Organic electroluminescence devices and electronic devices

Abstract

An organic electroluminescence device (1) having an anode (3), a cathode (4), and a light-emitting layer (5), wherein the light-emitting layer (5) comprises a first compound represented by general formula (1) and a second compound with delayed fluorescence represented by general formula (2), and wherein the singlet energy S1 (M1) of the first compound and the singlet energy S1 (M2) of the second compound satisfy the relationship of the following formula (Formula 1). S1(M2)>S1(M1) … (number 1) Rings A, B, D, E, and F are each independently ring structures selected from the group consisting of a substituted or unsubstituted ring-forming aryl ring having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming complex ring having 5 to 30 atoms, and either one of rings B and D is present, or both of rings B and D are present, and either one of rings E and F is present, or both of rings E and F are present.

Description

Technology Field

[0001] The present invention relates to an organic electroluminescence device and an electronic device. Background Technology

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

[0003] Fluorescent organic EL devices that utilize light emission from singlet excitons are applied to full-color displays such as mobile phones and televisions, but their internal quantum efficiency is considered to be limited to 25%. Therefore, efforts are being made to improve the performance of organic EL devices.

[0004] For example, it is expected that organic EL devices will emit light more efficiently by using triplet excitons in addition to singlet excitons. Against this backdrop, high-efficiency fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter simply referred to as "delayed fluorescence") have been proposed and are being researched.

[0005] The TADF (Thermally Activated Delayed Fluorescence) mechanism is a mechanism that utilizes the phenomenon in which a thermal transition between a triplet exciton and a singlet exciton occurs when a material with a small energy difference (ΔST) between the singlet level and the triplet level is used. Thermally activated delayed fluorescence is described, for example, in *Chihaya Adachi (ed.), "Device Properties of Organic Semiconductors," Kodansha, published April 1, 2012, pp. 261-268.

[0006] As for compounds exhibiting heat-activated delayed fluorescence (TADF-like) (hereinafter also referred to as TADF-like compounds), for example, compounds in which a donor site and an acceptor site are combined within the molecule are known.

[0007] For example, Patent Document 1 describes an organic electroluminescence device using a TADF compound.

[0008] In addition, for example, Patent Documents 2 and 3 describe an organic electroluminescence device using a condensed ring compound containing nitrogen atoms and boron atoms. Prior art literature

[0009] Patent Document 1: International Publication No. 2018 / 181188 Patent Document 2: International Publication No. 2020 / 106032 Patent Document 3: International Publication No. 2020 / 135953 The problem to be solved

[0010] The object of the present invention is to provide an organic electroluminescence device capable of improving performance, particularly extending its lifespan, and to provide an electronic device equipped with said organic electroluminescence device. means of solving the problem

[0011] According to one embodiment of the present invention, an organic electroluminescence device is provided having an anode, a cathode, and a light-emitting layer included between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by the following general formula (1) and a second compound with delayed fluorescence represented by the following general formula (2), and wherein the singlet energy S1 (M1) of the first compound and the singlet energy S1 (M2) of the second compound satisfy the relationship of the following formula (1).

[0012] S1(M2)>S1(M1) … (number 1)

[0013] [Painting 1]

[0014]

[0015] (In the above general formula (1),

[0016] Rings A, B, D, E, and F are, respectively, independently

[0017] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0018] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0019] It is a ring structure selected from a group consisting of, and

[0020] Either ring B or ring D exists, or both ring B and ring D exist,

[0021] If both ring B and ring D are present, ring B and ring D share the bond connecting Zc and Zh, and

[0022] Either ring E or ring F exists, or both ring E and ring F exist,

[0023] If both ring E and ring F are present, ring E and ring F share the bond connecting Zf and Zi, and

[0024] Za is a nitrogen atom or a carbon atom, and

[0025] Zb is,

[0026] If ring B is present, it is a nitrogen atom or a carbon atom, and

[0027] If ring B is absent, it is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), and

[0028] Zc is a nitrogen atom or a carbon atom, and

[0029] Zd is,

[0030] If ring D is present, it is a nitrogen atom or a carbon atom, and

[0031] If ring D is absent, it is an oxygen atom, a sulfur atom, or NRd, and

[0032] Ze is,

[0033] If ring E is present, it is a nitrogen atom or a carbon atom, and

[0034] If ring E is absent, it is an oxygen atom, a sulfur atom, or NRe, and

[0035] Zf is a nitrogen atom or a carbon atom, and

[0036] Zg is,

[0037] If ring F is present, it is a nitrogen atom or a carbon atom, and

[0038] In the case where ring F is absent, it is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), and

[0039] Zh is a nitrogen atom or a carbon atom,

[0040] Zi is a nitrogen atom or a carbon atom, and

[0041] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0042] Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently hydrogen atoms or substituents, and

[0043] Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4 and Rh as substituents are, respectively, independently

[0044] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0045] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[0046] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0047] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[0048] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[0049] -O-(R 914 The one indicated by ),

[0050] -S-(R 915 The unit indicated by ), or

[0051] -N(R 916 )(R 917 It is a device indicated by ), and

[0052] However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0053] [Painting 2]

[0054]

[0055] (In the above general formula (2),

[0056] k is 1, 2, 3, 4, or 5, and

[0057] Dx is a device represented by the following general formula (21), general formula (22), or general formula (23), provided that at least one Dx is a device represented by the following general formula (22) or general formula (23).

[0058] m is 1, 2, 3, or 4, and

[0059] When m is 2, 3, or 4, multiple Dx are identical or different from each other, and

[0060] n is 0, 1, 2, or 3, and

[0061] When n is 2 or 3, multiple Rs are identical or different from each other, and

[0062] However, the sum of m and n is 2 or greater, and

[0063] R is, each independently, a halogen atom or a substituent, and

[0064] R as a substituent, each independently,

[0065] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0066] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[0067] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0068] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[0069] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[0070] -O-(R 914 The one indicated by ),

[0071] -S-(R 915 The unit indicated by ), or

[0072] -N(R 916 )(R 917 It is a device indicated by ).

[0073] [Tuesday 3]

[0074]

[0075] [Painting 4]

[0076]

[0077] [Tuesday 5]

[0078]

[0079] (R1 to R8 in the above general formula (21) are each independently a hydrogen atom, a halogen atom, or a substituent, and

[0080] R in the above general formula (22) 21 ~R 28 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 21 and R 22 of, R 22 and R 23 of, R 23 and R 24 of, R25 and R 26 of, R 26 and R 27 of, and R 27 and R 28 One or more of the groups combine with each other to form a ring,

[0081] R in the above general formula (23) 211 ~R 218 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 211 and R 212 of, R 212 and R 213 of, R 213 and R 214 of, R 215 and R 216 of, R 216 and R 217 of, and R 217 and R 218 One or more of the groups combine with each other to form a ring,

[0082] R1–R8 as substituents, R as a substituent 21 ~R 28 and R as a substituent 211 ~R 218 Each independently,

[0083] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0084] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[0085] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0086] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[0087] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[0088] -O-(R 914 The one indicated by ),

[0089] -S-(R 915 The unit indicated by ), or

[0090] -N(R 916 )(R 917 It is a device indicated by ), and

[0091] In the above general formula (22) and the above general formula (23),

[0092] Rings G, J and K are each independently selected from the group of ring structures represented by the following general formulas (24), (25) and (26), and

[0093] Rings G, J, and K condense with adjacent rings at any position, and

[0094] pa, px, and py are, independently, 1, 2, 3, or 4, and

[0095] If pa is 2, 3, or 4, the multiple rings G are identical or different from each other, and

[0096] If px is 2, 3, or 4, multiple rings J are identical or different from each other, and

[0097] If py is 2, 3, or 4, multiple rings K are identical or different from each other, and

[0098] However, at least one Dx is a group represented by the general formula (22) including any ring structure selected from the group consisting of ring structures represented by the following general formulas (25) and (26), where pa is 2, 3 or 4 and as ring G, or a group represented by the general formula (23) including any ring structure selected from the group consisting of ring structures represented by the following general formulas (25) and (26), where at least one of px and py is 2, 3 or 4 and as ring J or ring K, and

[0099] In the above general formulas (21) to (23), * indicates the bonding position with the benzene ring in the above general formula (2).

[0100] [Tuesday 6]

[0101]

[0102] (In the above general formula (24),

[0103] R 19 and R 20 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups of combine with each other to form a ring,

[0104] In the above general formula (25) and general formula (26),

[0105] X 21 and X 22 are, respectively, sulfur atom, oxygen atom, NR 220 , CR 221 R 222 or SiR 223 R 224 And,

[0106] R 220 It is silver, a hydrogen atom, a halogen atom, or a substituent, and

[0107] R 221 and R 222 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 221 and R 222 The groups of combine with each other to form a ring,

[0108] R 223 and R 224 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 223 and R 224 The groups of combine with each other to form a ring,

[0109] R as a substituent 19 , R 20 , R 220 , R 221 , R222 , R 223 and R 224 Each has the same meaning as R1–R8 as substituents, independently.)

[0110] (In the first compound and the second compound above, R 911 ~R 917 Each independently,

[0111] hydrogen atom,

[0112] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0113] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0114] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0115] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0116] R 911 If this plural exists, the plural R 911 They are identical or different from each other,

[0117] R 912 If there are multiple instances of , multiple R 912 are identical or different from each other,

[0118] R 913 If this plural exists, the plural R 913 They are identical or different from each other,

[0119] R 914 If there are multiple instances of , multiple R 914 are identical or different from each other,

[0120] R 915 If there are multiple instances of , multiple R 915 are identical or different from each other,

[0121] R 916 If this plural exists, the plural R 916 They are identical or different from each other,

[0122] R 917 If this plural exists, the plural R 917 They are identical or different from each other.

[0123] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescence element according to one aspect of the present invention described above is provided.

[0124] According to one aspect of the present invention, an organic electroluminescence element capable of improving performance, particularly extending the lifespan, and an electronic device equipped with said organic electroluminescence element can be provided. Brief explanation of the drawing

[0125] FIG. 1 is a diagram illustrating the schematic configuration of an example of an organic electroluminescence device according to a first embodiment of the present invention. Figure 2 is a schematic diagram of a device for measuring transient PL. Figure 3 is a diagram illustrating an example of the damping curve of transient PL. FIG. 4 is a diagram illustrating the relationship between the energy levels of a first compound and a second compound in an example light-emitting layer of an organic electroluminescence device according to a first embodiment of the present invention. FIG. 5 is a diagram illustrating the relationship between the energy levels and energy transfer of a first compound, a second compound, and a third compound in an example light-emitting layer of an organic electroluminescence device according to a second embodiment of the present invention. Specific details for implementing the invention

[0126] [definition]

[0127] In this specification, the term hydrogen atom includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0128] 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.

[0129] 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. Unless otherwise noted, the “ring-forming carbon number” described below 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.

[0130] In addition, when a benzene ring is substituted with, for example, an alkyl group, the number of carbon atoms of this 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, the number of carbon atoms of this 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.

[0131] 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. Unless otherwise noted, the "number of ring-forming atoms" described below shall be the same. 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 the number of atoms constituting a substituent are not included in the number of ring-forming atoms of a pyridine ring. For this reason, the number of ring-forming atoms of a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Also, for example, hydrogen atoms or atoms constituting substituents bonded to carbon atoms of a quinazoline ring are not included in the number of ring-forming atoms of the quinazoline ring. For this reason, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0132] In the present specification, “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having carbon number XX to YY” indicates the number of carbons when the ZZ group is unsubstituted and does not include the number of carbons 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.

[0133] In the present specification, the expression “ZZ group having XX to YY number of substituted or unsubstituted atoms” indicates 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.

[0134] 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."

[0135] In this specification, when referring to a "substituted or unsubstituted ZZ group," "unsubstituted" 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.

[0136] 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.

[0137] "Substituents described in this specification"

[0138] The substituents described in this specification will be explained below.

[0139] 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.

[0140] The number of ring-forming atoms of the “unsubstituted complex ring” described in this specification is 5 to 50 unless otherwise specified in this specification, preferably 5 to 30, more preferably 5 to 18.

[0141] 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.

[0142] 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.

[0143] 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.

[0144] The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described in this specification is 3 to 50 unless otherwise specified in this specification, preferably 3 to 20, more preferably 3 to 6.

[0145] 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.

[0146] The number of ring-forming atoms of the “unsubstituted divalent complex circulator” described in this specification is 5 to 50 unless otherwise specified in this specification, preferably 5 to 30, more preferably 5 to 18.

[0147] 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.

[0148] · "Substitution or non-substitution aryl"

[0149] 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.”

[0150] "Substituted aryl group" refers to 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.

[0151] ·Muchan's Arilgi (Special Example Group G1A):

[0152] phenyl group,

[0153] p-biphenyl group,

[0154] m-biphenyl group,

[0155] o-biphenyl group,

[0156] p-terphenyl-4-diary,

[0157] p-terphenyl-3-diary,

[0158] p-terphenyl-2-diary,

[0159] m-terphenyl-4-diary,

[0160] m-terphenyl-3-diary,

[0161] m-terphenyl-2-diary,

[0162] o-terphenyl-4-diary,

[0163] o-terphenyl-3-diary,

[0164] o-terphenyl-2-diyl,

[0165] 1-Naphthyl group,

[0166] 2-Naphthyl group,

[0167] Anthrill,

[0168] Benzoanthryl group,

[0169] phenanthril group,

[0170] Benzophenanthrile group,

[0171] Penalenyl group,

[0172] Pyreneyl group,

[0173] Crysenyl group,

[0174] benzocrysenyl group,

[0175] triphenylenyl group,

[0176] benzotriphenylenyl group,

[0177] tetracenyl group,

[0178] Pentacenyl group,

[0179] Fluorenyl group,

[0180] 9,9'-spirobifluorenyl group,

[0181] benzofluorenyl group,

[0182] dibenzofluorenyl group,

[0183] Fluoranthenyl group,

[0184] benzofluranthenyl group,

[0185] perylenyl group, and

[0186] 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).

[0187] [Tuesday 7]

[0188]

[0189] [Tue 8]

[0190]

[0191] · Substitution Aryl group (Specific example group G1B):

[0192] o-tollil group,

[0193] m-tolyl group,

[0194] p-tolyl group,

[0195] Para-xyl group,

[0196] meta-xylyl group,

[0197] Ortho-xyl group,

[0198] para-isopropylphenyl group,

[0199] meta-isopropylphenyl group,

[0200] Ortho-isopropylphenyl group,

[0201] para-t-butylphenyl group,

[0202] meta-t-butylphenyl group,

[0203] Ortho-t-butylphenyl group,

[0204] 3,4,5-trimethylphenyl group,

[0205] 9,9-dimethylfluorenyl group,

[0206] 9,9-diphenylfluorenyl group

[0207] 9,9-bis(4-methylphenyl)fluorenyl group,

[0208] 9,9-bis(4-isopropylphenyl)fluorenyl group,

[0209] 9,9-bis(4-t-butylphenyl)fluorenyl group,

[0210] cyanophenyl group,

[0211] triphenylsilylphenyl group,

[0212] trimethylsilylphenyl group,

[0213] phenylnaphthyl group,

[0214] Naphthylphenyl group, and

[0215] 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.

[0216] · "Substitutional or Non-substitutional Complex Recall"

[0217] The “complex circulating group” described in this specification is a cyclic group comprising at least one heteroatom in a ring-forming atom. Specific examples of heteroatoms include nitrogen atoms, oxygen atoms, sulfur atoms, silicon atoms, phosphorus atoms, and boron atoms.

[0218] The “complex ring” described in this specification is a simple ring or a condensed ring.

[0219] The “complex generator” described in this specification is an aromatic complex generator or a non-aromatic complex generator.

[0220] 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.”

[0221] "Substituted complex group" refers to a group in which one or more hydrogen atoms of an "unsubstituted complex group" are substituted with substituents. Specific examples of a "substituted complex group" include a group in which a hydrogen atom of an "unsubstituted complex group" of the following group of examples G2A is substituted, and an example of a substituted complex group of the following group of examples G2B. Furthermore, the examples of "unsubstituted complex groups" and "substituted complex groups" listed herein are merely examples, and the "substituted complex group" described in this specification includes a group in which a hydrogen atom bonded to the ring-forming atom of the complex group itself in the "substituted complex group" 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 group" of the following group of examples G2B is further substituted with a substituent.

[0222] 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 removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33).

[0223] 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 are substituted as substituents among monovalent complex groups derived from ring structures represented by the following general formulas (TEMP-16) to (TEMP-33).

[0224] · Unsubstituted complex saturators containing nitrogen atoms (Specific example group G2A1):

[0225] pyrrolyl group,

[0226] Imidajorilgi,

[0227] pyrazolyl group,

[0228] triazolyl group,

[0229] tetrazolyl group,

[0230] Oxazoligi,

[0231] Isooxazolilgi,

[0232] Oxadiazolyl group,

[0233] Thiazolyl group,

[0234] isothiazolyl group,

[0235] Thiadiazolylgi,

[0236] Piridilgi,

[0237] Piridajinilgi,

[0238] pyrimidinyl group,

[0239] Pyrazinyl group,

[0240] triazinyl group,

[0241] Indolil,

[0242] Isoindolilgi,

[0243] Indolezinyl group,

[0244] Quinolidinyl group,

[0245] Quinolyl group,

[0246] isoquinolyl group,

[0247] Sinnolilgi,

[0248] Phthalaginyl group,

[0249] Quinazolinyl group,

[0250] Quinoxalinyl group,

[0251] benzimidazolyl group,

[0252] Indazolillgi,

[0253] phenanthrolinyl group,

[0254] phenanthridinyl group,

[0255] Acridinyl group,

[0256] phenazinyl group,

[0257] Carbazolyl group,

[0258] benzocarbazolyl group,

[0259] Morpolinogi,

[0260] phenoxazinyl group,

[0261] Phenothiazinyl group,

[0262] Azacarbazolyl group, and diazcarbazolyl group.

[0263] · Unsubstituted complex circulators containing oxygen atoms (specific example group G2A2):

[0264] Purilgi,

[0265] Oxazoligi,

[0266] Isooxazolilgi,

[0267] Oxadiazolyl group,

[0268] xanthenyl group,

[0269] benzofuranyl group,

[0270] isobenzofuranyl group,

[0271] dibenzofuranyl group,

[0272] Naphthobenzofuranyl group,

[0273] Benzooxazolyl group,

[0274] Benzoisooxazolyl group,

[0275] phenoxazinyl group,

[0276] Morpolinogi,

[0277] dinaphthofranyl group,

[0278] Azadibenzofuranyl group,

[0279] Diazadibenzofuranyl group,

[0280] Azanaptobenzofuranyl group, and

[0281] Diazanaptobenzofuranyl group.

[0282] · Unsubstitutable complex circulators containing sulfur atoms (Specific example group G2A3):

[0283] thienyl group,

[0284] Thiazolyl group,

[0285] isothiazolyl group,

[0286] Thiadiazolylgi,

[0287] benzothiophenyl group (benzothienyl group),

[0288] isobenzothiophenyl group (isobenzothienyl group),

[0289] dibenzothiophenyl group (dibenzothienyl group),

[0290] Naphthobenzothiophenyl group (naphthobenzothienyl group),

[0291] benzothiazolyl group,

[0292] Benzoisothiazolyl group,

[0293] Phenothiazinyl group,

[0294] dinaphthothiophenyl group (dinaphthienyl group),

[0295] Azadibenzothiophenyl group (azadibenzothienyl group),

[0296] Diazadibenzothiophenyl group (diazadibenzothienyl group),

[0297] Azanapthobenzothiophenyl group (azanaphthobenzothienyl group), and

[0298] Diazanaptobenzothiophenyl group (diazanaptobenzothienyl group).

[0299] · A monovalent complex circulator induced by removing one hydrogen atom from a ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

[0300] [Tue 9]

[0301]

[0302] [Tuesday 10]

[0303]

[0304] 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 AAt least one of them is an oxygen atom, a sulfur atom, or NH.

[0305] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A In cases where at least one of them is NH or CH2, the monovalent complex circulating group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

[0306] · Substitutional complex vacancies containing nitrogen atoms (Specific example group G2B1):

[0307] (9-phenyl)carbazolyl group,

[0308] (9-biphenylyl)carbazolyl group,

[0309] (9-phenyl)phenylcarbazolyl group,

[0310] (9-naphthyl)carbazolyl group,

[0311] Diphenylcarbazole-9-diary,

[0312] Phenylcarbazole-9-diary,

[0313] methylbenzimidazolyl group,

[0314] Ethylbenzimidazolyl group,

[0315] phenyltriazinyl group,

[0316] biphenyltriazinyl group,

[0317] diphenyltriazinyl group,

[0318] Phenylquinazolinyl group, and biphenylquinazolinyl group.

[0319] · Substitutional complex mutators containing oxygen atoms (Specific example group G2B2):

[0320] Phenyldibenzofuranyl group,

[0321] methyldibenzofuranyl group,

[0322] t-butyldibenzofuranyl group, and

[0323] The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

[0324] · Complex substitutions containing sulfur atoms (Specific example group G2B3):

[0325] Phenyldibenzothiophenyl group,

[0326] methyldibenzothiophenyl group,

[0327] t-butyldibenzothiophenyl group, and

[0328] A monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

[0329] · 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):

[0330] The above "one or more hydrogen atoms of a monovalent complex group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent complex group, X A and Y A A hydrogen atom bonded to a nitrogen atom in the case where at least one of them is NH, and X A and Y A It means one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of them is CH2.

[0331] · Substituted or unsubstituted alkyl group

[0332] 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.

[0333] "Substituted alkyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkyl group" are substituted with substituents. Specific examples of "substituted alkyl group" include a group in which one or more hydrogen atoms of an "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.

[0334] · Unsubstituted alkyl group (Specific Example Group G3A):

[0335] methyl group,

[0336] ethyl group,

[0337] n-Profilter,

[0338] isopropyl group,

[0339] n-butyl group,

[0340] isobutyl group,

[0341] s-butyl group, and

[0342] t-butyl group.

[0343] · Substituted alkyl group (Specific Example Group G3B):

[0344] heptafluoropropyl group (including isomers),

[0345] pentafluoroethyl group,

[0346] 2,2,2-trifluoroethyl group, and

[0347] Trifluoromethyl group.

[0348] · "Substituted or unsubstituted alkenyl group"

[0349] 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.”

[0350] "Substituted alkenyl group" refers to a group in which one or more hydrogen atoms of 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.

[0351] · Non-substitutional alkenyl group (Special Example Group G4A):

[0352] vinyl,

[0353] Alilgi,

[0354] 1-butenyl group,

[0355] 2-butenyl group, and

[0356] 3-butenyl group.

