Compounds, materials for organic electroluminescent elements, organic electroluminescent elements and electronic devices

Abstract

To provide a compound that can improve the performance of organic electroluminescent elements. [Solution] A compound represented by general formula (D1). In general formula (D1), R1~R 11 Each of these is independently a hydrogen atom or a substituent, however R1 to R 11 Of these, at least one is a group represented by general formula (D11). R12 and R 13 Each of these is independently a group represented by general formula (D12), or a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, provided that R 12 and R 13 Of these, at least one is a group represented by the general formula (D12). TIFF2026086952000228.tif61159

Description

[Technical Field]

[0001] The present invention relates to compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices. [Background technology]

[0002] When a voltage is applied to an organic electroluminescent device (hereinafter sometimes 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 laws of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%. Fluorescent organic light-emitting diodes (OLEDs), which use light emission from singlet excitons, are being applied to full-color displays in mobile phones and televisions, but their internal quantum efficiency is said to be limited to 25%. Various studies are being conducted on compounds used in OLEDs to improve their performance (see, for example, Patent Documents 1 to 6). Examples of OLED performance include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] U.S. Patent Application Publication No. 2021 / 013423 [Patent Document 2] European Patent Application Publication No. 3723151 [Patent Document 3] International Publication No. 2021 / 213972 [Patent Document 4] International Publication No. 2021 / 151532 [Patent Document 5] International Publication No. 2021 / 228114 [Patent Document 6] International Publication No. 2021 / 199948 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] Further improvements in the performance of organic EL elements are needed to enhance the performance of electronic devices such as displays.

[0005] An object of the present invention is to provide a compound that can improve the luminescence efficiency of an organic electroluminescent element. Another object of the present invention is to provide a material for an organic electroluminescent element and an organic electroluminescent element containing the compound, and to provide an electronic device equipped with the organic electroluminescent element. [Means for solving the problem]

[0006] According to one aspect of the present invention, a compound represented by the following general formula (D1) is provided.

[0007] [ka]

[0008] (In the above general formula (D1), R1~R 11 Each of them operates independently. hydrogen atom, The group represented by the following general formula (D11), Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 131 )(R 132 A base represented by ) -Si(R 133 )(R 134 )(R135 a group represented by -O-(R 136 a group represented by -S-(R 137 a group represented by a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 138 a group represented by -COOR 139 a group represented by a halogen atom, a cyano group, a nitro group, -P(=O)(R 140 )(R 141 a group represented by -Ge(R 142 )(R 143 )(R 144 a group represented by -B(R 145 )(R 146 a group represented by a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that, ​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​At least one of these is a group represented by the following general formula (D12).

[0009] [ka]

[0010] (In the above general formula (D11), R A , R B , R C , R D , R E , R F And one or more pairs of adjacent Y members, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring A , R B , R C , R D , R E , R F And one of Y is a single bond that connects to *a, L1 is a ring-forming arylene group with 6 to 50 carbon atoms, either single-bonded, substituted, or unsubstituted. *b indicates the bonding position with the ring structure represented by the general formula (D1), R A and R B When a set consisting of these elements is bonded to each other to form a substituted or unsubstituted carbazole ring, and Y is a single bond to *a and L1 is a single bond, then a substituted or unsubstituted amino group and a substituted or unsubstituted N-carbazolyl group will not be bonded to the carbazole ring. In the above general formula (D12), R G , R H , R I , R J and R K Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, *c indicates the bonding position with the ring structure represented by the general formula (D1) above. In the above general formulas (D11) and (D12), R does not form the aforementioned substituted or unsubstituted monoring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a single bond attached to *a. A , R B , R C , R D , R E , R F and Y, and R which does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. G , R H , R I , R J and R K Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 131 )(R 132 A base represented by ) -Si(R 133 )(R 134 )(R 135 A base represented by ) -O-(R 136 A base represented by ) -S-(R 137 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 138 A base represented by -COOR 139A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 140 )(R 141 A base represented by ) -Ge(R 142 )(R 143 )(R 144 A base represented by ) -B(R 145 )(R 146 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. however, R G and R H However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R K It is not a hydrogen atom, R J and R K However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R G It is not a hydrogen atom, R G and R H They do not combine with each other, and R J and R K If they do not combine with each other, R G and R K (It is neither a hydrogen atom nor a substituted or unsubstituted aryl group with 6-50 carbon atoms forming a ring.) (In the compound represented by the general formula (D1) above, R 131 ~R 146 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, R 131 When there are a plurality of R's, the plurality of R's 131 are the same as or different from each other, R 132 When there are a plurality of R's, the plurality of R's 132 are the same as or different from each other, R 133 When there are a plurality of R's, the plurality of R's 133 are the same as or different from each other,<( R 134 When there are a plurality of R's, the plurality of R's 134 are the same as or different from each other, R 135 When there are a plurality of R's, the plurality of R's 135 are the same as or different from each other, R 136 When there are a plurality of R's, the plurality of R's 136 are the same as or different from each other, R 137 When there are a plurality of R's, the plurality of R's 137 are the same as or different from each other, R 138 When there are a plurality of R's, the plurality of R's 138 are the same as or different from each other, R 139 When there are a plurality of R's, the plurality of R's 139 are the same as or different from each other, R 140 When there are a plurality of R's, the plurality of R's 140 are the same as or different from each other, R 141 When there are a plurality of R's, the plurality of R's 141 are the same as or different from each other, R 142 When there are a plurality of R's, the plurality of R's[[ID=7{2]] 142 are the same as or different from each other, R 143 When there are a plurality of R's, the plurality of R's 143 are the same as or different from each other, R 144If multiple R 144 They are either identical or different from one another. R 145 If multiple R 145 They are either identical or different from one another. R 146 If multiple R 146 They are either identical or different to one another.

[0011] According to one aspect of the present invention, a material for an organic electroluminescent device containing a compound according to one aspect of the present invention is provided.

[0012] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising a cathode, an anode, and an organic layer contained between the cathode and the anode, wherein at least one layer of the organic layer contains a compound according to one aspect of the present invention as compound M3.

[0013] According to one aspect of the present invention, an electronic device equipped with an organic electroluminescent element according to one aspect of the present invention is provided. [Effects of the Invention]

[0014] According to one aspect of the present invention, a compound capable of improving the performance of an organic electroluminescent element can be provided. According to one aspect of the present invention, a material for an organic electroluminescent element and an organic electroluminescent element containing a compound according to one aspect of the present invention can be provided, as well as an electronic device equipped with the organic electroluminescent element. [Brief explanation of the drawing]

[0015] [Figure 1] This figure shows a schematic configuration of an example of an organic electroluminescent element according to the third embodiment of the present invention. [Figure 2] This is a schematic diagram of a device for measuring transient PL (Power Level). [Figure 3]This figure shows an example of a transient PL decay curve. [Figure 4] This figure shows the relationship between the energy levels of the sensitizing material and the fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the third embodiment of the present invention, as well as the relationship between energy transfer. [Figure 5] This figure shows the relationship between the energy levels and energy transfer of the host material, sensitizing material, and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the fourth embodiment of the present invention. [Modes for carrying out the invention]

[0016] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0017] In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" representing a deuterium atom are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms.

[0018] In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, 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. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in that alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10.

[0019] In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring aggregates) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

[0020] In this specification, the expression "substituted or unsubstituted ZZ group having XX to YY carbon atoms" means that "XX to YY carbon atoms" represents the number of carbon atoms when the ZZ group is unsubstituted, and does not include the number of carbon atoms of substituents 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.

[0021] In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" means that "atom count XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and does not include the number of substituent atoms when it is substituted. Here, "YY" is greater than "XX", where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more.

[0022] In this specification, an unsubstituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "unsubstituted ZZ group," and a substituted ZZ group refers to a case where "substituted or unsubstituted ZZ group" is "substituted ZZ group." In this specification, "unsubstituted" in the context of a "substituted or unsubstituted ZZ group" means that the hydrogen atoms in the ZZ group are not replaced by substituents. The hydrogen atoms in an "unsubstituted ZZ group" are light hydrogen atoms, deuterium atoms, or tritium atoms. Furthermore, in this specification, "substituted" in the context of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. Similarly, "substituted" in the context of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced by an AA group.

[0023] "Substituents as described herein" The substituents described herein will be explained below.

[0024] The number of ring-forming carbon atoms in the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkyl group" as described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted cycloalkyl groups" described herein is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise specified herein. The number of ring-forming carbon atoms in the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein. The number of ring-forming atoms in the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified herein. The number of carbon atoms in the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

[0025] • "substituted or unsubstituted aryl groups" Specific examples of "substituted or unsubstituted aryl groups" as described herein (Specific Examples Group G1) include the following unsubstituted aryl groups (Specific Examples Group G1A) and substituted aryl groups (Specific Examples Group G1B), etc. (Here, "unsubstituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is an "unsubstituted aryl group," and "substituted aryl group" refers to the case where "substituted or unsubstituted aryl group" is a "substituted aryl group.") In this specification, the term "aryl group" simply includes both "unsubstituted aryl groups" and "substituted aryl groups." A "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced by substituents. Examples of "substituted aryl groups" include the groups in which one or more hydrogen atoms of an "unsubstituted aryl group" in specific example group G1A below are replaced by substituents, and the examples of substituted aryl groups in specific example group G1B below. Note that the examples of "unsubstituted aryl groups" and "substituted aryl groups" listed here are merely examples, and the "substituted aryl groups" described herein also include groups in which the hydrogen atoms bonded to the carbon atom of the aryl group itself in the "substituted aryl group" in specific example group G1B below are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted aryl group" in specific example group G1B below are further replaced by substituents.

[0026] • Unsubstituted aryl groups (specific examples group G1A): Phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-Naphthyl group, 2-Naphthyl group, anthryl group, Benzoantryl group, Phenanthryl group, Benzophenanthryl group, Phenalenyl group, Pyrenyl group, Chrysenyl group, Benzocrisenyl group, Triphenylenyl group, benzotriphenylenyl group, Tetraceryl group, Pentacenyl group, Fluorenyl group, 9,9'-Spirobifluorenyl group, Benzofluorenyl group, Dibenzofluorenyl group, Fluoranthenyl group, Benzofluoranthenyl group, Perilenyl group, and A monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

[0027] [ka]

[0028] [ka]

[0029] • Substitutive aryl groups (Specific examples group G1B): o-Tryl group, m-tolyl group, p-tril group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, Meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, Cyanophenyl group, Triphenylsilylphenyl group, Trimethylsilylphenyl group, Phenylnaphthyl group, Naphthylphenyl group, and A group obtained by replacing one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) above with substituents.

[0030] • "Substitutable or unsubstituted heterocyclic groups" The “heterocyclic group” as described herein is a cyclic group containing at least one heteroatom in its ring-forming atoms. Specific examples of heteroatoms include nitrogen, oxygen, sulfur, silicon, phosphorus, and boron. The "heterocyclic group" as described herein is either a monocyclic group or a fused-cyclic group. The term "heterocyclic group" as used herein refers to either an aromatic heterocyclic group or a non-aromatic heterocyclic group. Specific examples of "substituted or unsubstituted heterocyclic groups" as described herein (Specific Examples Group G2) include the following unsubstituted heterocyclic groups (Specific Examples Group G2A) and substituted heterocyclic groups (Specific Examples Group G2B), etc. (Here, "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group," and "substituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "substituted heterocyclic group.") In this specification, the term "heterocyclic group" simply includes both "unsubstituted heterocyclic groups" and "substituted heterocyclic groups." A "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by substituents. Specific examples of "substituted heterocyclic groups" include the groups in specific example group G2A below in which hydrogen atoms of an "unsubstituted heterocyclic group" are replaced, and the examples of substituted heterocyclic groups in specific example group G2B below. Note that the examples of "unsubstituted heterocyclic groups" and "substituted heterocyclic groups" listed here are merely examples, and the "substituted heterocyclic groups" described herein also include groups in which hydrogen atoms bonded to the ring-forming atoms of the heterocyclic group itself are further replaced by substituents, and groups in which hydrogen atoms of substituents are further replaced by substituents.

[0031] The specific examples group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

[0032] Specific examples group G2B includes, for example, substituted heterocyclic groups containing a nitrogen atom (Specific Examples Group G2B1), substituted heterocyclic groups containing an oxygen atom (Specific Examples Group G2B2), substituted heterocyclic groups containing a sulfur atom (Specific Examples Group G2B3), and groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (Specific Examples Group G2B4).

[0033] • Unsubstituted heterocyclic groups containing a nitrogen atom (specific examples group G2A1): Pyrrolyl group, imidazolyl group, Pyrazolyl group, Triazolyl group, Tetrazolyl group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Pyridyl group, Pyridazinyl group, Pyrimidinyl group, pyrazinyl group, Triazinyl group, Indolyl group, isoindolyl group, indolidinyl group, Quinolidinyl group, quinolyl group, Isoquinolyl group, cinnolyl group, Phthalazinyl group, Quinazolinyl group, Quinoxalinyl group, Benzimidazolyl group, Indazolyl group, Phenanthrolinyl group, Phenantridinyl group, Acridinyl group, Phenazinyl group, Carbazolyl group, Benzocarbazolyl group, Morpholino group, Phenoxadinyl group, Phenothiazinyl group, Azacarbazolyl group and diazacarbazolyl group.

[0034] • Unsubstituted heterocyclic groups containing an oxygen atom (specific examples group G2A2): Frill group, Oxazolyl group, isoxazolyl group, Oxadiazolyl group, xanthenyl group, Benzofuranyl group, Isobenzofuranyl group, Dibenzofuranyl group, Naphthobenzofuranyl group, Benzoxazolyl group, Benzoisoxazolyl group, Phenoxadinyl group, Morpholino group, Dinaphthofuranyl group, Azadibenzofuranyl group, Diazadibenzofuranyl group, Azanaftobenzofuranyl group, and Diazanaphthobenzofuranyl group.

[0035] • Unsubstituted heterocyclic groups containing a sulfur atom (specific examples group G2A3): Thienyl group, Thiazolyl group, isothiazolyl group, Thiadianzolyl group, Benzothiophenyl group (benzothienyl group), Isobenzothiophenyl group (isobenzothienyl group), Dibenzothiophenyl group (dibenzothienyl group), Naphthobenzothiophenyl group (naphthobenzothienyl group), Benzothiazolyl group, Benzoisothiazolyl group, Phenothiazinyl group, Dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), Diazadibenzothiophenyl group (diazadibenzothienyl group), Azanaphtobenzothiophenyl group (azanaphthobenzothienyl group), and Diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

[0036] • Monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (Specific examples group G2A4):

[0037] [ka]

[0038] [ka]

[0039] In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A Each of these is independently an oxygen atom, a sulfur atom, NH, or CH2. However, X A and Y A At least one of them is an oxygen atom, a sulfur atom, or NH. In the above general formulas (TEMP-16) to (TEMP-33), X A and Y A If at least one of the members is NH or CH2, the monovalent heterocyclic groups derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) include monovalent groups obtained by removing one hydrogen atom from these NH or CH2 members.

[0040] • Heterocyclic groups with substitutions containing a nitrogen atom (Specific examples group G2B1): (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, Phenylcarbazole-9-yl group, Methyl benzimidazolyl group, Ethyl benzimidazolyl group, Phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, Phenylquinazolinyl group, and Biphenylylquinazolinyl group.

[0041] • Heterocyclic groups with substitutions containing an oxygen atom (Specific examples group G2B2): Phenyldibenzofuranyl group, Methyldibenzofuranyl group, t-butyldibenzofuranyl group, and A monovalent residue of spiro[9H-xanthene-9,9'-[9H]fluorene].

[0042] • Heterocyclic groups with substitutions containing a sulfur atom (specific examples group G2B3): Phenyldibenzothiophenyl group, Methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and A monovalent residue of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

[0043] • Groups in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced by substituents (specific examples group G2B4):

[0044] The aforementioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to hydrogen atoms bonded to the ring-forming carbon atoms of the monovalent heterocyclic group, X A and Y A A hydrogen atom bonded to a nitrogen atom when at least one of them is NH, and X A and Y A This refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.

[0045] • "Substituted or unsubstituted alkyl groups" Specific examples of "substituted or unsubstituted alkyl groups" as described herein (Specific Examples Group G3) include the following unsubstituted alkyl groups (Specific Examples Group G3A) and substituted alkyl groups (Specific Examples Group G3B). (Here, "unsubstituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "unsubstituted alkyl group," and "substituted alkyl group" refers to the case where "substituted or unsubstituted alkyl group" is "substituted alkyl group.") Hereafter, "alkyl group" simply refers to both "unsubstituted alkyl groups" and "substituted alkyl groups." A "substituted alkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl group" are replaced by substituents. Specific examples of "substituted alkyl groups" include the groups in which one or more hydrogen atoms in the "unsubstituted alkyl groups" (specific example group G3A) below are replaced by substituents, and examples of substituted alkyl groups (specific example group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" refers to a linear alkyl group. Therefore, "unsubstituted alkyl groups" include both linear "unsubstituted alkyl groups" and branched "unsubstituted alkyl groups". The examples of "unsubstituted alkyl groups" and "substituted alkyl groups" listed here are merely examples, and the "substituted alkyl groups" described herein also include groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl groups" of specific example group G3B are further replaced by substituents.

[0046] • Unsubstituted alkyl groups (specific examples group G3A): Methyl group, Ethyl group, n-propyl group, Isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.

[0047] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0048] • "Substituted or unsubstituted alkenyl groups" Specific examples of "substituted or unsubstituted alkenyl groups" as described herein (Specific Examples Group G4) include the following unsubstituted alkenyl groups (Specific Examples Group G4A) and substituted alkenyl groups (Specific Examples Group G4B), etc. (Here, "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is an "unsubstituted alkenyl group," and "substituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group.") In this specification, the term "alkenyl group" simply includes both "unsubstituted alkenyl groups" and "substituted alkenyl groups." A "substituted alkenyl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted alkenyl group" are replaced by substituents. Specific examples of "substituted alkenyl groups" include groups in which the "unsubstituted alkenyl group" (Specific Example Group G4A) has substituents, and examples of substituted alkenyl groups (Specific Example Group G4B). Note that the examples of "unsubstituted alkenyl groups" and "substituted alkenyl groups" listed here are merely examples, and the "substituted alkenyl groups" described herein also include groups in which the hydrogen atoms of the alkenyl group itself in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents, and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl group" of Specific Example Group G4B are further replaced by substituents.

[0049] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0050] • Substitutive alkenyl groups (specific examples group G4B): 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.

[0051] • "Substituted or unsubstituted alkynyl groups" Specific examples of "substituted or unsubstituted alkynyl groups" as described herein (Specific Examples Group G5) include the following unsubstituted alkynyl groups (Specific Examples Group G5A), etc. (Here, "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereafter, when simply referred to as "alkynyl group," it includes both "unsubstituted alkynyl groups" and "substituted alkynyl groups." A "substituted alkynyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl group" are replaced by substituents. Specific examples of "substituted alkynyl groups" include groups in which one or more hydrogen atoms in an "unsubstituted alkynyl group" (specific example group G5A) are replaced by substituents.

