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

Abstract

To provide compounds that enable organic electroluminescent elements to emit light with high efficiency. [Solution] A compound having a structure in which an orthobiphenyl group is introduced at at least one position of the biscarbazole skeleton, for example, the following compound Host-1 is shown. TIFF2026094506000187.tif75160

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. Patent Document 7 discloses an organic EL device that utilizes the TTF (Triplet-Triplet Fusion) mechanism, one of the mechanisms of delayed fluorescence. The TTF mechanism utilizes the phenomenon in which a singlet exciton is generated by the collision of two triplet excitons. [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] U.S. Patent Application Publication No. 2022 / 0135601 [Patent Document 2] Korean Published Patent No. 10-2015-0105201 [Patent Document 3] U.S. Patent Application Publication No. 2022 / 0112163 [Patent Document 4] U.S. Patent Application Publication No. 2022 / 0140255 [Patent Document 5] International Publication No. 2017 / 111543 [Patent Document 6] Korean Published Patent No. 10-2016-0095667 [Patent Document 7] International Publication No. 2010 / 134350 [Overview of the project] [Problems that the invention aims to solve]

[0004] It is believed that by utilizing the TTF mechanism for delayed fluorescence described in Patent Document 7, the internal quantum efficiency can theoretically be increased to 40% even in fluorescence emission. However, further improvements in the performance of organic EL elements are desired in order to improve the performance of electronic devices such as displays.

[0005] An object of the present invention is to provide a compound that can enable an organic electroluminescent element to emit light with high efficiency. Another object of the present invention is to provide a material for an organic electroluminescent element containing the compound. Another object of the present invention is to provide an organic electroluminescent element that emits light with high efficiency, 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 (1) is provided.

[0007] [ka]

[0008] [ka]

[0009] (In the above general formula (1), Ar1 is a group represented by the general formula (11) or (12) above, A set consisting of two or more adjacent elements from R1 to R4, and one or more sets consisting of R6 and R7, 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, R8~R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 Of these, one or more pairs consisting of two or more adjacent items, 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, The compound represented by the general formula (1) satisfies either condition i or condition ii. (Condition i): A set of two or more adjacent tiles from R1 to R4, a set of R6 and R7, R8 to R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 When one or more pairs of adjacent rings combine, the substituted or unsubstituted monorings and the substituted or unsubstituted fused rings formed are, independently of each other, The ring is represented by the general formula (14) above, or A substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, R5, and R1-R4 and R6-R, which do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted condensed ring. 15 Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, In the above general formula (14), Y1 is an oxygen atom or a sulfur atom, R 16 ~R 19 are each independently, a hydrogen atom, the group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, -Si(R 41 )(R 42 )(R 43 ) or a group represented by -Ge(R 44 )(R 45 )(R 46 ), and the two * indicate the bonding positions to the carbazole ring in the general formula (1). However, among R1 to R 19 , at least one is the group represented by the general formula (13). When there are a plurality of groups represented by the general formula (13), the plurality of groups represented by the general formula (13) are the same as or different from each other. When there are a plurality of rings represented by the general formula (14), the plurality of rings represented by the general formula (14) are the same as or different from each other. (Condition ii): Among the groups consisting of two or more adjacent ones of R1 to R4, the group consisting of R6 and R7, the group consisting of two or more adjacent ones of R8 to R 11 , and the group consisting of two or more adjacent ones of R 12 ~R 15 do not bond to each other. R1 to R 15 are each independently, a hydrogen atom, the group represented by the general formula (13), a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring-forming carbon atoms, and However, R1 to R 15Of these, at least one is a group represented by the general formula (13), and if there are multiple groups represented by the general formula (13), the multiple groups represented by the general formula (13) are either identical or different from each other. (In the above general formulas (11) and (12), R 21 ~R 25 Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not bind to each other, R 26 ~R 29 Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not bind to each other, Multiple R 30 Of the sets of two or more adjacent items, one or more sets are They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not bind to each other, The aforementioned substituted or unsubstituted ring-forming aliphatic hydrocarbon rings with 3 to 20 carbon atoms do not form R 21 ~R 30 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), Multiple R 30 They are either identical to each other or different to each other. X1 consists of an oxygen atom, a sulfur atom, and C(R) 51 )(R 52), or Si(R 53 )(R 54 ) and R 51 and R 52 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 bind to each other, R 53 and R 54 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 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 51 ~R 54 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or These are heterocyclic groups with 5 to 60 substituted or unsubstituted ring-forming atoms. In the general formula (11), * represents the bonding position of Ar1 with the nitrogen atom to which it is bonded in the general formula (1). In the general formula (12), the asterisk (*) indicates the bonding position of Ar1 with the nitrogen atom to which it is bonded in the general formula (1). (In the above general formula (13), R 31 ~R 39 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), * indicates a bond position. (In the compound represented by the general formula (1) above, R 41 ~R 43 One of the pairs of adjacent items is 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 44 ~R 46 One of the pairs of adjacent items is 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 41 ~R 46 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 60 carbon atoms, A heterocyclic group with 5 to 60 substituted or unsubstituted ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, (These are substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms forming a ring.)

