fabricated as follows.

[0895] A glass substrate (manufactured by Geomatec Co., Ltd.) equipped with an ITO transparent electrode (anode) with a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[0896] A glass substrate equipped with a transparent electrode after cleaning was mounted in a substrate holder of a vacuum deposition apparatus, and first, the transparent electrode was placed over the side on which the transparent electrode was formed, so that compounds HT-1 and HI-1 were co-deposited such that the ratio of compound HI-1 was 3 mass%, thereby forming a first hole transport layer with a film thickness of 10 nm.

[0897] Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm.

[0898] Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[0899] Compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer such that the ratio of compound BD-1 was 4 mass%, and an emissive layer with a thickness of 25 nm was formed.

[0900] Compound HBL-1 was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0901] On the first electron transport layer, compound ET-1 and 8-hydroxyquinolinolato-lithium (Liq) were co-deposited such that the ratio of Liq was 50 mass% to form a second electron transport layer with a film thickness of 20 nm.

[0902] On the second electron transport layer, metal Yb and LiF were co-deposited such that the ratio of Yb was 50 mass% to form an electron injection layer with a film thickness of 1 nm.

[0903] A cathode with a thickness of 50 nm was formed by depositing metallic Al on the electron injection layer.

[0904] The device configuration of the organic EL device of Example 1 can be briefly represented as follows.

[0905] ITO(130) / HT-1:HI-1(10:3%) / HT-1(80) / EBL-1(5) / BH-1:BD-1(25:4%) / HBL-1(5) / ET-1:Liq(20:50%) / LiF:Yb(1:50%) / Al(50)

[0906] The number in parentheses indicates the film thickness (unit: nm). Also, the number in parentheses indicated by a percentage represents the proportion (mass%) of the latter compound in the layer.

[0907] Evaluation of Organic EL Devices

[0908] (External quantum efficiency)

[0909] Current density is 1.0 mA / cm² 2 A voltage was applied to the organic EL device to such an extent, and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Kabuki Kaisha). From the obtained spectroradiometer, the external quantum efficiency EQE (%) was calculated. The results are shown in Table 1.

[0910] Comparative Example 1

[0911] Organic EL devices were fabricated and evaluated in the same manner as in Example 1, except that the compounds listed in Table 1 were used instead of compound ET-1. The results are shown in Table 1.

[0912]

[0913] Example 2

[0914] Fabrication of Organic EL Devices

[0915] An organic EL device was fabricated as follows.

[0916] A glass substrate (manufactured by Geomatec Co., Ltd.) equipped with an ITO transparent electrode (anode) with a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[0917] A glass substrate equipped with a transparent electrode after cleaning was mounted in a substrate holder of a vacuum deposition apparatus, and first, the transparent electrode was placed over the side on which the transparent electrode was formed, so that compounds HT-2 and HI-1 were co-deposited such that the ratio of compound HI-1 was 3 mass%, thereby forming a first hole transport layer with a film thickness of 10 nm.

[0918] Compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm.

[0919] Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[0920] Compound BH-2 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer such that the ratio of compound BD-1 was 4 mass%, thereby forming an emissive layer with a thickness of 25 nm.

[0921] Compound HBL-2 ​​was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0922] Compound ET-1 and Liq were co-deposited on the first electron transport layer such that the ratio of Liq was 50 mass% to form a second electron transport layer with a film thickness of 20 nm.

[0923] Metal Yb was deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0924] A cathode with a thickness of 50 nm was formed by depositing metallic Al on the electron injection layer.

[0925] The device configuration of the organic EL device of Example 2 can be briefly represented as follows.

[0926] ITO(130) / HT-2:HI-1(10:3%) / HT-2(80) / EBL-1(5) / BH-2:BD-1(25:4%) / HBL-2(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50)

[0927] The number in parentheses indicates the film thickness (unit: nm). Also, the number in parentheses indicated by a percentage represents the proportion (mass%) of the latter compound in the layer.

[0928] Evaluation of Organic EL Devices

[0929] (Driving voltage)

[0930] Initial characteristics of the organic EL device, at room temperature, DC constant current 50 mA / cm² 2 Measurements were taken by driving. The results are shown in Table 2.

[0931] Examples 3-5

[0932] Organic EL devices were fabricated and evaluated in the same manner as in Example 2, except that the compound listed in Table 2 was used instead of compound ET-1. The results are shown in Table 2.