[0052] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0053] • "Substituted or unsubstituted cycloalkyl groups" Specific examples of "substituted or unsubstituted cycloalkyl groups" as described herein (Specific Examples Group G6) include the following unsubstituted cycloalkyl groups (Specific Examples Group G6A) and substituted cycloalkyl groups (Specific Examples Group G6B), etc. (Here, "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group," and "substituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "substituted cycloalkyl group.") In this specification, the term "cycloalkyl group" simply includes both "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups." A "substituted cycloalkyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" are replaced by a substituent. Specific examples of "substituted cycloalkyl groups" include the groups in which one or more hydrogen atoms in an "unsubstituted cycloalkyl group" (specific example group G6A) are replaced by a substituent, and examples of substituted cycloalkyl groups (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl groups" and "substituted cycloalkyl groups" listed here are merely examples, and the "substituted cycloalkyl groups" described herein also include groups in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted cycloalkyl group" of specific example group G6B are further replaced by a substituent.

[0054] • Unsubstituted cycloalkyl groups (specific examples group G6A): Cyclopropyl group, Cyclobutyl group, Cyclopentyl group, Cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.

[0055] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0056] · "-Si(R 901 )(R 902 )(R 903 ) a base represented by -Si(R 901 )(R 902 )(R 903 ) Examples of the base represented by (Example Group G7) are: -Si(G1)(G1)(G1), -Si(G1)(G2)(G2), -Si(G1)(G1)(G2), -Si(G2)(G2)(G2), -Si(G3)(G3)(G3), and -Si(G6)(G6)(G6) Here are some examples. G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -Si(G1)(G1)(G1), the multiple G1s are either identical or different from one another. In -Si(G1)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G1)(G1)(G2), the multiple G1s are either identical or different from one another. In -Si(G2)(G2)(G2), the multiple G2s are either identical or different from one another. In -Si(G3)(G3)(G3), the multiple G3s are either identical or different from one another. In -Si(G6)(G6)(G6), the multiple G6s are either identical or different from one another.

[0057] ·「-O-(R 904 ) a base represented by The following information pertains to the -O-(R 904 ) Examples of the base represented by (Example Group G8) are: -O(G1), -O(G2), -O(G3), and -O(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0058] · "-S-(R 905 ) a base represented by The following information pertains to this specification -S-(R 905 ) Examples of the base represented by (example group G9) are: -S(G1), -S(G2), -S(G3), and -S(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6.

[0059] · "-N(R 906 )(R 907 ) a base represented by -N(R) as described in this specification 906 )(R 907 ) Examples of the base represented by (Example Group G10) are: -N(G1)(G1), -N(G2)(G2), -N(G1)(G2), -N(G3)(G3), and -N(G6)(G6) These are some examples. Here, G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. G2 is a "substituted or unsubstituted heterocyclic group" as described in specific example group G2. G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. G6 is a "substituted or unsubstituted cycloalkyl group" as described in specific example group G6. In -N(G1)(G1), multiple G1s are either identical or different from one another. In -N(G2)(G2), multiple G2s are either identical or different from one another. In -N(G3)(G3), multiple G3s are either identical or different from one another. In -N(G6)(G6), multiple G6s are either identical or different from one another.

[0060] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0061] • "Substituted or unsubstituted fluoroalkyl groups" The terms "substituted or unsubstituted fluoroalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a fluorine atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by fluorine atoms (perfluoro groups). The number of carbon atoms in an "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced by substituents. The terms "substituted fluoroalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted fluoroalkyl groups" include the example of a group in which one or more hydrogen atoms in the aforementioned "alkyl group" (specific example group G3) are replaced by fluorine atoms.

[0062] • "Substituted or unsubstituted haloalkyl groups" The terms "substituted or unsubstituted haloalkyl groups" as used herein refer to groups in which at least one hydrogen atom bonded to the carbon atoms constituting the alkyl group is replaced by a halogen atom, and also include groups in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group are replaced by halogen atoms. The number of carbon atoms in an "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein. A "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced by substituents. The terms "substituted haloalkyl groups" as used herein also include groups in which one or more hydrogen atoms bonded to the carbon atoms of the alkyl chain are further replaced by substituents, and groups in which one or more hydrogen atoms of a substituent are further replaced by substituents. Specific examples of "unsubstituted haloalkyl groups" include groups in which one or more hydrogen atoms of the aforementioned "alkyl group" (specific example group G3) are replaced by halogen atoms. Haloalkyl groups are sometimes referred to as alkyl halogens.

[0063] • "Substituted or unsubstituted alkoxy groups" A specific example of a "substituted or unsubstituted alkoxy group" as described herein is a group represented by -O(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The number of carbon atoms in the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0064] • "substituted or unsubstituted alkylthio groups" A specific example of the "substituted or unsubstituted alkylthio group" described herein is the group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3. The number of carbon atoms in the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified herein.

[0065] • "Substituted or unsubstituted aryloxy groups" A specific example of a "substituted or unsubstituted aryloxy group" as described herein is a group represented by -O(G1), where G1 is a "substituted or unsubstituted aryl group" as described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0066] • "Substituted or unsubstituted arylthio groups" A specific example of the "substituted or unsubstituted arylthio group" described herein is the group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. The number of ring-forming carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

[0067] • "Substituted or unsubstituted trialkylsilyl groups" A specific example of the "trialkylsilyl group" described herein is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" as described in specific example group G3. The multiple G3s in -Si(G3)(G3)(G3) are either identical or different from one another. Unless otherwise specified herein, 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.

[0068] • "Substituted or unsubstituted aralkyl groups" Specific examples of the "substituted or unsubstituted aralkyl group" described herein include the group represented by -(G3)-(G1), where G3 is the "substituted or unsubstituted alkyl group" described in specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in specific example group G1. Therefore, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced by an "aryl group" as a substituent, and is one form of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" in which an "unsubstituted aryl group" is substituted, and the number of carbon atoms in the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise specified herein. Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

[0069] Unless otherwise specified herein, the substituted or unsubstituted aryl groups are preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, pyrenyl, chrysenyl, triphenylenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl, and 9,9-diphenylfluorenyl.

[0070] Unless otherwise specified herein, the substituted or unsubstituted heterocyclic groups are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothiophenyl, naphthobenzothiophenyl, aza These include dibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group, etc.

[0071] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0072] [ka]

[0073] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0074] [ka]

[0075] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0076] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0077] [ka]

[0078] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0079] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0080] • "Substituted or unsubstituted arylene group" Unless otherwise specified, the "substituted or unsubstituted arylene group" described herein is a divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described above. Specific examples of the "substituted or unsubstituted arylene group" (Specific Examples Group G12) include the divalent group derived by removing one hydrogen atom from the aryl ring of the "substituted or unsubstituted aryl group" described in Specific Examples Group G1.

[0081] • "Substitutable or unsubstituted divalent heterocyclic groups" Unless otherwise specified, the “substituted or unsubstituted divalent heterocyclic groups” described herein refer to divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described above. Specific examples of “substituted or unsubstituted divalent heterocyclic groups” (Specific Examples Group G13) include the divalent groups derived by removing one hydrogen atom from the heterocycle of the “substituted or unsubstituted heterocyclic groups” described in Specific Examples Group G2.

[0082] • "Substituted or unsubstituted alkylene groups" Unless otherwise specified, the "substituted or unsubstituted alkylene groups" described herein are divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described above. Specific examples of "substituted or unsubstituted alkylene groups" (Specific Examples Group G14) include the divalent groups derived by removing one hydrogen atom from the alkyl chain of the "substituted or unsubstituted alkyl groups" described in Specific Examples Group G3.

[0083] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0084] [ka]

[0085] [ka]

[0086] In the above general formulas (TEMP-42) to (TEMP-52), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. In the general formulas (TEMP-42) to (TEMP-52) above, * represents a bond position.

[0087] [ka]

[0088] In the above general formulas (TEMP-53) to (TEMP-62), Q1 to Q 10 Each of these is independently either a hydrogen atom or a substituent. Equations Q9 and Q 10 These elements may be bonded to each other via single bonds to form a ring. In the general formulas (TEMP-53) to (TEMP-62) above, * represents a bond position.

[0089] [ka]

[0090] In the general formulas (TEMP-63) to (TEMP-68) above, Q1 to Q8 are each independently a hydrogen atom or a substituent. In the general formulas (TEMP-63) to (TEMP-68) above, * represents a bond position.

[0091] Unless otherwise specified herein, the substituted or unsubstituted divalent heterocyclic groups described herein are preferably any of the following general formulas (TEMP-69) to (TEMP-102).

[0092] [ka]

[0093] [ka]

[0094] [ka]

[0095] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0101] The above is a description of the substituents described herein.

[0102] • "When they combine to form a ring" In this specification, the phrase "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring, join together to form a substituted or unsubstituted fused ring, or do not join together" means the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted monoring," the case where "one or more pairs of adjacent elements join together to form a substituted or unsubstituted fused ring," and the case where "one or more pairs of adjacent elements do not join together." In this specification, the cases in which "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements bond to each other to form a substituted or unsubstituted fused ring" (hereinafter, these cases may be collectively referred to as "cases where elements bond to form a ring") will be explained below. An example will be given of an anthracene compound represented by the following general formula (TEMP-103), whose parent skeleton is an anthracene ring.

[0103] [ka]

[0104] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.

[0105] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0106] [ka]

[0107] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which 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 R 922 Share.

[0108] [ka]

[0109] The formed "mono-ring" or "condensed-ring" may be saturated or unsaturated, based solely on the structure of the formed ring. Even when "a pair of adjacent rings" forms a "mono-ring" or "condensed-ring," the "mono-ring" or "condensed-ring" can be saturated or unsaturated. For example, ring Q formed in the general formula (TEMP-104) A and ring Q B These are, respectively, a "single ring" or a "condensed ring". Also, ring Q formed in the general formula (TEMP-105) is A , and ring Q C This is a "condensed ring". The ring Q of the general formula (TEMP-105) A and Q C This refers to the Q environment. A and Q C The ring Q of the general formula (TMEP-104) is formed by the condensation of the two rings. A If it is a benzene ring, then ring Q A It is a single ring. The ring Q of the general formula (TMEP-104) A If it is a naphthalene ring, then ring Q A It is a condensed ring.

[0110] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.

[0111] Here, "any element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur, unless otherwise specified herein. In any element (for example, carbon or nitrogen), bonds that do not form a ring may be terminated with a hydrogen atom or the like, or substituted with "any substituent" as described later. If any element other than carbon is included, the formed ring is a heterocycle. The "one or more arbitrary elements" constituting the monoring or fused ring are preferably 2 to 15, more preferably 3 to 12, and even more preferably 3 to 5, unless otherwise specified herein. Unless otherwise specified herein, the preferred form is a "mono-ring" and a "condensed ring." Unless otherwise specified herein, the "unsaturated ring" is preferred over the "saturated ring". Unless otherwise specified herein, “monocyclic” is preferably a benzene ring. Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring. When "one or more sets of two or more adjacent elements" "bond to each other to form a substituted or unsubstituted monoring" or "bond to each other to form a substituted or unsubstituted fused ring", unless otherwise specified herein, preferably, one or more sets of two or more adjacent elements bond to each other to form a substituted or unsubstituted "unsaturated ring" consisting of multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur elements, ranging from one to fifteen.

[0112] When the above-mentioned "monocyclic ring" or "fused ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "monocyclic ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. When the above-mentioned "saturated ring" or "unsaturated ring" has substituents, the substituents are, for example, "any substituents" as described later. Specific examples of substituents when the above-mentioned "mono-ring" or "fused ring" has substituents are the substituents described in the section "Substituents as described herein" above. The above explains the cases in which "one or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring" and "one or more pairs of adjacent elements combine to form a substituted or unsubstituted fused ring" ("the case of combining to form a ring").

[0113] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), Halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. R903 If there are two or more of them, then there are two or more R 903 They are either identical or different from each other. R 904 If there are two or more of them, then there are two or more R 904 They are either identical or different from each other. R 905 If there are two or more of them, then there are two or more R 905 They are either identical or different from each other. R 906 If there are two or more of them, then there are two or more R 906 They are either identical or different from each other. R 907 If there are two or more of them, then there are two or more R 907 They are either identical or different from one another.

[0114] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.

[0115] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, Ring-forming aryl groups with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.

[0116] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0117] Unless otherwise specified herein, adjacent substituents may form a "saturated ring" or an "unsaturated ring," preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, and more preferably a benzene ring. Unless otherwise specified herein, any substituent may have further substituents, such as those described above.

[0118] In this specification, a numerical range expressed using "AA~BB" means a range that includes the numerical value AA, which is listed before "AA~BB", as the lower limit, and the numerical value BB, which is listed after "AA~BB", as the upper limit.

[0119] In this specification, the expression "A≧B" means that the value of A is equal to the value of B, or that the value of A is greater than the value of B. In this specification, the expression "A ≤ B" means that the value of A is equal to the value of B, or that the value of A is less than the value of B.

[0120] [First Embodiment] The compound according to the first embodiment is a compound represented by the following general formula (D1).

[0121] [ka]

[0122] (In the above general formula (D1), R1~R 11 Each of them operates independently. hydrogen atom, The group represented by the following general formula (D11), Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 131 )(R 132 A base represented by ) -Si(R 133 )(R 134 )(R 135 A base represented by ) -O-(R 136 A base represented by ) -S-(R 137 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 138 A base represented by -COOR 139 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 140 )(R 141 A base represented by ) -Ge(R 142 )(R 143 )(R 144 A base represented by ) -B(R 145 )(R 146 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. however, R1~R 11 Of these, at least one is a group represented by the following general formula (D11), There are no cases where two or more of R1 to R4 are not hydrogen atoms. There are no cases where two or more of R5 to R8 are not hydrogen atoms. R9~R 11 There are no cases where two or more of them are not hydrogen atoms. R9 and R 11 It does not contain substituted or unsubstituted carbazolyl groups. R 12 and R 13 Each of them operates independently. A group represented by the following general formula (D12), or A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, However, R 12 and R 13 At least one of these is a group represented by the following general formula (D12).

[0123] [ka]

[0124] (In the above general formula (D11), R A , R B , R C , R D , R E , R F And one or more pairs of adjacent Y members, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring A , R B , R C , R D , R E , R F And one of Y is a single bond that connects to *a, L1 is a ring-forming arylene group with 6 to 50 carbon atoms, either single-bonded, substituted, or unsubstituted. *b indicates the bonding position with the ring structure represented by the general formula (D1), R A and R BWhen a set consisting of these elements is bonded to each other to form a substituted or unsubstituted carbazole ring, and Y is a single bond to *a and L1 is a single bond, then a substituted or unsubstituted amino group and a substituted or unsubstituted N-carbazolyl group will not be bonded to the carbazole ring. In the above general formula (D12), R G , R H , R I , R J and R K Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, *c indicates the bonding position with the ring structure represented by the general formula (D1) above. In the above general formulas (D11) and (D12), R does not form the aforementioned substituted or unsubstituted monoring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a single bond attached to *a. A , R B , R C , R D , R E , R F and Y, and R which does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. G , R H , R I , R J and R K Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 131 )(R132 A base represented by ) -Si(R 133 )(R 134 )(R 135 A base represented by ) -O-(R 136 A base represented by ) -S-(R 137 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 138 A base represented by -COOR 139 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 140 )(R 141 A base represented by ) -Ge(R 142 )(R 143 )(R 144 A base represented by ) -B(R 145 )(R 146 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. however, R G and R H However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R K It is not a hydrogen atom, R J and R K However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R G It is not a hydrogen atom, R G and R H They do not combine with each other, and R J and R K If they do not combine with each other, R G and RK (It is neither a hydrogen atom nor a substituted or unsubstituted aryl group with 6-50 carbon atoms forming a ring.) (In the compound represented by the general formula (D1) above, R 131 ~R 146 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 131 If multiple R 131 They are either identical or different from one another. R 132 If multiple R 132 They are either identical or different from one another. R 133 If multiple R 133 They are either identical or different from one another. R 134 If multiple R 134 They are either identical or different from one another. R 135 If multiple R 135 They are either identical or different from one another. R 136 If multiple R 136 They are either identical or different from one another. R 137 If multiple R 137 They are either identical or different from one another. R 138 If multiple R 138 They are either identical or different from one another. R 139 If multiple R 139 They are either identical or different from one another. R 140 If multiple R140 They are either identical or different from one another. R 141 If multiple R 141 They are either identical or different from one another. R 142 If multiple R 142 They are either identical or different from one another. R 143 If multiple R 143 They are either identical or different from one another. R 144 If multiple R 144 They are either identical or different from one another. R 145 If multiple R 145 They are either identical or different from one another. R 146 If multiple R 146 They are either identical or different to one another.

[0125] The compound according to this embodiment has a fused ring containing a boron atom and two nitrogen atoms as its parent skeleton, and a group represented by general formula (D12) is bonded to at least one of the nitrogen atoms of the parent skeleton. G and R K Since the group represented by the general formula (D12) is not a hydrogen atom but forms a substituted or unsubstituted monocycle, a substituted or unsubstituted fused ring, or is a substituent, the group represented by the general formula (D12) is a bulky substituent. Thus, the compound according to this embodiment has a structure in which a bulky substituent is bonded to at least one of the nitrogen atoms of the parent skeleton, so that intermolecular interactions are suppressed and the full width at half maximum of the emission spectrum is narrowed and improved. Furthermore, by using the compound according to this embodiment in the organic layer of an organic EL element, the luminescence efficiency can be improved.

[0126] Furthermore, the statement "There are no cases where two or more of R1 to R4 are not hydrogen atoms" means that three of R1 to R4 are hydrogen atoms, and the remaining one is either a hydrogen atom or something other than a hydrogen atom (i.e., a substituent). The statement "There are no cases where two or more of R5 to R8 are not hydrogen atoms" means that three of R5 to R8 are hydrogen atoms, and the remaining one is either a hydrogen atom or something other than a hydrogen atom (i.e., a substituent). "R9~R 11 "There are no cases where two or more of them are not hydrogen atoms" means R9~R 11 This means that three of them are hydrogen atoms, and the remaining one is either a hydrogen atom or something other than a hydrogen atom (i.e., a substituent).

[0127] In one embodiment of this present invention, R in the general formula (D11) A and R B A set consisting of these elements can combine with each other to form a substituted or unsubstituted monoring, or combine with each other to form a substituted or unsubstituted fused ring. In the compound according to this embodiment, R A and R B The substituted or unsubstituted monorings and substituted or unsubstituted fused rings formed by the bonding of sets consisting of these elements are preferably, independently, substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring-forming carbon atoms, substituted or unsubstituted heterorings with 5 to 50 (preferably 5 to 30, more preferably 5 to 18) ring-forming carbon atoms, or substituted or unsubstituted aliphatic hydrocarbon rings with 3 to 50 (preferably 3 to 20, more preferably 3 to 6) ring-forming carbon atoms.