[0357] · Substitutional alkenyl group (Specific example group G4B):

[0358] 1,3-butanedienyl group,

[0359] 1-methylvinyl group,

[0360] 1-methylallyl group,

[0361] 1,1-dimethylallyl group,

[0362] 2-methylallyl group, and

[0363] 1,2-dimethylallyl group.

[0364] · "Substituted or unsubstituted alkynyl group"

[0365] 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.

[0366] "Substituted alkynyl group" means a group in which one or more hydrogen atoms of an "unsubstituted alkynyl group" are substituted with substituents. Specific examples of "substituted alkynyl group" include a group in which one or more hydrogen atoms of an "unsubstituted alkynyl group" (specific example group G5A) are substituted with substituents.

[0367] · Unsubstituted alkynyl group (Specific example group G5A):

[0368] Ethinyl group.

[0369] · Substituted or unsubstituted cycloalkyl group

[0370] Specific examples of the “substituted or unsubstituted cycloalkyl group” described in this specification (Specific Example Group G6) include the following unsubstituted cycloalkyl group (Specific Example Group G6A) and substituted cycloalkyl group (Specific Example Group 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.”

[0371] "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.

[0372] · Unsubstituted cycloalkyl group (Specific Example Group G6A):

[0373] cyclopropyl group,

[0374] cyclobutyl group,

[0375] Cyclopentyl group,

[0376] cyclohexyl group,

[0377] 1-adamantyl group,

[0378] 2-adamantyl group,

[0379] 1-norbornyl group, and

[0380] 2-Norbornilgi.

[0381] · Substituted cycloalkyl group (Specific Example Group G6B):

[0382] 4-methylcyclohexyl group.

[0383] ·「-Si(R 901 )(R 902 )(R 903 The device indicated by )

[0384] -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),

[0385] -Si(G1)(G1)(G1),

[0386] -Si(G1)(G2)(G2),

[0387] -Si(G1)(G1)(G2),

[0388] -Si(G2)(G2)(G2),

[0389] -Si(G3)(G3)(G3), and

[0390] -Si(G6)(G6)(G6)

[0391] ...can be cited. Here,

[0392] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0393] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0394] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0395] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0396] In -Si(G1)(G1)(G1), multiple G1s are either identical or different from each other.

[0397] In -Si(G1)(G2)(G2), multiple G2s are either identical or different from each other.

[0398] In -Si(G1)(G1)(G2), multiple G1s are either identical or different from each other.

[0399] In -Si(G2)(G2)(G2), multiple G2s are either identical or different from each other.

[0400] In -Si(G3)(G3)(G3), multiple G3s are either identical or different from each other.

[0401] In -Si(G6)(G6)(G6), multiple G6s are either identical or different from each other.

[0402] ·「-O-(R 904 The unit indicated by )

[0403] -O-(R as described in this specification 904 As for a specific example of the device indicated by ) (specific example group G8),

[0404] -O(G1),

[0405] -O(G2),

[0406] -O(G3), and

[0407] -O(G6)

[0408] ...can be cited.

[0409] Here,

[0410] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0411] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0412] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0413] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0414] ·「-S-(R 905 The unit indicated by )

[0415] -S-(R as described in this specification 905 As for a specific example of the device indicated by ) (specific example group G9),

[0416] -S(G1),

[0417] -S(G2),

[0418] -S(G3), and

[0419] -S(G6)

[0420] ...can be cited.

[0421] Here,

[0422] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0423] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0424] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0425] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0426] ·「-N(R 906 )(R 907 The unit indicated by )

[0427] -N(R as described in this specification 906 )(R 907 As for a specific example of the device indicated by ) (specific example group G10),

[0428] -N(G1)(G1),

[0429] -N(G2)(G2),

[0430] -N(G1)(G2),

[0431] -N(G3)(G3), and

[0432] -N(G6)(G6)

[0433] ...can be cited.

[0434] Here,

[0435] G1 is a “substituted or non-substituted aryl group” as described in Specific Example Group G1.

[0436] G2 is a "complex circulator of permutation or non-permutation" described in the specific example group G2.

[0437] G3 is a “substituted or unsubstituted alkyl group” as described in Specific Example Group G3.

[0438] G6 is a "substituted or unsubstituted cycloalkyl group" as described in Specific Example Group G6.

[0439] In -N(G1)(G1), multiple G1s are either identical or different from each other.

[0440] In -N(G2)(G2), multiple G2s are either identical or different from each other.

[0441] In -N(G3)(G3), multiple G3s are either identical or different from each other.

[0442] In -N(G6)(G6), multiple G6s are either identical or different from each other.

[0443] · "Halogen atom"

[0444] Specific examples of the “halogen atoms” described in this specification (Specific example group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0445] · "Substituted or unsubstituted fluoroalkyl group"

[0446] The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is 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 in the "substituted or unsubstituted alkyl group" are substituted with fluorine atoms. Unless otherwise specified in this specification, the number of carbon atoms in 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.

[0447] · "Substituted or unsubstituted haloalkyl group"

[0448] The "substituted or unsubstituted haloalkyl group" described in this specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is substituted with a halogen atom, and also includes a group in which all hydrogen atoms bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" are substituted with halogen atoms. Unless otherwise specified in this specification, the number of carbon atoms in 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. Furthermore, the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl group" are further substituted with a substituent, and a group in which one or more hydrogen atoms of a 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 halogen atoms. A haloalkyl group is sometimes referred to as an alkyl halide group.

[0449] · "Substitutional or non-substitutional alkoxyl group"

[0450] A specific example of the “substituted or unsubstituted alkoxy group” described in this specification is a group represented by -O(G3), where 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.

[0451] · "Substituted or unsubstituted alkylthio groups"

[0452] A specific example of the “substituted or unsubstituted alkylthio group” described in this specification is a group represented by -S(G3), where G3 is the “substituted or unsubstituted alkyl group” described in the group of specific examples G3. The number of carbon atoms of the “unsubstituted alkylthio group” is 1 to 50 unless otherwise specified in this specification, preferably 1 to 30, and more preferably 1 to 18.

[0453] · "Substituted or unsubstituted aryloxy groups"

[0454] A specific example of the “substituted or unsubstituted aryloxy group” described in this specification is a group represented by -O(G1), where 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.

[0455] · "Substitution or non-substitution arylthioge"

[0456] A specific example of the “substituted or unsubstituted arylthio group” described in this specification is a group represented by -S(G1), where 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.

[0457] · Substituted or unsubstituted trialkylsilyl group

[0458] A specific example of the “trialkylsilyl group” described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a “substituted or unsubstituted alkyl group” described in the group of specific examples G3. The plurality of G3s in -Si(G3)(G3)(G3) may be identical or different from each other. Unless otherwise specified in this specification, the number of carbon atoms in each alkyl group of the “trialkylsilyl group” is 1 to 50, preferably 1 to 20, and more preferably 1 to 6.

[0459] · "Substitution or non-substitution Aralkilgi"

[0460] 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 unless otherwise specified in this specification, preferably 7 to 30, and more preferably 7 to 18.

[0461] 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.

[0462] 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.

[0463] The substituted or unsubstituted complex groups described herein, unless otherwise specified herein, 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.

[0464] In this specification, the carbazolyl group is, specifically, any one of the following, unless otherwise specified in this specification.

[0465] [Tuesday 11]

[0466]

[0467] In this specification, the (9-phenyl)carbazolyl group is, specifically, any one of the following groups, unless otherwise specified in this specification.

[0468] [Tuesday 12]

[0469]

[0470] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * indicates the bonding position.

[0471] In this specification, the dibenzofuranyl group and the dibenzothiophenyl group are, specifically, any one of the following groups, unless otherwise specified in this specification.

[0472] [Tuesday 13]

[0473]

[0474] In the above general formulas (TEMP-34) to (TEMP-41), * indicates the bonding position.

[0475] 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.

[0476] · "Substitutional or non-substitutional arylen groups"

[0477] 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.

[0478] · "Divination of Substitution or Non-Substitution of a Bivalent Complex Call"

[0479] The “substituted or unsubstituted divalent complex ring” described in this specification is, unless otherwise noted, a divalent ring derived by removing 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 removing one hydrogen atom from the “substituted or unsubstituted complex ring” described in Specific Example Group G2.

[0480] · "Substituted or unsubstituted alkylene group"

[0481] 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.

[0482] 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).

[0483] [Tuesday 14]

[0484]

[0485] [Tuesday 15]

[0486]

[0487] Among the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0488] In the above general formulas (TEMP-42) to (TEMP-52), * indicates the bonding position.

[0489] [Tuesday 16]

[0490]

[0491] Among the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each is independently a hydrogen atom or a substituent.

[0492] Formula Q9 and Q 10 They may also join together through single bonds to form a ring.

[0493] In the above general formulas (TEMP-53) to (TEMP-62), * indicates the bonding position.

[0494] [Tuesday 17]

[0495]

[0496] In the above general formulas (TEMP-63) to (TEMP-68), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0497] In the above general formulas (TEMP-63) to (TEMP-68), * indicates the bonding position.

[0498] 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.

[0499] [Tuesday 18]

[0500]

[0501] [Tue 19]

[0502]

[0503] [Tue 20]

[0504]

[0505] In the above general formulas (TEMP-69) to (TEMP-82), Q1 to Q9 are each independently hydrogen atoms or substituents.

[0506] [Tue 21]

[0507]

[0508] [Tue 22]

[0509]

[0510] [Tue 23]

[0511]

[0512] [Tue 24]

[0513]

[0514] In the above general formulas (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently hydrogen atoms or substituents.

[0515] The above is an explanation of the “substituents described in this specification.”

[0516] · "When combined to form a ring"

[0517] In the present specification, the phrase “one or more of two or more adjacent groups combine to form a substituted or non-substituted 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 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.”

[0518] The following describes the cases in this specification where "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 "combining to form a ring"). The description is given by way of example by an anthracene compound represented by the following general formula (TEMP-103), in which the matrix is ​​an anthracene ring.

[0519] [Tue 25]

[0520]

[0521] 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 that make up one set are R 921 and R922 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, R 926 and R 927 of, R 927 and R 928 of, R 928 and R 929 The group of, and R 929 and R 921 It is the group of.

[0522] The above "one or more sets" means that two or more sets of the above 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).

[0523] [Tue 26]

[0524]

[0525] The case where "a group consisting of two or more adjacent units" forms a ring includes not only the case where a group consisting of "two" adjacent units combines as in the example above, but also the case 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 (R921 , R 922 and R 923 This refers to the case where groups composed 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 R 922 Share.

[0526] [Tue 27]

[0527]

[0528] 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 α is a benzene ring, then ring Q A is a single ring. The ring Q of the above general formula (TMEP-104) A If is a naphthalene ring, then ring Q A is a condensed ring.

[0529] "Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic complex ring. "Saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic complex ring.

[0530] As a specific example of an aromatic hydrocarbon ring, a structure in which the group given as a specific example in specific example group G1 is terminated by a hydrogen atom can be cited.

[0531] As a specific example of an aromatic complex ring, a structure in which an aromatic complex ring group is terminated by a hydrogen atom can be cited as a specific example in the specific example group G2.

[0532] As a specific example of an aliphatic hydrocarbon ring, a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom can be cited.

[0533] "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 additional arbitrary elements. 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 elements. 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.

[0534] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, unless otherwise specified in this specification. In any element (e.g., in the case of a carbon or nitrogen element), bonds that do not form a ring may be terminated by a hydrogen atom or the like, or substituted by an "any substituent" described below. When any element other than a carbon element is included, the ring formed is a complex ring.

[0535] Unless otherwise specified in this specification, “one or more of any elements” 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.

[0536] Unless otherwise specified in this specification, among "single ring" and "condensed ring," it is preferably "single ring".

[0537] Unless otherwise specified in this specification, among "saturated ring" and "unsaturated ring," it is preferably "unsaturated ring."

[0538] Unless otherwise stated in this specification, "single ring" is preferably a benzene ring.

[0539] Unless otherwise specified in this specification, the “unsaturated ring” is preferably a benzene ring.

[0540] In cases 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” composed of a plurality of atoms of the matrix and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

[0541] In the case where the above "single 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 "single ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."

[0542] In the case where the above "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 "mono-ring" or "condensed ring" has a substituent are the substituents described in the aforementioned section "Substituents described in this specification."

[0543] The above is an explanation of 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).

[0544] · Substituents in the case of "substituent or non-substituent"

[0545] In one embodiment of this specification, the substituent in the case of "substituted or non-substituted" (which may be referred to as "optional substituent" in this specification) is, for example

[0546] Unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0547] Unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0548] Unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0549] Unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0550] -Si(R 901 )(R 902 )(R 903 ),

[0551] -O-(R 904 ),

[0552] -S-(R 905 ),

[0553] -N(R 906 )(R 907 ),

[0554] Halogen atom, cyano group, nitro group,

[0555] An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, and

[0556] Unsubstituted complex circulators with 5 to 50 ring-forming atoms

[0557] It is a device selected from a group consisting of, and

[0558] Here, R 901 ~R 907 Each independently

[0559] hydrogen atom,

[0560] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0561] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0562] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0563] It is a complex circulator with 5 to 50 atoms forming a ring, either substituent or unsubstituent.

[0564] R 901 If there are 2 or more of these, 2 or more R 901 They are identical or different from each other,

[0565] R 902 If there are 2 or more, 2 or more R 902 are identical or different from each other,

[0566] R 903 If there are 2 or more of these, 2 or more R 903 They are identical or different from each other,

[0567] R 904 If there are 2 or more, 2 or more R 904are identical or different from each other,

[0568] R 905 If there are 2 or more, 2 or more R 905 are identical or different from each other,

[0569] R 906 If there are 2 or more of these, 2 or more R 906 They are identical or different from each other,

[0570] R 907 If there are 2 or more of these, 2 or more R 907 They are identical or different from each other.

[0571] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0572] alkyl group having 1 to 50 carbon atoms,

[0573] A ring-forming aryl group having 6 to 50 carbon atoms, and

[0574] Complex circulators with 5 to 50 ring-forming atoms

[0575] It is a group selected from a group consisting of

[0576] In one embodiment, the substituent in the case of "substituted or non-substituted" is,

[0577] alkyl group having 1 to 18 carbon atoms,

[0578] A ring-forming aryl group having 6 to 18 carbon atoms, and

[0579] Complex circulators with 5 to 18 ring-forming atoms

[0580] It is a group selected from a group consisting of

[0581] The specific examples of each of the above arbitrary substituents are specific examples of substituents described in the aforementioned section “Substituents described in this specification”.

[0582] Unless otherwise specified in this specification, any adjacent substituents may form a “saturated ring” or an “unsaturated ring,” preferably forming a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably forming a benzene ring.

[0583] Unless otherwise stated in this specification, any substituent may have additional substituents. The additional substituents of any substituent are identical to the said arbitrary substituent.

[0584] 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.

[0585] [First Embodiment]

[0586] The configuration of an organic EL device according to the first embodiment of the present invention will be described.

[0587] An organic EL device comprises an organic layer between two electrodes, a positive electrode and a negative electrode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer may be formed by stacking multiple layers composed of organic compounds. The organic layer may further include an inorganic compound. In the organic EL device of the present embodiment, at least one of the organic layers is a light-emitting layer. Accordingly, the organic layer may, for example, be composed of a single light-emitting layer, or may include a layer that can be employed in the organic EL device. The layer that can be employed in the organic EL device is not particularly limited, but may include, for example, at least any layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer.

[0588] An organic EL device according to the present embodiment has an anode, a cathode, and a light-emitting layer included between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by the following general formula (1) and a second compound with delayed fluorescence represented by the following general formula (2), and the singlet energy S1 (M1) of the first compound and the singlet energy S1 (M2) of the second compound satisfy the relationship of the following formula (Formula 1).

[0589] S1(M2)>S1(M1) … (number 1)

[0590] By combining a first compound represented by general formula (1) and a second compound with delayed fluorescence represented by general formula (2), recombination in the first compound is reduced and the probability of exciton generation in the second compound is improved. As a result, the degradation of the first compound can be suppressed, thereby enabling the realization of a device with a long lifespan. In addition, in one embodiment of the organic EL device of the present embodiment, the luminous efficiency is improved.

[0591] FIG. 1 illustrates a schematic configuration of an example of an organic EL element in the present embodiment.

[0592] An organic EL device (1) comprises a transparent substrate (2), an anode (3), a cathode (4), and an organic layer (10) disposed between the anode (3) and the cathode (4). The organic layer (10) is configured such that, starting from the anode (3) side, a hole injection layer (6), a hole transport layer (7), a light-emitting layer (5), an electron transport layer (8), and an electron injection layer (9) are stacked in this order. The present invention is not limited to an organic EL device with the configuration shown in FIG. 1.

[0593] <Luminous layer>

[0594] In the organic EL device of the present embodiment, the light-emitting layer comprises a first compound and a second compound. In this embodiment, the first compound is preferably a dopant material (which may also be referred to as a guest material, emitter, or light-emitting material), and the second compound is preferably a host material (which may also be referred to as a matrix material).

[0595] In one aspect of the present embodiment, the light-emitting layer may include a metal complex.

[0596] In addition, in one aspect of the present embodiment, it is preferable that the light-emitting layer does not include a phosphorescent light-emitting material (a phosphorescent light-emitting dopant material).

[0597] In addition, in one aspect of the present embodiment, it is preferable that the light-emitting layer does not include a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0598] In addition, in one aspect of the present embodiment, it is also preferable that the light-emitting layer does not include a metal complex.

[0599] (1st compound)

[0600] The first compound is represented by the following general formula (1).

[0601] [Tue 28]

[0602]

[0603] (In the above general formula (1),

[0604] Rings A, B, D, E, and F are, respectively, independently

[0605] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0606] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0607] It is a ring structure selected from a group consisting of, and

[0608] Either ring B or ring D exists, or both ring B and ring D exist,

[0609] If both ring B and ring D are present, ring B and ring D share the bond connecting Zc and Zh, and

[0610] Either ring E or ring F exists, or both ring E and ring F exist,

[0611] If both ring E and ring F are present, ring E and ring F share the bond connecting Zf and Zi, and

[0612] Za is a nitrogen atom or a carbon atom, and

[0613] Zb is,

[0614] If ring B is present, it is a nitrogen atom or a carbon atom, and

[0615] If ring B is absent, it is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), and

[0616] Zc is a nitrogen atom or a carbon atom, and

[0617] Zd is,

[0618] If ring D is present, it is a nitrogen atom or a carbon atom, and

[0619] If ring D is absent, it is an oxygen atom, a sulfur atom, or NRd, and

[0620] Ze is,

[0621] If ring E is present, it is a nitrogen atom or a carbon atom, and

[0622] If ring E is absent, it is an oxygen atom, a sulfur atom, or NRe, and

[0623] Zf is a nitrogen atom or a carbon atom, and

[0624] Zg is,

[0625] If ring F is present, it is a nitrogen atom or a carbon atom, and

[0626] In the case where ring F is absent, it is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), and

[0627] Zh is a nitrogen atom or a carbon atom,

[0628] Zi is a nitrogen atom or a carbon atom, and

[0629] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0630] Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently hydrogen atoms or substituents, and

[0631] Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4 and Rh as substituents are, respectively, independently

[0632] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0633] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[0634] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0635] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[0636] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[0637] -O-(R 914 The one indicated by ),

[0638] -S-(R 915 The unit indicated by ), or

[0639] -N(R 916 )(R 917It is a device indicated by ), and

[0640] However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0641] The bonds between Y and Za, Y and Zd, and Y and Ze are all single bonds, and these single bonds are covalent bonds and not coordinate bonds.

[0642] In this specification, complex rings may be, for example, ring structures (complex rings) excluding bonding hands from the “complex rings” exemplified in the aforementioned “substituents described in this specification.” These complex rings may have substituents or may be unsubstituents.

[0643] In this specification, an aryl ring may be, for example, a ring structure (aryl ring) excluding bonding members from an "aryl group" exemplified in the aforementioned "substituents described in this specification." These aryl rings may have substituents or may be unsubstituted.

[0644] In the above general formula (1), it is also preferable that both ring B and ring D are present, and both ring E and ring F are present. In this case, the compound of the above general formula (1) is represented by the following general formula (1-1).

[0645] [Tue 29]

[0646]

[0647] (In the above general formula (1-1),

[0648] Rings A, B, D, E, and F are, respectively, independently

[0649] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0650] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0651] It is a ring structure selected from a group consisting of, and

[0652] Rings B and D share the bond connecting Zc and Zh, and

[0653] Rings E and F share the bond connecting Zf and Zi, and

[0654] Za, Zb, Zc, Zd, Ze, Zf, Zg, Zh, and Zi are each independently nitrogen atoms or carbon atoms, and

[0655] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0656] However, the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds.

[0657] In the general formula of the first compound, it is preferable that Y be a boron atom.

[0658] It is preferable that Zb and Zg in the general formula of the first compound are nitrogen atoms.

[0659] In the present embodiment, it is preferable that Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming complex circulatory group having 5 to 30 atoms.

[0660] In the present embodiment, it is preferable that Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently hydrogen atoms or substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms.

[0661] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (11).

[0662] [Tue 30]

[0663]

[0664] (In the above general formula (11),

[0665] Rings A, D, and E, each independently,

[0666] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0667] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0668] It is a ring structure selected from a group consisting of, and

[0669] Za is a nitrogen atom or a carbon atom, and

[0670] Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), and

[0671] Zc is a nitrogen atom or a carbon atom, and

[0672] Zd is a nitrogen atom or a carbon atom, and

[0673] Ze is a nitrogen atom or a carbon atom, and

[0674] Zf is a nitrogen atom or a carbon atom, and

[0675] Zg is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), and

[0676] Zh is a nitrogen atom or a carbon atom,

[0677] Zi is a nitrogen atom or a carbon atom, and

[0678] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0679] Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh are each independently identical in meaning to Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh in the above general formula (1).

[0680] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (12).

[0681] [Tue 31]

[0682]

[0683] (In the above general formula (12),

[0684] Rings A, D, and E, each independently,

[0685] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0686] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0687] It is a ring structure selected from a group consisting of, and

[0688] Za, Zc, Zd, Ze, Zf, Zh, and Zi are each independently nitrogen atoms or carbon atoms, and

[0689] Rb and Rg are each independently identical in meaning to Rb and Rg in the above general formula (1).

[0690] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (13).

[0691] [Tue 32]

[0692]

[0693] (In the above general formula (13),

[0694] Zb is an oxygen atom, a sulfur atom, or NRb, and

[0695] Zg is an oxygen atom, a sulfur atom, or NRg, and

[0696] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0697] Rb, Rg, and Rh each have the same meaning as Rb, Rg, and Rh in the above general formula (1), independently.