[0933] Comparative Example 2

[0934] Organic EL devices were fabricated and evaluated in the same manner as in Example 2, except that the compound listed in Table 2 was used instead of compound ET-1. The results are shown in Table 2.

[0935]

[0936] Example 6

[0937] Fabrication of Organic EL Devices

[0938] An organic EL device was fabricated as follows.

[0939] A glass substrate (manufactured by Geomatec Co., Ltd.) equipped with an ITO transparent electrode (anode) with a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The thickness of the ITO film was set to 130 nm.

[0940] A glass substrate equipped with a transparent electrode after cleaning was mounted in a substrate holder of a vacuum deposition apparatus, and first, the transparent electrode was placed over the side on which the transparent electrode was formed, so that compounds HT-1 and HI-1 were co-deposited such that the ratio of compound HI-1 was 3 mass%, thereby forming a first hole transport layer with a film thickness of 10 nm.

[0941] Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm.

[0942] Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer with a film thickness of 5 nm.

[0943] Compound BH-1 (host material) and compound BD-1 (dopant material) were co-deposited on the third hole transport layer such that the ratio of compound BD-1 was 4 mass%, and an emissive layer with a thickness of 25 nm was formed.

[0944] Compound HBL-2 ​​was deposited on the light-emitting layer to form a first electron transport layer with a film thickness of 5 nm.

[0945] On the first electron transport layer, compound ET-1 and Liq were co-prepared such that the ratio of Liq was 50 mass%, thereby forming a second electron transport layer with a film thickness of 20 nm.

[0946] Metal Yb was deposited on the second electron transport layer to form an electron injection layer with a film thickness of 1 nm.

[0947] A cathode with a thickness of 50 nm was formed by depositing metallic Al on the electron injection layer.

[0948] The device configuration of the organic EL device of Example 6 can be briefly represented as follows.

[0949] ITO(130) / HT-1:HI-1(10:3%) / HT-1(80) / EBL-1(5) / BH-1:BD-1(25:4%) / HBL-2(5) / ET-1:Liq(20:50%) / Yb(1) / Al(50)

[0950] The number in parentheses indicates the film thickness (unit: nm). Also, the number in parentheses indicated by a percentage represents the proportion (mass%) of the latter compound in the layer.

[0951] Evaluation of Organic EL Devices

[0952] (External quantum efficiency)

[0953] Current density is 10 mA / cm² 2 A voltage was applied to the organic EL device to such an extent, and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation). From the obtained spectroradiometer, the external quantum efficiency EQE (%) was calculated. The results are shown in Table 3.

[0954] Examples 7–13

[0955] Organic EL devices were fabricated and evaluated in the same manner as in Example 6, except that the compound listed in Table 3 was used instead of compound ET-1. The results are shown in Table 3.

[0956]

[0957] Synthesis of Compounds

[0958] (Synthesis Example 1) Synthesis of ET-1

[0959] Compound ET-1 was synthesized via the following synthesis route.

[0960]

[0961] 4-([1,1'-biphenyl]-4-yl)-6-(4-bromophenyl)-2-phenylpyrimidine (4.00 g) and (Amphos)2PdCl2 (0.31 g) were placed in a flask and, after replacing with argon gas, 1,4-dioxane (108 mL) and 2M aqueous sodium carbonate solution (13.5 mL) were added. Under reflux conditions, a 1,4-dioxane solution (30 mL) of tetraphen-7-ylboronic acid (4.40 g) was added dropwise over 3 hours and 30 minutes, and the mixture was heated and stirred for 5 more hours. After cooling the reaction solution, the solvent was removed by distillation, and methanol was added to filter and collect the precipitated solid. The obtained crude product was purified by silica gel chromatography and then washed with ethyl acetate to obtain compound ET-1 as a white solid (5.20 g, yield 79%).

[0962] Mass spectrum analysis results showed that the molecular weight was 610.76 and m / e=611, and it was identified as the target substance.

[0963] (Synthesization Example 2) Synthesis of ET-2

[0964] Compound ET-2 was synthesized via the following synthesis route.