[0128] In one embodiment of this present invention, R in the general formula (D11) A and R B The sets consisting of these elements do not join together and do not form a ring.

[0129] In the compound according to this embodiment, it is preferable that Y is a single bond bonded to *a. When Y is a single bond bonded to *a, the nitrogen atom is bonded to L1 as shown in the following general formula (D111) or (D112).

[0130] In the compound according to this embodiment, it is preferable that at least one of the groups represented by the general formula (D11) is a group represented by the following general formula (D111) or (D112).

[0131] [ka]

[0132] (In the above general formula (D111), R A , R B , R C , R D , R E , R F L1 and *b are, respectively, R in the general formula (D11). A , R B , R C , R D , R E , R F , is synonymous with L1 and *b, however R A and R B They do not combine with each other, In the above general formula (D112), R C , R D , R E , R F L1 and *b are, respectively, R in the general formula (D11). C , R D , R E , R F , is synonymous with L1 and *b, R L , R M , R N and R O Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring L , R M , R N and R OEach of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R 131 )(R 132 A base represented by ) -Si(R 133 )(R 134 )(R 135 A base represented by ) -O-(R 136 A base represented by ) -S-(R 137 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 138 A base represented by -COOR 139 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 140 )(R 141 A base represented by ) -Ge(R 142 )(R 143 )(R 144 A base represented by ) -B(R 145 )(R 146 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. However, if L1 in the above general formula (D112) is a single bond, R C , R D , R E , R F , R L , R M , RN and R O is -N(R 131 )(R 132 (This does not refer to the group represented by ) or the substituted or unsubstituted N-carbazolyl group.)

[0133] The group represented by the general formula (D11) is represented by the general formula (D111) or the general formula (D112) when Y is bonded to *a as a single bond.

[0134] In the compound according to this embodiment, at least one of the groups represented by the general formula (D11) is R A , R B , R C , R D , R E and R F It is also preferable that one of them is a single bond to *a.

[0135] The compound according to this embodiment preferably has one or two groups represented by the general formula (D11) in its molecule.

[0136] In the compound according to this embodiment, it is preferable that one of R2 and R7 is a group represented by the general formula (D11), or that both R2 and R7 are groups represented by the general formula (D11).

[0137] In the compound according to this embodiment, R 10 However, it is also preferable that the group be represented by the general formula (D11) mentioned above.

[0138] In the compound according to this embodiment, R 10 However, it is also preferable that the atom be a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0139] In the compound according to this embodiment, R9~R 11 If one of these is a group represented by the general formula (D11), it is preferable that neither R1 to R4 nor R5 to R8 are both hydrocarbon groups.

[0140] In the compound according to this embodiment, R1, R3, R4, R5, R6, R8, R9 and R 11 It is also preferable that it be a hydrogen atom.

[0141] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D103). The compound represented by the following general formula (D103) is one in which R1, R3, R4, R5, R6, R8, R9 and R in the general formula (D1) 11 This corresponds to a compound where the atom is a hydrogen atom.

[0142] [ka]

[0143] (In the above general formula (D103), R2, R7, R 10 , R 12 and R 13 These are R2, R7, and R in the general formula (D1) mentioned above, respectively. 10 , R 12 and R 13 (This is synonymous with...)

[0144] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D101). The compound represented by the following general formula (D101) is the one in which R in the general formula (D1) 12 and R 13 This corresponds to a compound where the group is represented by the general formula (D12).

[0145] [ka]

[0146] (In the above general formula (D101), R1 to R 11 , R G , R H , R I , R J and R KThese are R1 to R in the general formulas (D1) and (D12) mentioned above, respectively. 11 , R G , R H , R I , R J and R K It is synonymous with multiple R G These are either identical or different from each other, and multiple R H These are either identical or different from each other, and multiple R I These are either identical or different from each other, and multiple R J These are either identical or different from each other, and multiple R K They are either identical or different to one another.

[0147] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D102). The compound represented by the following general formula (D102) corresponds to the compound in which R2 and R7 in the general formula (D101) are groups represented by the general formula (D112), and R1, R3, R4, R5, R6, and R8 are hydrogen atoms.

[0148] [ka]

[0149] (In the above general formula (D102), R9~R 11 , R G , R H , R I , R J and R K These are R9~R in the general formulas (D1) and (D12) mentioned above, respectively. 11 , R G , R H , R I , R J and R K It is synonymous with, R C , R D , R E , R F , R L , R M , R N , RO And L1 are, respectively, R in the general formula (D112) C , R D , R E , R F , R L , R M , R N , R O And it is synonymous with L1, Multiple L1s may be identical or different from each other, and multiple R C These are either identical or different from each other, and multiple R D These are either identical or different from each other, and multiple R E These are either identical or different from each other, and multiple R F These are either identical or different from each other, and multiple R G These are either identical or different from each other, and multiple R H These are either identical or different from each other, and multiple R I These are either identical or different from each other, and multiple R J These are either identical or different from each other, and multiple R K These are either identical or different from each other, and multiple R L These are either identical or different from each other, and multiple R M These are either identical or different from each other, and multiple R N These are either identical or different from each other, and multiple R O They are either identical or different to one another.

[0150] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D104). The compound represented by the following general formula (D104) is one in which R9 and R in the general formula (D102) 11 This corresponds to a compound where the atom is a hydrogen atom.

[0151] [ka]

[0152] (In the above general formula (D104), R 10 , R G, R H , R I , R J and R K These are R in the general formulas (D1) and (D12) mentioned above, respectively. 10 , R G , R H , R I , R J and R K It is synonymous with, R C , R D , R E , R F , R L , R M , R N , R O And L1 are, respectively, R in the general formula (D112) C , R D , R E , R F , R L , R M , R N , R O (And synonymous with L1.)

[0153] In the compound according to this embodiment, R H and R J It is preferable that it be a hydrogen atom.

[0154] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D105). The compound represented by the following general formula (D105) is the one in which R in the general formula (D104) H and R J This corresponds to a compound where the atom is a hydrogen atom.

[0155] [ka]

[0156] (In the above general formula (D105), R 10 , R G , R I , and R KThese are R in the general formulas (D1) and (D12) mentioned above, respectively. 10 , R G , R I , and R K It is synonymous with, R C , R D , R E , R F , R L , R M , R N , R O And L1 are, respectively, R in the general formula (D112) C , R D , R E , R F , R L , R M , R N , R O (And synonymous with L1.)

[0157] In the compound according to this embodiment, it is preferable that L1 is a single bond.

[0158] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D106). The compound represented by the following general formula (D106) corresponds to the compound in which L1 in the general formula (D104) is a single bond.

[0159] [ka]

[0160] (In the above general formula (D106), R 10 , R G , R H , R I , R J and R K These are R in the general formulas (D1) and (D12) mentioned above, respectively. 10 , R G , R H , R I , R J and R K is synonymous with, RC , R D , R E , R F , R L , R M , R N and R O These are, respectively, R in the general formula (D112) above. C , R D , R E , R F , R L , R M , R N and R O (This is synonymous with...)

[0161] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D107). The compound represented by the following general formula (D107) corresponds to the compound in which L1 in the general formula (D105) is a single bond.

[0162] [ka]

[0163] (In the above general formula (D107), R 10 , R G , R I , and R K These are R in the general formulas (D1) and (D12) mentioned above, respectively. 10 , R G , R I , and R K It is synonymous with, R C , R D , R E , R F , R L , R M , R N and R O These are, respectively, R in the general formula (D112) above. C , R D , R E , R F , R L , R M , R N and RO (This is synonymous with...)

[0164] In this embodiment, the compound represented by the general formula (D1) may also be represented by the following general formula (D108). The compound represented by the following general formula (D108) is the one in which R in the general formula (D107) C , R D , R E , R F , R L , R M , R N and R O This corresponds to a compound where the atom is a hydrogen atom.

[0165] [ka]

[0166] (In the above general formula (D108), R 10 , R G , R I , and R K These are R in the general formulas (D1) and (D12) mentioned above, respectively. 10 , R G , R I , and R K (This is synonymous with...)

[0167] In the compound according to this embodiment, R1 to R 11 Each of them operates independently. hydrogen atom, The base represented by the general formula (D11) above, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms, however, R1 to R 11 Of these, at least one is a group represented by the following general formula (D11).

[0168] In the compound according to this embodiment, R A , R B , R C , R D , R E and R F Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0169] In the compound according to this embodiment, R C , R D , R E , R F , R L , R M , R N and R O Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0170] In the compound according to this embodiment, R G and R H A set consisting of R J and R K It is also preferable that one of the pairs consists of two rings that combine to form a substituted or unsubstituted monoring, or a substituted or unsubstituted fused ring, while the other ring does not combine with the other ring.

[0171] In the compound according to this embodiment, R G and R H A set consisting of R J and RK Each of these pairs may independently combine with one another to form a substituted or unsubstituted monoring, or combine with one another to form a substituted or unsubstituted fused ring.

[0172] In the compound according to this embodiment, R G and R H A set consisting of R J and R K The substituted or unsubstituted monorings and substituted or unsubstituted fused rings formed by the bonding of sets consisting of these elements are preferably, independently, substituted or unsubstituted aromatic hydrocarbon rings with 6 to 50 (preferably 6 to 30, more preferably 6 to 18) ring-forming carbon atoms, substituted or unsubstituted heterorings with 5 to 50 (preferably 5 to 30, more preferably 5 to 18) ring-forming carbon atoms, or substituted or unsubstituted aliphatic hydrocarbon rings with 3 to 50 (preferably 3 to 20, more preferably 3 to 6) ring-forming carbon atoms.

[0173] In the compound according to this embodiment, the group represented by the general formula (D12) is also preferably a group represented by the following general formulas (D121), (D122), or (D123).

[0174] [ka]

[0175] (In the above general formulas (D121), (D122), and (D123), R I R in the general formula (D12) is I It is synonymous with, R 121 ~R 128 , R 151 ~R 158 R 161 ~R 168 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. X A and X B These are, independently, either an oxygen atom or a sulfur atom. *c indicates the bonding position with the ring structure represented by the general formula (D1) above.

[0176] In the compound according to this embodiment, the group represented by the general formula (D12) is also preferably a group represented by the following general formulas (D124), (D125), (D126), or (D127).

[0177] [ka]

[0178] (In the above general formulas (D124), (D125), (D126), and (D127), R G , R H and R I These are, respectively, R in the general formula (D12) above. G , R H and R I This is synonymous with, however, R G It is not a hydrogen atom, R 121 ~R 124 , R 151 ~R 158 R 171 ~R 180 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. X A is an oxygen atom or a sulfur atom, *c indicates the bonding position with the ring structure represented by the general formula (D1) above.

[0179] In the compound according to this embodiment, R G and R K Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R H , R I and R J Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0180] In the compound according to this embodiment, R G and R K Preferably, each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.

[0181] In the compound according to this embodiment, R G and R K Each of these is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0182] In the compound according to this embodiment, R G and R K Each is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, and R IPreferably, this is a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.

[0183] In the compound according to this embodiment, R G , R I and R K Each of these is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

[0184] The compounds according to this embodiment may also preferably not contain substituted or unsubstituted amino groups in their molecules.

[0185] In the compound according to this embodiment, the substituent in the phrase "substituted or unsubstituted" is halogen atom, Unsubstituted alkyl groups with 1 to 20 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, or It is preferable that the group is an unsubstituted heterocyclic group with 5 to 30 ring-forming atoms.

[0186] In the compound according to this embodiment, the substituent in the phrase "substituted or unsubstituted" is Unsubstituted alkyl groups with 1 to 6 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 6 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 18 carbon atoms, or It is more preferable that the group is an unsubstituted heterocyclic group with 5 to 18 ring-forming atoms.

[0187] In the compounds according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0188] (Method for producing the compound according to this embodiment) The compounds according to this embodiment can be produced by following the synthesis method described in the examples below, or by using known alternative reactions and raw materials tailored to the target product, in accordance with that synthesis method.

[0189] (Specific examples of compounds according to this embodiment) Specific examples of compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted from the description. In this specification, methyl groups may be denoted as Me, and phenyl groups as Ph.

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[0230] [Second Embodiment] <Materials for organic electroluminescent devices> The material for an organic electroluminescent device according to this embodiment contains the compound according to the first embodiment. One embodiment is a material for an organic electroluminescent device that contains only the compound according to the first embodiment, and another embodiment is a material for an organic electroluminescent device that contains the compound according to the first embodiment and other compounds different from the compound in the first embodiment. In the organic electroluminescent element material of this embodiment, it is preferable that the compound according to the first embodiment is a dopant material. In this case, the organic electroluminescent element material may include the compound according to the first embodiment as a dopant material (preferably a fluorescent compound) and other compounds such as a host material and a sensitizer.

[0231] [Third Embodiment] <Organic electroluminescent element> An organic EL element according to the third embodiment will be described. The organic EL element according to the third embodiment includes a cathode, an anode, and an organic layer contained between the cathode and the anode. This organic layer includes at least one layer composed of an organic compound. Alternatively, this organic layer is formed by stacking multiple layers composed of organic compounds. The organic layer may further contain an inorganic compound. At least one layer of the organic layer contains the compound according to the first embodiment as compound M3. Compound M3 may be referred to as the third compound.

[0232] (organic layer) In the third embodiment of the organic EL element, it is preferable that the organic layer includes an emissive layer, and that the emissive layer contains compound M3 (the third compound). In the third embodiment of the organic EL element, the organic layer may consist of, for example, one emissive layer, or it may include layers that can be used in the organic EL element. The layers that can be used in the organic EL element are not particularly limited, but examples include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron barrier layer, a hole barrier layer, an electron transport layer, and an electron injection layer.

[0233] An organic EL element according to one aspect of the third embodiment includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a sensitizing material and compound M3. The sensitizing material and compound M3 are different compounds from each other.

[0234] In the organic EL element of the third embodiment, a hole transport layer may be disposed between the anode and the light-emitting layer.

[0235] In the organic EL element of the third embodiment, an electron transport layer may be disposed between the cathode and the light-emitting layer.

[0236] Figure 1 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is constructed by stacking a hole injection layer 6, a hole transport layer 7, an emissive layer 5, an electron transport layer 8, and an electron injection layer 9 in that order, starting from the anode 3 side. The present invention is not limited to the configuration of the organic EL element shown in Figure 1.

[0237] (Emitting layer) In one embodiment, the sensitizing material and compound M3 are contained in a single layer. For example, if the organic EL element has one light-emitting layer, the sensitizing material and compound M3 are contained in that single light-emitting layer; if it has multiple light-emitting layers, the sensitizing material and compound M3 are contained in one of the single light-emitting layers. In one embodiment, compound M3 (the third compound) is contained in the light-emitting layer as a fluorescent material.

[0238] In one embodiment, the light-emitting layer contains a sensitizing material and compound M3 as a fluorescent material. In this embodiment, the sensitizing material is preferably one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds, and more preferably a delayed-fluorescence compound. In this embodiment, if the light-emitting layer contains a delayed-fluorescence compound as a sensitizing material, it is preferable that the light-emitting layer does not contain a phosphorescent metal complex.

[0239] In the light-emitting layer, recombination of holes and electrons is more likely to occur on the molecules of the sensitizing material rather than on the fluorescent material. If the sensitizing material is a delayed-fluorescence compound, it is thought that the lowest excited triplet state undergoes reverse intersystem crossing to the lowest excited singlet state. Thus, after the energy state transition to the lowest excited singlet state occurs in the sensitizing material, energy transfer occurs from the sensitizing material to the fluorescent material, and fluorescence emission occurs from the lowest excited singlet state of the fluorescent material. In this embodiment, if the sensitizing material is a delayed-fluorescence compound in which reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state occurs efficiently, energy loss is small, and the fluorescent material that receives that energy is thought to emit light with high efficiency.

[0240] [Fluorescent materials] In this embodiment, the fluorescent material is preferably a compound that does not exhibit thermally activated delayed fluorescence. In this embodiment, the fluorescent material is not a phosphorescent metal complex. In this embodiment, the fluorescent material is preferably not a metal complex.

[0241] (Maximum peak wavelength) In the third embodiment, the maximum peak wavelength of the third compound (compound M3) as a fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less. In the third embodiment, the maximum peak wavelength of the third compound (compound M3) as a fluorescent material is preferably 430 nm or higher, and more preferably 440 nm or higher. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum peak wavelength of fluorescence emission. In the organic EL element of the third embodiment, the third compound (compound M3) preferably exhibits blue light emission. In this specification, blue light emission refers to light emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 430 nm or more and 480 nm or less.

[0242] (Emission spectrum half-width) In the third embodiment, the emission spectrum full width at half maximum (FWHM) of the third compound (compound M3) as a fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. FWHM is an abbreviation for full width at half maximum.

[0243] In this specification, the method for measuring the maximum peak wavelength of a compound is as follows: The compound to be measured is 10 -6 mol / L or more, 10 -5 Prepare a toluene solution with a concentration of mol / L or less and place it in a quartz cell. At room temperature (300K), measure the emission spectrum of this sample (toluene solution) using a spectrofluorometer (vertical axis: emission intensity, horizontal axis: wavelength). The emission spectrum can be measured using a spectrofluorometer (model name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the one used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum is defined as the maximum peak wavelength. In this specification, the maximum peak wavelength of fluorescence emission may be referred to as the maximum peak wavelength of fluorescence emission (FL-peak). The emission spectrum half-width FWHM is the full width at half maximum at the maximum peak of the emission spectrum.

[0244] (Stokes shift) In this embodiment, the Stokes shift of the third compound (compound M3) as a fluorescent material is preferably 25 nm or less, and more preferably 20 nm or less. In this embodiment, the Stokes shift of the third compound (compound M3) as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. The Stokes shift of the third compound (compound M3) is less than 20 nm, which allows for a reduction in excitation energy. The Stokes shift of the third compound (compound M3) is 10 nm or greater, which suppresses self-absorption and reduces efficiency loss. The Stokes shift can be measured by the following method: 2.0 × 10⁻⁶ of the compound to be measured. -5 Prepare the sample for measurement by dissolving the compound in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with continuous ultraviolet-visible light at room temperature (300K) and measure the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength). A spectrophotometer can be used for absorption spectrum measurement; for example, Hitachi High-Tech Science's U-3900 / 3900H spectrophotometer can be used. Also, the compound to be measured should be 4.9 × 10⁻⁶ -6Prepare a sample for measurement by dissolving the substance in toluene at a concentration of mol / L. Irradiate the sample, placed in a quartz cell, with excitation light at room temperature (300K) and measure the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength). A spectrophotometer can be used for fluorescence spectrum measurement; for example, the Hitachi High-Tech Science F-7000 spectrofluorometer can be used. From these absorption and fluorescence spectra, calculate the difference between the absorption maximum wavelength and the fluorescence maximum wavelength to determine the Stokes shift (SS). The unit of Stokes shift SS is nm.

[0245] [Sensitizing material] In this specification, the compound used as a sensitizer may be referred to as the second compound or compound M2.