[0698] R 101 ~R 111 Each is independently a hydrogen atom or a substituent, and

[0699] R as a substituent 101 ~R 111 Each independently,

[0700] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0701] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[0702] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0703] Substituted or unsubstituted haloalkyl groups having 1 to 30 carbon atoms,

[0704] Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms,

[0705] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[0706] -N(R 906 )(R 907 The one indicated by ),

[0707] Cyanogi, and

[0708] Halogen atoms

[0709] It is a group selected from the group consisting of, and

[0710] In the first compound, R 901 , R 902 , R 903 , R 906 and R 907 Each is 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 heterocyclic group with 5–50 atoms.

[0711] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (14).

[0712] [Tue 33]

[0713]

[0714] (In the above general formula (14),

[0715] R 101 ~R 111 Each independently, R in the above general formula (13) 101 ~R 111 It has the same meaning as,

[0716] Rb and Rg are each independently identical in meaning to Rb and Rg in the above general formula (1).

[0717] In the above general formulas (12) to (14), Rb and Rg are each preferably independently a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and more preferably a substituted or unsubstituted phenyl group.

[0718] In the first compound, R 101 ~R 111 Each independently,

[0719] hydrogen atom,

[0720] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0721] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[0722] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0723] In the first compound, R 101 ~R 111 Each independently,

[0724] hydrogen atoms, or

[0725] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0726] In the first compound, R 101 ~R 111 It is preferable that it be a hydrogen atom.

[0727] In the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (15).

[0728] [Tue 34]

[0729]

[0730] (In the above general formula (15),

[0731] Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), and

[0732] X1 is, CR 121 This, or a nitrogen atom, or X 12 It is a carbon atom bonded to by a single bond, and

[0733] X2 is, CR 122 Or it is a nitrogen atom,

[0734] X3 is CR 123 Or it is a nitrogen atom,

[0735] X4 is CR 124 Or it is a nitrogen atom,

[0736] X5 is CR 125 Or it is a nitrogen atom,

[0737] X6 is CR 126 Or it is a nitrogen atom,

[0738] X7 is CR 127 Or it is a nitrogen atom,

[0739] X8 is CR 128 Or it is a nitrogen atom,

[0740] X9 is CR 129 Or it is a nitrogen atom,

[0741] X 10 silver, CR 130 Or it is a nitrogen atom,

[0742] X11 silver, CR 131 Or it is a nitrogen atom,

[0743] X 12 is, CR 132 It is either a nitrogen atom, or a carbon atom bonded to X1 by a single bond, and

[0744] Q is, CR Q Or it is a nitrogen atom,

[0745] R 122 ~R 131 One or more of the groups consisting of two or more adjacent groups,

[0746] They combine with each other to form a substituted or unsubstituted ring,

[0747] They combine with each other to form substituted or unsubstituted condensed rings, or

[0748] Without combining with each other,

[0749] R 124 , R 125 One or more sets consisting of two or more adjacent elements among , Rb, Rb1, Rb2, Rb3, and Rb4,

[0750] They combine with each other to form a substituted or unsubstituted ring,

[0751] They combine with each other to form substituted or unsubstituted condensed rings, or

[0752] Without combining with each other,

[0753] R 124 , R 125 At least one hydrogen in a monocyclic or condensed ring formed by the bonding of one or more sets of two or more adjacent groups among Rb, Rb1, Rb2, Rb3, and Rb4 is,

[0754] alkyl group having 1 to 50 carbon atoms,

[0755] Ring-forming aryl group having 6 to 50 carbon atoms,

[0756] Complex circulators with 5 to 50 ring-forming atoms,

[0757] -O-(R 151 The unit indicated by ), and

[0758] -N(R 152 )(R 153 It is substituted with or not substituted by at least one substituent selected from the group consisting of the group represented by ). and at least one hydrogen in the substituent is substituted with or not substituted by a ring-forming aryl group having 6 to 50 carbon atoms or an alkyl group having 1 to 50 carbon atoms.

[0759] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 121 ~R 132 , R 150 and R Q are, each independently,

[0760] hydrogen atom,

[0761] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0762] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0763] -Si(R 951 )(R 952 )(R 953 The one indicated by ),

[0764] -O-(R 954 The one indicated by ),

[0765] -S-(R 955 The one indicated by ),

[0766] -N(R 956 )(R 957 The one indicated by ),

[0767] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[0768] -C(=O)R 958 The one indicated by,

[0769] -COOR 959 The one indicated by,

[0770] Halogen atoms,

[0771] Cyanogi,

[0772] Nitro,

[0773] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0774] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0775] Rb, Rb1, Rb2, Rb3, and Rb4, which do not form the above-mentioned substituted or unsubstituted single ring and also do not form the above-mentioned substituted or unsubstituted condensed ring, are each independently,

[0776] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0777] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0778] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0779] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0780] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0781] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0782] R 151 ~R 153 and R 951 ~R 959 are, each independently,

[0783] hydrogen atom,

[0784] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0785] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0786] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0787] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0788] R 151 If this plural exists, the plural R 151 They are identical or different from each other,

[0789] R 152 If there are multiple instances of R 152 are identical or different from each other,

[0790] R 153 If this plural exists, the plural R 153 They are identical or different from each other,

[0791] R 951 If this plural exists, the plural R 951 They are identical or different from each other,

[0792] R 952 If there are multiple instances of R 952 are identical or different from each other,

[0793] R 953 If this plural exists, the plural R 953 They are identical or different from each other,

[0794] R 954 If there are multiple instances of R 954 are identical or different from each other,

[0795] R 955 If there are multiple instances of , multiple R 955 are identical or different from each other,

[0796] R 956 If this plural exists, the plural R 956 They are identical or different from each other,

[0797] R 957 If this plural exists, the plural R 957 They are identical or different from each other,

[0798] R 958If this plural exists, the plural R 958 They are identical or different from each other,

[0799] R 959 If there are multiple instances of , multiple R 959 are identical or different from each other.

[0800] In the first compound of the above general formula (15), X1 is X 12 It is a carbon atom bonded to by a single bond, and X 12 If is a carbon atom that is bonded to X1 by a single bond, the first compound is represented by the following general formula (15A).

[0801] [Tue 35]

[0802]

[0803] (In the above general formula (15A), Zb, X2~X 11 , R 150 and Q are each as defined in the above general formula (15).)

[0804] In the first compound of the above general formula (15), R 121 ~R 132 , R 150 and R Q are, each independently,

[0805] hydrogen atom,

[0806] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0807] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[0808] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0809] In the first compound of the above general formula (15), R 121 ~R 132 , R 150 and R Q are, each independently,

[0810] hydrogen atoms, or

[0811] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0812] In the first compound of the above general formula (15), R 121 ~R 132 , R 150 and R Q It is preferable that it be a hydrogen atom.

[0813] It is also preferable that the first compound of the above general formula (15) is a compound represented by the following general formula (151).

[0814] [Tue 36]

[0815]

[0816] (In the above general formula (151),

[0817] X1~X 12 Each is X1 to X in the above general formula (15). 12 It has the same meaning as,

[0818] R 150 , R Q and Rb are, respectively, R in the general formula (15) above. 150 , R Q and has the same meaning as Rb.)

[0819] It is also preferable that the first compound of the above general formula (15) is a compound represented by the following general formula (152).

[0820] [Tue 37]

[0821]

[0822] (In the above general formula (152),

[0823] X1~X3, X5~X 12 are, respectively, X1~X3, X5~X in the above general formula (15). 12 It has the same meaning as,

[0824] X 13 silver, CR 133 Or it is a nitrogen atom,

[0825] X 14 is, CR 134 Or it is a nitrogen atom,

[0826] X 15 is, CR 135 Or it is a nitrogen atom,

[0827] X 16 silver, CR 136 Or it is a nitrogen atom,

[0828] R 133 ~R 136 Each independently,

[0829] hydrogen atom,

[0830] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0831] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0832] -Si(R 951 )(R 952 )(R 953 The one indicated by ),

[0833] -O-(R 954 The one indicated by ),

[0834] -S-(R 955 The one indicated by ),

[0835] -N(R 956 )(R 957 The one indicated by ),

[0836] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[0837] -C(=O)R 958 The one indicated by,

[0838] -COOR 959 The one indicated by,

[0839] Halogen atoms,

[0840] Cyanogi,

[0841] Nitro,

[0842] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0843] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0844] R 150 and R Q are, respectively, R in the above general formula (15) 150 and R Q It has the same meaning as.)

[0845] In the first compound of the above general formula (15), R 133 ~R 136 Each independently,

[0846] hydrogen atom,

[0847] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0848] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[0849] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0850] In the first compound of the above general formula (15), R 133 ~R 136 Each independently,

[0851] hydrogen atoms, or

[0852] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0853] In the first compound, R 133 ~R 136 It is preferable that it be a hydrogen atom.

[0854] It is also preferable that the first compound of the above general formula (15) is a compound represented by the following general formula (153).

[0855] [Tue 38]

[0856]

[0857] (In the above general formula (153), R 122 , R 126 , R 134 , R150 and R Q are, each independently,

[0858] hydrogen atom,

[0859] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0860] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0861] -Si(R 951 )(R 952 )(R 953 The one indicated by ),

[0862] -O-(R 954 The one indicated by ),

[0863] -S-(R 955 The one indicated by ),

[0864] -N(R 956 )(R 957 The one indicated by ),

[0865] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[0866] -C(=O)R 958 The one indicated by,

[0867] -COOR 959 The one indicated by,

[0868] Halogen atoms,

[0869] Cyanogi,

[0870] Nitro,

[0871] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0872] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and R 951 ~R 959 is as defined in the above general formula (15).)

[0873] In the above general formula (153), R 122 , R 126 , R 134 , R 150 and R Qare, each independently,

[0874] hydrogen atom,

[0875] Substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms,

[0876] A substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or

[0877] It is also desirable to have a complex circulating group with 5 to 18 substituent or non-substituent ring-forming atoms.

[0878] In the above general formula (153), R 122 and R 134 are, each independently, hydrogen atoms

[0879] Alternatively, it is also preferable to have a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0880] In the above general formula (153), R 126 , R 150 and R Q It is also preferable that each be a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms.

[0881] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (16).

[0882] [Tue 39]

[0883]

[0884] (In the above general formula (16),

[0885] R 161 ~R 177 One or more of the groups consisting of two or more adjacent groups,

[0886] They combine with each other to form a substituted or unsubstituted ring,

[0887] They combine with each other to form substituted or unsubstituted condensed rings, or

[0888] Without combining with each other,

[0889] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 161 ~R 177 Each independently,

[0890] hydrogen atom,

[0891] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0892] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0893] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0894] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0895] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[0896] -Si(R 961 )(R 962 )(R 963 The one indicated by ),

[0897] -O-(R 964 The one indicated by ),

[0898] -S-(R 965 The one indicated by ),

[0899] -N(R 966 )(R 967 The one indicated by ),

[0900] -C(=O)R 968 The one indicated by,

[0901] -COOR 969 The one indicated by,

[0902] Halogen atoms,

[0903] Cyanogi,

[0904] Nitro,

[0905] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0906] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0907] R 961 ~R 969 are, each independently,

[0908] hydrogen atom,

[0909] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0910] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0911] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[0912] R 961 If this plural exists, the plural R 961 They are identical or different from each other,

[0913] R 962 If there are multiple instances of , multiple R 962 are identical or different from each other,

[0914] R 963 If this plural exists, the plural R 963 They are identical or different from each other,

[0915] R 964 If there are multiple instances of , multiple R 964 are identical or different from each other,

[0916] R 965 If there are multiple instances of , multiple R 965 are identical or different from each other,

[0917] R 966 If this plural exists, the plural R 966 They are identical or different from each other,

[0918] R 967 If this plural exists, the plural R 967 They are identical or different from each other,

[0919] R 968 If this plural exists, the plural R 968 They are identical or different from each other,

[0920] R 969 If there are multiple instances of , multiple R 969 are identical or different from each other.

[0921] In the first compound of the above general formula (16), R 161 ~R 177 Each independently,

[0922] hydrogen atom,

[0923] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[0924] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[0925] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0926] In the first compound of the above general formula (16), R 168 ~R 170 At least one of them,

[0927] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0928] It is preferable that the complex circulator has 5 to 50 substituent or non-substituent ring-forming atoms.

[0929] In the first compound of the above general formula (16), R 161 ~R 177 Each independently,

[0930] hydrogen atoms, or

[0931] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0932] In the first compound of the above general formula (16), R 161 ~R 177 It is also desirable that it be a hydrogen atom.

[0933] In the first compound of the above general formula (16), R 161 ~R 177It is also desirable that at least one set of two or more adjacent sets be combined to form a ring represented by the following general formula (16A).

[0934] [Tue 40]

[0935]

[0936] (The dotted line in the above general formula (16A) represents the joint area, and

[0937] R X1 ~R X4 are, each independently,

[0938] hydrogen atom,

[0939] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[0940] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[0941] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[0942] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[0943] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[0944] -Si(R 961 )(R 962 )(R 963 The one indicated by ),

[0945] -O-(R 964 The one indicated by ),

[0946] -S-(R 965 The one indicated by ),

[0947] -N(R 966 )(R 967 The one indicated by ),

[0948] -C(=O)R 968 The one indicated by,

[0949] -COOR 969 The one indicated by,

[0950] Halogen atoms,

[0951] Cyanogi,

[0952] Nitro,

[0953] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[0954] It is a complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms.

[0955] R X1 If this plural exists, the plural R X1 They are identical or different from each other,

[0956] R X2 If there are multiple instances of , multiple R X2 are identical or different from each other,

[0957] R X3 If this plural exists, the plural R X3 They are identical or different from each other,

[0958] R X4 If there are multiple instances of , multiple R X4 They are identical or different from each other.

[0959] In the first compound of the above general formula (16),

[0960] R 161 and R 162 A group consisting of,

[0961] R 165 and R 166 A group consisting of,

[0962] R 172 and R 173 A group consisting of, and

[0963] R 176 and R 177 It is also desirable that at least one set of sets made of the above be combined to form a ring represented by the general formula (16A).

[0964] In the first compound of the above general formula (16), R 161 and R 162 A group consisting of, and R176 and R 177 It is preferable that the group consisting of does not simultaneously form a ring represented by the above general formula (16A).

[0965] In the first compound of the above general formula (16), R 165 and R 166 A group composed of such and such is combined to form a ring represented by the general formula (16A), and R 172 and R 173 It is also desirable for the groups composed of to combine with each other to form a ring represented by the above general formula (16A), in which case the first compound is represented by the following general formula (161).

[0966] It is also preferable that the first compound of the above general formula (16) is a compound represented by the following general formula (161).

[0967] [Tue 41]

[0968]

[0969] (In the above general formula (161), R 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R X1 ~R X4 R in the above general formula (16) is, respectively, independently 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R in the above general formula (16A) X1 ~R X4 It has the same meaning as.)

[0970] It is also preferable that the first compound of the above general formula (16) is a compound represented by the following general formula (162).

[0971] [Tue 42]

[0972]

[0973] (In the above general formula (162), R 161 ~R 163 , R 168 ~R 170 and R 175 ~R 177 R in the above general formula (16) is, each independently 161 ~R 163 , R 168 ~R 170 and R 175 ~R 177 It has the same meaning as.)

[0974] It is also preferable that the first compound of the above general formula (16) is a compound represented by the following general formula (163).

[0975] [Tuesday 43]

[0976]

[0977] (In the above general formula (163), R 162 , R 169 and R 176 R in the above general formula (16) is, each independently 162 , R 169 and R 176 It has the same meaning as.)

[0978] In the above general formulas (16), (161) to (163) of the first compound, R 169 It is also desirable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0979] In the above general formulas (16), (161) to (163) of the first compound, R 169 It is also desirable that it be a substituted or unsubstituted phenyl group.

[0980] In the present embodiment, it is also preferable that the first compound is a compound represented by the following general formula (171) or general formula (172).

[0981] [Tuesday 44]

[0982]

[0983] [Tuesday 45]

[0984]

[0985] (In the above general formula (171) and general formula (172),

[0986] Rings A, D, and E, each independently,

[0987] Substituted or unsubstituted ring-forming aryl rings having 6 to 30 carbon atoms, and

[0988] Complex ring with 5 to 30 atoms forming a ring, either substituted or unsubstituted

[0989] It is a ring structure selected from a group consisting of, and

[0990] Za is a nitrogen atom or a carbon atom, and

[0991] Zb is an oxygen atom, a sulfur atom, or NRb, and

[0992] Zc is a nitrogen atom or a carbon atom, and

[0993] Zd is a carbon or nitrogen atom, and

[0994] Ze is a carbon atom or a nitrogen atom, and

[0995] Zf is a nitrogen atom or a carbon atom, and

[0996] Zh is a nitrogen atom or a carbon atom,

[0997] Zi is a nitrogen atom or a carbon atom, and

[0998] Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and

[0999] Rb and Rh, each independently, are hydrogen atoms or substituents, and

[1000] Rb and Rh as substituents, respectively, independently

[1001] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1002] A complex circulating ring-forming group having 5 to 30 substituted or unsubstituted atoms, and

[1003] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms

[1004] Selected from a group consisting of,

[1005] R 181 and R 182 A group consisting of,

[1006] They combine with each other to form a substituted or unsubstituted ring,

[1007] They combine with each other to form substituted or unsubstituted condensed rings, or

[1008] Without combining with each other,

[1009] R 183 and R 184 A group consisting of,

[1010] They combine with each other to form a substituted or unsubstituted ring,

[1011] They combine with each other to form substituted or unsubstituted condensed rings, or

[1012] Without combining with each other,

[1013] R that does not form the above-mentioned substituted or non-substituted single ring and does not form the above-mentioned substituted or non-substituted condensed ring 181 ~R 184 are, each independently,

[1014] hydrogen atom,

[1015] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1016] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1017] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1018] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[1019] Substituted or unsubstituted araclel groups having 7 to 50 carbon atoms,

[1020] -Si(R 971 )(R 972 )(R 973 The one indicated by ),

[1021] -O-(R 974 The one indicated by ),

[1022] -S-(R 975 The one indicated by ),

[1023] -N(R 976 )(R 977 The one indicated by ),

[1024] -C(=O)R 978 The one indicated by,

[1025] -COOR 979 The one indicated by,

[1026] Halogen atoms,

[1027] Cyanogi,

[1028] Nitro,

[1029] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[1030] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[1031] R 971 ~R 979 are, each independently,

[1032] hydrogen atom,

[1033] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1034] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[1035] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[1036] R 971 If this plural exists, the plural R 971 They are identical or different from each other,

[1037] R 972 If there are multiple instances of , multiple R972 are identical or different from each other,

[1038] R 973 If this plural exists, the plural R 973 They are identical or different from each other,

[1039] R 974 If there are multiple instances of , multiple R 974 are identical or different from each other,

[1040] R 975 If there are multiple instances of , multiple R 975 are identical or different from each other,

[1041] R 976 If this plural exists, the plural R 976 They are identical or different from each other,

[1042] R 977 If this plural exists, the plural R 977 They are identical or different from each other,

[1043] R 978 If this plural exists, the plural R 978 They are identical or different from each other,

[1044] R 979 If there are multiple instances of , multiple R 979 are identical or different from each other.

[1045] In the first compound of the above general formula (171) or the above general formula (172), R 181 ~R 184 are, each independently,

[1046] hydrogen atom,

[1047] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1048] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[1049] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1050] In the first compound of the above general formula (171) or the above general formula (172), R 181 ~R 184 are, each independently,

[1051] hydrogen atoms, or

[1052] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[1053] In the first compound of the above general formula (171) or the above general formula (172), R 181 ~R 184 It is preferable that it be a hydrogen atom.

[1054] In this embodiment, it is also preferable that the first compound is a compound represented by the following general formula (18).

[1055] [Tuesday 46]

[1056]

[1057] (In the above general formula (18),

[1058] r is 0 or 1, and

[1059] When r is 0, p and q are 1, and R W1 and R W2 There exists,

[1060] When r is 1, p and q are 0, and R W1 and R W2 does not exist,

[1061] X 81 Silver, nitrogen atoms, or CR 191 And,

[1062] X 82 is, a nitrogen atom or CR 192 And,

[1063] X 83 Silver, single bond, oxygen atom, sulfur atom, Si(R 193 )(R 194 ), C(R 195 )(R 196 ) or BR197 And,

[1064] X 84 is, R 801 This or, or X 85 It is a carbon atom bonded to by a single bond, and

[1065] X 85 is, R 812 This or, or X 84 It is a carbon atom bonded to by a single bond, and

[1066] R 191 , R 192 , R 193 , R 194 , R 195 , R 196 , R 197 , R 801 , R 802 , R 803 , R 804 , R 805 , R 806 , R 807 , R 808 , R 809 , R 810 , R 811 , R 812 , R W1 , R W2 and R W3 One or more of the groups consisting of two or more adjacent groups,

[1067] They combine with each other to form a substituted or unsubstituted ring,

[1068] They combine with each other to form substituted or unsubstituted condensed rings, or

[1069] Without combining with each other,

[1070] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. W3 silver,

[1071] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,

[1072] A complex circulator with 5 to 50 substituent or unsubstituent ring-forming atoms, or

[1073] It is a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, and

[1074] R that does not form the above-mentioned substituted or non-substituted single ring, and also does not form the above-mentioned substituted or non-substituted condensed ring. 191 , R 192 , R 193 , R 194 , R 195 , R 196 , R 197 , R 801 , R 802 , R 803 , R 804 , R 805 , R 806 , R 807 , R 808 , R 809 , R 810 , R 811 , R 812 , R W1 and R W2 are, each independently,

[1075] hydrogen atom,

[1076] deuterium atom,

[1077] -Si(R 981 )(R 982 )(R 983 The one indicated by ),

[1078] -O-(R 984 The one indicated by ),

[1079] -S-(R 985 The one indicated by ),

[1080] -N(R 986 )(R 987 The one indicated by ),

[1081] -B(R 988 )(R 989 The one indicated by ),

[1082] -OSO2(R 990 The one indicated by ),

[1083] Cyanogi,

[1084] Halogen atoms,

[1085] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1086] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[1087] Substituted or unsubstituted fluoroalkyl groups having 1 to 50 carbon atoms,

[1088] Substituted or unsubstituted thioalkoxy groups having 1 to 50 carbon atoms,

[1089] Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms,

[1090] Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms,

[1091] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[1092] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[1093] R 981 ~R 990 Each independently,

[1094] hydrogen atom,

[1095] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1096] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[1097] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[1098] R 981 If this plural exists, the plural R 981 They are identical or different from each other,

[1099] R 982 If there are multiple instances of , multiple R 982 are identical or different from each other,

[1100] R 983 If this plural exists, the plural R 983 They are identical or different from each other,

[1101] R 984 If there are multiple instances of , multiple R 984 are identical or different from each other,

[1102] R 985 If there are multiple instances of , multiple R 985 are identical or different from each other,

[1103] R 986 If this plural exists, the plural R 986 They are identical or different from each other,

[1104] R 987 If this plural exists, the plural R 987 They are identical or different from each other,

[1105] R 988 If this plural exists, the plural R 988 They are identical or different from each other,

[1106] R 989 If there are multiple instances of , multiple R 989 are identical or different from each other,

[1107] R 990 If this plural exists, the plural R 990 They are identical or different from each other.