[0965]

[0966] 4-(4-bromophenyl)-2,6-diphenylpyrimidine (5.70 g) and (Amphos)2PdCl2 (0.42 g) were placed in a flask and, after replacing the gas with argon, 1,4-dioxane (98 mL) and a 2 M aqueous sodium carbonate solution (18.4 mL) were added. Under reflux conditions, a 1,4-dioxane solution (49 mL) of tetraphen-7-ylboronic acid (6.01 g) was added dropwise over 3 hours and 30 minutes, and the mixture was heated and stirred for 2 more hours. After cooling the reaction solution, the solvent was removed by distillation, and methanol was added to filter and collect the precipitated solid. The obtained crude product was purified by silica gel chromatography and then washed with ethyl acetate to obtain compound ET-2 as a white solid (6.26 g, yield 79%).

[0967] Mass spectrum analysis results showed that the molecular weight was 534.66 and m / e=535, and it was identified as the target substance.

[0968] (Synthesis Example 3) Synthesis of ET-3

[0969] Compound ET-3 was synthesized via the following synthesis route.

[0970] (3-1) Intermediate A was synthesized via the following synthesis pathway.

[0971]

[0972] 4-(3-bromophenyl)-6-(4-chlorophenyl)-2-phenylpyrimidine (5.53 g), (4-cyanophenyl)boronic acid (1.93 g), and Pd(PPh3)4 (0.30 g) were placed in a flask, and after replacing with argon gas, DME (66 mL) and 2 M aqueous sodium carbonate solution (19.7 mL) were added, and the mixture was heated and stirred for 5 hours under reflux conditions. After cooling the reaction solution, MeOH was added, and the precipitated solid was filtered and collected. The obtained crude product was washed with cyclohexane and toluene and purified by silica gel chromatography to obtain 3'-(6-(4-chlorophenyl)-2-phenylpyrimidine-4-yl)-[1,1'-biphenyl]-4-carbonitrile (intermediate A) as a white solid (4.80 g, yield 82%).

[0973] Mass spectrum analysis results showed that m / e=444 for a molecular weight of 443.93, and it was identified as the target substance.

[0974] (3-2) Compound ET-3 was synthesized via the following synthesis route.

[0975]

[0976] Compound ET-3 was obtained as a pale yellow solid (3.29 g, yield 53%) by using the 3'-(6-(4-chlorophenyl)-2-phenylpyrimidine-4-yl)-[1,1'-biphenyl]-4-carbonitrile (4.30 g) and tetraphen-7-ylboronic acid (3.95 g) obtained in (3-1) above, respectively, and following the conditions described in Synthesis Example 1.

[0977] Mass spectrum analysis results showed that m / e=636 for a molecular weight of 635.77, and it was identified as the target substance.

[0978] (Synthesis Example 4) Synthesis of ET-4

[0979] Compound ET-4 was synthesized via the following synthesis route.

[0980]

[0981] 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (3.43 g), tetraphen-7-ylboronic acid (2.99 g), Pd2(dba)3 (0.18 g), SPhos (0.32 g), and K2CO3 (2.76 g) were placed in a flask, and after replacing with argon gas, 1,4-dioxane (43 mL) and H2O (7.1 mL) were added, and the mixture was heated and stirred for 6.5 hours under reflux conditions. After cooling the reaction solution, MeOH was added, and the precipitated solid was collected by filtration and washed with water and methanol. The obtained crude product was purified by silica gel chromatography and then recrystallized with toluene to obtain compound ET-4 as a pale yellow solid (4.51 g, yield 84%).

[0982] Mass spectrum analysis results showed that the molecular weight was 534.66 and m / e=535, and it was identified as the target substance.

[0983] (Synthesis Example 5) Synthesis of ET-5

[0984] Compound ET-5 was synthesized via the following synthesis route.

[0985] (5-1) Intermediate B was synthesized via the following synthesis pathway.

[0986]

[0987] Penchlorim (7.94 g), tetraphen-7-ylboronic acid (8.00 g), and Pd(PPh3)4 (1.70 g) were placed in a flask, and after replacing with argon gas, DME (147 mL) and 2 M sodium carbonate aqueous solution (29.4 mL) were added, and the mixture was heated and stirred for 5.5 hours under reflux conditions. After cooling the reaction solution, the solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography and then washed with hexane to obtain 4-chloro-2-phenyl-6-(tetraphen-7-yl)pyrimidine (intermediate B) as a white solid (6.07 g, yield 50%).

[0988] Mass spectrum analysis results showed that the molecular weight was 416.91 and m / e=417, and it was identified as the target substance.

[0989] (5-2) Compound ET-5 was synthesized via the following synthesis route.