[0246] (Delayed fluorescence compounds) In this embodiment, the delayed-fluorescence compound is not a phosphorescent metal complex. In this embodiment, it is preferable that the delayed-fluorescence compound is not a metal complex.

[0247] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H1).

[0248] [ka]

[0249] (In the above general formula (H1), A H This is a group having at least one substructure selected from the group consisting of the following general formulas (a-1), (a-2), (a-3), (a-4), (a-5), (a-6), (a-7), and (a-8), D H This is a group represented by the following general formulas (221), (222), or (223): L H teeth, single bond, A substituted or unsubstituted aryl ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. m is 1, 2, 3, 4 or 5, and multiple A H They are either identical or different from one another. n is 1, 2, 3, 4, or 5, and there are multiple D H They are either identical or different to one another.

[0250] [ka]

[0251] (In the general formulas (a-1) to (a-8) above, * independently indicates the bonding position with other atoms in the molecule of the delayed-fluorescence compound.)

[0252] [ka]

[0253] [ka]

[0254] [ka]

[0255] (R in the above general formula (221) 21 ~R 28 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (222), R 221 ~R 228 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (223), R 231 ~R 238 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form a substituted or unsubstituted monoring in the general formula (221) and does not form a substituted or unsubstituted fused ring 21 ~R 28 R that does not form a substituted or unsubstituted monoring in the general formula (222) and does not form a substituted or unsubstituted condensed ring. 221 ~R 228 Furthermore, R that does not form a substituted or unsubstituted monoring in the general formula (223) and does not form a substituted or unsubstituted condensed ring. 231 ~R 238 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the above general formulas (222) and (223), Rings A, B, and C are each independently selected from the group consisting of ring structures represented by the following general formulas (224) and (225). Rings A, B, and C condense with adjacent rings at any position. p, px, and py are each independently 1, 2, 3, or 4. If p is 2, 3, or 4, then multiple rings A are either identical or different from one another. If px is 2, 3, or 4, then multiple rings B are either identical or different from one another. If py is 2, 3, or 4, then multiple rings C are either identical or different from one another. In the above general formulas (221) to (223), * represents L H (This indicates the bonding position.)

[0256] [ka]

[0257] (In the above general formula (224), r is 0, 2, or 4. Multiple R 29 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (225), X A is a sulfur atom, an oxygen atom, or C(R 291 )(R 292 ) and R 291 and R 292 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 29 , R 291 and R 292 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by halogen atom, Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. Multiple R 29 They are either identical or different from one another. Multiple R 291 They are either identical or different from one another. Multiple R 292 They are either identical or different from one another. Multiple X A They are either identical or different to one another.

[0258] (In the aforementioned delayed-fluorescence compound, R 901 , R 902 , R 903 , R 904 , R 905 , R 906 , R 907 , R 908 , R 909 , R 931 , R 932 , R 933 , R 934 , R 935 , R 936 and R 937 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 908 If multiple R 908 They are either identical or different from one another. R 909 If multiple R 909 They are either identical or different from one another. R 931 If multiple R 931 They are either identical or different from one another. R 932 If multiple R 932 They are either identical or different from one another. R 933 If multiple R 933 They are either identical or different from one another. R 934 If multiple R 934 They are either identical or different from one another. R 935 If multiple R 935 They are either identical or different from one another. R 936If multiple R 936 They are either identical or different from one another. R 937 If multiple R 937 They are either identical or different to one another.

[0259] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H10).

[0260] [ka]

[0261] (In the above general formula (H10), CN is a cyano group, L H This is a substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 30 carbon atoms. D 11 and D 12 Each of these is independently a group represented by the general formula (221), (222), or (223), m is 1, 2, 3, 4, or 5. nx is 0, 1, 2, 3, 4, or 5. ny is 0, 1, 2, 3, 4, or 5. nx+ny is 1, 2, 3, 4, or 5. D 11 and D 12 They are either identical or different from one another. Multiple D 11 They are either identical or different from one another. Multiple D 12 They are either identical or different to one another.

[0262] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H100).

[0263] [ka]

[0264] (In the above general formula (H100), L H , D 11 , D 12 m, nx, and ny are, respectively, L in the general formula (H10). H , D 11 , D 12 , is synonymous with m, nx and ny, R is independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by Cyano group, Nitro group, -P(=O)(R 931 )(R 932 A base represented by ) -Ge(R 933 )(R 934 )(R 935 A base represented by ) -B(R 936 )(R 937 A base represented by ) A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. However, at least one R is a substituent, and at least one R as a substituent is L of the compound represented by the general formula (H100). H It is bonded to it by a carbon-carbon bond, k is an integer greater than or equal to 1. Multiple Rs are either identical or different from one another.

[0265] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H101).

[0266] [ka]

[0267] (In the above general formula (H101), D 11 and D 12 These are, respectively, D in the general formula (H10) above. 11 and D 12 It is synonymous with, Each R is independently equivalent to R in the general formula (H100) above, m is 1, 2, 3, or 4. nx is 0, 1, 2, 3, or 4. ny is 0, 1, 2, 3, or 4. k is 1, 2, 3, or 4. nx+ny is 1, 2, 3, or 4. m + nx + ny + k = 6.

[0268] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H110), (H120), or (H130).

[0269] [ka]

[0270] (In the above general formulas (H110), (H120), and (H130), D 11 and D 12 These are, respectively, D in the general formula (H10) above. 11 and D 12 It is synonymous with, Each R is independently equivalent to R in the general formula (H100) above, nx is 0, 1, 2, or 3. ny is 0, 1, 2, or 3. k is 1, 2, or 3. nx+ny is 1, 2, or 3. nx + ny + k = 4.

[0271] In this embodiment, the group represented by the general formula (222) in the delayed-fluorescence compound is preferably one of the groups selected from the group consisting of the following general formulas (22A), (22B), (22C), (22D), (22E), and (22F).

[0272] [ka]

[0273] [ka]

[0274] [ka]

[0275] [ka]

[0276] [ka]

[0277] [ka]

[0278] (In the above general formulas (22A), (22B), (22C), (22D), (22E), and (22F), R 221 ~R 228 These are, respectively, R in the general formula (222) above. 221 ~R 228 It is synonymous with, R 229 and R 230 Each of these independently corresponds to R in the general formula (224) 29 It is synonymous with, X A X in the general formula (225) is A It is synonymous with, In the general formulas (22A), (22B), (22C), (22D), (22E), and (22F) above, * indicates the bond position.

[0279] In the organic EL element according to this embodiment, when the delayed fluorescence compound is a compound represented by general formula (H101), the * in general formulas (22A), (22B), (22C), (22D), (22E), and (22F) is bonded to the benzene ring itself, as explicitly shown in general formula (H101).

[0280] In the delayed fluorescence compound of this embodiment, X A It is also preferable that this atom be a sulfur atom or an oxygen atom.

[0281] In the delayed fluorescence compound of this embodiment, X A However, C(R 291 )(R 292 ) If R 291 and R 292Each of these is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, a substituted or unsubstituted ring-forming C6-C50 aryl group, or a substituted or unsubstituted ring-forming C5-C50 heterocyclic group, and more preferably a substituted or unsubstituted C1-C50 alkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.

[0282] In the delayed fluorescence compound of this embodiment, R 21 ~R 28 It is also preferable that any set of two or more adjacent elements does not combine with each other. In the delayed fluorescence compound of this embodiment, R 221 ~R 228 It is also preferable that any set of two or more adjacent elements does not combine with each other. In the delayed fluorescence compound of this embodiment, R 231 ~R 238 It is also preferable that any set of two or more adjacent elements does not combine with each other.

[0283] In the delayed-fluorescence compound of this embodiment, R is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0284] In the delayed-fluorescence compound of this embodiment, R is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.

[0285] R in the delayed fluorescence compound of this embodiment 21 ~R 28 , R 221 ~R 228 , R 231 ~R 238、 R29 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0286] R in the delayed fluorescence compound of this embodiment 21 ~R 28 , R 221 ~R 228 , R 231 ~R 238、 R 29 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group.

[0287] In the delayed-fluorescence compound of this embodiment, R is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group. R in the delayed fluorescence compound of this embodiment 21 ~R 28 , R 221 ~R 228 , R 231 ~R 238、 R 29 Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted ring-forming C6-C30 aryl group, or a substituted or unsubstituted ring-forming C5-C30 heterocyclic group.

[0288] In the delayed-fluorescence compound of this embodiment, R is independently a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C6-C18 aryl group, or a substituted or unsubstituted ring-forming C5-C18 heterocyclic group. R in the delayed fluorescence compound of this embodiment 21 ~R 28 , R221 ~R 228 、R 231 ~R 238、 and R 29 are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.

[0289] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) group represented by -O-(R 904 ) group represented by -S-(R 905 ) group represented by -N(R 906 )(R 907 ) group represented by an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 ) group represented by -COOR 909 ) group represented by -P(=O)(R 931 )(R 932 ) group represented by -Ge(R 933 )(R 934 )(R 935 ) group represented by -B(R 936 )(R 937 ) group represented by -S(=O)2R 938 ) group represented by a halogen atom, a cyano group, a nitro group, An aryl group having 6 to 25 ring-forming carbon atoms without substitution, or a heterocyclic group having 5 to 25 ring-forming atoms without substitution, R 901 ~R 909 , and R 931 ~R 938 are each independently a hydrogen atom, an alkyl group having 1 to 25 carbon atoms without substitution, an aryl group having 6 to 25 ring-forming carbon atoms without substitution, or a heterocyclic group having 5 to 25 ring-forming atoms without substitution is preferable.

[0290] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is a halogen atom, an alkyl group having 1 to 25 carbon atoms without substitution, an aryl group having 6 to 25 ring-forming carbon atoms without substitution, or a heterocyclic group having 5 to 25 ring-forming atoms without substitution is preferable.

[0291] In the compound according to this embodiment, when the substituent in the case of "substituted or unsubstituted" is an alkyl group having 1 to 10 carbon atoms without substitution, an aryl group having 6 to 12 ring-forming carbon atoms without substitution, or a heterocyclic group having 5 to 12 ring-forming atoms without substitution is preferable.

[0292] In the compound according to this embodiment, it is also preferable that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0293] In this specification, the group represented by -O-(R 904 ) is a hydroxy group when R 904 is a hydrogen atom. In this specification, the group represented by -S-(R 905 ) is a thiol group when R 905 is a hydrogen atom. In this specification, the group represented by -P(=O)(R 931 )(R 932 ) is a substituted phosphine oxide group when R 931 and R 932 are substituents. In this specification, -Ge(R 933 )(R 934 )(R 935 The group represented by ) is R 933 , R 934 and R 935 If it is a substituent, it is a substituted germanium group. In this specification, -B(R 936 )(R 937 The group represented by ) is R 936 and R 937 If it is a substituent, it is a substituted boryl group.

[0294] (Thermal-activated delayed fluorescence) In this specification, thermally activated delayed fluorescence may be referred to as delayed fluorescence. Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, published by Kodansha). In that document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is described. 13 It is explained that if the threshold (ΔST) can be reduced, the reverse energy transfer from the excited triplet state to the excited singlet state, which normally has a low transition probability, can occur with high efficiency, resulting in thermally activated delayed fluorescence (TADF). Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 of the relevant literature. The TADF mechanism is a mechanism that utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. As for compounds that exhibit thermally activated delayed fluorescence (TADF), compounds in which a donor site and an acceptor site are bound within the molecule are known.

[0295] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[0296] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurement is a technique in which a sample is excited by irradiating it with a pulsed laser, and the decay behavior (transient characteristics) of the PL emission after the irradiation is stopped is measured. PL emission in TADF compounds can be 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 the singlet excitons generated by the initial PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from these singlet excitons decays rapidly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it originates from singlet excitons generated via long-lived triplet excitons. Thus, there is a significant time difference between the emission from singlet excitons generated by the initial PL excitation and the emission from singlet excitons generated via triplet excitons. Therefore, the emission intensity originating from delayed fluorescence can be determined.

[0297] Figure 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL. An example of a transient PL measurement method using Figure 2, and an example of delayed fluorescence behavior analysis, will be explained.

[0298] The transient PL measurement device 100 shown in Figure 2 comprises a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for housing the measurement sample, a spectrometer 103 for spectrally analyzing the light emitted from the measurement sample, a streak camera 104 for forming a two-dimensional image, and a personal computer 105 for capturing and analyzing the two-dimensional image. Note that the measurement of transient PL is not limited to the device shown in Figure 2.

[0299] The sample to be placed in sample chamber 102 is obtained by depositing a thin film on a quartz substrate in which a doping material is doped to a matrix material at a concentration of 12% by mass.

[0300] A pulsed laser is irradiated from the pulsed laser unit 101 onto a thin film sample housed in the sample chamber 102 to excite the doping material. The emitted light is extracted at a 90-degree angle to the direction of the excitation light irradiation, and the extracted light is spectrally analyzed by the spectrometer 103 to form a two-dimensional image in the streak camera 104. As a result, a two-dimensional image is obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spots correspond to emission intensity. By cropping this two-dimensional image along a predetermined time axis, an emission spectrum is obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cropping this two-dimensional image along the wavelength axis, a decay curve (transient PL) is obtained in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is time.

[0301] For example, thin film sample A was prepared as described above using compound HX1 as the matrix material and compound DX1 as the doping material, and transient PL measurements were performed.

[0302] [ka]

[0303] Here, the decay curves were analyzed using the thin film samples A and B described above. Thin film sample B was prepared using compound HX2 as the matrix material and compound DX1 as the doping material, as described above.

[0304] Figure 3 shows the decay curves obtained from transient PL measurements for thin film sample A and thin film sample B.

[0305] [ka]

[0306] As described above, transient PL measurement allows us to obtain an emission decay curve with emission intensity on the vertical axis and time on the horizontal axis. Based on this emission decay curve, we can estimate the fluorescence intensity ratio between fluorescence emitted from a singlet excited state generated by photoexcitation and delayed fluorescence emitted from a singlet excited state generated by reverse energy transfer via a triplet excited state. In materials exhibiting delayed fluorescence, the ratio of the intensity of the slowly decaying delayed fluorescence to the intensity of the rapidly decaying fluorescence is relatively large.

[0307] Specifically, there are two types of emission from delayed-fluorescence materials: prompt emission and delayed emission. Prompt emission is emission observed immediately after the delayed-fluorescence material is excited by pulsed light (light emitted from a pulsed laser) at a wavelength absorbed by the material. Delayed emission is emission that is not observed immediately after excitation by the pulsed light, but is observed later.

[0308] The amounts and ratios of prompt emission and delayed emission can be determined using a method similar to that described in “Nature 492, 234-238, 2012” (Reference 1). The apparatus used to calculate the amounts of prompt emission and delayed emission is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 2.

[0309] Furthermore, to measure the delayed fluorescence of the delayed fluorescence compound according to this embodiment, a sample prepared by the following method is used. For example, the delayed fluorescence compound according to this embodiment is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption. In addition, to prevent quenching by oxygen, the sample solution is frozen and degassed, then sealed in a lidded cell under an argon atmosphere to obtain an argon-saturated, oxygen-free sample solution. The fluorescence spectrum of the above sample solution was measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. The total fluorescence quantum yield was calculated using the fluorescence area intensities of both spectra and equation (1) in Morris et al. J.Phys.Chem.80(1976)969.

[0310] In this embodiment, the amount of prompt emission (immediate emission) of the compound to be measured is X P Let X be the amount of delayed emission. D When X D / X P It is preferable that the value of is 0.05 or greater. The measurement of the amount and ratio of Prompt emission and Delay emission of compounds other than delayed-fluorescence compounds in this specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of delayed-fluorescence compounds in this embodiment.

[0311] (ΔST) In this embodiment, the lowest excitation singlet energy S1 and the energy gap T at 77[K] are used. 77K The difference between (S1-T) 77K Define ) as ΔST.

[0312] In this embodiment, the lowest excitation singlet energy S1(M2) of the delayed-fluorescence compound and the energy gap T at 77[K] of the delayed-fluorescence compound are used. 77K The difference ΔST(M2) from (M2) is preferably less than 0.5eV, more preferably less than 0.3eV, even more preferably less than 0.2eV, even more preferably less than 0.1eV, and still more preferably less than 0.01eV. That is, ΔST(M2) preferably satisfies the following formulas (Equation 2), (Equation 2A), (Equation 2B), (Equation 2C), or (Equation 2D). ΔST(M2)=S1(M2)-T 77K (M2)<0.5eV…(Math 2) ΔST(M2)=S1(M2)-T 77K (M2) < 0.3 eV …(Math 2A) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV…(Several 2B) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV…(Several 2C) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV …(Math 2D)

[0313] (Relationship between triplet energy and the energy gap at 77 K) Here, we will explain the relationship between triplet energy and the energy gap at 77[K]. In this embodiment, the energy gap at 77[K] differs from the triplet energy as it is normally defined. The triplet energy is measured as follows: First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum of this sample is measured at a low temperature (77 K) (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength). A tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from the wavelength value at the intersection of the tangent line and the horizontal axis using a predetermined conversion formula. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77[K]), and excited singlet states and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes emission from both excited singlet states and excited triplet states, and it is difficult to distinguish which state emitted the light, but basically the triplet energy value is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as that for the usual triplet energy T, in order to distinguish that it is different in a strict sense, the value measured as follows is the energy gap T 77KThis method is called [name of method]. The compound to be measured is dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to obtain a solution with a concentration of 10 μmol / L, and this solution is placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at a low temperature (77 [K]), and a tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent line and the horizontal axis is measured. edge Based on [nm], the energy amount calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let's assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0314] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurement, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer can be used. However, the measuring apparatus is not limited to this; measurements may also be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light-receiving device.

[0315] (Lowest excitation singlet energy S1) The following methods can be used to measure the lowest excited singlet energy S1 using a solution (sometimes referred to as the solution method). A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) is measured at room temperature (300 K). A tangent line is drawn to the falling edge on the long-wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge Examples of absorption spectrum measuring devices include, but are not limited to, Hitachi's spectrophotometer (device name: U3310).

[0316] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum absorbance values ​​of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.

[0317] (Method for producing delayed-fluorescence compounds) Delayed fluorescence compounds can be produced by known methods. Furthermore, delayed fluorescence compounds can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target compound.

[0318] (Specific examples of delayed-fluorescence compounds) Specific examples of delayed-fluorescence compounds include the following compounds. However, the present invention is not limited to these specific examples.

[0319] [ka]

[0320] [ka]

[0321] [ka]

[0322] [ka]

[0323] [ka]

[0324] [ka]

[0325] (Relationship between sensitizing material and fluorescent material in the light-emitting layer) In one embodiment, the sensitizing material is the delayed-fluorescence compound. In one embodiment, the light-emitting layer contains the delayed-fluorescence compound as the sensitizing material and does not necessarily contain the phosphorescent metal complex.