[0010] 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.

[0011] According to one aspect of the present invention, an organic electroluminescent element is provided, comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer contains a host material and a sensitizing material, the host material being a compound according to one aspect of the present invention, and the sensitizing material and the host material being different compounds from each other.

[0012] 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]

[0013] According to one aspect of the present invention, a compound can be provided that enables an organic electroluminescent element to emit light with high efficiency. According to one aspect of the present invention, a material for an organic electroluminescent element containing the compound can be provided. According to one aspect of the present invention, an organic electroluminescent element that emits light with high efficiency can be provided, as well as an electronic device equipped with the organic electroluminescent element. [Brief explanation of the drawing]

[0014] [Figure 1] This figure shows a schematic configuration of an example of an organic electroluminescent element according to the first 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 energy levels and energy transfer relationships of the host material, sensitizing material (delayed fluorescence compound), and fluorescent material in the light-emitting layer of an example of an organic electroluminescent element according to the first embodiment of the present invention. [Modes for carrying out the invention]

[0015] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] "Substituents as described herein" The substituents described herein will be explained below.

[0023] 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.

[0024] • "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.

[0025] • 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).

[0026] [ka]

[0027] [ka]

[0028] • 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.

[0029] • "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.

[0030] 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).

[0031] 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).

[0032] • 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.

[0033] • 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.

[0034] • 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).

[0035] • 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):

[0036] [ka]

[0037] [ka]

[0038] 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.

[0039] • 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.

[0040] • 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].

[0041] • 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].

[0042] • 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):

[0043] 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 AThis refers to one or more hydrogen atoms selected from the hydrogen atoms of the methylene group when one of the atoms is CH2.

[0044] • "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.

[0045] • 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.

[0046] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0047] • "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.

[0048] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0049] • 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.

[0050] • "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.

[0051] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group.

[0052] • "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.

[0053] • 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.

[0054] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0055] · "-Si(R 901 )(R 902 )(R 903 ) represented by the base -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.

[0056] ·「-O-(R 904 ) represented by the base The following information pertains to the -O-(R904 ) 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.

[0057] · "-S-(R 905 ) represented by the base -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.

[0058] · "-N(R 906 )(R 907 ) represented by the base -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.

[0059] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0060] • "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.

[0061] • "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.

[0062] • "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.

[0063] • "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.

[0064] • "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.

[0065] • "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.

[0066] • "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.

[0067] • "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.

[0068] 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.

[0069] 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.

[0070] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0071] [ka]

[0072] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0073] [ka]

[0074] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0075] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups:

[0076] [ka]

[0077] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0078] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0079] • "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.

[0080] • "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.

[0081] • "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.

[0082] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0083] [ka]

[0084] [ka]

[0085] 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.

[0086] [ka]

[0087] 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.

[0088] [ka]

[0089] 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.

[0090] 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).

[0091] [ka]

[0092] [ka]

[0093] [ka]

[0094] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0095] [ka]

[0096] [ka]

[0097] [ka]

[0098] [ka]

[0099] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0100] The above is a description of the substituents described herein.

[0101] • "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.

[0102] [ka]

[0103] For example, R921 ~R 930 Among them, in the case of "one or more of the pairs consisting of two or more adjacent ones are combined with each other to form a ring", the pair consisting of two adjacent ones that forms one pair is R 921 and R 922 and the pair of R 922 and R 923 and the pair of R 923 and R 924 and the pair of R 924 and R 930 and the pair of R 930 and R 925 and the pair of R 925 and R 926 and the pair of R 926 and R 927 and the pair of R 927 and R 928 and the pair of R 928 and R 929 and the pair of R, and R 929 and R 921 and the pair of R.