[0990]

[0991] 2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-3-yl]dibenzofuran (3.54 g), 4-chloro-2-phenyl-6-(tetraphen-7-yl)pyrimidine obtained from (5-1) above (3.15 g), and (Amphos)2PdCl2 (0.21 g) were placed in a flask, and after replacing with argon gas, DME (76 mL) and 2 M sodium carbonate aqueous solution (9.4 mL) were added, and the mixture was heated and stirred for 6 hours under reflux conditions. After cooling the reaction solution, the solvent was removed by distillation, and the resulting crude product was purified by silica gel chromatography and then washed with ethyl acetate to obtain ET-5 as a white solid (3.73 g, yield 70%).

[0992] Mass spectrum analysis results showed that the molecular weight was 700.84 and m / e=701, and it was identified as the target substance.

[0993] (Synthesis Example 6) Synthesis of ET-6

[0994] Compound ET-6 was synthesized via the following synthesis route.

[0995]

[0996] Compound ET-6 was obtained as a pale yellow solid (4.27 g, yield 73%) by using 4-(4-bromophenyl)-6-(4-dibenzo[b, d]thiophene-4-yl)-2-phenyl-pyrimidine (4.50 g) and tetraphen-7-ylboronic acid (2.73 g), respectively, according to the conditions described in Synthesis Example 4.

[0997] Mass spectrum analysis results showed that m / e=641 for a molecular weight of 640.80, and it was identified as the target substance.

[0998] (Synthesis Example 7) Synthesis of ET-7

[0999] Compound ET-7 was synthesized via the following synthesis route.

[1000]

[1001] Compound ET-7 was obtained as a white solid (3.52 g, yield 62%) by using 4-(4-bromophenyl)-6-[4-(dibenzo[b,d]thiophene-4-yl)phenyl]-2-phenyl-pyrimidine (4.50) and tetraphen-7-ylboronic acid (2.36 g), respectively, according to the conditions described in Synthesis Example 4.

[1002] Mass spectrum analysis results showed that m / e=717 for a molecular weight of 716.90, and it was identified as the target substance.

[1003] (Synthesization Example 8) Synthesis of ET-8

[1004] Compound ET-8 was synthesized via the following synthesis route.

[1005]

[1006] Compound ET-8 was obtained as a white solid (4.94 g, yield 78%) by using 2-(4-bromophenyl)-6-(4-(dibenzo[b,d]furan-4-yl)phenyl)-2-phenylpyrimidine (5.00 g) and tetraphen-7-ylboronic acid (2.70 g) respectively, according to the conditions described in Synthesis Example 4.

[1007] Mass spectrum analysis results showed that the molecular weight was 700.81 and m / e=701, and it was identified as the target substance.

[1008] (Synthesis Example 9) Synthesis of ET-9

[1009] Compound ET-9 was synthesized via the following synthesis route.

[1010]

[1011] Compound ET-9 was obtained as a white solid (2.84 g, yield 44%) by using 4-([1,1'-biphenyl]-4-yl)-6-(4-bromonaphthalene-1-yl)-2-phenylpyrimidine (5.00 g) and tetraphen-7-ylboronic acid (2.91 g), respectively, according to the conditions described in Synthesis Example 4.

[1012] Mass spectrum analysis results showed that m / e=661 for a molecular weight of 660.82, and it was identified as the target substance.

[1013] (Synthesis Example 10) Synthesis of ET-10

[1014] Compound ET-10 was synthesized via the following synthesis route.

[1015]

[1016] Compound ET-10 was obtained as a white solid (2.47 g, yield 52%) by using 4-([1,1'-biphenyl]-4-yl)-2-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (3.50 g) and 12-bromo-7-phenyltetraphene (2.63 g) respectively, according to the conditions described in Synthesis Example 4.

[1017] Mass spectrum analysis results showed that m / e=687 for a molecular weight of 686.86, and it was identified as the target substance.

[1018] (Synthesis Example 11) Synthesis of ET-11

[1019] Compound ET-11 was synthesized via the following synthesis route.

[1020]

[1021] Compound ET-10 was obtained as a white solid (2.36 g, yield 42%) by using 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (4.00 g) and 12-bromo-7-phenyltetraphene (3.53 g), respectively, according to the conditions described in Synthesis Example 4.

[1022] Mass spectrum analysis results showed that the molecular weight was 610.76 and m / e=611, and it was identified as the target substance.