[0326] Figure 4 shows an example of the relationship between the energy levels of a sensitizing material and a fluorescent material when the light-emitting layer includes a delayed-fluorescence compound (second compound (compound M2)) as a sensitizing material and a fluorescent material (third compound (compound M3)). In Figure 4, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of the delayed-fluorescence compound, and T1(M2) represents the lowest excited triplet state of the delayed-fluorescence compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow from S1(M2) to S1(M3) in Figure 4 represents the Förster-type energy transfer from the lowest excited singlet state of the delayed-fluorescence compound to the lowest excited singlet state of the fluorescent material. As shown in Figure 4, when a compound with a small ΔST(M2) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing delayed fluorescence through this TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0327] In the organic EL element according to the third embodiment, it is preferable that the lowest excitation singlet energy S1(M2) of the sensitizing material and the lowest excitation singlet energy S1(M3) of the fluorescent material satisfy the following equation (Equation 4). S1(M2)>S1(M3)…(Math 4)

[0328] In one embodiment, the energy gap T at 77[K] of the sensitizing material 77K (M2) and the energy gap T at 77[K] for fluorescent materials. 77K It is also preferable that (M3) and the following equation (Equation 6A) satisfy the relationship. T 77K (M2)>T 77K (M3) …(Number 6A)

[0329] When the organic EL element of the third embodiment is made to emit light, it is preferable that the light-emitting layer mainly consists of a fluorescent material.

[0330] The maximum peak wavelength of light emitted from an organic EL element is measured as follows. Current density is 10 mA / cm² 2The spectral radiance spectrum of an organic EL element is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta) when a voltage is applied to the element in such a manner. The peak wavelength of the emission spectrum with the maximum emission intensity is measured from the obtained spectral radiance spectrum and defined as the maximum peak wavelength (unit: nm).

[0331] (Compound content in the luminescent layer) The content of the sensitizing material (compound M2) and the fluorescent material (compound M3) contained in the light-emitting layer is preferably within the following ranges, for example. The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. Furthermore, the content of compound M2 may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or 99% by mass or more and 99.9% by mass or less. The content of compound M3 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. This embodiment does not exclude the inclusion of materials other than compound M2 and compound M3 in the light-emitting layer. The light-emitting layer may contain only one type of compound M2, or two or more types. The light-emitting layer may contain only one type of compound M3, or two or more types.

[0332] Let's further explain the configuration of the organic EL element.

[0333] (substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), such as a plastic substrate. Examples of materials for forming a plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic vapor-deposited film may also be used.

[0334] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, examples include indium tin oxide (ITO), indium tin oxide containing silicon or silicon oxide, indium zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, etc. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of metallic materials (e.g., titanium nitride).

[0335] These materials are typically deposited by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target containing 1% to 10% by mass of zinc oxide relative to indium oxide. Similarly, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5% to 5% by mass of tungsten oxide and 0.1% to 1% by mass of zinc oxide relative to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used.

[0336] Of 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 anode's work function. Therefore, any material suitable for electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, as well as elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0337] Materials with low work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), as well as alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Furthermore, when using silver paste or similar materials, coating methods or inkjet methods can be employed.

[0338] When the organic EL element is of the bottom emission type, the anode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. In this specification, light-transmitting or semi-transparent means the property of transmitting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The metallic material having light-transmitting or semi-transparent properties can be appropriately selected from the materials listed in the anode section.

[0339] When the organic EL element is of the top-emission type, the anode is a reflective electrode having a reflective layer. The reflective layer is preferably formed of a light-reflecting metallic material. In this specification, light reflectivity means the property of reflecting 50% or more (preferably 80% or more) of the light emitted from the light-emitting layer. The light-reflecting metallic material can be appropriately selected and used from the materials listed in the anode section. The anode may consist only of a reflective layer, or it may have a multilayer structure comprising a reflective layer and a conductive layer (preferably a transparent conductive layer). When the anode has a reflective layer and a conductive layer, it is preferable that the conductive layer is positioned between the reflective layer and the hole transport band. The conductive layer can be appropriately selected from the materials listed in the anode section.

[0340] (cathode) For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, and mixtures thereof with 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) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing these.

[0341] Furthermore, when forming a cathode using alkali metals, alkaline earth metals, or alloys containing these, vacuum deposition or sputtering methods can be used. Additionally, when using silver paste or similar materials, coating or inkjet methods can be employed.

[0342] Furthermore, by providing an electron injection layer, cathodes 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 methods such as sputtering, inkjet printing, or spin coating.

[0343] When the organic EL element is of the bottom emission type, the cathode is a reflective electrode. The reflective electrode is preferably formed from a metallic material that has light-reflecting properties. The metallic material with light-reflecting properties can be appropriately selected from the materials listed in the cathode section.

[0344] When the organic EL element is of the top-emission type, the cathode is preferably formed of a metallic material that is light-transmitting or semi-transparent, allowing light from the light-emitting layer to pass through. The light-transmitting or semi-transparent metallic material can be appropriately selected from the materials listed in the cathode section.

[0345] The organic EL element according to this embodiment may be a bottom-emission type organic EL element. Alternatively, the organic EL element according to this embodiment may be a top-emission type organic EL element. When the organic EL element is of the bottom emission type, it is preferable that the anode is a light-transmitting electrode and the cathode is a light-reflecting electrode. When the organic EL element is of the top-emission type, it is preferable that the anode is a light-reflecting electrode with light-reflecting properties and the cathode is a light-transmitting electrode with light-transmitting properties.

[0346] (Capping layer) When an organic EL element is of the top-emission type, the organic EL element typically has a capping layer above the cathode. The capping layer may contain, for example, at least one compound selected from the group consisting of polymer compounds, metal oxides, metal fluorides, metal borides, silicon nitride, and silicon compounds (such as silicon oxide). Furthermore, the capping layer may contain, for example, at least one compound selected from the group consisting of aromatic amine derivatives, anthracene derivatives, pyrene derivatives, fluorene derivatives, or dibenzofuran derivatives. Furthermore, laminates formed by stacking layers containing these materials can also be used as capping layers.

[0347] (Hole injection layer) The hole injection layer is a layer containing a material with high hole injection properties. Suitable materials with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. Furthermore, substances with high hole injection potential include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviated as DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), 1, Aromatic amine compounds such as 3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviated as DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviated as PCzPCN1) are also examples. Furthermore, polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used as materials with high hole injection properties. Examples of polymer compounds include poly(N-vinylcarbazole) (abbreviated as PVK), poly(4-vinyltriphenylamine) (abbreviated as PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviated as PTPDMA), and poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviated as Poly-TPD). In addition, polymer compounds to which acids such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly(styrenesulfonic acid) (PAni / PSS) have been added can also be used.

[0348] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used in the hole transport layer. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviated as BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl Aromatic amine compounds such as phenyl (abbreviated as DFLDPBi), 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviated as TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviated as MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviated as BSPB) can be used. The substances described here are mainly 10 -6 cm 2 It is a substance with a hole mobility of / Vs or greater. The hole transport layer may use carbazole derivatives such as CBP, CzPA, and PCzPA, or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. High molecular weight compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) can also be used. However, other materials may be used as long as they have higher hole transport capabilities than electron transport capabilities. Furthermore, the layer containing the material with high hole transport capabilities may be a single layer or a layer consisting of two or more layers of the above-mentioned materials stacked together.

[0349] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ, among others, can be used. In addition to metal complexes, there are also 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances described here are mainly 10 -6 cm 2The material has an electron mobility of 1 / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may be a single layer or a layer consisting of two or more layers of the above material stacked together. Furthermore, polymer compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[0350] (electron injection layer) The electron injection layer is a layer containing a material with high electron injection potential. The electron injection layer can contain 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). Alternatively, a material containing an alkali metal, alkaline earth metal, or compound thereof in an electron-transporting material, specifically one containing magnesium (Mg) in Alq, may also be used. In this case, electron injection from the cathode can be performed more efficiently. Alternatively, a composite material formed by mixing an organic compound and an electron donor may be used in the electron injection layer. Such a composite material exhibits excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material that is excellent at transporting the generated electrons, and specifically, for example, the substances that constitute the electron transport layer described above (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor can be any substance that exhibits electron-donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, such as lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferred, such as lithium oxide, calcium oxide, and barium oxide. Lewis bases such as magnesium oxide can also be used. Organic compounds such as tetrathiafulvalene (abbreviated as TTF) can also be used.

[0351] (Layer formation method) The method for forming each layer of the organic EL element according to any of the embodiments described above is not limited to those specifically mentioned above, but known methods such as dry deposition methods such as vacuum deposition, sputtering, plasma deposition, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet deposition can be employed.

[0352] (film thickness) The film thickness of each organic layer in the organic EL element according to the third embodiment is not limited unless otherwise specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness of each organic layer in the organic EL element is usually preferably in the range of a few nanometers to 1 μm.

[0353] The organic EL element according to the third embodiment has a light-emitting layer that contains the compound according to the first embodiment (compound M3 (third compound)), and therefore, according to the third embodiment, the luminous efficiency of the organic EL element can be improved. The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0354] [Fourth Embodiment] The configuration of the organic EL element according to the fourth embodiment will now be described. In the description of the fourth embodiment, components identical to those in the third embodiment will be given the same reference numerals and names, and their descriptions will be omitted or simplified. Furthermore, in the fourth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third embodiment.

[0355] The organic EL element according to the fourth embodiment is characterized in that the light-emitting layer further includes a host material. This differs from the organic EL element according to the third embodiment. Other aspects are the same as those of the third embodiment. In this specification, the compound used as the host material may be referred to as the first compound or compound M1. In other words, in the fourth embodiment, the light-emitting layer contains a host material (first compound (compound M1)), a sensitizing material (second compound (compound M2)), and a fluorescent material (third compound (compound M3)).

[0356] (Emitting layer) In one embodiment, a host material, a sensitizing material, and a fluorescent material are contained in a single layer. For example, if the organic EL element has one light-emitting layer, the host material, the sensitizing material, and the fluorescent material are contained in that single light-emitting layer; if the element has multiple light-emitting layers, they are contained in one of the single light-emitting layers.

[0357] In one embodiment, when the light-emitting layer contains a delayed-fluorescence compound as a sensitizing material, the light-emitting layer does not contain a phosphorescent metal complex.

[0358] [Host Materials] In the fourth embodiment, the host material is a first compound (compound M1) containing one or more substructures selected from the group consisting of substructures represented by the following general formulas (101) to (118) in a single molecule.

[0359] [ka]

[0360] [ka]

[0361] (In the above general formula (101), A 11 ~A 16 Each of these is independently a nitrogen atom and CR. 11 , or a carbon atom that is bonded to another atom or other structure in the molecule of the first compound, However, A 11 ~A 16 At least one of these is a carbon atom that is bonded to other atoms or other structures in the molecule of the first compound, R 11 If multiple R 11 These are either identical or different from each other, and multiple R 11 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formula (102), A1 to A4 are each independently nitrogen atoms, CR 12 , or a carbon atom that is bonded to another atom or other structure in the molecule of the first compound, R 12 Each of these is independently either a hydrogen atom or a substituent, or adjacent to R 12 One or more pairs of elements can join with each other to form a ring. R 12 When there are a plurality of R's, the plurality of R's 12 may be the same as or different from each other, and one or more sets of adjacent two or more among the plurality of R's 12 are combined with each other to form a substituted or unsubstituted monocyclic ring, combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, In the general formula (103), X 10 is NR 13 , C(R 14 )(R 15 ), Si(R 16 )(R 17 ), an oxygen atom, a sulfur atom, a nitrogen atom bonded to another atom or another structure in the molecule of the first compound, a carbon atom bonded to R 18 and another atom or another structure in the molecule of the first compound respectively, or a silicon atom bonded to R 19 and another atom or another structure in the molecule of the first compound respectively, provided that at least one or more of the carbon atoms in A1 to A4, the nitrogen atom in X 10 , the carbon atom in X 10 , and the silicon atom in X<s 10 are bonded to another atom or another structure in the molecule of the first compound, R 14 and R 15 form a set that is combined with each other to form a substituted or unsubstituted monocyclic ring, combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, R 16 and R 17 form a set that is combined with each other to form a substituted or unsubstituted monocyclic ring, combined with each other to form a substituted or unsubstituted condensed ring, or not combined with each other, In the general formula (103), R115 and R 116 A group consisting of, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, In the above general formulas (101) to (104), R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 11 , R 12 , R 14 , R 15 , R 16 , R 17 , R 115 and R 116 , and R 13 , R 18 , R 19 and R 117 Each of them operates independently. hydrogen atom Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) -C(=O)R 908 A base represented by -COOR 909 A base represented by -P(=O)(R 910 )(R 911 A base represented by ) -P(=O)(OR912 )(OR 913 A base represented by ) -Ge(R 914 )(R 915 )(R 916 A base represented by ) -B(R 917 )(R 918 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the above general formulas (103) to (118), * indicates a bonding site with another atom or structure within the molecule of the first compound. If the first compound has multiple substructures represented by the general formulas (101) to (104), The multiple substructures represented by the general formula (101) are either identical or different from one another. The multiple substructures represented by the general formula (102) are either identical or different from one another. The multiple substructures represented by the general formula (103) are either identical or different from one another. The substructures represented by the aforementioned general formula (104) are either identical or different from one another.

[0362] (In the first compound mentioned above, R 901 ~R 918 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901If multiple R 901 They are either identical or different from one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 908 If multiple R 908 They are either identical or different from one another. R 909 If multiple R 909 They are either identical or different from one another. R 910 If multiple R 910 They are either identical or different from one another. R 911 If multiple R 911 They are either identical or different from one another. R 912 If multiple R 912 They are either identical or different from one another. R 913 If multiple R 913 They are either identical or different from one another. R 914 If multiple R 914 They are either identical or different from one another. R 915If multiple R 915 They are either identical or different from one another. R 916 If multiple R 916 They are either identical or different from one another. R 917 If multiple R 917 They are either identical or different from one another. R 918 If multiple R 918 They are either identical or different to one another.

[0363] In the above general formula (102), X 10 When is "a nitrogen atom bonded to another atom or structure in the molecule of the first compound", then the above general formula (102) is represented by the following general formula (102-1). In the above general formula (102), X 10 R 18 When it is "and carbon atoms bonded to other atoms or other structures in the molecule of the first compound", the above general formula (102) is represented by the following general formula (102-2). In the above general formula (102), X 10 R 19 When it is "and silicon atoms bonded to other atoms or other structures in the molecule of the first compound", the above general formula (102) is represented by the following general formula (102-3). In general formulas (102-1) to (102-3), A1 to A4 are each independently equivalent to A1 to A4 in the aforementioned general formula (102), and R 18 and R 19 Each of these independently corresponds to R in the general formula (102) 12 This is synonymous with *, where * represents a bonding site with another atom or structure within the molecule of the first compound.

[0364] [ka]

[0365] In one embodiment, the host material has at least one substructure represented by the general formula (101). In one embodiment, the substructure represented by general formula (101) is at least one selected from the group consisting of substructures represented by the following general formulas (A11) to (A19).

[0366] [ka]

[0367] [ka]

[0368] (In the above general formulas (A11) to (A16), A 12 ~A 16 Each of these independently comprises a nitrogen atom or CR 11 And R 11 R in the general formula (101) is 11 This is synonymous with, and * represents a bonding site with another atom or other structure within the molecule of the first compound. In the above general formulas (A17) and (A18), A 11 ~A 22 Each of these is independently a nitrogen atom or CR 11 R is either a carbon atom that bonds with other atoms or structures in the molecule of the first compound, 11 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with A 11 ~A 22 At least one of these is a carbon atom that is bonded to other atoms or other structures in the molecule of the first compound, In the above general formula (A19), A 11 ~A 18 Each of these is independently a nitrogen atom or CR 11 It is either a carbon atom that bonds with other atoms or other structures in the molecule of the first compound, R 11 Each of these independently corresponds to R in the general formula (101)11 It is synonymous with X 11 and X 12 Each of these independently corresponds to X in the general formula (102) above. 10 It is synonymous with A 11 ~A 18 Carbon atoms in X 11 and X 12 Nitrogen atom in X 11 and X 12 The carbon atoms in, and X 11 and X 12 At least one of the silicon atoms in is bonded to other atoms or structures in the molecule of the first compound, In the general formulas (A11) to (A19) above, * represents a bonding site with another atom or structure within the molecule of the first compound.

[0369] In one embodiment, the host material has at least one substructure represented by the general formula (102). In one embodiment, the substructure represented by the general formula (102) is at least one selected from the group consisting of substructures represented by the following general formulas (B11) to (B24).

[0370] [ka]

[0371] (In the above general formulas (B11) to (B16), Ax1 to Ax4 are each independently a nitrogen atom or CR 12 And R 12 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with X 10 X in the general formula (102) is 10 This is synonymous with, and * represents a bonding site with another atom or other structure within the molecule of the first compound. In the general formula (B17) above, Ax1, Ax2, and Ay1 to Ay4 are each independently a nitrogen atom or CR 12It is either a carbon atom that bonds with other atoms or other structures in the molecule of the first compound, R 12 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with X 10 X in the general formula (102) is 10 This is synonymous, however, the carbon atoms in Ax1, Ax2 and Ay1~Ay4, X 10 Nitrogen atom in X 10 Carbon atoms and X in 10 At least one of the silicon atoms in is bonded to other atoms or structures in the molecule of the first compound, In the general formula (B18) above, Ay1 to Ay8 are each independently a nitrogen atom or CR 12 It is either a carbon atom that bonds with other atoms or other structures in the molecule of the first compound, R 12 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with X 10 X in the general formula (102) is 10 This is synonymous with carbon atoms in Ay1 to Ay8, X 10 Nitrogen atom in X 10 Carbon atoms and X in 10 At least one of the silicon atoms in is bonded to other atoms or structures in the molecule of the first compound, In the general formulas (B11) to (B18) above, * represents a bonding site with another atom or structure within the molecule of the first compound.

[0372] [ka]

[0373] (In the above general formulas (B19) to (B24), Ay1 to Ay8 and Ay9 to Ay 12 Each of these is independently a nitrogen atom or CR 12 It is either a carbon atom that bonds with other atoms or other structures in the molecule of the first compound, R12 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with X9 and X 10 Each of these independently corresponds to X in the general formula (102) above. 10 It is synonymous with, Ay1-Ay8 and Ay9-Ay 12 Carbon atoms, X9 and X 10 Nitrogen atoms, X9 and X in 10 The carbon atoms in, as well as X9 and X 10 At least one of the silicon atoms in the first compound is bonded to another atom or structure in the molecule.