[0104] The above "one or more" means that two or more of the pairs consisting of two or more adjacent ones may form a ring at the same time. For example, R 921 and R 922 are combined with each other to form ring Q A , and at the same time R 925 and R 926 are combined with each other to form ring Q B is formed, then the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[0105]

Chemical formula

[0106] The case where a "pair consisting of two or more adjacent ones" forms a ring includes not only the case where a pair consisting of "two" adjacent ones is combined as in the above example, but also the case where a pair consisting of "three or more" adjacent ones is combined. For example, R 921 and R 922 are combined with each other to form ring Q A , and 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.

[0107] [ka]

[0108] 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.

[0109] 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 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.

[0110] 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 monoring or a fused 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.

[0111] 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").

[0112] • 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 These are groups selected from the group consisting of unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, 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, It is a substituted or unsubstituted aryl group with 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group with 5 to 50 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. R 903 If there are two or more of them, then there are two or more R903 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.

[0113] 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 It is a group selected from the group consisting of heterocyclic groups with 5 to 50 ring-forming atoms.

[0114] 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 It is a group selected from the group consisting of heterocyclic groups with 5 to 18 ring-forming atoms.

[0115] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] [First Embodiment] <Compound> The compound according to this embodiment is a compound represented by the following general formula (1).

[0120] [ka]

[0121] [ka]

[0122] (In the above general formula (1), Ar1 is a group represented by the general formula (11) or (12) above, A set consisting of two or more adjacent elements from R1 to R4, and one or more sets consisting of R6 and R7, 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, R8~R 11 A set consisting of two or more adjacent items, and R 12 ~R15 Of these, one or more pairs consisting of two or more adjacent items, 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, The compound represented by the general formula (1) satisfies either condition i or condition ii. (Condition i): A set of two or more adjacent tiles from R1 to R4, a set of R6 and R7, R8 to R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 When one or more pairs of adjacent rings combine, the substituted or unsubstituted monorings and the substituted or unsubstituted fused rings formed are, independently of each other, The ring is represented by the general formula (14) above, or A substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, R5, and R1-R4 and R6-R, which do not form the substituted or unsubstituted monoring and do not form the substituted or unsubstituted condensed ring. 15 Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, In the above general formula (14), Y1 is either an oxygen atom or a sulfur atom. R 16 ~R 19 Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), The two *s indicate the bond position with the carbazole ring in the general formula (1) above. However, R1~R 19 Of these, at least one is a group represented by the general formula (13), and if there are multiple groups represented by the general formula (13), the multiple groups represented by the general formula (13) are either identical or different from each other, and if there are multiple rings represented by the general formula (14), the multiple rings represented by the general formula (14) are either identical or different from each other. (Condition ii): A set of two or more adjacent tiles from R1 to R4, a set of R6 and R7, R8 to R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 If any of the pairs of adjacent elements do not combine with each other, R1~R 15 Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, However, R1~R 15 Of these, at least one is a group represented by the general formula (13), and if there are multiple groups represented by the general formula (13), the multiple groups represented by the general formula (13) are either identical or different from each other. (In the above general formulas (11) and (12), R 21 ~R 25 Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not connect with each other, R 26 ~R 29 Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not connect with each other, Multiple R 30 Of the sets of two or more adjacent items, one or more sets are They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring with 3 to 20 carbon atoms, or They do not connect with each other, The aforementioned substituted or unsubstituted ring-forming aliphatic hydrocarbon rings with 3 to 20 carbon atoms do not form R 21 ~R 30 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), Multiple R 30 They are either identical to each other or different to each other. X1 consists of an oxygen atom, a sulfur atom, and C(R) 51 )(R 52 ), or Si(R 53 )(R 54 ) and R 51 and R 52 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 53 and R 54 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 the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 51 ~R 54 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or These are heterocyclic groups with 5 to 60 substituted or unsubstituted ring-forming atoms. In the general formula (11), * represents the bonding position of Ar1 with the nitrogen atom to which it is bonded in the general formula (1). In the general formula (12), the asterisk (*) indicates the bonding position of Ar1 with the nitrogen atom to which it is bonded in the general formula (1). (In the above general formula (13), R 31 ~R 39 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), * indicates a bond position. (In the compound represented by the general formula (1) above, R 41 ~R 43 One of the pairs of adjacent items is 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 44 ~R 46One of the pairs of adjacent items is 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 41 ~R 46 Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 60 carbon atoms, A heterocyclic group with 5 to 60 substituted or unsubstituted ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, (These are substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms forming a ring.)