[1108] In the above general formula (18), X 84 Ga X 85 It is a carbon atom bonded to by a single bond, and X 85 Ga X 84 In the case where the carbon atom is bonded by a single bond, the first compound is represented by the following general formula (18A).

[1109] [Tue 47]

[1110]

[1111] (In the above general formula (18A), r, p, q, R 802 ~R 811 , R W1 , R W2 , RW3 , X 81 , X 82 , X 83 Each is as defined in the above general formula (18).)

[1112] In the first compound of the above general formula (18), R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 are, each independently,

[1113] hydrogen atom,

[1114] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1115] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[1116] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1117] In the first compound of the above general formula (18), R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 are, each independently,

[1118] hydrogen atoms, or

[1119] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[1120] In the first compound of the above general formula (18), R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 It is preferable that it be a hydrogen atom.

[1121] It is also preferable that the first compound of the above general formula (18) is a compound represented by the following general formula (181).

[1122] [Tue 48]

[1123]

[1124] (In the above general formula (181),

[1125] X 81 , X 82 , X 84 and X 85 are, respectively, X in the above general formula (18) 81 , X 82 , X 84 and X 85 It has the same meaning as,

[1126] R 802 ~R 811 and R W3 Each is R in the above general formula (18). 802 ~R 811 and R W3 It has the same meaning as.)

[1127] It is also preferable that the first compound of the above general formula (18) is a compound represented by the following general formula (182).

[1128] [Tue 49]

[1129]

[1130] (In the above general formula (182),

[1131] X 81 and X 82 are, respectively, X in the above general formula (18) 81 and X 82 It has the same meaning as,

[1132] R 802 ~R 811 and R W3 Each is R in the above general formula (18). 802 ~R 811 and R W3 It has the same meaning as.)

[1133] In the first compound, the substituent in the case of "substituted or unsubstituted" is,

[1134] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1135] Unsubstituted alkenyl groups having 2 to 25 carbon atoms,

[1136] Unsubstituted alkynyl groups having 2 to 25 carbon atoms,

[1137] Unsubstituted ring-forming cycloalkyl groups having 3 to 25 carbon atoms,

[1138] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[1139] -O-(R 904 The one indicated by ),

[1140] -S-(R 905 The one indicated by ),

[1141] -N(R 906 )(R 907 The one indicated by ),

[1142] Unsubstituted araclel groups with 7–50 carbon atoms,

[1143] -C(=O)R 908 The one indicated by,

[1144] -COOR 909 The one indicated by,

[1145] -S(=O)2R 941 The one indicated by,

[1146] -P(=O)(R 942 )(R 943 The one indicated by ),

[1147] -Ge(R 944 )(R 945 )(R 946 The one indicated by ),

[1148] Halogen atoms,

[1149] Cyanogi,

[1150] Nitro,

[1151] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1152] It is a non-substituting complex circulator with 5 to 25 ring-forming atoms, and

[1153] R 901 ~R 909 and R 941 ~R 946 Each independently,

[1154] hydrogen atom,

[1155] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1156] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1157] It is preferable that it be a complex circulator with 5 to 25 ring-forming atoms that are unsubstituted.

[1158] In the first compound, the substituent in the case of "substituted or unsubstituted" is,

[1159] Halogen atoms,

[1160] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1161] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1162] It is preferable that it be a complex circulator with 5 to 25 ring-forming atoms that are unsubstituted.

[1163] In the first compound, the substituent in the case of "substituted or unsubstituted" is,

[1164] Unsubstituted alkyl groups having 1 to 10 carbon atoms,

[1165] An unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or

[1166] It is preferable that it be a complex circulator with 5 to 12 ring-forming atoms that are unsubstituted.

[1167] In the first compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[1168] The maximum peak wavelength of the first compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 500 nm or more and 530 nm or less.

[1169] In this specification, the maximum peak wavelength of a compound refers to a compound to be measured that is 10 -6 10 moles / liter or more -5 It refers to the peak wavelength of the fluorescence spectrum at which the luminescence intensity in the measured fluorescence spectrum is maximum for a toluene solution dissolved at a concentration of mol / liter or less. As a measuring device, a spectrofluorescence photometer (Hitachi, F-7000) can be used.

[1170] The first compound is preferably a compound that exhibits green fluorescent emission.

[1171] It is preferable that the first compound be a material with a high luminescence quantum yield.

[1172] · Method for preparing the first compound

[1173] The first compound according to the present embodiment can be prepared by using a known alternative reaction and raw materials suited to the target product, according to the synthesis method described in the example below, or according to the said synthesis method.

[1174] · Specific example of the first compound

[1175] Specific examples of the first compound of the present embodiment include, for instance, the following compounds. However, the present invention is not limited to specific examples of these compounds.

[1176] In the present specification, among the embodiments of the compound, D represents a deuterium atom, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[1177] [Tue 50]

[1178]

[1179] [Tue 51]

[1180]

[1181] [Tue 52]

[1182]

[1183] [Tuesday 53]

[1184]

[1185] [Tue 54]

[1186]

[1187] [Tue 55]

[1188]

[1189] [Tuesday 56]

[1190]

[1191] [Tue 57]

[1192]

[1193] [Tue 58]

[1194]

[1195] [Tue 59]

[1196]

[1197] [Tuesday 60]

[1198]

[1199] [Tuesday 61]

[1200]

[1201] [Tuesday 62]

[1202]

[1203] [Tuesday 63]

[1204]

[1205] [Tuesday 64]

[1206]

[1207] [Tuesday 65]

[1208]

[1209] [Tuesday 66]

[1210]

[1211] [Tuesday 67]

[1212]

[1213] [Tuesday 68]

[1214]

[1215] [Tue 69]

[1216]

[1217] [Tue 70]

[1218]

[1219] [Tue 71]

[1220]

[1221] [Tue 72]

[1222]

[1223] [Tue 73]

[1224]

[1225] [Tue 74]

[1226]

[1227] [Tue 75]

[1228]

[1229] [Tue 76]

[1230]

[1231] [Tue 77]

[1232]

[1233] [Tue 78]

[1234]

[1235] [Tue 79]

[1236]

[1237] [Tue 80]

[1238]

[1239] [Tue 81]

[1240]

[1241] [Tue 82]

[1242]

[1243] [Tue 83]

[1244]

[1245] [Tue 84]

[1246]

[1247] [Tue 85]

[1248]

[1249] (Compound 2)

[1250] The second compound of this embodiment is a heat-activated delayed fluorescent compound.

[1251] The second compound is represented by the following general formula (2).

[1252] [Tue 86]

[1253]

[1254] (In the above general formula (2),

[1255] k is 1, 2, 3, 4, or 5, and

[1256] Dx is a device represented by the following general formula (21), general formula (22) or general formula (23), and

[1257] m is 1, 2, 3, or 4, and

[1258] When m is 2, 3, or 4, multiple Dx are identical or different from each other, and

[1259] n is 0, 1, 2, or 3, and

[1260] When n is 2 or 3, multiple Rs are identical or different from each other, and

[1261] However, the sum of m and n is 2 or greater, and

[1262] R is, each independently, a halogen atom or a substituent, and

[1263] R as a substituent, each independently,

[1264] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1265] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[1266] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[1267] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[1268] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[1269] -O-(R 914 The one indicated by ),

[1270] -S-(R 915 The unit indicated by ), or

[1271] -N(R 916 )(R 917 It is a device indicated by ).

[1272] [Tue 87]

[1273]

[1274] [Tue 88]

[1275]

[1276] [Tue 89]

[1277]

[1278] (R1 to R8 in the above general formula (21) are each independently a hydrogen atom, a halogen atom, or a substituent, and

[1279] R in the above general formula (22) 21 ~R 28Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 21 and R 22 of, R 22 and R 23 of, R 23 and R 24 of, R 25 and R 26 of, R 26 and R 27 of, and R 27 and R 28 One or more of the groups combine with each other to form a ring,

[1280] R in the above general formula (23) 211 ~R 218 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 211 and R 212 of, R 212 and R 213 of, R 213 and R 214 of, R 215 and R 216 of, R 216 and R 217 of, and R 217 and R 218 One or more of the groups combine with each other to form a ring,

[1281] R1–R8 as substituents, R as a substituent 21 ~R 28 and R as a substituent 211 ~R 218 Each independently,

[1282] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1283] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[1284] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[1285] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[1286] -Si(R 911 )(R 912 )(R 913 The one indicated by ),

[1287] -O-(R 914 The one indicated by ),

[1288] -S-(R 915 The unit indicated by ), or

[1289] -N(R 916 )(R 917 It is a device indicated by ), and

[1290] In the above general formula (22) and the above general formula (23),

[1291] Rings G, J and K are each independently selected from the group of ring structures represented by the following general formulas (24), (25) and (26), and

[1292] Rings G, J, and K condense with adjacent rings at any position, and

[1293] pa, px, and py are, independently, 1, 2, 3, or 4, and

[1294] If pa is 2, 3, or 4, the multiple rings G are identical or different from each other, and

[1295] If px is 2, 3, or 4, multiple rings J are identical or different from each other, and

[1296] If py is 2, 3, or 4, multiple rings K are identical or different from each other, and

[1297] In the above general formulas (21) to (23), * indicates the bonding position with the benzene ring in the above general formula (2).

[1298] [Tue 90]

[1299]

[1300] (In the above general formula (24),

[1301] R 19 and R 20 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups of combine with each other to form a ring,

[1302] In the above general formula (25) and general formula (26),

[1303] X 21 and X 22 are, respectively, sulfur atom, oxygen atom, NR 220 , CR 221 R 222 or SiR 223 R 224 And,

[1304] R 220 It is silver, a hydrogen atom, a halogen atom, or a substituent, and

[1305] R 221 and R 222 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 221 and R 222 The groups of combine with each other to form a ring,

[1306] R 223 and R 224 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 223 and R 224 The groups of combine with each other to form a ring,

[1307] R as a substituent 19 , R 20 , R 220 , R 221 , R 222 , R 223 and R 224 Each has the same meaning as R1–R8 as substituents, independently.)

[1308] (In the first compound and the second compound above, R 911 ~R 917 Each independently,

[1309] hydrogen atom,

[1310] Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,

[1311] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 50 carbon atoms,

[1312] Substituted or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms, or

[1313] It is a complex circulating group with 5 to 50 substituent or unsubstituent ring-forming atoms, and

[1314] R 911 If this plural exists, the plural R 911 They are identical or different from each other,

[1315] R 912 If there are multiple instances of , multiple R 912 are identical or different from each other,

[1316] R 913 If this plural exists, the plural R 913 They are identical or different from each other,

[1317] R 914 If there are multiple instances of , multiple R 914 are identical or different from each other,

[1318] R 915 If there are multiple instances of , multiple R 915 are identical or different from each other,

[1319] R 916 If this plural exists, the plural R 916 They are identical or different from each other,

[1320] R 917 If this plural exists, the plural R 917 They are identical or different from each other.

[1321] In an organic EL device of one embodiment (first embodiment) of the present embodiment, at least one Dx in the general formula (2) of the second compound is a group represented by general formula (22) or general formula (23). In the case of this first embodiment, at least one Dx is a group represented by general formula (22) which includes a ring structure selected from the group consisting of ring structures represented by general formula (25) and general formula (26), where pa is 2, 3, or 4 and is ring G, or a group represented by general formula (23) which includes a ring structure selected from the group consisting of ring structures represented by general formula (25) and general formula (26), where at least one of px and py is 2, 3, or 4 and is ring J or ring K. In the case of this first embodiment, the light-emitting layer contains a combination of the second compound having at least one group represented by general formula (22) or general formula (23) and any of the aforementioned first compounds.

[1322] In an organic EL device of another embodiment (second embodiment) of the present embodiment, the second compound is a compound represented by general formula (2). In this second embodiment, the light-emitting layer contains a combination of the compound represented by general formula (2) and any one of the first compounds of general formulas (15), (16), (171), (172) or (18).

[1323] In an organic EL device of another embodiment (third embodiment) of the present embodiment, the second compound is a compound represented by general formula (2) and is a compound that does not contain a group represented by general formula (22) or general formula (23). In the case of this third embodiment, the light-emitting layer contains a combination of the second compound that does not contain a group represented by general formula (22) or general formula (23) and any one of the first compounds of general formulas (15), (16), (171), (172) or (18).

[1324] In this embodiment, it is preferable that m in the general formula (2) is 2.

[1325] In the present embodiment, the compound represented by the above general formula (2) is preferably represented by the following general formula (210), general formula (220), or general formula (230).

[1326] [Tue 91]

[1327]

[1328] (In the above general formulas (210), (220) and (230), Dx, m, R and n each have the same meaning as Dx, m, R and n in the above general formula (2).)

[1329] In the present embodiment, the compound represented by the general formula (2) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (211) to (218).

[1330] [Tue 92]

[1331]

[1332] (In the above general formulas (211) and (212),

[1333] D 11 is a device represented by the above general formula (22) or general formula (23), and

[1334] R 231 ~R 233 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 ~R 233 At least one of them is a substituent, and R as a substituent 231 ~R 233 ...is the same meaning as R as a substituent in the above general formula (2).)

[1335] [Tue 93]

[1336]

[1337] (In the above general formulas (213) to (216),

[1338] D 11 and D 12 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 and D 12 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1339] R 231 and R 232 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 and R 232 At least one of them is a substituent, and R as a substituent 231 and R 232 is the same meaning as R as a substituent in the above general formula (2).)

[1340] [Tue 94]

[1341]

[1342] (In the above general formulas (217) and (218),

[1343] D 11 ~D 13 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 ~D 13 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1344] R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (2).)

[1345] In the present embodiment, the compound represented by the general formula (2) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (221) to (229).

[1346] [Tue 95]

[1347]

[1348] (In the above general formulas (221) to (223),

[1349] D 11 is a device represented by the above general formula (22) or general formula (23), and

[1350] R 231 ~R 233 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 ~R 233 At least one of them is a substituent, and R as a substituent 231 ~R 233 ...is the same meaning as R as a substituent in the above general formula (2).)

[1351] [Tue 96]

[1352]

[1353] (In the above general formulas (224) to (226),

[1354] D 11 and D 12 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 and D 12 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1355] R 231 and R 232 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 and R 232 At least one of them is a substituent, and R as a substituent 231 and R 232 is the same meaning as R as a substituent in the above general formula (2).)

[1356] [Tue 97]

[1357]

[1358] (In the above general formulas (227) to (229),

[1359] D 11 ~D 13 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 ~D 13 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1360] R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (2).)

[1361] In this embodiment, the compound represented by the general formula (2) is also preferably the compound represented by the general formula (226).

[1362] In the present embodiment, the compound represented by the general formula (2) is preferably any compound selected from the group consisting of compounds represented by the following general formulas (231) to (235).

[1363] [Tue 98]

[1364]

[1365] (In the above general formula (231),

[1366] D 11 is a device represented by the above general formula (22) or general formula (23), and

[1367] R 231 ~R 233 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 ~R 233 At least one of them is a substituent, and R as a substituent 231 ~R 233 ...is the same meaning as R as a substituent in the above general formula (2).)

[1368] [Tue 99]

[1369]

[1370] (In the above general formulas (232) to (234),

[1371] D 11 and D 12 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 and D 12 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1372] R 231 and R 232 Each has the same meaning as R in the above general formula (2), independently, provided that R 231 and R 232 At least one of them is a substituent, and R as a substituent 231 and R 232 is the same meaning as R as a substituent in the above general formula (2).)

[1373] [Tue 100]

[1374]

[1375] (In the above general formula (235),

[1376] D 11 ~D 13 Each has the same meaning as Dx in the above general formula (2), independently, provided that D 11 ~D 13 At least one of them is a device represented by the above general formula (22) or general formula (23), and

[1377] R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (2).)

[1378] In this embodiment, it is also preferable that the compound represented by the general formula (2) is the compound represented by the general formula (234).

[1379] In this embodiment, it is also preferable that the compound represented by the above general formula (2) is a compound represented by the following general formula (236).

[1380] [Tue 101]

[1381]

[1382] (In the above general formula (236),

[1383] D 11 is a device represented by the following general formulas (22A), (22B), (22C), (22D), (22E) or (22F), and

[1384] 3 Ds 12 is a device represented by the above general formula (21), each independently, and

[1385] However, D 11 and D 12 They are different from each other.)

[1386] [Tue 102]

[1387]

[1388] [Tue 103]

[1389]

[1390] [Tue 104]

[1391]

[1392] [Tue 105]

[1393]

[1394] [Tue 106]

[1395]

[1396] [Tue 107]

[1397]

[1398] (In the above general formulas (22A), (22B), (22C), (22D), (22E) and (22F),

[1399] R 21 ~R28 R in the above general formula (22) is, each independently 21 ~R 28 It has the same meaning as,

[1400] R 19 and R 20 R in the above general formula (24), each independently 19 and R 20 It has the same meaning as,

[1401] X 21 is X in the above general formula (25). 21 It has the same meaning as,

[1402] In the above general formulas (22A), (22B), (22C), (22D), (22E) and (22F), * indicates the bonding position with the benzene ring in the above general formula (2).

[1403] R in the above general formulas (22A), (22B), (22C), (22D), (22E) and (22F) 21 and R 22 of, R 22 and R 23 of, R 23 and R 24 of, R 25 and R 26 of, R 26 and R 27 of, R 27 and R 28 of the group and R 19 and R 20 It is desirable that the groups of the group do not combine with each other.

[1404] In the second compound, the group represented by the general formula (22) is preferably any group selected from the group consisting of the general formulas (22A), (22D), and (22F).

[1405] In the second compound, X 21 It is preferable that it be an oxygen atom or a sulfur atom.

[1406] The compound according to the present embodiment preferably has at least one group selected from the group consisting of the groups represented by the general formulas (22A), (22B), (22C), (22D), (22E) and (22F) as Dx in the general formula (2).

[1407] The compound according to the present embodiment is any group selected from the group consisting of the groups represented by the general formulas (22A), (22B), (22C), (22D), (22E), and (22F), as Dx in the general formula (2), and also X 21 It is more desirable to have at least one group that is an oxygen atom or a sulfur atom.

[1408] Dx in the above general formula (210), general formula (220) and general formula (230) is preferably any one selected from the group consisting of the general formulas (22A), (22B), (22C), (22D), (22E) and (22F), each independently.

[1409] D in the above general formulas (211) to (218), (221) to (229), (231) to (235) 11 , D 12 and D 13 It is preferable that each be any one of the groups consisting of the groups represented by the general formulas (22A), (22B), (22C), (22D), (22E) and (22F), respectively.

[1410] In this embodiment, R as a substituent of the second compound is, respectively, independently

[1411] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1412] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[1413] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[1414] In this embodiment, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 Each independently,

[1415] hydrogen atom,

[1416] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1417] A complex circulator with 5 to 30 substituent or unsubstituent ring-forming atoms, or

[1418] It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[1419] In this embodiment, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 Each independently,

[1420] hydrogen atoms, or

[1421] It is preferable that it be a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[1422] In this embodiment, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 It is preferable that it be a hydrogen atom.

[1423] In the second compound, the substituent in the case of "substituted or unsubstituted" is,

[1424] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1425] Unsubstituted alkenyl groups having 2 to 25 carbon atoms,

[1426] Unsubstituted alkynyl groups having 2 to 25 carbon atoms,

[1427] Unsubstituted ring-forming cycloalkyl groups having 3 to 25 carbon atoms,

[1428] -Si(R 901 )(R 902 )(R903 The one indicated by ),

[1429] -O-(R 904 The one indicated by ),

[1430] -S-(R 905 The one indicated by ),

[1431] -N(R 906 )(R 907 The one indicated by ),

[1432] Unsubstituted araclel groups with 7–50 carbon atoms,

[1433] -C(=O)R 908 The one indicated by,

[1434] -COOR 909 The one indicated by,

[1435] -S(=O)2R 941 The one indicated by,

[1436] -P(=O)(R 942 )(R 943 The one indicated by ),

[1437] -Ge(R 944 )(R 945 )(R 946 The one indicated by ),

[1438] Halogen atoms,

[1439] Cyanogi,

[1440] Nitro,

[1441] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1442] It is a non-substituting complex circulator with 5 to 25 ring-forming atoms, and

[1443] R 901 ~R 909 and R 941 ~R 946 Each independently,

[1444] hydrogen atom,

[1445] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1446] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1447] It is preferable that it be a complex circulator with 5 to 25 ring-forming atoms that are unsubstituted.

[1448] In the second compound, the substituent in the case of "substituted or unsubstituted" is,

[1449] Halogen atoms,

[1450] Unsubstituted alkyl groups having 1 to 25 carbon atoms,

[1451] An unsubstituted ring-forming aryl group having 6 to 25 carbon atoms, or

[1452] It is preferable that it be a complex circulator with 5 to 25 ring-forming atoms that are unsubstituted.

[1453] In the second compound, the substituent in the case of "substituted or unsubstituted" is,

[1454] Unsubstituted alkyl groups having 1 to 10 carbon atoms,

[1455] An unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, or

[1456] It is preferable that it be a complex circulator with 5 to 12 ring-forming atoms that are unsubstituted.

[1457] In the second compound, it is preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[1458] In the organic EL device of the present embodiment, it is preferable that the delayed fluorescent light-emitting material as the second compound is a host material.

[1459] In the organic EL device of the present embodiment, it is preferable that the delayed fluorescent light-emitting material as the second compound is the host material, and the compound according to the first embodiment as the first compound is the dopant material.

[1460] (Delayed fluorescence)

[1461] Delayed fluorescence is explained on pages 261–268 of *Device Properties of Organic Semiconductors* (edited by Adachi Chihaya, published by Kodansha). In that document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent emitting material 13 It is explained that if the value can be reduced, reverse energy transfer from the excited triplet state, which typically has a low transition probability, to the excited singlet state occurs with high efficiency, and Thermally Activated Delayed Fluorescence (TADF) is expressed. Additionally, the mechanism of delayed fluorescence generation is described in Fig. 10.38 of the aforementioned literature. In the present embodiment, the delayed fluorescence-emitting material is preferably a compound that exhibits thermally activated delayed fluorescence generated by this mechanism.