[0374] In the first compound of the fourth embodiment, R 11、 R 12 and R 115 ~R 117 Preferably, each of these is independently a hydrogen atom, a halogen atom, a cyano group, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 carbon atoms, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an amino group, an unsubstituted alkylamino group having 2 to 30 carbon atoms, an unsubstituted arylamino group having 6 to 60 carbon atoms, a thiol group, an unsubstituted alkylthio group having 1 to 30 carbon atoms, or an unsubstituted arylthio group having 6 to 30 carbon atoms. In the first compound of the fourth embodiment, R 11、 R 12 and R 115 ~R 117It is more preferable that each of these groups independently be a hydrogen atom, a halogen atom, a cyano group, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 14 carbon atoms, an unsubstituted C1 to 6 alkyl group, an unsubstituted C1 to 6 halogenated alkyl group, an unsubstituted C3 to 6 alkylsilyl group, an unsubstituted ring-forming arylsilyl group having 6 to 60 carbon atoms, an unsubstituted ring-forming arylphosphoryl group having 6 to 60 carbon atoms, an unsubstituted C1 to 6 alkoxy group, an unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms, an amino group, an unsubstituted C2 to 12 alkylamino group, an unsubstituted ring-forming arylamino group having 6 to 60 carbon atoms, a thiol group, an unsubstituted C1 to 6 alkylthio group, or an unsubstituted ring-forming arylthio group having 6 to 14 carbon atoms. In the first compound of the fourth embodiment, R 11、 R 12 and R 115 ~R 117 It is even more preferable that it be a hydrogen atom.

[0375] In the first compound of the fourth embodiment, X 10 In R 13 ~R 19 , and R in X9 13 ~R 19 (X 10 In R 13 ~R 19 (Synonymous with) preferably each independently be a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. In the first compound of the fourth embodiment, X 10 In R 13 ~R 19 , and R in X9 13 ~R 19 It is more preferable that each of these is independently a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 14 carbon atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. In the first compound of the fourth embodiment, X10 In R 13 ~R 19 , and R in X9 13 ~R 19 It is even more preferable that each of these is independently an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0376] Examples of substructures represented by any of the above general formulas (101) to (118) include the substructures represented by the following general formulas (A101) to (A121) and (B101) to (B125). The first compound may also preferably contain at least one of the substructures represented by the following general formulas (A101) to (A121) and (B101) to (B125) within a single molecule.

[0377] [ka]

[0378] In the above general formulas (A101) to (A107), R 101 ~R 106 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with R 101 ~R 106 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound. In the above general formulas (A101) to (A107), adjacent R 101 and R 102 The group, R 102 and R 103 The group, R 103 and R 104 The group, R 104 and R 105 The group, R 105 and R 106 The set, and R 106 and R 101 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0379] [ka]

[0380] In the above general formulas (A108) to (A109), R 110 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with R 110 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound, and multiple R 110 These are identical or different from each other, and multiple R 110 One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0381] [ka]

[0382] In the above general formulas (A110) to (A114), R 110 and R 112 ~R 114 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with X 110 Each of these independently corresponds to X in the general formula (102) above. 10 It is synonymous with R 110 and R 112 ~R 114 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound, or X 110 At least one of the nitrogen, carbon, and silicon atoms in the first compound is bonded to other atoms or structures in the molecule, and multiple R 110 They are either identical or different from one another. In the above general formulas (A110) to (A114), multiple R 110 A set of two or more adjacent items, R112 and R 113 The set of, and X 110 In R 14 and R 15 The group (X 10 In R 15 and R 15 (Synonymous with the group), X 110 In R 16 and R 17 The group (X 10 In R 16 and R 17 One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0383] [ka]

[0384] In the above general formulas (A115) to (A119), R 110 and R 112 ~R 114 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with R 110 and R 112 ~R 114 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound, and multiple R 110 They are either identical or different from one another. In the above general formulas (A115) to (A119), multiple R 110 A set of two or more adjacent items, and R 112 and R 113 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, a substituted or unsubstituted fused ring, or do not combine with each other.

[0385] [ka]

[0386] In the above general formulas (A120) to (A121), R 110 Each of these independently corresponds to R in the general formula (101) 11 It is synonymous with R 110 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound, and multiple R 110 They are either identical or different from one another. In the above general formulas (A120) to (A121), multiple R 110 One or more pairs of adjacent elements from among them either combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0387] [ka]

[0388] In the above general formulas (B101) to (B109), R 114 and R 121 ~R 131 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with R 114 and R 121 ~R 131 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound. In the above general formulas (B101) to (B102), R 122 and R 123 The group, R 123 and R 114 The set, and R 114 and R 121 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other. In the above general formulas (B105) to (B106), R 124 and R 125 The group, R 125 and R 126 The group, R 126 and R127 The group, R 127 and R 128 The set, and R 128 and R 129 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other. In the above general formula (B107), R 124 and R 125 The group, R 125 and R 126 The group, R 126 and R 127 The group, R 127 and R 128 The group, R 128 and R 129 The group, R 129 and R 114 The set, and R 114 and R 124 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other. In the above general formulas (B108) to (B109), R 124 and R 125 The group, R 125 and R 126 The group, R 130 and R 131 The set, and R 131 and R 129 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0389] [ka]

[0390] In the above general formulas (B110) to (B117), R 110 and R 132 ~R 135 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with R 110 and R132 ~R 135 At least one of these is a single bond that connects to another atom or structure in the molecule of the first compound, and multiple R 110 They are either identical or different from one another. In the above general formulas (B110) to (B117), multiple R 110 A set of two or more adjacent items, and R 132 and R 133 One or more pairs of these elements combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0391] [ka]

[0392] In the above general formulas (B118) to (B123), R 110 Each of these independently corresponds to R in the general formula (102) 12 This is synonymous with Xa and Xb, which are each independently of X in the general formula (102). 10 It is synonymous with R 110 At least one of them is a single bond that connects to another atom or structure in the molecule of the first compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa and Xb is bonded to another atom or structure in the molecule of the first compound, and multiple R 110 They are either identical or different from one another. In the above general formulas (B118) to (B123), multiple R 110 A set of two or more adjacent items from among them, R in Xa 14 and R 15 The set and R in Xb 14 and R 15 The group (X 10 In R 14 and R 15 (Synonymous with the pair), and R in Xa 16 and R 17 The set and R in Xb 16 and R17 The group (X 10 In R 16 and R 17 One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0393] [ka]

[0394] In the above general formulas (B124) to (B125), R 110 Each of these independently corresponds to R in the general formula (102) 12 This is synonymous with Xa, Xb, and Xc, each independently, being X in the general formula (102) above. 10 It is synonymous with R 110 At least one of them is a single bond that connects to another atom or structure in the molecule of the first compound, or at least one of the nitrogen, carbon, and silicon atoms in Xa, Xb, and Xc is bonded to another atom or structure in the molecule of the first compound, and multiple R 110 They are either identical or different from one another. In the above general formulas (B124) to (B125), multiple R 110 A set of two or more adjacent items among them, Xa, Xb, and Xc, in R 14 and R 15 The group (X 10 In R 14 and R 15 (Synonymous with the set of), and R in Xa, Xb and Xc 16 and R 17 The group (X 10 nioke R 16 and R 17 One or more pairs (synonymous with a pair) combine to form a substituted or unsubstituted monoring, combine to form a substituted or unsubstituted fused ring, or do not combine with each other.

[0395] In the above general formulas (A101) to (A121) and (B101) to (B125), R 110 , R 101 ~R 106 , R 112 ~R 114 , R 121 ~R 131 and R 132 ~R 135 Each of these is preferably independently a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. It is more preferably a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. It is even more preferable that the ring-forming aryl group has 6 to 14 carbon atoms, or that the alkyl group has 1 to 6 carbon atoms, and is unsubstituted.

[0396] In the above general formulas (A101) to (A121) and (B101) to (B125), Xa, Xb, Xc and X 110 In R 13 ~R 19 (X 10 In R 13 ~R 19 (Synonymous with) each is preferably independently a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, an unsubstituted ring-forming heterocyclic group having 5 to 30 carbon atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms. It is more preferably a hydrogen atom, an unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, or an unsubstituted halogenated alkyl group having 1 to 6 carbon atoms. It is even more preferable that the ring-forming aryl group has 6 to 14 carbon atoms, or that the alkyl group has 1 to 6 carbon atoms, and is unsubstituted.

[0397] In the fourth embodiment, the first compound preferably has at least one monovalent or greater residue derived from any of the following: (I) a cyano group, an amino group, a substituted or unsubstituted C2-C30 alkylamino group, or a substituted or unsubstituted ring-forming C6-C60 arylamino group; or (II) a monovalent or greater residue derived from any of the following: substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted indole, substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted imidazole, substituted or unsubstituted benzimidazole, substituted or unsubstituted phenanthrene, or substituted or unsubstituted triphenylene.

[0398] In the fourth embodiment, the first compound is more preferably having (III) at least one cyano group, or (IV) at least one monovalent or greater residue derived from any of the following: substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted silafluorene, substituted or unsubstituted triazine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridine, and substituted or unsubstituted triphenylene.

[0399] In the fourth embodiment, the first compound is more preferably monovalent or greater residues derived from any of the following: substituted or unsubstituted carbazole, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted triazine, and substituted or unsubstituted pyrimidine.

[0400] In the fourth embodiment, the first compound preferably has at least one monovalent or greater residue derived from a substituted or unsubstituted carbazole.

[0401] In the fourth embodiment, the first compound preferably has at least one substructure represented by the following general formula (15).

[0402] [ka]

[0403] (In the above general formula (15), R 150 ~R 158 Of these, at least one is a single bond that connects to another atom or structure in the molecule of the first compound, R is not a single bond 150 ~R 158 Each of them operates independently. hydrogen atom Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -O-(R 904 A base represented by ) -S-(R 905 A base represented by ) -N(R 906 )(R 907 A base represented by ) -C(=O)R 908 A base represented by -COOR 909 A base represented by -P(=O)(R 910 )(R 911A base represented by ) -Ge(R 912 )(R 913 )(R 914 A base represented by ) -B(R 915 )(R 916 A base represented by ) Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0404] In the above general formula (15), R 150 It is preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, more preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and even more preferably a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms.

[0405] (The first compound represented by general formula (161) or (162)) In the fourth embodiment, the first compound may also be a compound represented by the following general formula (161) or the following general formula (162).

[0406] [ka]

[0407] (In the above general formula (161), Ar 161 teeth, A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or These are heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms. m1 is 1, 2, 3, 4, 5, or 6. R 161 It is an electron-donating base, and R 161 These are, respectively, Ar 161 Bonded to the constituent elements, If m1 is 2 or more, multiple R 161 They are either identical or different from one another. However, Ar 161 It is not an electron-accepting aromatic hydrocarbon ring or heterocycle, but Ar 161 If the substituent has a substituent, that substituent is not an electron-accepting group, In the above general formula (162), Ar 162 teeth, A substituted or unsubstituted ring-forming aromatic hydrocarbon ring having 6 to 30 carbon atoms, or These are heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms. n1 is 1, 2, 3, 4, 5, or 6. R 162 R is an electron-accepting group, 162 These are, respectively, Ar 162 Bonded to the constituent elements, If n1 is 2 or greater, multiple R 162 They are either identical or different from each other. However, Ar 162 It is not an electron-donating aromatic hydrocarbon ring or heterocycle, but Ar 162 If the compound has substituents, those substituents are not electron-donating groups.

[0408] In the above general formulas (161) and (162), Ar 161 and Ar 162 Preferably, each of these is a monovalent or greater residue derived independently from one of the compounds represented by the following general formulas (A61), (A62), and (A63).

[0409] [ka]

[0410] (In the above general formulas (A61) to (A63), XD is an oxygen atom or a sulfur atom, and R D (This is a hydrogen atom or a substituent.)

[0411] In the above general formula (A3), R D If is a substituent, the substituent may be, for example, R in the general formula (101). 11 Similar bases can be cited.

[0412] In the fourth embodiment, R in the general formula (161) 161 Preferably, each of these is either a monovalent or greater residue derived from any of the compounds represented by the following general formulas (DN1) to (DN6) and (DN8) to (DN10), or a group represented by the following general formula (DN7).

[0413] [ka]

[0414] (In the above general formula (DN7), * represents Ar 161 (This represents the bonding site with the constituent elements.)

[0415] In the fourth embodiment, R in the general formula (162) 162 Each of these is preferably a monovalent or greater residue derived from any of the compounds represented by the following general formulas (AC4) to (AC18) and (AC22) to (AC23), or one of the groups represented by the following general formulas (AC1) to (AC3), (AC19) to (AC21), and (AC24).

[0416] [ka]

[0417] [ka]

[0418] (In the above general formula (AC1), n A is 1, 2, or 3, In the above general formulas (AC22) to (AC23), X1 to X8 are each independent of CR. 163 It is either or a carbon atom bonded to another atom or other structure in the molecule of the first compound, wherein at least one of the carbon atoms in X1 to X8 is Ar 162 It combines with the elements that make up the structure, In the general formula (AC24) above, X1 to X8 are each independently a nitrogen atom or CR 163 is or Ar 162 It is a carbon atom that bonds with the elements that make up the structure. In the above general formulas (AC22) to (AC24), R 163 If multiple R 163 These are either identical or different from each other, and multiple R 163 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 163 Each of these independently corresponds to R in the general formula (102) 12 It is synonymous with, In the above general formulas (AC1) to (AC3), (AC19) to (AC21), and (AC24), * represents Ar 162 (This represents the bonding site with the constituent elements.)

[0419] In the fourth embodiment, the first compound may also be a compound represented by the following general formula (13).

[0420] [ka]

[0421] (In the above general formula (13), X 13 This is a group represented by an oxygen atom, a sulfur atom, or N-Rb, Z1~Z 12 These are, independently, groups represented by a nitrogen atom or C-Rc, Ar 14 and Ar 15 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 14 and L 15 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, Rb and Rc are independent of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) -C(=O)R 908 A base represented by -COOR 909 A base represented by -P(=O)(R 910 )(R 911 A base represented by ) -Ge(R 912 )(R 913 )(R 914 A base represented by ) Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. If multiple Rc values ​​exist, they may be either identical or different from one another.

[0422] In the compound represented by the general formula (13) above, -L 14 -Ar 14 The group represented by -L 15 -Ar 15 If the group represented by is the same substituent, then Z1 and Z 12 Z2 and Z 11 Z3 and Z 10 It is also preferable that Z4 and Z9, Z5 and Z8, and Z6 and Z7 are not all the same base. In this case, in the general formula (13), X 13 A structure condensed on the right side of a 5-membered ring containing X 13 Unlike the structure in which the 5-membered ring containing the compound is condensed on the left side, the compound represented by the general formula (13) is a compound having an asymmetric structure.

[0423] In the compound represented by the general formula (13) above, -L 14 -Ar 14 The group represented by -L 15 -Ar 15 It is preferable that the group represented by and are different from each other. In this case as well, as described above, the compound represented by the general formula (13) is a compound having an asymmetric structure.

[0424] In the fourth embodiment, the first compound is also preferably a compound represented by the following general formula (12).

[0425] [ka]

[0426] (In the above general formula (12), Ar 11 and Ar 12 Each of them operates independently. A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L 11 and L 12 Each of them operates independently. single bond, A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, or A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, L 13 teeth, A substituted or unsubstituted monocyclic hydrocarbon group with 6 or fewer carbon atoms forming a ring, or A monocyclic heterocyclic group having 6 or fewer ring-forming atoms, whether substituted or unsubstituted. m is 0, 1, 2, or 3, and multiple L 13 They are either identical or different from one another. X1-X8 and Y1-Y8 are each independently N or CRa. However, one of X5 to X8 and one of Y1 to Y4 are L 13 It is a carbon atom bonded via or directly bonded to Ra is independent of each other. hydrogen atom Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 A base represented by ) halogen atom, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. If multiple Ra values ​​exist, are the multiple Ra values ​​identical or different from each other? The compound represented by the general formula (12) satisfies one or both of the following conditions (i) and (ii). (i)Ar 11 and Ar 12 At least one of these is an aryl group with 6 to 50 ring-forming carbon atoms substituted with a cyano group, or a heterocyclic group with 5 to 50 ring-forming atoms substituted with a cyano group. (ii) At least one of X1-X4 and Y5-Y8 is CRa, and at least one of the Ra in X1-X4 and Y5-Y8 is an aryl group with 6-50 ring-forming carbon atoms substituted with a cyano group, or a heterocyclic group with 5-50 ring-forming atoms substituted with a cyano group.

[0427] In the compound represented by the general formula (12), the aromatic hydrocarbon group having 6 to 50 ring-forming carbon atoms substituted with a cyano group, and the heterocyclic group having 5 to 50 ring-forming atoms substituted with a cyano group, may further have substituents other than cyano groups.

[0428] In the compound represented by the general formula (12), m is preferably 0, 1, or 2, and more preferably 0 or 1. In the compound represented by the general formula (12), when m is 0, one of X5 to X8 and one of Y1 to Y4 are directly bonded via a single bond.

[0429] In the compound represented by the general formula (12), any set selected from the group consisting of the set of X6 and Y3, the set of X6 and Y2, and the set of X7 and Y3 is L 13 It is preferable that the carbon atom is bonded via or directly bonded to the atom.

[0430] The combination of X6 and Y3 is L 13 If the carbon atom is bonded via or directly bonded, the compound represented by general formula (12) can be represented by the following general formula (121).

[0431] [ka]

[0432] (In the above general formula (121), Ar 11 Ar 12 , L 11 , L 12 , L 13 , m, X1~X5, X7~X8, Y1~Y2 and Y4~Y8 are, respectively, the general formula (12) Ar 11 Ar 12 , L 11 , L 12 , L 13 , m, X1~X5, X7~X8, Y1~Y2 and Y4~Y8 are synonymous, and the compound represented by the general formula (121) satisfies at least one of the conditions of (i) and (ii) above.

[0433] In the compound represented by the general formula (12) above, -Ar 11 -L 11 The group represented by -Ar 12 -L 12 It is preferable that the groups represented by are different from each other.

[0434] L 13 The monocyclic hydrocarbon group having 6 or fewer carbon atoms that forms the ring is preferably at least one group selected from the group consisting of, for example, phenylene, cyclopentenylene, cyclopentadienylene, cyclohexylene, and cyclopentylene, and more preferably a phenylene group. L 13 The monocyclic heterocyclic group with 6 or fewer ring-forming atoms is preferably at least one group selected from the group consisting of, for example, a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a flirene group, and a thiophenylene group.

[0435] In one embodiment, the light-emitting layer may contain two or more first compounds with different molecular structures. Mixing compounds with different charge transport properties is expected to improve the charge balance within the light-emitting layer and enhance the luminescence efficiency. Furthermore, the formation of an excyplex by two or more first compounds (host materials) reduces the excitation energy, enabling lower voltage operation than when only one host material is contained in the light-emitting layer.

[0436] (Method for producing the first compound (compound M1)) The first compound (compound M1) can be produced by known methods. Furthermore, the first compound can also be produced by following known methods and using known alternative reactions and starting materials tailored to the target product.

[0437] (Specific example of the first compound (compound M1)) Specific examples of the first compound (compound M1) of the fourth embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of compounds.

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[0524] (Relationship between host material, sensitizing material, and fluorescent material in the light-emitting layer) In one embodiment, the sensitizing material is the delayed-fluorescence compound. In one embodiment, the light-emitting layer contains the delayed-fluorescence compound as the sensitizing material and does not contain the phosphorescent metal complex.