[0123] The compound according to this embodiment (the compound represented by the general formula (1)) has a structure in which an orthobiphenyl group (the group represented by the general formula (13)) is introduced at at least one position of the biscarbazole skeleton. Due to this structure, the compound according to this embodiment has a higher glass transition temperature (Tg) compared to the compound before the introduction of the orthobiphenyl group. Therefore, by including this compound in the light-emitting layer, the thermal stability of the film (light-emitting layer) is improved. Furthermore, the compound according to this embodiment has a structure in which an ortho-biphenyl group is introduced to the biscarbazole skeleton, which increases the overall steric bulk of the compound. Due to this steric bulk, when the compound is used as a host compound, steric hindrance occurs between it and the dopant compound, suppressing their interaction. As a result, the compound according to the embodiment of the present invention can reduce the energy loss related to the luminescence of the dopant compound, enabling the organic EL element to emit light with high efficiency. Furthermore, since the molecular weight of the compound according to this embodiment does not increase as much as that of compounds into which terphenyl groups, etc., are introduced, it is possible to suppress the rise in deposition temperature when depositing the compound to form a light-emitting layer, thereby reducing the thermal load on the compound. In addition, since the rise in deposition temperature can be suppressed, the difference between the deposition temperature and the decomposition temperature of the compound can be widened, and as a result, the heat resistance margin of the compound during deposition can be improved. According to one embodiment of the compound of this embodiment, when used as a host compound, it is possible to make an organic EL element emit light with high efficiency. According to one embodiment of the compound of this embodiment, when included in the light-emitting layer together with a blue light-emitting material, the organic EL element can be made to emit light with high efficiency.

[0124] In one embodiment of the compound according to this embodiment, for example, in the general formula (1), the pair of R1 and R2 are bonded to each other to form a "substituted or unsubstituted condensed ring," and the formed condensed ring is a ring represented by the general formula (14), then the compound according to this embodiment is represented by the following general formula (1A) or (1E). In the following general formula (1A), R3~R 19 Of these, at least one is a group represented by the general formula (13). In the general formula (1E) below, R3 to R 19 Of these, at least one is a group represented by the general formula (13). In one embodiment of the compound according to this embodiment, for example, in the general formula (1), if the pair of R3 and R4 are bonded to each other to form a "substituted or unsubstituted monoring," and the formed ring is a "substituted or unsubstituted aliphatic hydrocarbon ring with 6 carbon atoms," then the compound according to this embodiment is represented by the following general formula (1X). In the following general formula (1X), Rx is not a group represented by the general formula (13), but rather R1~R2 and R5~R 15 Of these, at least one is a group represented by the general formula (13). In one embodiment of the compound according to this embodiment, for example, in the general formula (1), if the pair of R3 and R4 are bonded to each other to form a "substituted or unsubstituted condensed ring," and the formed condensed ring is a "substituted or unsubstituted ring-forming aliphatic hydrocarbon ring with 20 carbon atoms," then the compound according to this embodiment is a compound in which the "substituted or unsubstituted ring-forming aliphatic hydrocarbon ring with 6 carbon atoms" in the following general formula (1X) is replaced with a "substituted or unsubstituted ring-forming aliphatic hydrocarbon ring with 20 carbon atoms." If the aliphatic hydrocarbon ring has substituents, none of the substituents are groups represented by the general formula (13), but rather R1~R2 and R5~R 15 Of these, at least one is a group represented by the general formula (13).

[0125] [ka]

[0126] (In the above general formulas (1A) and (1E), Ar1 and R3~R 15 These are, independently, Ar1 and R3~R in the general formula (1) above. 15 This is synonymous with Y1 and R 16 ~R 19 These are, independently, Y1 and R in the general formula (14) above. 16 ~R 19 (This is synonymous with...) (In the above general formula (1X), Ar1, R1~R2 and R5~R 15 These are, independently, Ar1, R1~R2 and R5~R in the general formula (1) above. 15 It is synonymous with, One or more pairs of adjacent Rx elements 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, Rx that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted fused ring is, hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R 41 )(R 42 )(R 43 A base represented by ) or -Ge(R 44 )(R 45 )(R 46 It is a base represented by ), Multiple Rx values ​​are either identical or different from one another.

[0127] One embodiment of the compound according to this embodiment (the compound represented by the general formula (1)) is the compound represented by the following general formula (10).