[1462] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[1463] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement is a method of irradiating a sample with a pulsed laser to excite it, and then measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF materials is classified into a emission component from singlet excitons generated by the initial PL excitation and a emission component from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the initial PL excitation is very short, on the order of nanoseconds. Therefore, the emission from the singlet excitons decays rapidly after irradiation with a pulsed laser.

[1464] On the other hand, delayed fluorescence decays gradually because it is emission from a singlet exciton generated via a long-lived triplet exciton. As such, there is a significant temporal difference between the emission from a singlet exciton generated by the initial PL excitation and the emission from a singlet exciton generated via a triplet exciton. Therefore, the emission intensity derived from delayed fluorescence can be determined.

[1465] Figure 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL. An example of a method for measuring transient PL using Figure 2 and an analysis of the behavior of delayed fluorescence are described.

[1466] The transient PL measuring device (100) of FIG. 2 comprises a pulse laser unit (101) capable of irradiating light of a predetermined wavelength, a sample chamber (102) for receiving a measurement sample, a spectrometer (103) for spectrally analyzing light emitted from the measurement sample, a streak camera (104) for forming a two-dimensional image, and a personal computer (105) for receiving and analyzing the two-dimensional image. In addition, the measurement of transient PL is not limited to the device described in FIG. 2.

[1467] The sample received in the sample chamber (102) is obtained by forming a thin film on a quartz substrate in which the doping material is doped at a concentration of 12 mass% with respect to the matrix material.

[1468] A pulse laser is irradiated from a pulse laser unit (101) onto a thin film sample contained in a sample chamber (102) to excite a doping material. Light emission is emitted in a direction 90 degrees to the direction of irradiation of the excitation light, the emitted light is spectrally analyzed by a spectrometer (103), and a two-dimensional image is formed within a streak camera (104). As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to the light emission intensity. If this two-dimensional image is cut along a predetermined time axis, a light emission spectrum can be obtained in which the vertical axis is the light emission intensity and the horizontal axis is the wavelength. Additionally, if the above two-dimensional image is cut along the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of the light emission intensity and the horizontal axis is time.

[1469] For example, thin film sample A was prepared as described above by using the following reference compound H1 as the matrix material and the following reference compound D1 as the doping material, and transient PL measurements were performed.

[1470] [Tuesday 108]

[1471]

[1472] Here, damping curves were analyzed using the aforementioned thin film samples A and B. Thin film sample B was prepared as described above by using the reference compound H2 below as the matrix material and the reference compound D1 above as the doping material.

[1473] Figure 3 shows the damping curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[1474] [Tuesday 109]

[1475]

[1476] As described above, by measuring transient PL, a luminescence decay curve can be obtained with luminescence intensity on the vertical axis and time on the horizontal axis. Based on this luminescence decay curve, the ratio of fluorescence intensity between the fluorescence emitted from the singlet excited state generated by light excitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescence materials, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the rapidly decaying fluorescence is somewhat large.

[1477] Specifically, regarding the emission from delayed fluorescent materials, there exist Prompt emission and Delay emission. Prompt emission refers to emission observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) of a wavelength absorbed by the delayed fluorescent material. Delay emission refers to emission that is not observed immediately after excitement by the pulsed light, but is observed thereafter.

[1478] In addition, for measuring the delayed fluorescence of a delayed fluorescence emitting material, a sample prepared by the method described below is used. For example, a delayed fluorescence emitting material is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. In addition, to prevent quenching by oxygen, the sample solution is frozen and degassed, and then sealed in a covered cell under an argon atmosphere to become an oxygen-free sample solution saturated with argon.

[1479] The fluorescence spectrum of the above sample solution is measured using a spectrofluorescence photometer FP-8600 (manufactured by Nippon Bunko Co., Ltd.), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. Using the fluorescence area intensity of both spectra, the total fluorescence quantum yield is calculated by equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[1480] The amounts of Prompt light emission and Delay light emission and their ratios can be obtained using the same method described in “Nature 492, 234-238, 2012” (Reference 1). Meanwhile, the device used to calculate the amounts of Prompt light emission and Delay light emission is not limited to the device described in Reference 1 or the device described in FIG. 2.

[1481] In this embodiment, the amount of Prompt emission (immediate emission) of the compound to be measured (delayed fluorescent emitting material) is X P Let it be, and the amount of delay emission (delayed emission) be X D When done as, X D / X P It is desirable that the value of be 0.05 or higher.

[1482] The measurement of the amount and ratio of Prompt emission and Delay emission of a compound other than the delayed fluorescent emitting material in this specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of a delayed fluorescent emitting material.

[1483] ·ΔST

[1484] In this embodiment, the lowest excitation singlet energy S1 and the energy gap T at 77[K] are 77K The difference of (S1-T 77K ) is defined as ΔST.

[1485] The lowest excitation singlet energy S1(H) of the delayed fluorescence emitting material and the energy gap T at 77[K] of the delayed fluorescence emitting material 77KThe difference ΔST(H) of (H) is preferably less than 0.3 eV, more preferably less than 0.2 eV, even more preferably less than 0.1 eV, and even more preferably less than 0.01 eV. That is, it is desirable for ΔST(H) to satisfy the relationship of the following formulas (Equation 10), (Equation 11), (Equation 12) or (Equation 13).

[1486] ΔST(H)=S1(H)-T 77K (H)<0.3 eV … (number 10)

[1487] ΔST(H)=S1(H)-T 77K (H)<0.2 eV … (number 11)

[1488] ΔST(H)=S1(H)-T 77K (H)<0.1 eV … (number 12)

[1489] ΔST(H)=S1(H)-T 77K (H)<0.01 eV … (number 13)

[1490] · Relationship between triplet energy and the energy gap at 77[K]

[1491] Here, the relationship between the triplet energy and the energy gap at 77[K] is explained. In this embodiment, the energy gap at 77[K] is different from the triplet energy as it is typically defined.

[1492] The measurement of triplet energy is performed as follows. First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing the solution inside a quartz glass tube. For this sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77[K]), a tangent line is drawn on the rise on the short-wavelength side of the phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength at the intersection point of the tangent line and the horizontal axis.

[1493] Here, among the compounds according to the present embodiment, it is preferable that the heat-activated delayed fluorescence compound is a compound with a small ΔST. If ΔST is small, interterm and inverse interterm crossings are likely to occur even at low temperatures (77[K]), and the excited singlet state and the excited triplet state are mixed.

[1494] As a result, the spectrum measured as described above includes emission from both the excited singlet state and the excited triplet state; although it is difficult to distinguish which state emitted the light, it is considered that the triplet energy value is fundamentally dominant.

[1495] Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish that it is different in the strict sense, the value measured as follows is the energy gap T 77K It is called [this]. The compound to be measured is dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to serve as the measurement sample. For this measurement sample, the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 K), a tangent line is drawn on the rising short-wavelength side of the phosphorescence spectrum, and the wavelength λ at the intersection point of that tangent line and the horizontal axis edge Based on [nm], the energy amount calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K ...does as.

[1496] Conversion formula (F1): T 77K [eV]=1239.85 / λ edge

[1497] The tangent line for the rise on the short-wavelength side of the phosphorescence spectrum is drawn as follows. When moving along the spectrum curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum of the spectrum, the tangent line at each point on the curve toward the long-wavelength side is considered. The slope of this tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where the value of this slope takes a maximum (i.e., the tangent line at the inflection point) is designated as the tangent line for the rise on the short-wavelength side of the phosphorescence spectrum.

[1498] In addition, the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side mentioned above, and the tangent line drawn from the point closest to the maximum value on the shortest wavelength side, where the slope value takes a maximum value, is the tangent line for the rise on the short wavelength side of the phosphorescence spectrum.

[1499] For the measurement of phosphorescence, the main body of the F-4500 spectrofluorescence photometer manufactured by Hitachi High Technology Corporation may be used. In addition, the measuring device is not limited thereto, and measurement may also be performed by combining a cooling device and a low-temperature container with an excitation light source and a light receiving device.

[1500] ·Minimum here singlet energy S1

[1501] The following methods are used to measure the lowest excitation singlet energy S1 using a solution (sometimes called the solution method).

[1502] A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300K). A tangent line is drawn on the downward slope of the long wavelength side of this absorption spectrum, and the wavelength edge λedge [nm] at the intersection point of the tangent line and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the lowest excitation singlet energy.

[1503] Conversion formula (F2): S1[eV]=1239.85 / λedge

[1504] As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi (device name: U3310) can be cited, but is not limited to this.

[1505] The tangent line for the descent on the long-wavelength side of the absorption spectrum is drawn as follows. When moving along the spectrum curve in the long-wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum, consider the tangent line at each point on the curve. As the curve descends (i.e., as the value of the vertical axis decreases), the slope of this tangent line decreases and then increases repeatedly. The tangent line drawn at the point where the slope value takes a minimum value on the longest wavelength side (except when the absorbance becomes 0.1 or less) is defined as the tangent line for the descent on the long-wavelength side of the absorption spectrum.

[1506] In addition, maximum points with an absorbance value of 0.2 or less are not included in the maximum values ​​on the longest wavelength side.

[1507] · Method for preparing the second compound

[1508] The second compound according to the present embodiment can be prepared by using a known alternative reaction and raw materials suited to the target object, according to the synthesis method described in the example below, or according to the said synthesis method.

[1509] · Specific example of the second compound

[1510] Specific examples of the second compound of the present embodiment include, for instance, the following compounds. However, the present invention is not limited to specific examples of these compounds.

[1511] [Tue 110]

[1512]

[1513] [Tue 111]

[1514]

[1515] [Tue 112]

[1516]

[1517] [Tue 113]

[1518]

[1519] [Tue 114]

[1520]

[1521] (Relationship between the first compound and the second compound in the light-emitting layer)

[1522] In the organic EL device of the present embodiment, the lowest excitation singlet energy S1 (M1) of the first compound and the lowest excitation singlet energy S1 (M2) of the second compound satisfy the relationship of the above formula (Equation 1).

[1523] Energy gap T of the second compound at 77[K] 77K (M2) is the energy gap T of the first compound at 77[K]. 77K It is desirable that it be greater than (M1). That is, it is desirable to satisfy the relationship of the following formula (No. 5).

[1524] T 77K (M2)>T 77K (M1) … (number 5)

[1525] When the organic EL element of the present embodiment emits light, it is preferable that the first compound mainly emits light in the light-emitting layer.

[1526] ·TADF mechanism

[1527] FIG. 4 is a diagram illustrating an example of the relationship between the energy levels of the first compound and the second compound in the light-emitting layer. In FIG. 4, S0 represents the ground state. S1 (M2) represents the lowest excited singlet state of the second compound. T1 (M2) represents the lowest excited triplet state of the second compound. S1 (M1) represents the lowest excited singlet state of the first compound. T1 (M1) represents the lowest excited triplet state of the first compound.

[1528] The dashed arrow pointing from S1(M2) to S1(M1) in Fig. 4 indicates a Foerster-type energy transfer from the lowest excited singlet state of the second compound to the first compound.

[1529] As shown in FIG. 4, if a compound with a small ΔST (M2) is used as the second compound, the lowest excited triplet state T1 (M2) can be reversed to the lowest excited singlet state S1 (M2) by thermal energy. Then, a Foerster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of the second compound to the first compound, and the lowest excited singlet state S1 (M1) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of the first compound can be observed. It is thought that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence by this TADF mechanism.

[1530] It is preferable that the organic EL device of the present embodiment emits green light. When the organic EL device of the present embodiment emits green light, it is preferable that the maximum peak wavelength of the light emitted from the organic EL device is 500 nm or more and 560 nm or less.

[1531] The measurement of the maximum peak wavelength of light emitted from an organic EL device is performed as follows.

[1532] The spectroradiance spectrum of an organic EL element when voltage is applied to the element such that the current density is 10 mA / cm² is measured using a spectroradiance meter CS-2000 (manufactured by Konica Minolta).

[1533] In the obtained spectroscopic radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is set as the maximum peak wavelength (unit: nm).

[1534] · Film thickness of the light-emitting layer

[1535] The film thickness of the light-emitting layer in the organic EL device of the present embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the film thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and adjust the chromaticity, and if the film thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the rise in the driving voltage.

[1536] · Compound content in the light-emitting layer

[1537] The content of the first compound and the second compound included in the light-emitting layer is preferably, for example, within the following range.

[1538] The content of the second compound is preferably 10 mass% or more and 80 mass% or less, more preferably 10 mass% or more and 60 mass% or less, and even more preferably 20 mass% or more and 60 mass% or less. In addition, the content of the second compound may be 90 mass% or more and 99.9 mass% or less, 95 mass% or more and 99.9 mass% or less, or 99 mass% or more and 99.9 mass% or less.

[1539] The content of the first compound is preferably 0.01 mass% or more and 10 mass% or less, more preferably 0.01 mass% or more and 5 mass% or less, and even more preferably 0.01 mass% or more and 1 mass% or less.

[1540] In addition, the present embodiment does not exclude the inclusion of a material other than the first compound and the second compound in the light-emitting layer.

[1541] The light-emitting layer may include only one type of the first compound, or two or more types.

[1542] The light-emitting layer may include only one type of the second compound, or two or more types.

[1543] (Circuit board)

[1544] The substrate is used as a support for the organic EL device. For example, glass, quartz, plastic, etc., may be used as the substrate. Additionally, a flexible substrate may be used. A flexible substrate refers to a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. In addition, an inorganic deposition film may be used.

[1545] (anode)

[1546] 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, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[1547] These materials are typically formed by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1 mass% or more and 10 mass% or less of zinc oxide with respect to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass% or more and 5 mass% or less of tungsten oxide and 0.1 mass% or more and 1 mass% or less of zinc oxide with respect to indium oxide. Furthermore, they may be produced by vacuum deposition, coating, inkjet, spin coating, etc.

[1548] Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, so materials that are suitable as electrode materials (e.g., metals, alloys, electrically conductive compounds and mixtures thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[1549] Materials with a small work function, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals like lithium (Li) or cesium (Cs), alkaline earth metals like magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals like europium (Eu) and ytterbium (Yb), and alloys containing these may also be used. Furthermore, when forming an anode using alkali metals, alkaline earth metals, and alloys containing these, vacuum deposition or sputtering methods may be used. Additionally, when using silver paste, etc., coating methods or inkjet methods may be used.

[1550] (cathode)

[1551] 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.

[1552] In addition, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing them, vacuum deposition or sputtering methods may be used. In addition, when using silver paste, etc., coating methods or inkjet methods may be used.

[1553] In addition, by forming an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the magnitude of the work function. These conductive materials can be deposited using sputtering, inkjet, spin coating, etc.

[1554] (Hole injection layer)

[1555] 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, etc.

[1556] In addition, substances with high hole injection activity include low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated: DPA3B), and 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA1). Aromatic amine compounds such as 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated: PCzPCA2) and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated: PCzPCN1) can also be used.

[1557] In addition, polymer compounds (oligomers, dendrimers, polymers, etc.) may be used as materials with high hole injection properties. Examples include polymer compounds such as poly(N-vinylcarbazole) (abbreviated: PVK), poly(4-vinyltriphenylamine) (abbreviated: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated: PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated: Poly-TPD). Additionally, polymer compounds to which acids have been added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS), may also be used.

[1558] (Pure transport layer)

[1559] The hole transport layer is a layer containing a material with high hole transportability. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used for the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated: NPB) or N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviated: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated: MTDATA), Aromatic amine compounds such as 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviated: BSPB) can be used. The substances described herein are mainly 10 -6 It is a material having a hole mobility of ㎠ / (Vs) or more.

[1560] For the hole transport layer, carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used. Polymeric compounds such as poly(N-vinylcarbazole) (abbreviated: PVK) or poly(4-vinyltriphenylamine) (abbreviated: PVTPA) may also be used.

[1561] However, if the material has higher hole transport than electron transport, materials other than these may be used. Also, the layer containing the material with high hole transport may be a single layer, or a layer made of the above material may be a stack of two or more layers.

[1562] (Electron transport layer)

[1563] 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. Specifically, as low molecular weight organic compounds, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ may be used. In addition, in addition to metal complexes, 2-(4-biphenyll)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyll)-1,2,4-triazole (abbreviated: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyll)-1,2,4-triazole (abbreviated: p-EtTAZ), vasofenanthroline (abbreviated: BPhen), vasocuproin (abbreviated: BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated: Complex aromatic compounds such as BzOs) can also be used. The materials described herein are mainly 10 -6 It is a material having an electron mobility of cm² / (Vs) or higher. Additionally, if the material has higher electron transport than hole transport, other materials may be used as the electron transport layer. Furthermore, the electron transport layer may be a single layer, or a layer made of the above material may be a stack of two or more layers.

[1564] In addition, polymer compounds may be used for the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated: PF-BPy), etc. may be used.

[1565] (Electron injection layer)

[1566] The electron injection layer is a layer containing a material with high electron injection properties. In the electron injection layer, alkali metals, alkaline earth metals, or compounds thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), may be used. In addition, a material having electron transport properties may contain an alkali metal, an alkaline earth metal, or a compound thereof; specifically, a material containing magnesium (Mg) in Alq may be used. Furthermore, in this case, electron injection from the cathode can be performed more efficiently.

[1567] Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used in the electron injection layer. Since electrons are generated in the organic compound by the electron donor, such a composite material exhibits excellent electron injection and electron transport properties. In this case, it is desirable for the organic compound to be a material with excellent electron transport properties; specifically, for example, a material constituting the aforementioned electron transport layer (such as a metal complex or a complex aromatic compound) may be used. As for the electron donor, any material that exhibits electron-donating properties with respect to the organic compound is sufficient. Specifically, alkali metals, alkaline earth metals, or rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Additionally, alkali metal oxides or alkaline earth metal oxides are preferred, and examples include lithium oxide, calcium oxide, and barium oxide. Furthermore, Lewis bases such as magnesium oxide may be used. Additionally, organic compounds such as tetrathiafulvalene (abbreviated as TTF) may be used.

[1568] (Layer formation method)

[1569] As for the method of forming each layer of the organic EL device of the present embodiment, there are no limitations other than those specifically mentioned above, but known methods such as dry film deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, or wet film deposition methods such as spin coating, dipping, flow coating, and inkjet may be employed.

[1570] (Film thickness)

[1571] The film thickness of each organic layer of the organic EL device of the present embodiment is not limited except as specifically mentioned above, but generally, if the film thickness is excessively thin, defects such as pinholes are likely to occur, and conversely, if it is excessively thick, a high applied voltage is required and efficiency deteriorates, so a range of several nm to 1 μm is usually preferred.

[1572] According to the present embodiment, a high-performance organic EL device can be provided. Performance characteristics of the organic EL device include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. According to one aspect of the present embodiment, an organic EL device with a long lifespan can be provided. In addition, in one aspect of the organic EL device of the present embodiment, luminous efficiency is improved.

[1573] The organic EL element according to the present embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1574] [Second Embodiment]

[1575] (Organic Electroluminescence Device)

[1576] The configuration of an organic EL device according to a second embodiment is described. In the description of the second embodiment, components identical to those in the first embodiment are given the same reference numerals or names, and their descriptions are omitted or simplified. Additionally, in the second embodiment, for materials or compounds not specifically mentioned, materials or compounds identical to those described in the first embodiment may be used.

[1577] The organic EL device according to the second embodiment differs from the organic EL device according to the first embodiment in that the light-emitting layer further comprises a third compound. In other respects, it is identical to the first embodiment.

[1578] In the second embodiment, the light-emitting layer preferably comprises a first compound, a second compound, and a third compound. In this embodiment, the first compound is preferably a dopant material, and the second compound is preferably a host material. Additionally, the third compound is preferably not a dopant material. For example, the light-emitting layer of the second embodiment may contain the second compound and the third compound in total at least 50 mass% of the total mass of the light-emitting layer, and at least 60 mass% of the layer, at least 70 mass% of the layer, at least 80 mass% of the layer, at least 90 mass% of the layer, or at least 95 mass% of the layer.

[1579] (Third compound)

[1580] The third compound of the present embodiment may be a compound with heat-activated delayed fluorescence or a compound that does not exhibit heat-activated delayed fluorescence, but it is preferable that it be a compound that does not exhibit heat-activated delayed fluorescence.

[1581] The singlet energy S1 (M3) of the third compound and the singlet energy S1 (M2) of the second compound satisfy the relationship of the following formula (Equation 2).

[1582] S1(M3)>S1(M2) … (number 2)

[1583] As for the third compound, it is not particularly limited, but it is preferable that it be a compound other than an amine compound. That is, it is preferable that the third compound does not contain a substituted or unsubstituted amino group. In addition, for example, as the third compound, carbazole derivatives, dibenzofuran derivatives, and dibenzothiophene derivatives may be used, but are not limited to these derivatives.

[1584] It is also preferable that the third compound is a compound comprising at least one of the following substructures in one molecule, represented by the following general formula (31), the following substructure represented by the following general formula (32), the following substructure represented by the following general formula (33A), and the following substructure represented by the following general formula (34A).

[1585] [Tue 115]

[1586]

[1587] [Tuesday 116]

[1588]

[1589] In the above general formula (31),

[1590] Y 31 ~Y 36 Each is a carbon atom that independently bonds to a nitrogen atom or another atom in the molecule of the third compound, and

[1591] However, Y 31 ~Y 36 At least one of them is a carbon atom that bonds to another atom in the molecule of the third compound, and

[1592] In the above general formula (32),

[1593] Y 41 ~Y 48 Each is a carbon atom that independently bonds to a nitrogen atom or another atom in the molecule of the third compound, and

[1594] However, Y 41 ~Y 48 At least one of them is a carbon atom that bonds to another atom in the molecule of the third compound, and

[1595] X 30 It is a nitrogen atom, or an oxygen atom, or a sulfur atom that bonds with other atoms in the molecule of the third compound.

[1596] In the above general formulas (33A) and (34A), * each independently indicates a bonding location with another atom or other structure within the molecule of the third compound.

[1597] The third compound preferably has a total of 2 to 10 substructures represented by the general formula (31) and the general formula (32) in one molecule, and more preferably has 4 to 8 substructures.

[1598] In the above general formula (32), Y 41 ~Y 48 It is also desirable that at least two of them are carbon atoms that bond with other atoms in the molecule of the third compound, and that a ring structure containing said carbon atoms is constructed.

[1599] For example, it is preferable that the substructure represented by the above general formula (32) be any substructure selected from the group consisting of the substructures represented by the following general formulas (321), (322), (323), (324), (325) and (326).