[0525] Figure 5 shows an example of the relationship between the energy levels of the host material, sensitizer, and fluorescent material when the light-emitting layer includes a host material (first compound (compound M1)), a delayed-fluorescence compound as a sensitizer (second compound (compound M2)), and a fluorescent material (third compound (compound M3)). In Figure 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of the host material, and T1(M1) represents the lowest excited triplet state of the host material. S1(M2) represents the lowest excited singlet state of the delayed-fluorescence compound, and T1(M2) represents the lowest excited triplet state of the delayed-fluorescence compound. S1(M3) represents the lowest excited singlet state of the fluorescent material, and T1(M3) represents the lowest excited triplet state of the fluorescent material. The dashed arrow in Figure 5, pointing from S1(M2) to S1(M3), represents the Förster-type energy transfer from the lowest excited singlet state of the delayed-fluorescence compound to the lowest excited singlet state of the fluorescence-emitting material. As shown in Figure 5, when a compound with a small ΔST(M2) is used as the delayed fluorescence compound, the lowest excited triplet state T1(M2) can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. Then, a Förster-type energy transfer occurs from the lowest excited singlet state S1(M2) of the delayed fluorescence compound to the fluorescent material, generating the lowest excited singlet state S1(M3). As a result, fluorescence emission from the lowest excited singlet state S1(M3) of the fluorescent material can be observed. It is believed that by utilizing this delayed fluorescence due to the TADF mechanism, the internal quantum efficiency can theoretically be increased to 100%.

[0526] In one embodiment, the energy gap T of the host material at 77[K] 77K (M1) and the energy gap T at 77[K] in the sensitizing material. 77K It is preferable that (M2) and (Equation 1) satisfy the following relationship. T 77K (M1>T 77K (M2) …(Number 1)

[0527] In one embodiment, it is also preferable that the lowest singlet excitation energy S1(M1) of the host material and the lowest singlet excitation energy S1(M2) of the sensitizing material satisfy the following equation (Equation 4A). S1(M1)>S1(M2)…(Math 4A)

[0528] In one embodiment, it is also preferable that the lowest excitation singlet energy S1 of the host material, sensitizing material, and fluorescent material satisfy the following equation (Equation 4B). S1(M1)>S1(M2)>S1(M3)…(Number 4B)

[0529] In one embodiment, the energy gap T at 77[K] of the host material, sensitizing material, and fluorescent material is 77K It is also preferable that the following equation (Mathematics 6B) satisfies the relationship. T 77K (M1>T 77K (M2)>T 77K(M3) …(Number 6B)

[0530] (Compound content in the luminescent layer) The content of the host material (compound M1), sensitizing material (compound M2), and fluorescent material (compound M3) contained in the light-emitting layer is preferably within the following ranges, for example. The content of the host material (compound M1) in the light-emitting layer is preferably 50% by mass or more, and more preferably 70% by mass or more. The content of the host material (compound M1) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0531] The content of the sensitizing material (compound M2) is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the sensitizing material (compound M2) is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0532] The content of the fluorescent material (compound M3) in the light-emitting layer is preferably 0.5% by mass or more, and more preferably 1% by mass or more. The content of the fluorescent material (compound M3) in the light-emitting layer is preferably 10% by mass or less, and more preferably 5% by mass or less. The upper limit of the total content of the host material (compound M1), sensitizing material (compound M2), and fluorescent material (compound M3) in the light-emitting layer is 100% by mass. This embodiment does not exclude the inclusion of materials other than the host material, sensitizing material, and fluorescent material in the light-emitting layer. In this embodiment, the light-emitting layer may contain only one type of host material, or two or more types.

[0533] The organic EL element according to the fourth embodiment has a light-emitting layer that contains the compound according to the first embodiment (compound M3 (third compound)), and therefore, according to the fourth embodiment, the light-emitting efficiency of the organic EL element can be improved. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0534] [Fifth Embodiment] (electronic equipment) The electronic device according to the fifth embodiment incorporates an organic EL element of any embodiment described herein. The electronic device according to the fifth embodiment may also incorporate an organic EL element of any other embodiment described later. Examples of electronic devices include display devices and light-emitting devices. Examples of display devices include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lights. Light-emitting devices can also be used in display devices, for example, as a backlight for a display device.

[0535] The display device as an electronic device according to the fifth embodiment is preferably an organic EL display device equipped with organic EL elements as red pixels, green pixels, and blue pixels. In this organic EL display device, the red pixels are preferably organic EL elements according to the first embodiment.

[0536] [Other embodiments] An organic EL element according to one embodiment includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer may include a phosphorescent metal complex as a sensitizing material and a fluorescent material (compound M3 (third compound)) as a dopant material. An organic EL element according to one embodiment includes an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer may include a first compound as a host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material (a third compound (compound M3)) as a dopant material.

[0537] (Phosphorescent metal complex) In one embodiment, the phosphorescent metal complex preferably contains heavy metal atoms.

[0538] In one embodiment, the phosphorescent metal complex preferably contains one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Au), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0539] In one embodiment, the phosphorescent metal complex is preferably a compound represented by the following general formula (21). M(L1) n1 (L2) n2 …(twenty one)

[0540] [ka]

[0541] (In the above general formulas (21), (211), (212), (213), M is a transition metal selected from the group consisting of first transition metals, second transition metals, and third transition metals. L1 is at least one ligand selected from the group consisting of ligands represented by the general formula (211), ligands represented by the general formula (212), and ligands represented by the general formula (213), n1 is 1, 2, or 3. L2 is at least one ligand selected from the group consisting of monosessate ligands, disessate ligands, and trisessate ligands. n2 is 0, 1, 2, 3, or 4. The CY1, CY2, CY3, and CY4 rings are each independently selected from the group consisting of a carbocyclic group with 5 to 30 ring-forming carbon atoms and a heterocyclic group with 1 to 30 ring-forming carbon atoms. Y1 to Y4 are independent of each other. single bond, double bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, Divalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, *aO-*b, *aS-*b, *aC(=O)-*b, *aS(=O)-*b, *aC(R5)(R6)-*b, *aC(R5)=C(R6)-*b, *aC(R5)=*b, *a-Si(R5)(R6)-*b, *aB(R5)-*b, *aN(R5)-*b, and Selected from the group consisting of *aP(R5)-*b, a1, a2, and a3 are each independently 1, 2, or 3. a4 is 0, 1, 2, or 3, and when a4 is 0, the CY2 ring and CY4 ring are not connected to each other. T1, T2, T3, and T4 are each independent of each other. chemical bond, *aO-*b, *aS-*b, *aB(R7)-*b, *aN(R7)-*b, *aP(R7)-*b, *aC(R7)(R8)-*b, *a-Si(R7)(R8)-*b, *a-Ge(R7)(R8)-*b, *aC(=O)-*b and Selected from the group consisting of *aC(=S)-*b, *a and *b are, independently, bond positions with adjacent atoms. *1, *2, *3 and *4 are the bonding sites with M. R1 to R8 are each independent of each other. hydrogen atom, halogen atom, Cyano group, Nitro group, Amidino group, Hydrazino group, Hydrazono group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl groups with 3 to 50 ring-forming atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, A heterocycloalkenyl group with 3 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, -Si(R 251 )(R 252 )(R 253 A base represented by ) -O-(R 254 A base represented by ) -S-(R 255 A base represented by ) -N(R 256 )(R 257 A base represented by ) -C(=O)R 258 A base represented by -C(=O)(OR 259 A base represented by ) -S(=O)2(OR 260 A base represented by ) -OP(=O)(OR 261 )(OR 262 A base represented by ) -C(R 263 )(R 264 )(R 265 A base represented by ) -B(R 266 )(R 267 A base represented by ) -P(R 268 )(R269 A base represented by ) -S(=O)(R 270 A base represented by ) -S(=O)2(R 271 A base represented by ) -P(=O)(R 272 )(R 273 A group represented by ) and -P(=S)(R 274 )(R 275 Selected from the bases represented by ), One or more pairs of adjacent R1-R8 are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, One or more pairs of adjacent elements from R1-R8 and Y1-Y4 are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not connect with each other, b1, b2, b3, and b4 are independently 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, R 251 ~R 275 Each of them operates independently. hydrogen atom, halogen atom, -O-(R 276 A base represented by ) -N(R 277 )(R 278 A base represented by ) Cyano group, Nitro group, Amidino group, Hydrazino group, Hydrazono group, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl groups with 3 to 50 ring-forming atoms, Substituted or unsubstituted ring-forming cycloalkenyl groups with 3 to 50 carbon atoms, A heterocycloalkenyl group with 3 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A ring-forming aryl group having 6 to 50 carbon atoms substituted with or unsubstituted alkyl groups having 1 to 50 carbon atoms, A ring-forming aryl group having 6 to 50 carbon atoms substituted with a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, Substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups, Selected from the group consisting of biphenylyl groups and terphenylyl groups, R 276 ~R 278 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0542] In this specification, a ring-forming carbon-numbered carbon-5 to carbon-30 carbon-12

[0543] In this specification, a heterocyclic group having 1 to 30 ring-forming carbon atoms means a group having the same structure as a carbocyclic group having 5 to 30 ring-forming carbon atoms, but containing, as ring-forming atoms, at least one heteroatom selected from N (carbon atom), O (oxygen atom), Si (silicon atom), P (phosphorus atom), and S (sulfur atom) in addition to carbon (the number of carbon atoms may be 1 to 30).

[0544] In this specification, heterocycloalkyl groups having 3 to 50 ring-forming atoms mean monovalent monocyclic groups having 3 to 50 ring-forming atoms, including at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom. Specific examples include 1,2,3,4-oxatriazolidinyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. In this specification, heterocycloalkylene groups having 3 to 50 ring-forming atoms mean divalent groups having the same structure as heterocycloalkyl groups having 3 to 50 ring-forming atoms.

[0545] In this specification, a ring-forming cycloalkenyl group having 3 to 50 carbon atoms refers to a monovalent monocyclic group having 3 to 50 carbon atoms and possessing at least one double bond within the ring, but lacking aromaticity. Specific examples include the cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group. In this specification, a ring-forming cycloalkenylene group having 3 to 50 carbon atoms refers to a divalent group having the same structure as a ring-forming cycloalkenyl group having 3 to 50 carbon atoms.

[0546] In this specification, a heterocycloalkenyl group having 3 to 50 ring-forming atoms is a monovalent monocyclic group having 3 to 50 ring-forming atoms, containing at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and having at least one double bond within the ring. Specific examples of heterocycloalkenyl groups having 3 to 50 ring-forming atoms include the 4,5-dihydro-1,2,3,4-oxatriazolyl group, the 2,3-dihydrofuranyl group, and the 2,3-dihydrothiophenyl group. In this specification, a heterocycloalkenylene group having 3 to 50 ring-forming atoms means a divalent group having the same structure as a heterocycloalkenyl group having 3 to 50 ring-forming atoms.

[0547] According to one embodiment, in the compound represented by the general formula (21), the substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms preferably has 3 to 10 ring-forming carbon atoms, the substituted or unsubstituted heterocycloalkyl group having 3 to 50 ring-forming atoms preferably has 3 to 10 ring-forming atoms, the substituted or unsubstituted cycloalkenyl group having 3 to 50 ring-forming carbon atoms preferably has 3 to 10 ring-forming carbon atoms, and the substituted or unsubstituted heterocycloalkenyl group having 3 to 50 ring-forming atoms preferably has 3 to 10 ring-forming atoms.

[0548] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused to each other, containing only carbon as the ring-forming atom, and having non-aromaticity as a whole molecule. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0549] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are fused to each other, and which contains at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to carbon, and the entire molecule is non-aromatic. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic heterocondensed polycyclic group.

[0550] In this specification, "biphenylyl group" means "phenyl group substituted with a phenyl group." A "biphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is an "aryl group having 6 to 50 ring-forming carbon atoms."

[0551] In this specification, "terphenylyl group" means "phenyl group substituted with a biphenylyl group." A "terphenylyl group" belongs to the category of "substituted phenyl groups" whose substituent is "an aryl group having 6 to 50 ring-forming carbon atoms substituted with an aryl group having 6 to 50 ring-forming carbon atoms."

[0552] In the compound represented by the general formula (21), the chemical bonds as T1, T2, T3, and T4 are preferably single bonds.

[0553] In the compound represented by the general formula (21) above, M is preferably one or more metal atoms selected from the group consisting of platinum (Pt), iridium (Ir), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Au), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm), and is more preferably platinum (Pt) or iridium (Ir).

[0554] According to one embodiment, in the compound represented by the general formula (21), the CY1 to CY4 rings are each independently benzene, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, chrysene, cyclopentadiene, 1,2,3,4-tetrahydronaphthalene, carbene, thiophene, furan, selenofen, indole, benzoboro, benzophosphole, indene, benzosilol, benzogermol, benzothiophene, benzoselenophene, benzofuran, carbazole, dibenzoboro, dibenzophosphole, fluorene, dibenzosilol, dibenzogermol, dibenzothiophene, dibenzoselenophene, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzobolol, azabenzophosphole, azaindene, azabenzosilol, azabenzogermol, azabenzothiophene, a Zabenzoselenophen, azabenzofuran, azacarbazole, azadibenzobolol, azadibenzophosphorus, azafluorene, azadibenzosilol, azadibenzogermol, azadibenzothiophene, azadibenzoselenophene, azadibenzofuran, azadibenzothiophene 5-oxide, aza-9H-fluoren-9-one, azadibenzothiophene 5,5-dioxide, pyridine, pyrimidine, pyrazine, pyridazine, triazine, quinoline, isoquinoli You may select from the group consisting of quinoxaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline and 5,6,7,8-tetrahydroquinoline.

[0555] According to one embodiment, at least one of the CY1 and CY2 rings in general formula (211), at least one of the CY1 to CY3 rings in general formula (212), and at least one of the CY1 to CY4 rings in general formula (213) may be a carbene.

[0556] According to one embodiment, Y1 to Y4 in general formulas (211) to (213) may each be at least one independently selected from the group consisting of a single bond, a double bond, *aO-*b, *aS-*b, *aC(R5)(R6)-*b, and *aN(R5)-*b.

[0557] According to one embodiment, in general formula (211), at least one of R1 and R2, in general formula (212), at least one of R1 to R3, and in general formula (213), at least one of R1 to R4 may be an electron donating group.

[0558] For example, the electron-donating group may be an iso-propyl group, a tert-butyl group, and a substituent selected from the group consisting of the following general formulas (10-1) to (10-61).

[0559] [ka]

[0560] [ka]

[0561] In the general formulas (10-1) to (10-61) above, * represents the bond position with an adjacent atom.

[0562] In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted. In this specification, methyl groups may be denoted as Me, phenyl groups as Ph, isopropyl groups as i-Pr, and t-butyl groups as t-Bu in chemical formulas.

[0563] According to one embodiment, at least one of R1 and R2 in the general formula (211) is a substituent other than hydrogen, and / or Y1 is *aN(R5)-*b, and R5 is a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0564] According to one embodiment, at least one of R1 to R3 in the general formula (212) is a substituent other than hydrogen, and / or at least one of Y1 and Y2 is *aN(R5)-*b, and R5 may be a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0565] According to one embodiment, at least one of R1 to R4 in the general formula (213) is a substituent other than hydrogen, and / or at least one of Y1 to Y4 is *aN(R5)-*b, and R5 may be a substituted ring-forming aryl group having 6 to 50 carbon atoms.

[0566] The luminescence efficiency of the organic EL element is improved by including the compound (third compound) according to the first embodiment and a phosphorescent metal complex as a sensitizing material in the light-emitting layer. The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0567] [Variations of the Embodiment] Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.

[0568] For example, the light-emitting layer is not limited to one layer, but may consist of multiple light-emitting layers stacked together. If the organic EL element has multiple light-emitting layers, it is sufficient that at least one light-emitting layer satisfies the conditions described in the above embodiment. For example, the other light-emitting layers may be fluorescent light-emitting layers or phosphorescent light-emitting layers that utilize light emission due to electron transitions from a triplet excited state to a direct ground state. Furthermore, if the organic EL element has multiple light-emitting layers, these light-emitting layers may be arranged adjacent to each other, or it may be a so-called tandem type organic EL element in which multiple light-emitting units are stacked with an intermediate layer in between.

[0569] Alternatively, for example, a barrier layer may be provided adjacent to at least one of the anode and cathode sides of the light-emitting layer. The barrier layer is preferably positioned in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, if a barrier layer is placed in contact with the cathode side of the light-emitting layer, the barrier layer transports electrons and prevents holes from reaching the layer on the cathode side of the barrier layer (e.g., the electron transport layer). If the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light-emitting layer and the electron transport layer. Furthermore, if a barrier layer is placed in contact with the anode side of the light-emitting layer, the barrier layer transports holes and prevents electrons from reaching the layer on the anode side of the barrier layer (for example, a hole transport layer). If the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light-emitting layer and the hole transport layer. Furthermore, a barrier layer may be provided adjacent to the light-emitting layer to prevent excitation energy from leaking from the light-emitting layer to the surrounding layers. This prevents excitons generated in the light-emitting layer from moving to layers closer to the electrodes than the barrier layer (for example, electron transport layers and hole transport layers). It is preferable that the light-emitting layer and the barrier layer are bonded together.

[0570] Furthermore, the specific structure and shape in the implementation of the present invention may be other structures, etc., to the extent that the objectives of the present invention can be achieved. [Examples]

[0571] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0572] <Compound> The structure of the compound represented by general formula (D1) used in the manufacture of the organic EL element according to Example 1 is shown below.

[0573] [ka]

[0574] The structure of the comparative compound used in the manufacture of the organic EL element related to Comparative Example 1 is shown below.

[0575] [ka]

[0576] The structures of other compounds used in the manufacture of the organic EL elements in Example 1 and Comparative Example 1 are shown below.

[0577] [ka]

[0578] [ka]

[0579] <Fabrication of Organic EL Devices> Organic EL elements were fabricated and evaluated as follows.

[0580] (Example 1) A glass substrate with a 25mm x 75mm x 1.1mm thick ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The ITO film thickness was set to 130 nm. The glass substrate with the transparent electrode line, after cleaning, was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-1 and compound HA were co-deposited onto the surface on which the transparent electrode line was formed, covering the transparent electrode, to form a hole injection layer with a thickness of 10 nm. The proportion of compound HT-1 in the hole injection layer was 97% by mass, and the proportion of compound HA was 3% by mass. Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer with a thickness of 80 nm. Next, compound HT-2 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 5 nm. Next, compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer (also called an electron barrier layer) with a thickness of 5 nm. Next, compound HOST-1 as a host material (first compound), compound STZ-1 as a sensitizing material (delayed fluorescence compound), and compound BD-1 as a fluorescent material (third compound) were co-deposited on the third hole transport layer to form a light-emitting layer with a thickness of 30 nm. The proportion of compound HOST-1 in the light-emitting layer was set to 74% by mass, compound STZ-1 to 25% by mass, and compound BD-1 to 1% by mass. Next, compound HBL-1 was deposited onto the light-emitting layer to form a hole barrier layer with a thickness of 10 nm. Next, compound ET-1 was co-deposited onto the hole barrier layer to form an electron transport layer with a thickness of 20 nm. Next, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was deposited onto the electron injection layer to form a metallic Al cathode with a thickness of 50 nm. As described above, an organic EL element according to Example 1 was fabricated. The element configuration of the organic EL element according to Example 1 is schematically shown below. ITO(130) / HT-1:HA(10,97%:3%) / HT-1(80) / HT-2(5) / EBL-1(5) / HOST-1:STZ-1:BD-1(30,74%:25%:1%) / HBL-1(10) / ET-1(20) / LiF(1) / Al(50) In the above device configuration, the numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the above device configuration, the percentages in parentheses (97%:3%) indicate the proportion (mass%) of compound HT-1 and compound HA in the hole injection layer, and the percentages (74%:25%:1%) indicate the proportion (mass%) of compound HOST-1, compound STZ-1, and compound BD-1 in the light-emitting layer.