[0128] [ka]

[0129] (In the above general formula (10), R1 to R 15 Each of these independently corresponds to R1 to R in the general formula (1) above. 15 It is synonymous with R 21 ~R 25 Each of these independently corresponds to R in the general formula (11) above. 21 ~R 25 (This is synonymous with...)

[0130] In one embodiment of the compound according to this embodiment, a set consisting of two or more adjacent R1 to R4, a set of R6 and R7, and R8 to R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 One or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring. In this embodiment, R1~R 19 Of these, at least one is a group represented by the general formula (13). R1~R 19Preferably, one of them is a group represented by the general formula (13), and R1 to R4, R6 to R 11 and R 16 ~R 18 It is more preferable that one of them is a group represented by the general formula (13), R 10 , R 11 , R 16 or R 18 It is even more preferable that R is a group represented by the general formula (13), 10 or R 11 It is even more preferable that the group is represented by the general formula (13).

[0131] In one embodiment of the compound according to this embodiment, a set consisting of two or more adjacent R1 to R4, a set of R6 and R7, and R8 to R 11 A set consisting of two or more adjacent items, and R 12 ~R 15 No two or more adjacent pairs of these pairs are connected to each other. In this embodiment, R1~R 15 Of these, at least one is a group represented by the general formula (13). R1~R 15 Preferably, one of them is a group represented by the general formula (13), and R1 to R4 and R6 to R 11 It is more preferable that one of them is a group represented by the general formula (13), R 10 or R 11 It is even more preferable that the group is represented by the general formula (13).

[0132] One embodiment of the compound according to this embodiment (the compound represented by the general formula (1)) is a compound represented by the following general formulas (1A), (1B), (1C), or (1D). The compound represented by the following general formula (1A) is synonymous with the compound represented by the aforementioned general formula (1A).

[0133] [ka]

[0134] (In the above general formulas (1A), (1B), (1C), and (1D), Ar1 is synonymous with Ar1 in the general formula (1) above, R1~R 15 Each of these independently corresponds to R1 to R in the general formula (1) above. 15 It is synonymous with, Y1 and R 16 ~R 19 These are, independently, Y1 and R in the general formula (14) above. 16 ~R 19 (This is synonymous with...)

[0135] In the above general formulas (1A), (1B), (1C), and (1D), R1 to R 19 Preferably, one of them is a group represented by the general formula (13), and R1 to R4, R6 to R 11 and R 16 ~R 18 It is more preferable that one of them is a group represented by the general formula (13), R 10 , R 11 , R 16 or R 18 It is even more preferable that R is a group represented by the general formula (13), 10 or R 11 It is even more preferable that the group is represented by the general formula (13).

[0136] One embodiment of the compound according to this embodiment (the compound represented by the general formula (1)) is a compound represented by any of the following general formulas (2A), (2B), (2C), (2D), (2E), and (2F).

[0137] [ka]

[0138] [ka]

[0139] (In the above general formulas (2A), (2B), (2C), (2D), (2E), and (2F), Ar1 is synonymous with Ar1 in the above general formula (1), and R1~R 15 Each of these independently corresponds to R1 to R in the general formula (1) above. 15 This is synonymous with Y1 and R 16 ~R 19 These are, independently, Y1 and R in the general formula (14) above. 16 ~R 19 It is synonymous with [the above]. In the above general formula (2F), the two Y1s are either identical or different, and the two Rs are 16 They are either identical or different, and the two R 17 They are either identical or different from each other, and the two R's 18 They are either identical or different, and the two R 19 They are either identical or different.

[0140] In the above general formulas (2A), (2B), (2C), (2D), (2E), and (2F), R1 to R 19 Preferably, one of them is a group represented by the general formula (13), and R1 to R4, R6 to R 11 and R 16 ~R 18 It is more preferable that one of them is a group represented by the general formula (13), R 10 , R 11 , R 16 or R 18 It is even more preferable that R is a group represented by the general formula (13), 10 or R 11 It is even more preferable that the group is represented by the general formula (13).

[0141] In the compound according to this embodiment, R 31 ~R 39Each of these is preferably independently a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, or a substituted or unsubstituted ring-forming C3-C20 cycloalkyl group; more preferably a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, or a substituted or unsubstituted ring-forming C3-C12 cycloalkyl group; and even more preferably a hydrogen atom. In the compound according to this embodiment, R 31 ~R 39 At least one of them may be a deuterium atom.