[1600] [Tue 117]

[1601]

[1602] [Tuesday 118]

[1603]

[1604] [Tue 119]

[1605]

[1606] In the above general formulas (321) to (326),

[1607] X 30 Each is a nitrogen atom, or an oxygen atom, or a sulfur atom that is independently bonded to another atom in the molecule of the third compound, and

[1608] Y 41 ~Y 48Each is a carbon atom that independently bonds to a nitrogen atom or another atom in the molecule of the third compound, and

[1609] X 31 Each is independently a nitrogen atom, an oxygen atom, a sulfur atom, or a carbon atom that bonds to another atom in the molecule of the third compound, and

[1610] Y 61 ~Y 64 Each is a carbon atom that independently bonds with a nitrogen atom or another atom in the molecule of the third compound.

[1611] In this embodiment, the third compound preferably has a partial structure represented by the general formula (323) among the general formulas (321) to (326).

[1612] The substructure represented by the above general formula (31) is preferably included in the third compound as at least one group selected from the group consisting of the group represented by the following general formula (33) and the group represented by the following general formula (34).

[1613] It is also preferable that the third compound has at least one of the substructures represented by the following general formula (33) and the following general formula (34). Since the bonding sites are located at meta positions relative to each other, as in the substructures represented by the following general formulas (33) and (34), the energy gap T at 77[K] of the third compound 77K (M3) can be kept high.

[1614] [Tue 120]

[1615]

[1616] In the above general formula (33), Y 31 , Y 32 , Y 34 and Y 36 Silver, each independently, a nitrogen atom or CR31 am.

[1617] In the above general formula (34), Y 32 , Y 34 and Y 36 Silver, each independently, a nitrogen atom or CR 31 am.

[1618] In the above general formulas (33) and (34),

[1619] R 31 Each is independently a hydrogen atom or a substituent, and

[1620] R as a substituent 31 Each independently,

[1621] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1622] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[1623] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[1624] Substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms,

[1625] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[1626] Substituted or unsubstituted araclel groups having 7 to 30 carbon atoms,

[1627] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[1628] Substituted germanium group,

[1629] Substituted phosphine oxide group,

[1630] Halogen atoms,

[1631] Cyanogi,

[1632] Nitro group, and

[1633] Substituted or unsubstituted carboxyl group

[1634] It is selected from a group consisting of.

[1635] However, the above R 31 It is preferable that the aryl group having 6 to 30 carbon atoms forming a substituted or unsubstituted ring in the above be a non-condensed ring.

[1636] In the above general formula (33) and the above general formula (34), * each independently indicates a bonding location with another atom or other structure within the molecule of the third compound.

[1637] In the third compound, R 901 ~R 903 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.

[1638] In the above general formula (33), Y 31 , Y 32 , Y 34 and Y 36 uneun, each independently, CR 31 It is desirable that it is a plurality of R 31 They are identical or different from each other.

[1639] In addition, in the above general formula (34), Y 32 , Y 34 and Y 36 uneun, each independently, CR 31 It is desirable that it is a plurality of R 31 They are identical or different from each other.

[1640] The substituted germanium group is -Ge(R 301 It is preferable to represent it as )3. R 301 Each is an independent substituent. Substituent R 301 It is preferable that it be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Multiple R 301They are identical or different from each other.

[1641] The substructure represented by the above general formula (32) is preferably included in the third compound as at least one group selected from the group consisting of the following general formulas (35) to (39) and the following general formula (30a).

[1642] [Tue 121]

[1643]

[1644] [Tue 122]

[1645]

[1646] [Tue 123]

[1647]

[1648] In the above general formula (35), Y 41 to Y 48 Silver, each independently, a nitrogen atom or CR 32 am.

[1649] In the above general formulas (36) and (37), Y 41 ~Y 45 , Y 47 and Y 48 Silver, each independently, a nitrogen atom or CR 32 am.

[1650] In the above general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 and Y 48 Silver, each independently, a nitrogen atom or CR 32 am.

[1651] In the above general formula (39), Y 42 ~Y 48 Silver, each independently, a nitrogen atom or CR 32 am.

[1652] In the above general formula (30a), Y 42 ~Y47 Silver, each independently, a nitrogen atom or CR 32 am.

[1653] In the above general formulas (35) to (39) and (30a),

[1654] R 32 are, each independently, hydrogen atoms or substituents, and

[1655] R as a substituent 32 Is,

[1656] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1657] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[1658] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[1659] Substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms,

[1660] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[1661] Substituted or unsubstituted araclel groups having 7 to 30 carbon atoms,

[1662] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[1663] Substituted germanium group,

[1664] Substituted phosphine oxide group,

[1665] Halogen atoms,

[1666] Cyanogi,

[1667] Nitro group, and

[1668] Substituted or unsubstituted carboxyl group

[1669] Selected from a group consisting of,

[1670] Multiple R 32 are identical or different from each other.

[1671] In the above general formulas (37) to (39) and (30a),

[1672] X 30 Silver, NR 33 , is an oxygen atom or a sulfur atom,

[1673] R 33 silver,

[1674] Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,

[1675] Complex circulators with 5 to 30 substituent or unsubstituent ring-forming atoms,

[1676] Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[1677] Substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms,

[1678] Substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,

[1679] Substituted or unsubstituted araclel groups having 7 to 30 carbon atoms,

[1680] -Si(R 901 )(R 902 )(R 903 The one indicated by ),

[1681] Substituted germanium group,

[1682] Substituted phosphine oxide group,

[1683] Fluorine atom,

[1684] Cyanogi,

[1685] Nitro group, and

[1686] Substituted or unsubstituted carboxyl group

[1687] Selected from a group consisting of,

[1688] Multiple R 33 They are identical or different from each other.

[1689] However, the above R 33 It is preferable that the aryl group having 6 to 30 carbon atoms forming a substituted or unsubstituted ring in the above be a non-condensed ring.

[1690] In the above general formulas (35) to (39) and (30a), * each independently indicates a bonding location with another atom or other structure within the molecule of the third compound.

[1691] In the above general formula (35), Y 41 ~Y 48 uneun, each independently, CR 32 It is preferable that, in the above general formula (36) and the above general formula (37), Y 41 ~Y 45 , Y 47 and Y 48 uneun, each independently, CR 32 It is preferable that, in the above general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 and Y 48 uneun, each independently, CR 32 It is preferable that, in the above general formula (39), Y 42 ~Y 48 uneun, each independently, CR 32 It is preferable that, in the above general formula (30a), Y 42 ~Y 47 uneun, each independently, CR 32 It is desirable that it is a plurality of R 32 They are identical or different from each other.

[1692] In the third compound, X 30 It is preferable that it be silver, oxygen, or sulfur atoms.

[1693] In the third compound, R 31 and R 32 are, respectively, hydrogen atoms or substituents, and R as a substituent 31 and R as a substituent 32Preferably, each independently is any group selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted cyclic group having 5 to 30 atoms. R 31 and R 32 It is more preferable that is a hydrogen atom, a cyano group, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 30 atoms. However, R as a substituent 31 and R as a substituent 32 In the case where the aryl group is a substituted or unsubstituted ring-forming group having 6 to 30 carbon atoms, it is preferable that the aryl group be a non-condensed ring.

[1694] It is also preferable that the third compound be an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[1695] It is also preferable that the substituted phosphine oxide group be a substituted or unsubstituted diarylphosphine oxide group.

[1696] Specific examples of substituted or unsubstituted diarylphosphine oxide groups include diphenylphosphine oxide groups and ditolylphosphine oxide groups.

[1697] Examples of substituted carboxyl groups include, for instance, benzoyloxy groups.

[1698] · Method for preparing the third compound

[1699] The third compound can be prepared by methods described, for example, in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650, etc. Additionally, the third compound can be prepared by using known alternative reactions and raw materials suited to the target product, for example.

[1700] · Specific example of the third compound

[1701] Specific examples of the third compound according to the present embodiment are shown below. Furthermore, the third compound in the present invention is not limited to these specific examples.

[1702] [Tue 124]

[1703]

[1704] [Tue 125]

[1705]

[1706] [Tuesday 126]

[1707]

[1708] [Tue 127]

[1709]

[1710] (Relationship between the first, second, and third compounds in the light-emitting layer)

[1711] In the organic EL device of the present embodiment, the lowest excitation singlet energy S1 (M2) of the second compound and the lowest excitation singlet energy S1 (M3) of the third compound satisfy the relationship of the following formula (Equation 2).

[1712] Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T of the first compound at 77[K]. 77K It is desirable that it be larger than (M1).

[1713] Energy gap T at 77[K] of the third compound 77K (M3) is the energy gap T of the second compound at 77[K]. 77K It is desirable that it be larger than (M2).

[1714] It is desirable that the lowest excitation singlet energy S1 (M1) of the first compound, the lowest excitation singlet energy S1 (M2) of the second compound, and the lowest excitation singlet energy S1 (M3) of the third compound satisfy the relationship of the following formula (Equation 2A).

[1715] S1(M3)>S1(M2)>S1(M1) … (number 2A)

[1716] Energy gap T of the first compound at 77[K] 77K (M1) and the energy gap T of the second compound at 77[K] 77K (M2) and the energy gap T of the third compound at 77[K] 77K (M3) is desirable to satisfy the relationship of the following formula (2B).

[1717] T 77K (M3)>T 77K (M2)>T 77K (M1) … (Number 2B)

[1718] When the organic EL element of the present embodiment emits light, it is preferable that the first compound emits light in the light-emitting layer.

[1719] It is preferable that the organic EL element of the present embodiment emits green light, just like the organic EL element of the first embodiment.

[1720] When the organic EL element of the present embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less.

[1721] The maximum peak wavelength of light emitted from the organic EL element can be measured in the same way as the organic EL element of the first embodiment.

[1722] · Compound content in the light-emitting layer

[1723] When the light-emitting layer comprises a first compound, a second compound, and a third compound, the content of the first compound, the second compound, and the third compound in the light-emitting layer is preferably within the following range, for example.

[1724] The content of the first compound is preferably 0.01 mass% or more and 10 mass% or less, more preferably 0.01 mass% or more and 5 mass% or less, and even more preferably 0.01 mass% or more and 2 mass% or less.

[1725] The content of the second compound is preferably 10 mass% or more and 80 mass% or less, more preferably 10 mass% or more and 60 mass% or less, and even more preferably 20 mass% or more and 60 mass% or less.

[1726] It is preferable that the content of the third compound be 10 mass% or more and 80 mass% or less.

[1727] The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass%. In addition, the present embodiment does not exclude the inclusion of materials other than the first compound, the second compound, and the third compound in the light-emitting layer.

[1728] The emitting layer may include only one type of the first compound or two or more types. The emitting layer may include only one type of the second compound or two or more types. The emitting layer may include only one type of the third compound or two or more types.

[1729] FIG. 5 is a diagram illustrating an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of the first compound, and T1 (M1) represents the lowest excited triplet state of the first compound. S1 (M2) represents the lowest excited singlet state of the second compound, and T1 (M2) represents the lowest excited triplet state of the second compound. S1 (M3) represents the lowest excited singlet state of the third compound, and T1 (M3) represents the lowest excited triplet state of the third compound. The dashed arrow pointing from S1 (M2) to S1 (M1) in FIG. 5 indicates a Foerster-type energy shift from the lowest excited singlet state of the second compound to the first compound.

[1730] As illustrated in FIG. 5, if a compound with a small ΔST (M2) (a delayed fluorescence emitting material) is used as the second compound, the lowest excited triplet state T1 (M2) can be reversed to the lowest excited singlet state S1 (M2) by thermal energy. Then, a Foerster-type energy transfer occurs from the lowest excited singlet state S1 (M2) of the second compound to the first compound, and the lowest excited singlet state S1 (M1) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (M1) of the first compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence through this TADF mechanism.

[1731] According to the present embodiment, a high-performance organic EL device can be provided. Performance characteristics of the organic EL device include, for example, brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. According to one aspect of the present embodiment, an organic EL device with a long lifespan can be provided. In addition, in one aspect of the organic EL device of the present embodiment, luminous efficiency is improved.

[1732] The organic EL element according to the present embodiment can be used in electronic devices such as display devices and light-emitting devices.

[1733] [Third Embodiment]

[1734] (Electronic devices)

[1735] The electronic device according to the present embodiment is equipped with any organic EL element of the above-described embodiment. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules, etc.), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lighting fixtures.

[1736] [Change of Embodiment]

[1737] Meanwhile, the present invention is not limited to the aforementioned embodiments, and modifications, improvements, etc. within the scope of achieving the purpose of the present invention are included in the present invention.

[1738] For example, the light-emitting layer is not limited to a single layer, but may have multiple light-emitting layers stacked. When an organic EL device has multiple light-emitting layers, at least one organic layer satisfies the conditions described in the above embodiment, and it is preferable that at least one light-emitting layer contains the compound of the first embodiment. When one of the multiple light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer utilizing light emission by electron transition from a triplet excited state to a ground state.

[1739] In addition, when the organic EL device has a plurality of light-emitting layers, these light-emitting layers may be formed adjacent to each other, or it may be a so-called tandem type organic EL device in which a plurality of light-emitting units are stacked through an intermediate layer.

[1740] In addition, a barrier layer may be formed adjacent to, for example, at least one side of the anode and cathode of the light-emitting layer. The barrier layer is positioned in contact with the light-emitting layer and is preferably configured to block at least one of holes, electrons, and excitons.

[1741] For example, when a barrier layer is disposed in contact with the cathode side of the light-emitting layer, said barrier layer transports electrons and also prevents holes from reaching the layer on the cathode side (e.g., electron transport layer) above said barrier layer. When an organic EL device includes an electron transport layer, it is preferable to include said barrier layer between the light-emitting layer and the electron transport layer.

[1742] In addition, when a barrier layer is disposed in contact with the anode side of the light-emitting layer, said barrier layer transports holes and also prevents electrons from reaching the layer on the anode side of said barrier layer (e.g., a hole transport layer). When an organic EL device includes a hole transport layer, it is preferable to include said barrier layer between the light-emitting layer and the hole transport layer.

[1743] In addition, a barrier layer may be formed adjacent to the emissive layer to prevent excitation energy from leaking from the emissive layer to the surrounding layers. This prevents excitons generated in the emissive layer from moving to the electrode-side layer (e.g., electron transport layer and hole transport layer, etc.) relative to the barrier layer.

[1744] It is desirable for the light-emitting layer and the barrier layer to be bonded together.

[1745] Furthermore, specific structures and shapes in the implementation of the present invention may be other structures, etc., within the scope of achieving the purpose of the present invention.

[1746] Examples

[1747] Hereinafter, embodiments according to the present invention will be described. The present invention is not limited in any way by these embodiments.

[1748] <Compounds>

[1749] The structure of the compound represented by general formula (1) used in the manufacture of organic EL devices according to Examples 1 to 2 and Examples 2-1 to 2-8 is shown below.

[1750] [Tuesday 128]

[1751]

[1752] The structures of the comparative compounds used in the manufacture of organic EL devices according to Comparative Examples 1 to 3 and Comparative Example 2-1 are shown below.

[1753] [Tue 129]

[1754]

[1755] The structure of the compound represented by general formula (2) used in the manufacture of organic EL devices according to Examples 1 to 2 and Examples 2-1 to 2-8 is shown below.

[1756] [Tue 130]

[1757]

[1758] [Tue 131]

[1759]

[1760] The structures of other compounds used in the manufacture of organic EL devices according to Examples 1 to 2, Examples 2-1 to 2-8, Comparative Examples 1 to 3, and Comparative Example 2-1 are shown below.

[1761] [Tue 132]

[1762]

[1763] [Tue 133]

[1764]

[1765] [Tue 134]

[1766]

[1767] [Tue 135]

[1768]

[1769] [Tue 136]

[1770]

[1771] [Tue 137]

[1772]

[1773] Fabrication of Organic EL Devices

[1774] An organic EL device was fabricated and evaluated as follows.

[1775] (Example 1)

[1776] 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 1 minute. The ITO film thickness was set to 130 nm.

[1777] The glass substrate having a transparent electrode line after cleaning was mounted in a substrate holder of a vacuum deposition apparatus, and a transparent electrode was placed over the side on which the transparent electrode line is formed to co-deposit compound HT1 and compound HA, thereby forming a hole injection layer with a film thickness of 10 nm. The concentration of compound HT1 in the hole injection layer was set to 97 mass%, and the concentration of compound HA was set to 3 mass%.

[1778] Next, compound HT1 was deposited on the hole injection layer to form a first hole transport layer with a film thickness of 110 nm.

[1779] Next, compound HT2 was deposited on this first hole transport layer to form a second hole transport layer with a film thickness of 5 nm.

[1780] Next, a compound CBP was deposited on this second hole transport layer to form an electronic barrier layer with a thickness of 5 nm.

[1781] Next, on this electron barrier layer, compounds Matrix-1 and Matrix-2 as third compounds, TADF-1 as second compounds, and GD-1 as first compounds were co-deposited to form an emissive layer with a thickness of 25 nm. In the emissive layer, the concentration of compound Matrix-1 was set to 24 mass%, the concentration of compound Matrix-2 to 25 mass%, the concentration of compound TADF-1 to 50 mass%, and the concentration of compound GD-1 to 1 mass%.

[1782] Next, the compound HBL was deposited on this emissive layer to form a hole barrier layer with a thickness of 5 nm.

[1783] Next, compound ET was deposited on this hole barrier layer to form an electron transport layer with a thickness of 50 nm.

[1784] Next, lithium fluoride (LiF) was deposited on this electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1785] Then, metallic aluminum (Al) was deposited on this electron-injectable electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1786] The approximate configuration of the organic EL device according to Example 1 is as follows.

[1787] ITO(130) / HT1:HA(10,97%:3%) / HT1(110) / HT2(5) / CBP(5) / Matrix-1:Matrix-2:TADF-1:GD-1(25,24%:25%:50%:1%) / HBL(5) / ET(50) / LiF(1) / Al(80)

[1788] Also, the number in parentheses indicates the film thickness (unit: nm).

[1789] Likewise, within parentheses, the percentage numbers (97%:3%) represent the ratio (mass%) of Compound HT1 and Compound HA in the hole injection layer, and the percentage numbers (24%:25%:50%:1%) represent the ratio (mass%) of Compound Matrix-1, Compound Matrix-2, Compound TADF-1, and Compound GD-1 in the emissive layer. The same notation will be used hereinafter.

[1790] (Example 2)

[1791] The organic EL device according to Example 2 was prepared in the same manner as Example 1, except that the compound GD-1 in the light-emitting layer of Example 1 was changed to the first compound listed in Table 1.

[1792] (Comparative Examples 1–3)

[1793] The organic EL devices according to Comparative Examples 1 to 3 were each manufactured in the same manner as Example 1, except that the compound GD-1 in the light-emitting layer of Example 1 was changed to the first compound listed in Table 1.

[1794] (Example 2-1)

[1795] 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 1 minute. The ITO film thickness was set to 130 nm.

[1796] The glass substrate having a transparent electrode line after cleaning was mounted in a substrate holder of a vacuum deposition apparatus, and a transparent electrode was placed over the side on which the transparent electrode line is formed to co-deposit compound HT3 and compound HA, thereby forming a hole injection layer with a film thickness of 10 nm. The concentration of compound HT3 in the hole injection layer was set to 97 mass%, and the concentration of compound HA was set to 3 mass%.

[1797] Next, compound HT3 was deposited on this hole injection layer to form a hole transport layer with a film thickness of 90 nm.

[1798] Next, compound HT4 was deposited on this hole transport layer to form an electronic barrier layer with a thickness of 30 nm.

[1799] Next, compound Matrix-3 as the third compound, compound TADF-1 as the second compound, and compound GD-2 as the first compound were co-deposited on this electron barrier layer to form an emissive layer with a film thickness of 25 nm. The concentration of compound Matrix-3 in the emissive layer was set to 71.2 mass%, the concentration of compound TADF-1 to 28 mass%, and the concentration of compound GD-2 to 0.8 mass%.

[1800] Next, compound ET2 was deposited on this emissive layer to form a hole barrier layer with a thickness of 5 nm.

[1801] Next, compound ET3 and Liq were co-deposited on this hole barrier layer to form an electron transport layer with a thickness of 50 nm. The concentration of compound ET3 in the electron transport layer was set to 50 mass%, and the concentration of Liq was set to 50 mass%. Meanwhile, Liq is an abbreviation for (8-quinolinolato)lithium.

[1802] Next, ytterbium (Yb) was deposited on this electron transport layer to form an electron injection electrode (cathode) with a film thickness of 1 nm.

[1803] Then, metallic aluminum (Al) was deposited on this electron-injectable electrode to form a metallic Al cathode with a film thickness of 80 nm.

[1804] The approximate configuration of the organic EL device according to Example 2-1 is as follows.

[1805] ITO(130) / HT3:HA(10,97%:3%) / HT3(90) / HT4(30) / Matrix-3:TADF-1:GD-2(25,71.2%:28%:0.8%) / ET2(5) / ET3:Liq(50,50%:50%) / Yb(1) / Al(80)

[1806] (Examples 2-2 to 2-8)

[1807] The organic EL devices according to Examples 2-2 to 2-8 were each manufactured in the same manner as Example 2-1, except that the compound TADF-1 in the light-emitting layer of Example 2-1 was changed to the second compound listed in Table 2.

[1808] (Comparative Example 2-1)

[1809] The organic EL device according to Comparative Example 2-1 was prepared in the same manner as Example 2-5, except that the compound GD-2 in the light-emitting layer of Example 2-5 was changed to the first compound listed in Table 2.

[1810] Evaluation of Organic EL Devices

[1811] The following evaluations were performed on the fabricated organic EL devices. The evaluation results are shown in Tables 1 and 2. In addition, the singlet energy S1 of the first compound, the second compound, and the third compound used in the light-emitting layer of each example is also shown in Table 1 or Table 2.

[1812] (Maximum peak wavelength λ p and luminescence full width at half maximum (FWHM)

[1813] The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation) when a voltage was applied to the fabricated organic EL device to achieve a current density of 10 mA / cm². From the obtained spectral radiance spectrum, the maximum peak wavelength λ p (Unit: nm) and emission full width at half maximum (FWHM) (Unit: nm) were calculated.

[1814] (Lifespan LT95)

[1815] A voltage was applied to the fabricated organic EL device such that the current density was 50 mA / cm², and the time until the brightness reached 95% of the initial brightness (LT95 (unit: hours)) was measured as the lifetime. The brightness was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation).

[1816] "LT95 (relative value)" in Table 1 is the measured value of LT95 for each example (Example 1 to Example 2 and Comparative Examples 1 to 3) and the value calculated by the following formula (No. 1X).

[1817] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 … (numerical value 1X)

[1818] "LT95 (relative value)" in Table 2 is the measured value of LT95 for each example (Example 2-1 to Example 2-8 and Comparative Example 2-1) and the relative value calculated by the following formula (2X).