[1023] (Synthesis Example 12) Synthesis of ET-12

[1024] Compound ET-12 was synthesized via the following synthesis route.

[1025] (12-1) Intermediate C was synthesized via the following synthesis route.

[1026]

[1027] 4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-2-phenylpyrimidine (5.50 g), (4-chlorophenyl)boronic acid (3.67 g), and PdCl2(PPh3)2 (0.11 g) were placed in a flask, and after replacing with argon gas, toluene (156 mL) and 2 M sodium carbonate aqueous solution (19.5 mL) were added, and the mixture was heated and stirred at 60°C for 16 hours. After cooling the reaction solution, water and MeOH were added, and the precipitated solid was filtered and collected, and washed with water and methanol. The obtained crude product was purified by silica gel chromatography and recrystallization using toluene, and 4-([1,1'-biphenyl]-4-yl-d9)-6-(4-chlorophenyl)-2-phenylpyrimidine (intermediate C) was obtained as a white solid (4.82 g, yield 72%).

[1028] Mass spectrum analysis results showed that the molecular weight was 427.98 and m / e=428, and it was identified as the target substance.

[1029] (12-2) Compound ET-12 was synthesized via the following synthesis route.

[1030]

[1031] Compound ET-12 was obtained as a white solid (4.30 g, yield 66%) by using the 4-([1,1'-biphenyl]-4-yl-d9)-6-(4-chlorophenyl)-2-phenylpyrimidine (4.50 g) and tetraphen-7-ylboronic acid (3.15 g) obtained in (12-1) above, respectively, and following the conditions described in Synthesis Example 4.

[1032] Mass spectrum analysis results showed that the molecular weight was 619.82 and m / e=620, and it was identified as the target substance.

[1033] Although several embodiments and / or examples of the present invention have been described in detail above, those skilled in the art will easily make many modifications to these exemplary embodiments and / or examples without substantially departing from the novel teachings and effects of the present invention. Accordingly, such many modifications are included within the scope of the present invention.

[1034] All documents described in this specification and the contents of the application forming the basis of the priority of this application under the Paris Convention are adopted.