[0142] In the compound according to this embodiment, R 21 ~R 30 Each of these independently comprises a hydrogen atom, a group represented by the general formula (13), a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C3-C12 cycloalkyl group, and -Si(R 41 )(R 42 )(R 43 A group represented by ) or -Ge(R 44 )(R 45 )(R 46 It is preferable that the group is represented by ). In the compound according to this embodiment, R 21 ~R 30 At least one of them may be a deuterium atom.

[0143] In the compound according to this embodiment, R1 to R 19 Each of these independently comprises a hydrogen atom, a group represented by the general formula (13), a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C3-C12 cycloalkyl group, and -Si(R 41 )(R 42 )(R 43 A group represented by ) or -Ge(R 44 )(R 45 )(R 46 It is preferable that the group is represented by ). In the compound according to this embodiment, R1 to R 19 At least one of them may be a deuterium atom. R1~R19 Preferably, one of these is a group represented by the general formula (13).

[0144] In one embodiment of the compound according to this embodiment, Ar1 is Substituted or unsubstituted phenyl groups, The group represented by the following general formula (111), The base represented by the following general formula (112), The group represented by the following general formula (121), The group represented by the following general formula (122), The group represented by the following general formula (123), The group represented by the following general formula (124), The base represented by the following general formula (125), The group represented by the following general formula (126), A group represented by the following general formula (127), or It is a group represented by the following general formula (128).

[0145] [ka]

[0146] (In the above general formulas (111) to (112), R 21 ~R 23 and R 25 Each of these independently corresponds to R in the general formula (11) above. 21 ~R 23 and R 25 It is synonymous with, Each Rx is independently synonymous with Rx in the general formula (1X) above, * indicates the bonding position of Ar1 to the nitrogen atom in the general formula (1) above.

[0147] [ka]

[0148] [ka]

[0149] (In the above general formulas (121) to (128), X1 is the same as X1 in the above general formula (12), R 26 ~R 30 Each of these independently corresponds to R in the general formula (12) above. 26 ~R 30 It is synonymous with multiple R 30 They are either identical or different from one another. In the above general formulas (125) to (128), each Rx is independently equivalent to Rx in the above general formula (1X), and multiple Rx are either identical or different from one another. * indicates the bonding position of Ar1 to the nitrogen atom in the general formula (1) above.

[0150] In one embodiment of the compound according to this embodiment, Ar1 is not a substituted or unsubstituted naphthylene group. In one embodiment of the compound according to this embodiment, in the general formula (11), R 21 ~R 25 Of these, one or more pairs of adjacent elements 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. In one embodiment of the compound according to this embodiment, in the general formula (12), R 26 ~R 29 Of these, one or more pairs of adjacent elements 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. In one embodiment of the compound according to this embodiment, in the general formula (12), a plurality of R 30 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.

[0151] In the general formulas (121) to (128) above, X1 is preferably an oxygen atom or a sulfur atom. In the above general formulas (111) to (112) and (121) to (128), R 21 ~R 23 , R 25 , R 26 ~R 30 And Rx are, independently, a hydrogen atom, a substituted or unsubstituted C1-C6 alkyl group, a substituted or unsubstituted ring-forming C3-C12 cycloalkyl group, and -Si(R 41 )(R 42 )(R 43 A group represented by ) or -Ge(R 44 )(R 45 )(R 46 It is preferable that the group is represented by ).

[0152] In the compound according to this embodiment, R 51 and R 52 It is also preferable that the sets consisting of R do not combine with each other. 53 and R 54 It is also preferable that the pairs consisting of these elements do not combine with each other. In the compound according to this embodiment, R 41 ~R 43 It is also preferable that no two adjacent pairs of R are connected to each other. 44 ~R 46 It is also preferable that no two adjacent pairs of these pairs are connected to each other.

[0153] In the compounds according to this embodiment, examples of cycloalkyl groups having 3 to 20 ring-forming carbon atoms include monocycloalkanes (e.g., cyclopentane, cyclohexane, cycloheptane, and cyclooctane) and polycycloalkanes (e.g., adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane) from which one hydrogen atom has been removed. As for the cycloalkyl group having 3 to 20 carbon atoms that forms the ring, a group obtained by removing one hydrogen atom from adamantane is preferred.

[0154] In the compounds according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group.

[0155] In the compounds according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0156] In this specification, -Ge(R 44 )(R 45 )(R 46 The group represented by ) is R 44 , R 45 and R 46 If it is a substituent, it is a substituted germanium group.

[0157] The compound according to this embodiment is preferably a material used in a light-emitting layer. The compound according to this embodiment is preferably a host material.