[1819] LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 2-1) × 100 … (numerical value 2X)

[1820] (External Quantum Efficiency EQE)

[1821] The spectroradiance spectrum of the fabricated organic EL device was measured using a spectroradiance meter CS-2000 (manufactured by Konica Minolta Corporation) when a voltage was applied such that the current density was 10 mA / cm². From the obtained spectroradiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming Lambertian radiation was performed. Table 2 shows the "EQE" (unit: %) as a relative value.

[1822] "EQE (relative value)" in Table 2 is a relative value calculated based on the measured EQE of each example (Examples 2-1 to 2-8 and Comparative Example 2-1) and the following formula (3X).

[1823] EQE (relative value) = (EQE of each example / EQE of Comparative Example 2-1) × 100 … (3X)

[1824] (CIE1931 Color)

[1825] The CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the fabricated organic EL element such that the current density was 10 mA / cm² were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta Corporation).

[1826] (Driving voltage)

[1827] The voltage (unit: V) was measured when current was passed between the anode and cathode of an organic EL device fabricated to have a current density of 10 mA / cm².

[1828]

[1829]

[1830] Evaluation of Compounds

[1831] (Thermal-activated delayed fluorescence)

[1832] · Delayed fluorescence of compound TADF-1

[1833] Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Fig. 2. The compound TADF-1 was dissolved in toluene, and a dilute solution with an absorbance of 0.05 or less at the excitation wavelength was prepared to eliminate the contribution of self-absorption. In addition, to prevent quenching by oxygen, the sample solution was frozen and degassed, and then sealed in a covered cell under an argon atmosphere to make an oxygen-free sample solution saturated with argon.

[1834] The fluorescence spectrum of the above sample solution was measured using a spectrofluorescence spectrophotometer FP-8600 (manufactured by Nippon Bunko Co., Ltd.), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensity of both spectra, the total fluorescence quantum yield was calculated by equation (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[1835] After being excited by pulsed light of a wavelength absorbed by the compound TADF-1 (light irradiated from a pulsed laser), there exists Prompt emission (immediate emission) observed immediately from the excited state, and Delay emission (delayed emission) observed subsequently, rather than immediately after excitement. In this embodiment, delayed fluorescence emission means that the amount of Delay emission is 5% or more relative to the amount of Prompt emission. Specifically, the amount of Prompt emission is X P Let it be, and the amount of delay emission (delayed emission) be X D When done as, X D / X P It means that the value of is 0.05 or higher.

[1836] The amount of Prompt light emission and Delay light emission and their ratio can be obtained using the same method described in “Nature 492, 234-238, 2012” (Reference 1). In addition, the device used to calculate the amount of Prompt light emission and Delay light emission is not limited to the device described in Reference 1 or the device described in FIG. 2.

[1837] For compound TADF-1, it was confirmed that the amount of delay emission (delayed emission) was 5% or more of the amount of prompt emission (immediate emission).

[1838] Specifically, regarding compound TADF-1, X D / X P It was confirmed that the value of is 0.05 or higher.

[1839] For compounds TADF-2 to TADF-8 as well, the results of measurements performed in the same manner as for compound TADF-1 showed that X of compounds TADF-2 to TADF-8 D / X P The values ​​of were each greater than or equal to 0.05.

[1840] (Singlet energy S1)

[1841] The singlet energy S1 of compounds Matrix-1, Matrix-2, Matrix-3, compounds TADF-1 to TADF-8, compounds GD-1, GD-2, comparative compounds Ref-1, Ref-2, and Ref-3 was measured by the aforementioned solution method. The measurement results are shown in Table 1 or Table 2.

[1842] (ΔST)

[1843] T of compounds TADF-1 to TADF-8 77K T of compounds TADF-1 to TADF-8 was measured. 77K is the energy gap T described in the aforementioned "Relationship between triplet energy and the energy gap at 77[K]". 77K It was measured by the measurement method.

[1844] Measured lowest excitation singlet energy S1 and energy gap T at 77[K] 77K Based on this, the ΔST of compounds TADF-1 to TADF-8 was calculated. The ΔST values ​​of compound TADF-1 are shown in Table 1 or Table 2. In the table, the notation "<0.01" indicates that the ΔST is less than 0.01 eV.

[1845] (Maximum peak wavelength λ of the compound)

[1846] A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the fluorescence spectrum of the sample (vertical axis: fluorescence emission intensity, horizontal axis: wavelength) was measured at room temperature (300 K). In this example, the fluorescence spectrum was measured using a spectrofluorescence photometer manufactured by Hitachi (device name: F-7000). Furthermore, the fluorescence spectrum measurement device is not limited to the device used herein. In the fluorescence spectrum, the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum was set to the maximum peak wavelength λ of the compound.

[1847] Synthesis of Compounds

[1848] (Synthesization Example 1) Synthesis of Compound TADF-1

[1849] The synthesis method of compound TADF-1 is described below.

[1850] [Tue 138]

[1851]

[1852] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (50 g, 184 mmol), chlorotrimethylsilane (60 g, 552 mmol), and THF (200 mL) were added to a 1000 ml three-necked flask. In a dry ice / acetone bath, the material in the three-necked flask was cooled to -78°C, and then 230 ml of lithium diisopropylamide (2 M, THF solution) was added dropwise. The mixture was stirred at -78°C for 2 hours, then returned to room temperature and stirred for another 2 hours. After stirring, water (200 mL) was added to the three-necked flask, the organic layer was extracted with ethyl acetate, the extracted organic layer was washed with water and saline solution, dried with magnesium sulfate, and then the solvent was removed under reduced pressure using a rotary evaporator. The obtained intermediate M11 (73 g, 175 mmol, yield 95%) was used in the following reaction without purification. Chlorotrimethylsilane is sometimes abbreviated as TMS-Cl. In the chemical formula of intermediate M11, TMS is a trimethylsilyl group. LDA is an abbreviation for lithium diisopropyl amide.

[1853] Under a nitrogen atmosphere, intermediate M11 (73 g, 175 mmol) and dichloromethane (200 mL) were placed in a 1000 mL branched flask. Iodine monochloride (85 g, 525 mmol) was dissolved in dichloromethane (200 mL), added dropwise at 0°C, and stirred at 40°C for 4 hours. After stirring, the mixture was returned to room temperature, saturated sodium bisulfite aqueous solution (100 mL) was added, and the organic layer was extracted with dichloromethane. The extracted organic layer was washed with water and saline solution, the organic layer after washing was dried with magnesium sulfate, and the dried organic layer was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate M12 (65 g, 124 mmol, yield 71%).

[1854] Under a nitrogen atmosphere, intermediate M12 (22 g, 42 mmol), phenylboronic acid (12.8 g, 105 mmol), palladium acetate (0.47 g, 2.1 mmol), sodium carbonate (22 g, 210 mmol), and methanol (150 mL) were added to a 500 mL three-necked flask and stirred at 80°C for 4 hours. After stirring, the reaction solution was cooled to room temperature, then the organic layer was extracted with ethyl acetate, the extracted organic layer was washed with water and saline solution, and the organic layer after washing was concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain intermediate M13 (10 g, 24 mmol, yield 56%). In addition, the structure of the purified compound was identified by ASAP / MS. ASAP / MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[1855] Under a nitrogen atmosphere, intermediate M13 (10 g, 24 mmol), copper cyanide (10.6 g, 118 mmol), and DMF (15 mL) were placed in a 200 mL three-necked flask and heated and stirred at 150°C for 8 hours. After stirring, the mixture was cooled to room temperature, and the reaction solution was poured into 10 mL of ammonia water. Subsequently, the organic layer was extracted with methylene chloride, the extracted organic layer was washed with water and saline solution, and the washed organic layer was dried with magnesium sulfate. After drying, the solvent was removed under reduced pressure using a rotary evaporator, and the compound obtained after removal under reduced pressure was purified by silica gel column chromatography to obtain intermediate M14 (5.8 g, 18.34 mmol, yield 78%). DMF is an abbreviation for N,N-dimethylformamide.

[1856] Under a nitrogen atmosphere, intermediate M14 (1.0 g, 3.2 mmol), 12H-[1]benzothieno[2,3-a]carbazole (1.9 g, 7 mmol), potassium carbonate (1.3 g, 9.50 mmol), and 30 mL of DMF were added to a 100 mL three-necked flask and stirred at 120 °C for 6 hours. After stirring, the precipitated solid was filtered and purified by silica gel column chromatography to obtain compound TADF-1 (1.8 g, 2.2 mmol, yield 69%). The obtained compound was identified as compound TADF-1 by ASAP-MS analysis.

[1857] (Synthesization Example 2) Synthesis of Compound GD-1

[1858] The synthesis method of compound GD-1 is described below.

[1859] [Manufacture of Intermediate M21]

[1860] [Tue 139]

[1861]

[1862] Under an argon atmosphere, a mixture of 2-bromo-1,3-difluoro-5-iodobenzene (47.8 g), phenylboronic acid (18.29 g), tripotassium phosphate (39.8 g), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.09 g), 1,4-dioxane (250 mL), and water (125 mL) was stirred at room temperature for 4 hours. Toluene (250 mL) and water (200 mL) were added to the resulting mixture, the aqueous layer was extracted with toluene, the organic layer was washed with saturated saline solution, dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography to obtain 35.1 g (87%) of intermediate M21. In the reaction equation, Pd(dppf)Cl2 is [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[1863] [Manufacture of Intermediate M22]

[1864] [Tue 140]

[1865]

[1866] Under a nitrogen atmosphere, a mixture of intermediate M21 (2.69 g), benzo[b]carbazole (4.34 g), tripotassium phosphate (12.7 g), and dimethylformamide (50 mL) was stirred at 140°C for 3.5 hours. After cooling to room temperature, the mixture was added to water (200 mL), and the precipitated solid was separated by filtration and washed with water. The obtained solid was dissolved in dichloromethane, adsorbed onto silica gel, and purified by silica gel column chromatography to obtain 3.16 g (yield 47%) of intermediate M22. In the reaction scheme, DMF is dimethylformamide.

[1867] [Preparation of Compound GD-1]

[1868] [Tue 141]

[1869]

[1870] Under an argon atmosphere, intermediate M22 (1.2 g) was added to t-butylbenzene (18 mL) and cooled to 0°C, after which 1.9 M t-butyllithium pentane solution (1.9 mL) was added dropwise. After adding, the temperature was raised to 45°C and stirred for 15 minutes, then the reaction mixture was cooled to -55°C, boron tribromide (0.43 mL) was added, and the temperature was raised to room temperature and stirred for 1 hour. Afterward, the temperature was cooled to 0°C, N,N-diisopropylethylamine (0.79 mL) was added, and the mixture was stirred at room temperature until the exothermic reaction was contained, then the temperature was raised to 145°C and stirred for 2.5 hours. After cooling to room temperature, a 1 N aqueous potassium acetate solution was added, and the precipitated solid was filtered and washed with water and ethanol. The solid obtained by filtration was suspended in methylene chloride, and after filtering the solid, it was further washed with methylene chloride to obtain 527 mg (yield 49%) of an orange solid. As a result of mass spectrum analysis, this orange solid was identified as the target product (compound GD-1), with a molecular weight of 592.51 and a value of 593.3 [M+H] + It was. In the reaction equation, t-BuLi is tert-butyllithium and DIPEA is N,N-diisopropylethylamine.

[1871] (Synthesization Example 3) Synthesis of Compound GD-2

[1872] The method for synthesizing compound GD-2 is described below.

[1873] [Manufacture of Intermediate M23]

[1874] [Tue 142]

[1875]

[1876] Under an argon atmosphere, a mixture of 2-amino-3-iodonaphthalene (4.28 g), 1,2-diphenylacetylene (3.40 g), palladium(II) acetate (178 mg), tricyclohexylphosphine (446 mg), potassium carbonate (5.49 g), and N-methylpyrrolidone (360 mL) was stirred at 110°C for 5 hours. The resulting mixture was cooled to room temperature (25°C), and after removing some of the N-methylpyrrolidone by vacuum distillation, it was diluted with t-butylmethyl ether and added to water. The aqueous layer was extracted with t-butylmethyl ether, the organic layer was washed with saturated saline solution, dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography to obtain 2.78 g (55%) of intermediate M23. In the reaction equation, Pd(OAc)2 is palladium acetate (II), Cy3P is tricyclohexylphosphine, and NMP is N-methylpyrrolidone.

[1877] [Manufacture of Intermediate M24]

[1878] [Tue 143]

[1879]

[1880] Under an argon atmosphere, a mixture of 2-bromo-1,3-difluoro-5-iodobenzene (47.8 g), phenylboronic acid (18.29 g), tripotassium phosphate (39.8 g), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.09 g), 1,4-dioxane (250 mL), and water (125 mL) was stirred at room temperature for 4 hours. Toluene (250 mL) and water (200 mL) were added to the resulting mixture, the aqueous layer was extracted with toluene, the organic layer was washed with saturated saline solution, dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography to obtain 35.1 g (87%) of intermediate M24. In the reaction equation, Pd(dppf)Cl2 is [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride.

[1881] [Manufacture of Intermediate M25]

[1882] [Tue 144]

[1883]

[1884] Under an argon atmosphere, a mixture of intermediate M23 (6.39 g), intermediate M24 (10.76 g), tripotassium phosphate (21.23 g), and dimethylformamide (140 mL) was stirred at 105°C for 48 hours. After removing some of the dimethylformamide by vacuum distillation, the mixture was added to water and extracted with t-butylmethyl ether. The organic layer was washed with saturated saline solution, dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The resulting residue was purified by silica gel column chromatography to obtain 6.2 g (55%) of intermediate M25. In the reaction scheme, DMF is dimethylformamide.

[1885] [Manufacture of Intermediate M26]

[1886] [Tue 145]

[1887]

[1888] Under an argon atmosphere, a mixture of intermediate M25 (6.14 g), 3,6-di-tert-butyl-9H-carbazole (3.32 g), tripotassium phosphate (6.88 g), and dimethylformamide (96 mL) was stirred at 105°C for 20 hours. A portion of the dimethylformamide was removed by vacuum distillation, and the resulting mixture was added to 150 mL of water and stirred. The precipitated solid was filtered, washed with water, and then dried under vacuum. Additionally, the obtained solid was suspended in 220 mL of ethanol and heated under reflux for 1 hour; by filtering the solid, 7.31 g (82%) of intermediate M26 was obtained.

[1889] [Preparation of Compound GD-2]

[1890] [Tue 146]

[1891]

[1892] Under an argon atmosphere, intermediate M26 (2.23 g) was added to tert-butylbenzene (33 mL) and cooled to -20°C, after which 1.9 M tert-butyllithium-pentane solution (2.8 mL) was added dropwise. After adding, the temperature was raised to 70°C and stirred for 30 minutes, after which components with a lower boiling point than tert-butylbenzene were removed by vacuum distillation. The mixture was cooled to -55°C, boron tribromide (0.57 mL) was added, and the temperature was raised to room temperature and stirred for 1 hour. Afterward, the mixture was cooled to 0°C, N,N-diisopropylethylamine (1.19 mL) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided, after which the temperature was raised to 130°C and stirred overnight. After removing tert-butylbenzene by vacuum distillation, the residue was purified by flash chromatography to obtain 350 mg of an orange compound. This orange compound is the target (compound GD-2) as a result of mass spectrum analysis, with a molecular weight of 756.8 and 757.4 [M+H] + It was. In the reaction equation, t-BuLi is tert-butyllithium and DIPEA is N,N-diisopropylethylamine. Explanation of the symbols

[1893] 1… Organic EL device, 2… Substrate, 3… Anode, 4… Cathode, 5… Emitting layer, 6… Hole injection layer, 7… Hole transport layer, 8… Electron transport layer, 9… Electron injection layer.