Claims

Claim 1 A compound represented by the following formula (1). [In Equation (1), R7 represents a bond with L3. R1 to R6, and R8 to R 12 is a hydrogen atom. R1–R6, and R8–R 12 Among them, groups consisting of two or more adjacent groups do not bond with each other. Ar1 is a substituted or unsubstituted phenyl group, and Ar2 is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a monovalent complex cyclic group represented by the following formula (1-21). (Equation (1-21), X 21 is, N(R 29 ), O, or S.R 21 ~R 29 One of them indicates binding with L2. R that does not indicate binding with L2 21 ~R 29 One or more of the sets consisting of two or more adjacent elements combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring. R that does not exhibit combination with L2 and does not form the said substituted or unsubstituted saturated or unsaturated ring. 21 ~R 29 are, each independently, a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 911 )(R 912 )(R 913 ),-O-(R 914 ),-S-(R 915 ),-N(R 916 )(R 917 ),-P(=O)(R 918 )(R 919 ),(here, R 911 ~R 919 R is, each independently, a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming C5–50 non-nitrogen monovalent heterocyclic group. 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of the above may be the same or different), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted cyclic or unsubstituted monovalent complex group having 5 to 50 atoms that does not contain a nitrogen atom.) If there are multiple monovalent complex groups represented by the above formula (1-21), the multiple monovalent complex groups represented by the above formula (1-21) may be the same or different. L1 to L3 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group. n1 is an integer from 0 to 2, and if n1 is 0, (L1) n1 is a single bond. If there are 2 or more L1s, the 2 or more L1s may be identical or different. n2 is an integer from 0 to 2, and if n2 is 0, (L2) n2 is a single bond. If there are 2 or more L2s, the 2 or more L2s may be the same or different. n3 is 1. In Formula (1) and Formula (1-21), the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 carbon atoms, -Si(R 911 )(R 912 )(R 913 ),-O-(R 914 ),-S-(R 915 ),-N(R 916 )(R 917 ),-P(=O)(R 918 )(R 919 )(here, R 911 ~R 919 R is, each independently, a hydrogen atom, an unsubstituted C1–50 alkyl group, an unsubstituted ring-forming C3–50 cycloalkyl group, an unsubstituted ring-forming C6–50 aryl group, or an unsubstituted ring-forming C5–50 monovalent heterocyclic group that does not contain a nitrogen atom. 911 ~R 919 If there are 2 or more, 2 or more R 911 ~R 919 Each of the following may be identical or different), a halogen atom, a cyano group, a nitro group, an unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and an unsubstituted ring-forming monovalent heterocyclic group having 5 to 50 atoms that does not contain a nitrogen atom, are selected from the group consisting of these. Claim 2 A compound according to claim 1, wherein L3 is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalenediyl group. Claim 3 In paragraph 1, in the case of "substituted or non-substituted" in Ar1 and Ar2, the substituent is a non-substituted group, and R is the substituent in the above formula (1-21). 21 ~R 29 A compound with no substitution. Claim 4 A compound according to claim 1, wherein Ar2 is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. Claim 5 In claim 1, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzocrisenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted benzoflurenyl group, a substituted or unsubstituted dibenzoflurenyl group, a substituted A monovalent compound selected from the group consisting of an unsubstituted fluoranthenyl group, a substituted or unsubstituted benzofluranthenyl group, and a substituted or unsubstituted perylenyl group. Claim 6 A compound according to claim 1, wherein Ar2 is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted carbazolyl group. Claim 7 A compound according to claim 1, wherein Ar2 is selected from the group consisting of a substituted or unsubstituted phenyl group and a substituted or unsubstituted biphenyl group. Claim 8 In claim 1, in the above formula (1-21), R 21 ~R 24 Two adjacent atoms combine to form a substituted or unsubstituted benzene ring, and R 21 ~R 24 The other two do not form substituted or unsubstituted saturated or unsaturated rings, and also, R 25 ~R 28 A compound consisting of two or more adjacent groups that does not form a substituted or unsubstituted saturated or unsaturated ring. Claim 9 In claim 1, in the above formula (1-21), R 21 ~R 28 A compound consisting of two or more adjacent groups that does not form a substituted or unsubstituted saturated or unsaturated ring. Claim 10 A compound according to claim 1, wherein L1 and L2 are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthalenediyl group. Claim 11 A compound according to claim 1, wherein L1 and L2 are each independently substituted or unsubstituted naphthalenediyl groups. Claim 12 A compound in which n1 is 0, in claim 1. Claim 13 A compound in which n2 is 0, in claim 1. Claim 14 A compound that does not include an anthracene structure in claim 1. Claim 15 A compound according to claim 1 that, in addition to the pyrimidine backbone to which L1, L2, and L3 are bonded, does not include a nitrogen-containing six-membered ring structure or a condensation structure containing a nitrogen-containing six-membered ring backbone as a partial structure. Claim 16 In claim 1, the compound represented by the above formula (1) is a compound represented by the following formula (11). (In Equation (11), Ar1, Ar2, L3, R1 to R6, and R8 to R 11 is as defined in the above equation (1). Claim 17 In claim 1, the compound represented by the above formula (1) is a compound represented by the following formula (12). (In Equation (12), Ar1 and Ar2 are as defined in Equation (1) above.) Claim 18 In claim 1, the compound represented by the above formula (1) comprises at least one deuterium atom. Claim 19 A compound that is a material for an organic electroluminescence device, in any one of claims 1 to 18. Claim 20 An organic electroluminescence device having a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, wherein at least one layer of the organic layers comprises a compound described in any one of claims 1 to 18. Claim 21 An organic electroluminescence device according to claim 20, comprising an anode, a light-emitting layer, an electron transport band, and a cathode in this order, wherein the electron transport band comprises the compound. Claim 22 An organic electroluminescence device according to claim 21, wherein the electron transport band has a first layer and a second layer in this order from the light-emitting layer side, and the second layer comprises the compound. Claim 23 An organic electroluminescence device according to claim 22, wherein the second layer comprises one or more compounds selected from the group consisting of the above-mentioned compound, a compound comprising an alkali metal, and a compound comprising a metal belonging to Group 13 of the periodic table. Claim 24 An electronic device having an organic electroluminescence element as described in paragraph 20. Claim 25 delete Claim 26 delete Claim 27 delete Claim 28 delete Claim 29 delete Claim 30 delete Claim 31 delete Claim 32 delete Claim 33 delete Claim 34 delete Claim 35 delete Claim 36 delete Claim 37 delete Claim 38 delete

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