[0158] (Method for producing the compound according to this embodiment) The compound according to this embodiment (the compound represented by general formula (1)) can be produced according to the synthesis method described in the examples below, or by following that synthesis method and using known alternative reactions and raw materials suited to the target product.

[0159] (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.

[0160] [ka]

[0161] [ka]

[0162]

change

[0163]

change

[0164]

change

[0165]

change

[0166]

change

[0167]

change

[0168]

change

[0169]

change

[0170]

change

[0171]

change

[0172]

change

[0173]

change

[0174]

change

[0175]

change

[0176]

change

[0177]

change

[0178]

change

[0179]

change

[0180]

change

[0181]

change

[0182] [Second form] <Materials for Organic Elastomer Materials> 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. One embodiment of a material for an organic electroluminescent element includes a compound according to the first embodiment as a host material and another compound such as a sensitizing material (preferably a delayed-fluorescence compound). One embodiment of a material for an organic electroluminescent element includes a compound according to the first embodiment as a host material, a sensitizing material (preferably a delayed-fluorescence compound), and a fluorescent material.

[0183] [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 an organic layer between the anode and cathode electrodes. 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.

[0184] The organic EL element according to 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 host material, a sensitizing material, and a fluorescent material. The host material is a compound according to the first embodiment. The host material, sensitizing material, and fluorescent material are all different compounds.

[0185] In the light-emitting layer, recombination of holes and electrons is more likely to occur on the molecules of the host material or sensitizing material rather than the fluorescent material. In the sensitizing 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 an efficient 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. The compound according to the first embodiment (represented by general formula (1)) used as a host material has sterically bulky substituents, which reduces energy loss due to interaction with the dopant compound. As a result, the fluorescent material that receives energy from the sensitizing material is expected to emit light with high efficiency.

[0186] (organic layer) In the organic EL element of the third embodiment, the organic layer may consist of, for example, a single light-emitting 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, another hole barrier layer, an electron transport layer, and an electron injection layer.

[0187] In the organic EL element of the third embodiment, a hole transport layer may be disposed between the anode and the light-emitting layer.

[0188] In the organic EL element of the third embodiment, an electron transport layer may be disposed between the cathode and the light-emitting layer.

[0189] 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.

[0190] (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.

[0191] 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.

[0192] [Host Materials] In one embodiment, the host material is a compound according to the first embodiment. In this specification, the compound used as the host material may be referred to as the first compound.

[0193] [Sensitizing material] In one embodiment, the sensitizing material is one or more compounds selected from the group consisting of phosphorescent metal complexes and delayed-fluorescence compounds. In this specification, the compound used as the sensitizing material may be referred to as the second compound. In one embodiment, the sensitizing material is a delayed-fluorescence compound.

[0194] (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.

[0195] (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.

[0196] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H1).

[0197] [ka]

[0198] (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 each other. n is 1, 2, 3, 4, or 5, and multiple D H They are either identical or different to one another.

[0199] [ka]

[0200] (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.)

[0201] [ka]

[0202] [ka]

[0203] [ka]

[0204] (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 228Furthermore, 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 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. 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.)

[0205] [ka]

[0206] (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 , R291 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 each other. Multiple R 291 They are either identical or different from each other. Multiple R 292 They are either identical or different from each other. Multiple X A They are either identical or different to one another.

[0207] (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 901 If multiple R 901 They are either identical or different from each other. R 902 If multiple R 902 They are either identical or different from each other. R 903 If multiple R 903 They are either identical or different from each other. R 904 If multiple R 904 They are either identical or different from each other. R 905 If multiple R 905 They are either identical or different from each other. R 906 If multiple R 906 They are either identical or different from each other. R 907 If multiple R 907 They are either identical or different from each other. R 908 If multiple R 908 They are either identical or different from each other. R 909 If multiple R 909 They are either identical or different from each other. R 931 If multiple R 931 They are either identical or different from each other. R 932 If multiple R 932 They are either identical or different from each other. R 933 If multiple R 933 They are either identical or different from each other. R 934 If multiple R 934 They are either identical or different from each other. R 935 If multiple R 935 They are either identical or different from each other. R 936 If multiple R 936 They are either identical or different from each other. R 937 If multiple R 937 They are either identical or different to one another.

[0208] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H10).

[0209] [ka]

[0210] (In the above general formula (H10), CN is a cyano group, L HThis 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 each other. Multiple D 11 They are either identical or different from each other. Multiple D 12 They are either identical or different to one another.