[0581] (Comparative Example 1) The organic EL element of Comparative Example 1 was prepared in the same manner as in Example 1, except that compound BD-1, which was used as the fluorescent material in the light-emitting layer of Example 1, was replaced with one of the compounds listed in Table 1.

[0582] <Evaluation of Organic EL Devices> The fabricated organic EL elements were evaluated as follows. The evaluation results are shown in Table 1. The evaluation results of the compounds used in the light-emitting layer of each example are also shown in Table 1.

[0583] (External quantum efficiency EQE) The fabricated organic EL element has a current density of 10.00 mA / cm². 2 The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied in such a manner. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission occurred. The "EQE (relative value)" (unit: %) was calculated based on the following formula (Equation 1X). EQE (relative value) = (EQE of each example / EQE of comparison example 1) × 100 ... (Equation 1 x)

[0584] [Table 1]

[0585] As shown in Table 1, the organic EL element of Example 1 contained a sensitizing material and a fluorescent material represented by general formula (D1) in its light-emitting layer, and emitted light with higher efficiency compared to the organic EL element of Comparative Example 1.

[0586] <Evaluation of Compounds> The following evaluations were performed on the compound.

[0587] (Lowest excitation singlet energy S1) A 10 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The absorption spectrum of this sample (vertical axis: absorption intensity, horizontal axis: wavelength) was measured at room temperature (300 K). A tangent line was drawn to the falling edge on the long-wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis was substituted into the following conversion formula (F2) to calculate the lowest excited singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge A Hitachi spectrophotometer (model name: U3310) was used for measuring absorption spectra.

[0588] The tangent to the falling edge of an absorption spectrum on the longer wavelength side is drawn as follows: Consider the tangents at each point on the spectral curve as we move along the spectral curve in the longer wavelength direction from the maximum value on the longest wavelength side of the absorption spectrum. As the curve falls (i.e., as the value on the vertical axis decreases), the slope of this tangent decreases and then increases repeatedly. The tangent drawn at the point where the value of the slope is minimized on the longest wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the falling edge of the absorption spectrum on the longer wavelength side. Note that maximum absorbance values ​​of 0.2 or less are not included in the maximum value at the longest wavelength mentioned above.

[0589] (Energy gap T at 77[K]) 77K ) The compound to be measured was dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L to obtain a solution, which was then placed in a quartz cell to be used as the measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample was measured at a low temperature (77 [K]), and a tangent line was drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum. The wavelength value λ at the intersection of this tangent line and the horizontal axis was measured.edge Based on [nm], the energy amount calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K That's what I decided. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0590] The tangent to the rise of the phosphorescence spectrum on the short-wavelength side is drawn as follows: When moving along the spectral curve from the short-wavelength side of the phosphorescence spectrum to the shortest wavelength maximum value of the spectrum, consider the tangent at each point on the curve toward the long-wavelength side. The slope of this tangent increases as the curve rises (i.e., as the vertical axis increases). The tangent drawn at the point where this slope value is maximum (i.e., the tangent at the inflection point) is considered the tangent to the rise of the phosphorescence spectrum on the short-wavelength side. Furthermore, maxima with peak intensity less than 15% of the maximum peak intensity of the spectrum are not included in the shortest wavelength maxima mentioned above. Instead, the tangent line drawn at the point closest to the shortest wavelength maxima, where the slope value is at its maximum, is considered the tangent line to the rising edge of the phosphorescence spectrum on the short wavelength side. For phosphorescence measurements, a Hitachi High-Technologies Corporation F-4500 spectrofluorometer was used.

[0591] (ΔST) The measured lowest excited singlet energy S1 and energy gap T 77K Based on the value of , ΔST = S1 - T 77K The result was calculated.

[0592] (Delayed fluorescence of compounds) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 2. The compound STZ-1 was dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength to eliminate the contribution of self-absorption. Furthermore, to prevent quenching by oxygen, the sample solution was frozen and degassed, then sealed in a lidded cell under an argon atmosphere to obtain an argon-saturated, oxygen-free sample solution. The fluorescence spectra of the above sample solutions were measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was also measured under the same conditions. Using the fluorescence area intensities of both spectra, the total fluorescence quantum yield was calculated using equation (1) in Morris et al. J.Phys.Chem.80(1976)969. Compound STZ-1 is excited by pulsed light (light emitted from a pulsed laser) at a wavelength it absorbs. After excitation, there are two types of emission: Prompt emission (immediate emission), which is observed immediately from the excited state, and Delay emission (delayed emission), which is not observed immediately after excitation but is observed later. In this embodiment, delayed fluorescence emission means that the amount of Delay emission is 5% or more of the amount of Prompt emission (immediate emission). Specifically, the amount of Prompt emission (immediate emission) is X P Let X be the amount of delayed emission. D When X D / X P This means the value is 0.05 or greater. The amounts and ratios of prompt emission and delayed emission can be determined using a method similar to that described in “Nature 492, 234-238, 2012” (Reference 1). The apparatus used to calculate the amounts of prompt emission and delayed emission is not limited to the apparatus described in Reference 1 or the apparatus shown in Figure 2. For compound STZ-1, it was confirmed that the amount of delayed emission was 5% or more of the amount of prompt emission. Specifically, for compound STZ-1, X D / X P The value was 0.05 or higher.

[0593] (Maximum peak wavelength and full width at half maximum of the compound) The maximum peak wavelength λ and full width at half maximum (FWHM) of the compound were measured by the following method. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum at which the emission intensity is maximum was defined as the maximum peak wavelength λ, and the spectral width of the portion at half the maximum emission intensity was defined as the full width at half maximum (FWHM).

[0594] <Example of synthesis> (Synthesis of compound BD-1)

[0595] [ka]

[0596] (1) Synthesis of Compounds 1-2 Under an argon atmosphere, compound 1-1a (4.27 g, 15.0 mmol), compound 1-1b (11.3 g, 30.0 mmol), bis(tritertically butylphosphine)palladium (1.02 g, 2.00 mmol), sodium tertically butoxide (4.33 g, 45.0 mmol), and xylene (80 mL) were added, and the mixture was heated and stirred at 100 °C for 18 hours. After the reaction was complete, water and dichloromethane were added, the organic layer was extracted, and the solvent was removed by distillation. The resulting crude product was purified by column chromatography to obtain a white solid (4.60 g, yield 35%). The obtained solid was the target compound 1-2, and mass spectral analysis showed a molecular weight of 875.6 and a m / e ratio of 876.

[0597] (2) Synthesis of compound BD-1 Under an argon atmosphere, tert-butylbenzene (20 mL) was added to compound 1-2 (1.31 g, 1.50 mmol), and the mixture was cooled to -78°C. Tert-butyllithium pentane solution (1.88 mL, 1.60 M, 3.00 mmol) was added dropwise. After stirring for 1 hour, boron tribromide (1.50 g, 6.00 mmol) and diisopropylethylamine (388 mg, 3.00 mmol) were added, and the mixture was heated and stirred at 120°C for 6 hours. After the reaction was complete, water and dichloromethane were added, and the organic layer was extracted. The solvent was removed by distillation, and the resulting crude product was washed with ethanol to obtain a yellow solid (344 mg, yield 27%). The obtained solid was the target compound BD-1, and mass spectral analysis showed a molecular weight of 848.9 and a m / e ratio of 849. [Explanation of Symbols]

[0598] 1...Organic electroluminescent element, 10...Organic layer, 2...Substrate, 3...Anode, 4...Cathode, 5...Light-emitting layer, 6...Hole injection layer, 7...Hole transport layer, 8...Electron transport layer, 9...Electron injection layer.

Claims

1. A compound represented by the following general formula (D1). 【Chemistry 1】 (In the above general formula (D1), R １ ~R １１ Each of them operates independently. hydrogen atom, The group represented by the following general formula (D11), Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R) １３１ ) (Caution １３２ ) a base represented by -Si(R １３３ ) (Caution １３４ ) (Caution １３５ ) a base represented by -O-(R １３６ ) a base represented by -S-(R １３７ ) group represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R １３８ A base represented by - COOR １３９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R １４０ ) (Caution １４１ ) a base represented by -Ge(R) １４２ ) (Caution １４３ ) (Caution １４４ ) a base represented by -B(R) １４５ ) (Caution １４６ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, however, R １ ~R １１ Of these, at least one is a group represented by the following general formula (D11), R １ ~R ４ There are no cases where two or more of them are not hydrogen atoms. R ５ ~R ８ There are no cases where two or more of them are not hydrogen atoms. R ９ ~R １１ There are no cases where two or more of them are not hydrogen atoms. R ９ and R １１ It does not contain substituted or unsubstituted carbazolyl groups. R １２ and R １３ Each of them operates independently. A group represented by the following general formula (D12), or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, However, R １２ and R １３ At least one of these is a group represented by the following general formula (D12). 【Chemistry 2】 (In the above general formula (D11), R Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ , R Ｆ And one or more pairs of adjacent Y members, They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ , R Ｆ And one of Y is a single bond that connects to *a, L １ This is an arylene group having 6 to 50 carbon atoms, which is either single-bonded, substituted, or unsubstituted, forming a ring. *b indicates the bonding position with the ring structure represented by the general formula (D1) above. R Ａ and R Ｂ The set consists of two elements that bond to each other to form a substituted or unsubstituted carbazole ring, and Y is a single bond bonded to *a, and L １ When it is a single bond, a substituted or unsubstituted amino group and a substituted or unsubstituted N-carbazolyl group cannot be bonded to the carbazole ring. In the above general formula (D12), R Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, *c indicates the bonding position with the ring structure represented by the general formula (D1) above. In the above general formulas (D11) and (D12), R does not form the aforementioned substituted or unsubstituted monoring, does not form the aforementioned substituted or unsubstituted fused ring, and is not a single bond bonded to *a. Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ , R Ｆ and Y, and R which does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R) １３１ ) (Caution １３２ ) a base represented by -Si(R １３３ ) (Caution １３４ ) (Caution １３５ ) a base represented by -O-(R １３６ ) a base represented by -S-(R １３７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R １３８ A base represented by - COOR １３９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R １４０ ) (Caution １４１ ) a base represented by -Ge(R) １４２ ) (Caution １４３ ) (Caution １４４ ) a base represented by -B(R) １４５ ) (Caution １４６ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, however, R Ｇ and R Ｈ However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R Ｋ It is not a hydrogen atom, R Ｊ and R Ｋ However, if they bond to each other to form a substituted or unsubstituted monoring, or if they bond to each other to form a substituted or unsubstituted fused ring, then R Ｇ It is not a hydrogen atom, R Ｇ and R Ｈ are not bonded to each other, and when R Ｊ and R Ｋ are not bonded to each other, R Ｇ and R Ｋ is not a hydrogen atom, nor a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.) (In the compound represented by the general formula (D1), R １３１ ~R １４６ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R １３１ If multiple R １３１ They are either identical or different from one another. R １３２ When there are a plurality of R's １３２ they may be the same as or different from each other R １３３ If multiple R １３３ They are either identical or different from one another. R １３４ If multiple R １３４ They are either identical or different from one another. R １３５ If multiple R １３５ They are either identical or different from one another. R １３６ If multiple R １３６ They are either identical or different from one another. R １３７ If multiple R １３７ They are either identical or different from one another. R １３８ If multiple R １３８ They are either identical or different from one another. R １３９ If multiple R １３９ They are either identical or different from one another. R １４０ If multiple R １４０ They are either identical or different from one another. R １４１ If multiple R １４１ They are either identical or different from one another. R １４２ If multiple R １４２ They are either identical or different from one another. R １４３ If multiple R １４３ They are either identical or different from one another. R １４４ If multiple R １４４ They are either identical or different from one another. R １４５ If multiple R １４５ They are either identical or different from one another. R １４６ If multiple R １４６ (They are either identical or different to each other.)

2. Of the groups represented by the general formula (D11), at least one is a group represented by the following general formula (D111) or (D112): The compound according to claim 1. 【Transformation 3】 (In the above general formula (D111), R Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ , R Ｆ , L １ , and *b are R in the general formula (D11), respectively. Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ , R Ｆ , L １ , and *b are synonymous, however, R Ａ and R Ｂ They do not combine with each other, In the above general formula (D112), R Ｃ , R Ｄ , R Ｅ , R Ｆ , L １ , and *b are R in the general formula (D11), respectively. Ｃ , R Ｄ , R Ｅ , R Ｆ , L １ , and *b are synonymous, R Ｌ , R Ｍ , R Ｎ and R Ｏ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring Ｌ , R Ｍ , R Ｎ and R Ｏ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -N(R) １３１ ) (Caution １３２ ) a base represented by -Si(R １３３ ) (Caution １３４ ) (Caution １３５ ) a base represented by -O-(R １３６ ) a base represented by -S-(R １３７ ) a base represented by Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R １３８ A base represented by - COOR １３９ A base represented by halogen atom, Cyano group, Nitro group, -P (=O) (R １４０ ) (Caution １４１ ) a base represented by -Ge(R) １４２ ) (Caution １４３ ) (Caution １４４ ) a base represented by -B(R) １４５ ) (Caution １４６ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, L in the general formula (D112) １ If it is a single bond, R Ｃ , R Ｄ , R Ｅ , R Ｆ , R Ｌ , R Ｍ , R Ｎ and R Ｏ is -N(R １３１ ) (Caution １３２ (This does not include the group represented by ) and substituted or unsubstituted N-carbazolyl groups.)

3. In at least one of the groups represented by the general formula (D11), R Ａ , R Ｂ , R Ｃ , R Ｄ , R Ｅ and R Ｆ Either of these is a single bond that connects to *a. The compound according to claim 1.

4. L １ It is a single bond. The compound according to any one of claims 1 to 3.

5. The molecule has one or two groups represented by the general formula (D11) The compound according to any one of claims 1 to 4.

6. R ２ and R ７ One of them is a group represented by the general formula (D11), or R ２ and R ７ Both are groups represented by the general formula (D11), The compound according to any one of claims 1 to 5.

7. R １０ However, the group is represented by the general formula (D11) above. The compound according to any one of claims 1 to 6.

8. R １０ However, it is a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. The compound according to any one of claims 1 to 6.

9. R ９ ~R １１ If one of them is a group represented by the general formula (D11), then R １ ~R ４ Either of the following, R ５ ~R ８ It is not possible for either of them to be a hydrocarbon group. The compound according to any one of claims 1 to 8.

10. R １ , R ３ , R ４ , R ５ , R ６ , R ８ , R ９ and R １１ is a hydrogen atom, The compound according to any one of claims 1 to 9.

11. R Ｇ and R Ｋ Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. The compound according to any one of claims 1 to 10.

12. R Ｇ , R Ｉ and R Ｋ Each of these is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. The compound according to any one of claims 1 to 10.

13. R Ｈ and R Ｊ is a hydrogen atom, The compound according to any one of claims 1 to 12.

14. The compound represented by the above general formula (D1) is represented by the following general formula (D101), The compound according to any one of claims 1 to 13. 【Chemistry 4】 (In the above general formula (D101), R １ ~R １１ , R Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ These are R in the general formulas (D1) and (D12), respectively. １ ~R １１ , R Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ It is synonymous with multiple R's. Ｇ These are either identical or different from each other, and multiple R Ｈ These are either identical or different from each other, and multiple R Ｉ These are either identical or different from each other, and multiple R Ｊ These are either identical or different from each other, and multiple R Ｋ (They are either identical or different to each other.)

15. The compound represented by the above general formula (D1) is represented by the following general formula (D102), The compound according to claim 2. 【Transformation 5】 (In the above general formula (D102), R ９ ~R １１ , R Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ These are R in the general formulas (D1) and (D12), respectively. ９ ~R １１ , R Ｇ , R Ｈ , R Ｉ , R Ｊ and R Ｋ It is synonymous with, R Ｃ , R Ｄ , R Ｅ , R Ｆ , R Ｌ , R Ｍ , R Ｎ , R Ｏ and L １ These are, respectively, R in the general formula (D112) Ｃ , R Ｄ , R Ｅ , R Ｆ , R Ｌ , R Ｍ , R Ｎ , R Ｏ and L １ It is synonymous with, Multiple L １ These are either identical or different from each other, and multiple R Ｃ These are either identical or different from each other, and multiple R Ｄ These are either identical or different from each other, and multiple R Ｅ These are either identical or different from each other, and multiple R Ｆ These are either identical or different from each other, and multiple R Ｇ These are either identical or different from each other, and multiple R Ｈ These are either identical or different from each other, and multiple R Ｉ These are either identical or different from each other, and multiple R Ｊ These are either identical or different from each other, and multiple R Ｋ These are either identical or different from each other, and multiple R Ｌ These are either identical or different from each other, and multiple R Ｍ These are either identical or different from each other, and multiple R Ｎ These are either identical or different from each other, and multiple R Ｏ (They are either identical or different to each other.)

16. The compound represented by the above general formula (D1) is represented by the following general formula (D103): The compound according to any one of claims 1 to 13. 【Transformation 6】 (In the above general formula (D103), R ２ , R ７ , R １０ , R １２ and R １３ These are, respectively, R in the general formula (D1) ２ , R ７ , R １０ , R １２ and R １３ (This is synonymous with...)

17. A material for an organic electroluminescent device comprising the compound described in any one of claims 1 to 16.

18. An organic electroluminescent element, It comprises a cathode, an anode, and an organic layer contained between the cathode and the anode, At least one of the organic layers contains a compound according to any one of claims 1 to 16 as compound M3. Organic electroluminescent element.

19. The organic layer includes a light-emitting layer, The light-emitting layer contains the compound M3. The organic electroluminescent element according to claim 18.

20. The light-emitting layer contains a sensitizing material, The sensitizing material and compound M3 are different compounds. The organic electroluminescent element according to claim 19.

21. The sensitizing material is a delayed-fluorescence compound. The organic electroluminescent element according to claim 20.

22. The sensitizing material and the compound M3 are contained in a single layer. The organic electroluminescent element according to claim 20 or claim 21.

23. A hole transport layer is disposed between the anode and the light-emitting layer. An organic electroluminescent element according to any one of claims 20 to 22.

24. An electron transport layer is disposed between the cathode and the light-emitting layer. An organic electroluminescent element according to any one of claims 20 to 23.

25. An electronic device equipped with an organic electroluminescent element according to any one of claims 18 to 24.

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