Claims

Claim 1 An organic electroluminescence device having an anode, a cathode, and a light-emitting layer included between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by the following general formula (1) and a second compound having delayed fluorescence represented by the following general formula (210), general formula (220), or general formula (230), and wherein the singlet energy S1(M1) of the first compound and the singlet energy S1(M2) of the second compound satisfy the relationship of the following formula (Formula 1). S1(M2) > S1(M1) … (Formula 1) (In the above general formula (1), ring A, ring B, ring D, ring E and ring F are each independently ring structures selected from the group consisting of a substituted or unsubstituted ring-forming aryl ring having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming heterocyclic ring having 5 to 30 atoms, and if ring D is present, or if both ring B and ring D are present, and if both ring B and ring D are present, ring B and ring D share a bond connecting Zc and Zh, and if ring E is present, or if both ring E and ring F are present, and if both ring E and ring F are present, ring E and ring F share a bond connecting Zf and Zi, and at least one selected from the group consisting of ring A, ring D and ring E is a 1-naphthyl group, a 2-naphthyl group, anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, It is an aryl ring excluding the bonding hand from an aryl group selected from the group consisting of crisenyl, benzocrisenyl, triphenylenyl, benzotriphenylenyl, tetracenyl, pentacenyl, fluoranthenyl, benzofluranthenyl, and perylenyl groups, or a pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isooxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazolyl, indolyl, isoindolyl, indolizinyl, quinolidinyl, quinolyl, isoquinolidinyl, cinolyl, phthalazinyl, quinazolinyl, Quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenanthridinyl group, acrridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, azacarbazolyl group, diazazolyl group, furyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisooxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, diazanaphthobenzofuranyl group,A heterocyclic group selected from the group consisting of thienyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzothiazolyl, benzisothiazolyl, phenothiazinyl, dinaphthiophenyl, azadibenzothiophenyl, diazadibenzothiophenyl, azanaphthobenzothiophenyl, and diazanaphthobenzothiophenyl, excluding bonding hands, wherein these aryl rings and heterocyclic groups have substituents or are unsubstituted, and Za is a nitrogen atom or a carbon atom, Zb is a nitrogen atom or a carbon atom if ring B is present, and an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4) if ring B is absent, Zc is a nitrogen atom or a carbon atom, and Zd is a nitrogen atom or a carbon Atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is a nitrogen atom or a carbon atom if ring F is present, and an oxygen atom or a sulfur atom if ring F is absent, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom or a phosphorus atom, SiRh, P=O or P=S, Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh are each independently a hydrogen atom or a substituent, and Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh as substituents are each independently a substituted or unsubstituted ring-forming atom with 6 to 30 carbon atoms. Aryl group, substituted or unsubstituted ring-forming heterocyclic group with 5–30 atoms, substituted or unsubstituted alkyl group with 1–30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl group with 3–30 carbon atoms, -Si(R, 911 )(R 912 )(R 913 The unit indicated by ), -O-(R 914 The unit indicated by ), -S-(R 915 The unit indicated by ), or -N(R 916 )(R 917 It is a group represented by ), provided that the bond between Y and Za, the bond between Y and Zd, and the bond between Y and Ze are all single bonds. (In the above general formula (210), general formula (220), or general formula (230), Dx is a group represented by the following general formula (21), general formula (22), or general formula (23), provided that at least one Dx is a group represented by the following general formula (23), m is 1 or 2, and when m is 2, a plurality of Dx are identical or different from each other, n is 2 or 3, and when n is 2 or 3, a plurality of R are identical or different from each other, R is each independently a substituent, and R as a substituent is each independently a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.) (R1 to R8 in the above general formula (21) are each independently a hydrogen atom, a halogen atom, or a substituent, and R in the above general formula (22) 21 ~R 28 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 21 and R 22 of, R 22 and R 23 of, R 23 and R 24 of, R 25 and R 26 of, R 26 and R 27 of, and R 27 and R 28 One or more of the groups of the above combine to form a ring, and R in the general formula (23) 211 ~R 218 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 211 and R 212 of, R 212 and R 213 of, R 213 and R 214 of, R 215 and R 216 of, R 216 and R 217 of, and R 217 and R 218 One or more groups of the group combine with each other to form a ring, and R1 to R8 as substituents, and R as a substituent 21 ~R 28 and R as a substituent 211 ~R 218 Silver, each independently, a substituted or unsubstituted ring-forming aryl group having 6–30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5–30 carbon atoms, a substituted or unsubstituted alkyl group having 1–30 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3–30 carbon atoms, -Si(R 911 )(R 912 )(R 913 The unit indicated by ), -O-(R 914 The unit indicated by ), -S-(R 915 The unit indicated by ), or -N(R 916 )(R 917 A group represented by ), and in the above general formula (22) and the above general formula (23), ring G, ring J, and ring K are each independently any ring structure selected from the group consisting of ring structures represented by the following general formulas (24) and (25), ring G, ring J, and ring K are condensed with an adjacent ring at any position, pa, px, and py are each independently 1, 2, 3, or 4, and when pa is 2, 3, or 4, a plurality of rings G are identical or different from each other, when px is 2, 3, or 4, a plurality of rings J are identical or different from each other, and when py is 2, 3, or 4, a plurality of rings K are identical or different from each other, provided that at least one Dx is a group represented by the above general formula (23) where px and py are 2, where one of the two rings J is a ring structure represented by the general formula (24), and the other of the two rings J One side is a ring structure represented by general formula (25), one side of the two rings K is a ring structure represented by general formula (24), and the other side of the two rings K is a ring structure represented by general formula (25), and * in the above general formulas (21) to (23) indicates a bonding position with a benzene ring in the above general formula (210), general formula (220), or general formula (230). (In the above general formula (24), R 19 and R 20 Each is independently a hydrogen atom, a halogen atom, or a substituent, or R 19 and R 20 The groups of the ring combine to form a ring, and in the general formula (25), X 21 are, respectively, sulfur atom, oxygen atom, NR 220 , CR 221 R 222 or SiR 223 R 224 and R 220 It is silver, a hydrogen atom, a halogen atom, or a substituent, and R 221 and R 222 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 221 and R 222 The groups of combine with each other to form a ring, and R 223 and R 224 are, respectively, independently a hydrogen atom, a halogen atom, or a substituent, or R 223 and R 224 The groups of combine to form a ring, and R as a substituent 19 , R 20 , R 220 , R 221 , R 222 , R 223 and R 224 ..., each independently, has the same meaning as R1 to R8 as substituents.) (In the first compound and the second compound above, R 911 ~R 917 Each independently is 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 heterocyclic group with 5–50 atoms, and R 911 If this plural exists, the plural R 911 are identical or different from each other, and R 912 If there are multiple instances of , multiple R 912 are identical or different from each other, and R 913 If this plural exists, the plural R 913 are identical or different from each other, and R 914 If there are multiple instances of , multiple R 914 are identical or different from each other, and R 915 If there are multiple instances of , multiple R 915 are identical or different from each other, and R 916 If this plural exists, the plural R 916 are identical or different from each other, and R 917 If this plural exists, the plural R 917 They are identical or different from each other. Claim 2 An organic electroluminescence element according to claim 1, wherein Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh are each independently a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 30 atoms. Claim 3 In claim 1, Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh are each independently a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an organic electroluminescence element. Claim 4 In claim 1, the first compound is an organic electroluminescence element represented by the following general formula (11). (In the above general formula (11), ring A, ring D and ring E are each independently ring structures selected from the group consisting of a substituted or unsubstituted ring-forming aryl ring having 6 to 30 carbon atoms and a substituted or unsubstituted ring-forming heterocyclic ring having 5 to 30 atoms, and at least one selected from the group consisting of ring A, ring D and ring E is an aryl ring excluding bonding hands from an aryl group selected from the group consisting of 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, benzofluoranthenyl group, and perylenyl group, or a pyrrolyl group, imidazolyl group, pyrazolyl group, Triazolyl group, tetrazolyl group, oxazolyl group, isooxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenantridinyl group, acrridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, furyl group, xanthenyl group, benzofuranyl group, Excluding bonding hands in a complex circulating group selected from the group consisting of isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benziosooxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, diazanaphthobenzofuranyl group, thienyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, benzothiazolyl group, benzioisothiazolyl group, phenothiazinyl group, dinaphthiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, azanaphthobenzothiophenyl group, and diazanaphthobenzothiophenyl group. It is a complex call, andThese aryl and heterocyclic rings may have substituents or be unsubstituted, and Za is a nitrogen atom or a carbon atom, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, and Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh are each independently of the above general formula (1) has the same meaning as Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4 and Rh.), Claim 5 In paragraph 4, the first compound is an organic electroluminescence element represented by the following general formula (12). (In the above general formula (12), ring A, ring D and ring E are each independently ring structures selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic ring having 5 to 30 atoms, and at least one selected from the group consisting of ring A, ring D and ring E is an aryl ring excluding bonding hands from an aryl group selected from the group consisting of 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, benzofluoranthenyl group, and perylenyl group, or a pyrrolyl group, imidazolyl group, pyrazolyl group, Triazolyl group, tetrazolyl group, oxazolyl group, isooxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenantridinyl group, acrridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, furyl group, xanthenyl group, benzofuranyl group, Excluding bonding hands in a complex circulating group selected from the group consisting of isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benziosooxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, diazanaphthobenzofuranyl group, thienyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, benzothiazolyl group, benzioisothiazolyl group, phenothiazinyl group, dinaphthiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, azanaphthobenzothiophenyl group, and diazanaphthobenzothiophenyl group. It is a complex call, andThese aryl and heterocyclic rings may have substituents or be unsubstituents, and Za, Zc, Zd, Ze, Zf, Zh, and Zi are each independently nitrogen atoms or carbon atoms, and Rb and Rg are each independently identical in meaning to Rb and Rg in the above general formula (1). Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 delete Claim 10 delete Claim 11 In claim 1, the first compound is an organic electroluminescence element represented by the following general formula (15). (In the above general formula (15), Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), and X1 is CR 121 This, or it is a nitrogen atom, and X2 is, CR 122 Or it is a nitrogen atom, and X3 is, CR 123 Or it is a nitrogen atom, and X4 is CR 124 Or it is a nitrogen atom, and X5 is, CR 125 Or it is a nitrogen atom, and X6 is CR 126 Or it is a nitrogen atom, and X7 is CR 127 Or it is a nitrogen atom, and X8 is CR 128 Or it is a nitrogen atom, and X9 is CR 129 Or it is a nitrogen atom, and X 10 silver, CR 130 Or it is a nitrogen atom, and X 11 silver, CR 131 Or it is a nitrogen atom, and X 12 is, CR 132 This, or it is a nitrogen atom, and Q is CR Q Or it is a nitrogen atom, and R 122 ~R 131 One or more of the groups consisting of two or more adjacent groups combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other, R 124 , R 125 One or more sets of two or more adjacent groups among , Rb, Rb1, Rb2, Rb3, and Rb4 combine with each other to form a substituted or unsubstituted single ring, combine with each other to form a substituted or unsubstituted condensed ring, or do not combine with each other, R 124 , R 125 At least one hydrogen in a monocyclic or condensed ring formed by the bonding of one or more sets of two or more adjacent groups among Rb, Rb1, Rb2, Rb3, and Rb4 is a C1-50 alkyl group, a ring-forming C6-50 aryl group, a ring-forming heterocyclic group with 5-50 atoms, -O-(R 151 The unit indicated by ), and -N(R 152 )(R 153 R is substituted with or is not substituted by at least one substituent selected from the group consisting of the group represented by ). At least one hydrogen in the substituent is substituted with or is not substituted by a ring-forming aryl group having 6 to 50 carbon atoms or an alkyl group having 1 to 50 carbon atoms, and does not form the substituted or unsubstituted single ring and also does not form the substituted or unsubstituted condensed ring. 121 ~R 132 , R 150 and R Q Each independently, a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 951 )(R 952 )(R 953 The unit indicated by ), -O-(R 954 The unit indicated by ), -S-(R 955 The unit represented by ), -N(R 956 )(R 957 A group denoted by ), a substituted or unsubstituted aralkyl group with 7–50 carbon atoms, -C(=O)R 958 The one indicated by -COOR 959 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, wherein Rb, Rb1, Rb2, Rb3, and Rb4, which do not form the substituted or unsubstituted single ring and also do not form the substituted or unsubstituted condensed ring, are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, and R 151 ~R 153 and R 951 ~R 959 Each is 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 heterocyclic group with 5–50 atoms, and R 151 If this plural exists, the plural R 151 are identical or different from each other, and R 152 If there are multiple instances of , multiple R 152 are identical or different from each other, and R 153 If this plural exists, the plural R 153 are identical or different from each other, and R 951 If this plural exists, the plural R 951 are identical or different from each other, and R 952 If there are multiple instances of , multiple R 952 are identical or different from each other, and R 953 If this plural exists, the plural R 953 are identical or different from each other, and R 954 If there are multiple instances of , multiple R 954 are identical or different from each other, and R 955 If there are multiple instances of , multiple R 955 are identical or different from each other, and R 956 If this plural exists, the plural R 956 are identical or different from each other, and R 957 If this plural exists, the plural R 957 are identical or different from each other, and R 958 If this plural exists, the plural R 958 are identical or different from each other, and R 959 If there are multiple instances of , multiple R 959 are identical or different from each other. Claim 12 In Paragraph 11, R 121 ~R 132 , R 150 and R Q An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 13 In Paragraph 11, R 121 ~R 132 , R 150 and R Q An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 14 In Paragraph 11, R 121 ~R 132 , R 150 and R Q is an organic electroluminescence device that is a hydrogen atom. Claim 15 In claim 11, the above first compound is an organic electroluminescence device represented by the following general formula (151). (In the above general formula (151), X1 to X 12 Each is X1 to X in the above general formula (15). 12 It has the same meaning as, and R 150 , R Q and Rb are, respectively, R in the general formula (15) above. 150 , R Q and has the same meaning as Rb.) Claim 16 In claim 15, the above first compound is an organic electroluminescence device represented by the following general formula (152). (In the above general formula (152), X1 to X3, X5 to X 12 are, respectively, X1~X3, X5~X in the above general formula (15). 12 It has the same meaning as, and X 13 silver, CR 133 Or it is a nitrogen atom, and X 14 is, CR 134 Or it is a nitrogen atom, and X 15 is, CR 135 Or it is a nitrogen atom, and X 16 silver, CR 136 Or it is a nitrogen atom, and R 133 ~R 136 Silver, each independently, a hydrogen atom, a substituted or unsubstituted C1–30 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, -Si(R 951 )(R 952 )(R 953 The unit indicated by ), -O-(R 954 The unit indicated by ), -S-(R 955 The unit represented by ), -N(R 956 )(R 957 A group denoted by ), a substituted or unsubstituted aralkyl group with 7–50 carbon atoms, -C(=O)R 958 The one indicated by -COOR 959 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and R 150 and R Q are, respectively, R in the above general formula (15) 150 and R Q It has the same meaning as.) Claim 17 In Paragraph 16, R 133 ~R 136 An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 18 In Paragraph 16, R 133 ~R 136 An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 19 In Paragraph 16, R 133 ~R 136 An organic electroluminescence device in which the hydrogen atom is Claim 20 In claim 1, the organic electroluminescence element is a compound represented by the following general formula (16). (In the above general formula (16), R 161 ~R 177 One or more of the sets of two or more adjacent sets combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other to form the substituted or non-substituted single ring, and also do not form the substituted or non-substituted condensed ring. 161 ~R 177 Silver, each independently, hydrogen atom, substituted or unsubstituted C1–50 alkyl group, substituted or unsubstituted C2–50 alkenyl group, substituted or unsubstituted C2–50 alkynyl group, substituted or unsubstituted ring-forming C3–50 cycloalkyl group, substituted or unsubstituted C7–50 aralkyl group, -Si(R 961 )(R 962 )(R 963 The unit indicated by ), -O-(R 964 The unit indicated by ), -S-(R 965 The unit represented by ), -N(R 966 )(R 967 The unit indicated by ), -C(=O)R 968 The one indicated by -COOR 969 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and R 961 ~R 969 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted cyclic aryl group C6–50, or a substituted or unsubstituted cyclic heterocyclic group C5–50, and R 961 If this plural exists, the plural R 961 are identical or different from each other, and R 962 If there are multiple instances of , multiple R 962 are identical or different from each other, and R 963 If this plural exists, the plural R 963 are identical or different from each other, and R 964 If there are multiple instances of , multiple R 964 are identical or different from each other, and R 965 If there are multiple instances of , multiple R 965 are identical or different from each other, and R 966 If this plural exists, the plural R 966 are identical or different from each other, and R 967 If this plural exists, the plural R 967 are identical or different from each other, and R 968 If this plural exists, the plural R 968 are identical or different from each other, and R 969 If there are multiple instances of , multiple R 969 are identical or different from each other. Claim 21 In paragraph 20, R 161 ~R 177 An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 22 In paragraph 20, R 168 ~R 170 An organic electroluminescence element, wherein at least one of the elements is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms. Claim 23 In paragraph 20, R 161 ~R 177 An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 24 In paragraph 20, R 161 ~R 177 An organic electroluminescence device in which the hydrogen atom is Claim 25 In paragraph 20, R 161 ~R 177 An organic electroluminescence device comprising at least one set of two or more adjacent sets that combine with each other to form a ring represented by the following general formula (16A). (The dotted line in the above general formula (16A) indicates the joint area, and R X1 ~R X4 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 C3–50 cycloalkyl group, a substituted or unsubstituted C7–50 aralkyl group, -Si(R 961 )(R 962 )(R 963 The unit indicated by ), -O-(R 964 The unit indicated by ), -S-(R 965 The unit represented by ), -N(R 966 )(R 967 The unit indicated by ), -C(=O)R 968 The one indicated by -COOR 969 It is a group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group with 5 to 50 atoms. Claim 26 In paragraph 25, R 161 and R 162 A group consisting of, R 165 and R 166 A group consisting of, R 172 and R 173 A group consisting of, and R 176 and R 177 An organic electroluminescence device in which at least one of the sets of sets is combined with each other to form a ring represented by the general formula (16A). Claim 27 In claim 26, the above first compound is an organic electroluminescence device represented by the following general formula (161). (In the above general formula (161), R 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R X1 ~R X4 R in the above general formula (16) is, respectively, independently 161 ~R 164 , R 167 ~R 171 , R 174 ~R 177 and R in the above general formula (16A) X1 ~R X4 It has the same meaning as.) Claim 28 In claim 1, the organic electroluminescence device is a compound represented by the following general formula (171), wherein the first compound is an organic electroluminescence device. (In the above general formula (171), ring A, ring D and ring E are each independently ring structures selected from the group consisting of a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms and a substituted or unsubstituted heterocyclic ring having 5 to 30 atoms, and at least one selected from the group consisting of ring A, ring D and ring E is an aryl ring excluding bonding hands from an aryl group selected from the group consisting of 1-naphthyl group, 2-naphthyl group, anthryl group, benzoanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, crisenyl group, benzocrisenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, benzofluoranthenyl group, and perylenyl group, or a pyrrolyl group, imidazolyl group, pyrazolyl group, Triazolyl group, tetrazolyl group, oxazolyl group, isooxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenantridinyl group, acrridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, furyl group, xanthenyl group, benzofuranyl group, Excluding bonding hands in a complex circulating group selected from the group consisting of isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benziosooxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, diazanaphthobenzofuranyl group, thienyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, benzothiazolyl group, benzioisothiazolyl group, phenothiazinyl group, dinaphthiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, azanaphthobenzothiophenyl group, and diazanaphthobenzothiophenyl group. It is a complex call, andThese aryl and heterocyclic rings may have substituents or be unsubstituted, and Za is a nitrogen atom or a carbon atom, Zb is an oxygen atom, a sulfur atom or NRb, Zc is a nitrogen atom or a carbon atom, Zd is a carbon atom or a nitrogen atom, Ze is a carbon atom or a nitrogen atom, Zf is a nitrogen atom or a carbon atom, Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O or P=S, Rb and Rh are each independently a hydrogen atom or a substituent, and Rb and Rh as substituents are each independently selected from the group consisting of a substituted or unsubstituted cyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and R, 181 and R 182 A group composed of, which combines with one another to form a substituted or non-substituted single ring, or combines with one another to form a substituted or non-substituted condensed ring, or does not combine with one another to form the substituted or non-substituted single ring, or does not form the substituted or non-substituted condensed ring R 181 ~R 182 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 C3–50 cycloalkyl group, a substituted or unsubstituted C7–50 aralkyl group, -Si(R 971 )(R 972 )(R 973 The unit indicated by ), -O-(R 974 The unit indicated by ), -S-(R 975 The unit represented by ), -N(R 976 )(R 977 The unit indicated by ), -C(=O)R 978 The one indicated by -COOR 979 A group represented by, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming complex circulating group having 5 to 50 atoms, and R 971 ~R 979 Each is independently a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted cyclic aryl group C6–50, or a substituted or unsubstituted cyclic heterocyclic group C5–50, and R 971 If this plural exists, the plural R 971 are identical or different from each other, and R 972 If there are multiple instances of , multiple R 972 are identical or different from each other, and R 973 If this plural exists, the plural R 973 are identical or different from each other, and R 974 If there are multiple instances of , multiple R 974 are identical or different from each other, and R 975 If there are multiple instances of , multiple R 975 are identical or different from each other, and R 976 If this plural exists, the plural R 976 are identical or different from each other, and R 977 If this plural exists, the plural R 977 are identical or different from each other, and R 978 If this plural exists, the plural R 978 are identical or different from each other, and R 979 If there are multiple instances of , multiple R 979 are identical or different from each other. Claim 29 In paragraph 28, R 181 ~R 182 An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 30 In paragraph 28, R 181 ~R 182 An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 31 In paragraph 28, R 181 ~R 182 is an organic electroluminescence device consisting of hydrogen atoms. Claim 32 In claim 1, the first compound is an organic electroluminescence element represented by the following general formula (18). (In the above general formula (18), r is 0 or 1, and when r is 0, p and q are 1, and R W1 and R W2 exists, and when r is 1, p and q are 0, and R W1 and R W2 does not exist, and X 81 Silver, nitrogen atoms, or CR 191 and X 82 is, a nitrogen atom or CR 192 and X 83 Silver, single bond, oxygen atom, sulfur atom, Si(R 193 )(R 194 ), C(R 195 )(R 196 ) or BR 197 and X 84 is, R 801 and X 85 is, R 812 and R 191 , R 192 , R 193 , R 194 , R 195 , R 196 , R 197 , R 801 , R 802 , R 803 , R 804 , R 805 , R 806 , R 807 , R 808 , R 809 , R 810 , R 811 , R 812 , R W1 , R W2 and R W3 One or more of the sets of two or more adjacent sets combine with each other to form a substituted or non-substituted single ring, combine with each other to form a substituted or non-substituted condensed ring, or do not combine with each other to form the substituted or non-substituted single ring, and also do not form the substituted or non-substituted condensed ring. W3 R is a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, wherein R does not form the substituted or unsubstituted monocyclic ring and also does not form the substituted or unsubstituted condensed ring. 191 , R 192 , R 193 , R 194 , R 195 , R 196 , R 197 , R 801 , R 802 , R 803 , R 804 , R 805 , R 806 , R 807 , R 808 , R 809 , R 810 , R 811 , R 812 , R W1 and R W2 are, respectively, hydrogen atom, deuterium atom, -Si(R 981 )(R 982 )(R 983 The unit indicated by ), -O-(R 984 The unit indicated by ), -S-(R 985 The unit represented by ), -N(R 986 )(R 987 The unit represented by ), -B(R 988 )(R 989 The unit represented by ), -OSO2(R 990 A group represented by ), a cyano group, a halogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C3–50 cycloalkyl group, a substituted or unsubstituted C1–50 fluoroalkyl group, a substituted or unsubstituted C1–50 thioalkoxy group, a substituted or unsubstituted C2–50 alkenyl group, a substituted or unsubstituted C2–50 alkynyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 981 ~R 990 Each independently is a hydrogen atom, a substituted or unsubstituted C1–50 alkyl group, a substituted or unsubstituted ring-forming C6–50 aryl group, or a substituted or unsubstituted ring-forming heterocyclic group with 5–50 atoms, and R 981 If this plural exists, the plural R 981 are identical or different from each other, and R 982 If there are multiple instances of , multiple R 982 are identical or different from each other, and R 983 If this plural exists, the plural R 983 are identical or different from each other, and R 984 If there are multiple instances of , multiple R 984 are identical or different from each other, and R 985 If there are multiple instances of , multiple R 985 are identical or different from each other, and R 986 If this plural exists, the plural R 986 are identical or different from each other, and R 987 If this plural exists, the plural R 987 are identical or different from each other, and R 988 If this plural exists, the plural R 988 are identical or different from each other, and R 989 If there are multiple instances of , multiple R 989 are identical or different from each other, and R 990 If this plural exists, the plural R 990 They are identical or different from each other. Claim 33 In Paragraph 32, R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 34 In Paragraph 32, R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 35 In Paragraph 32, R 191 ~R 197 , R 801 ~R 812 , R W1 and R W2 is an organic electroluminescence device that is a hydrogen atom. Claim 36 In paragraph 32, the above first compound is an organic electroluminescence device represented by the following general formula (181). (In the above general formula (181), X 81 , X 82 , X 84 and X 85 are, respectively, X in the above general formula (18) 81 , X 82 , X 84 and X 85 It has the same meaning as, and R 802 ~R 811 and R W3 Each is R in the above general formula (18). 802 ~R 811 and R W3 It has the same meaning as.) Claim 37 delete Claim 38 An organic electroluminescence device according to claim 1, wherein m in the general formula (210), general formula (220), or general formula (230) is 2. Claim 39 delete Claim 40 An organic electroluminescence device, wherein in any one of claims 1 to 5, 11 to 36, and 38, the compound represented by the general formula (210) is any compound selected from the group consisting of compounds represented by the following general formulas (211) to (218). (In the above general formulas (211) and (212), D 11 is a group represented by the above general formula (23), and R 231 ~R 233 Each has the same meaning as R in the above general formula (210), independently.) (In the above general formulas (213) to (216), D 11 and D 12 Each has the same meaning as Dx in the above general formula (210), independently, provided that D 11 and D 12 At least one of them is a group represented by the above general formula (23), and R 231 and R 232 Each has the same meaning as R in the above general formula (210), independently.) (In the above general formulas (217) and (218), D 11 ~D 13 Each has the same meaning as Dx in the above general formula (210), independently, provided that D 11 ~D 13 At least one of them is a group represented by the above general formula (23), and R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (210).) Claim 41 An organic electroluminescence device, wherein in any one of claims 1 to 5, 11 to 36, and 38, the compound represented by the general formula (220) is any compound selected from the group consisting of compounds represented by the following general formulas (221) to (229). (In the above general formulas (221) to (223), D 11 is a group represented by the above general formula (23), and R 231 ~R 233 Each has the same meaning as R in the above general formula (220), independently.) (In the above general formulas (224) to (226), D 11 and D 12 Each has the same meaning as Dx in the above general formula (220), independently, provided that D 11 and D 12 At least one of them is a group represented by the above general formula (23), and R 231 and R 232 Each has the same meaning as R in the above general formula (220), independently.) (In the above general formulas (227) to (229), D 11 ~D 13 Each independently has the same meaning as Dx in the above general formula (220), provided that D 11 ~D 13 At least one of them is a group represented by the above general formula (23), and R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (220).) Claim 42 In claim 41, the compound represented by the general formula (220) is an organic electroluminescence element that is a compound represented by the general formula (226). Claim 43 An organic electroluminescence device, wherein in any one of claims 1 to 5, 11 to 36, and 38, the compound represented by the general formula (230) is any compound selected from the group consisting of compounds represented by the following general formulas (231) to (235). (In the above general formula (231), D 11 is a group represented by the above general formula (23), and R 231 ~R 233 Each has the same meaning as R in the above general formula (230), independently.) (In the above general formulas (232) to (234), D 11 and D 12 Each independently has the same meaning as Dx in the above general formula (230), provided that D 11 and D 12 At least one of them is a group represented by the above general formula (23), and R 231 and R 232 Each has the same meaning as R in the above general formula (230), independently.) (In the above general formula (235), D 11 ~D 13 Each has the same meaning as Dx in the above general formula (230), independently, provided that D 11 ~D 13 At least one of them is a group represented by the above general formula (23), and R 231 is a substituent, and R as a substituent 231 ...is the same meaning as R as a substituent in the above general formula (230).) Claim 44 In paragraph 43, the compound represented by the above general formula (230) is an organic electroluminescence device that is a compound represented by the above general formula (234). Claim 45 delete Claim 46 delete Claim 47 In any one of claims 1 to 5, 11 to 36, and 38, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 An organic electroluminescence element, each independently comprising a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Claim 48 In any one of claims 1 to 5, 11 to 36, and 38, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 An organic electroluminescence element, each independently comprising a hydrogen atom or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. Claim 49 In any one of claims 1 to 5, 11 to 36, and 38, R1 to R8 of the second compound, R 21 ~R 28 and R 211 ~R 218 An organic electroluminescence device in which the hydrogen atom is Claim 50 An organic electroluminescence device according to any one of claims 1 to 5, 11 to 36, and 38, wherein the light-emitting layer further comprises a third compound, and the singlet energy S1(M3) of the third compound and the singlet energy S1(M2) of the second compound satisfy the relationship of the following formula (Formula 2). S1(M3)>S1(M2) … (Formula 2) Claim 51 An electronic device equipped with an organic electroluminescence element as described in any one of claims 1 to 5, 11 to 36, and 38.

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