[0211] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H100).

[0212] [ka]

[0213] (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.

[0214] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H101).

[0215] [ka]

[0216] (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.

[0217] In this embodiment, the delayed-fluorescence compound is preferably a compound represented by the following general formula (H110), (H120), or (H130).

[0218] [ka]

[0219] (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.

[0220] 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).

[0221] [ka]

[0222] [ka]

[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] (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) isA It is synonymous with, In the general formulas (22A), (22B), (22C), (22D), (22E), and (22F) above, * indicates the bond position.

[0228] 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).

[0229] 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.

[0230] In the delayed fluorescence compound of this embodiment, X A However, C(R 291 )(R 292 ) If R 291 and R 292 Each 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.

[0231] 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 238It is also preferable that any set of two or more adjacent elements does not combine with each other.

[0232] 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.

[0233] 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.

[0234] 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.

[0235] 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.

[0236] 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.

[0237] 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 , 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.

[0238] In the delayed-fluorescence compound according to this embodiment, the substituent in the phrase "substituted or unsubstituted" is: Unsubstituted alkyl groups with 1 to 25 carbon atoms, Unsubstituted alkenyl groups with 2 to 25 carbon atoms, Unsubstituted alkynyl groups with 2 to 25 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 25 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 ) Unsubstituted aralkyl groups with 7 to 50 carbon atoms, -C(=O)R 908 A base represented by -COOR 909 A base represented by -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 ) -S(=O)2R 938 A base represented by halogen atom, Cyano group, Nitro group, Unsubstituted ring-forming aryl groups with 6 to 25 carbon atoms, or It is an unsubstituted heterocyclic group with 5 to 25 ring-forming atoms. R 901 ~R 909 , and R 931 ~R 938 Each of them operates independently. hydrogen atom, Unsubstituted alkyl groups with 1 to 25 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 25 carbon atoms, or It is preferable that the group is an unsubstituted heterocyclic group with 5 to 25 ring-forming atoms.

[0239] In the delayed-fluorescence compound according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably a halogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.

[0240] In the delayed-fluorescence compound according to this embodiment, the substituent in the case of "substituted or unsubstituted" is preferably an unsubstituted C1-C10 alkyl group, an unsubstituted ring-forming C6-C12 aryl group, or an unsubstituted ring-forming C5-C12 heterocyclic group.

[0241] In the delayed-fluorescence compound according to this embodiment, it is also preferable that all groups described as "substituted or unsubstituted" are "unsubstituted" groups.

[0242] In this specification, -O-(R 904 The group represented by ) is R 904 If it is a hydrogen atom, it is a hydroxyl group. In this specification, -S-(R 905 The group represented by ) is R 905 If it is a hydrogen atom, it is a thiol group. In this specification, -P(=O)(R 931 )(R 932 The group represented by ) is R 931 and R 932 If it is a substituent, it is a substituted phosphine oxide group. 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.

[0243] (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.

[0244] Generally, delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

[0245] 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.

[0246] 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.

[0247] 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.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] [ka]

[0252] 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.

[0253] Figure 3 shows the decay curves obtained from transient PL measurements for thin film sample A and thin film sample B.

[0254] [ka]

[0255] 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.

[0256] Specifically, there are two types of emission from delayed-fluorescence materials: prompt emission and delayed emission. Prompt emission is the 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 This refers to light emission that is not immediately observed after excitation by the pulsed light, but is observed later.

[0257] 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.

[0258] 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.

[0259] 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.

[0260] (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.

[0261] In this embodiment, the lowest excitation singlet energy S1(GT2) of the delayed-fluorescence compound and the energy gap T at 77[K] of the delayed-fluorescence compound are used. 77K The difference ΔST(GT2) from (GT2) 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 most preferably less than 0.05eV. That is, ΔST(GT2) preferably satisfies the following formulas (Equation 2), (Equation 2A), (Equation 2B), (Equation 2C), or (Equation 2D). ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.5 eV …(Math 2) ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.3eV …(Math 2A) ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.2eV …(Math 2B) ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.1eV …(Math 2C) ΔST(GT2)=S1(GT2)-T 77K (GT2) < 0.05 eV …(Math 2D)

[0262] (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. For this sample, the phosphorescence spectrum is measured at a low temperature (77 K) (vertical axis: phosphorescence intensity, horizontal axis: wavelength). The wavelength is measured, a tangent is drawn to the rising edge of the phosphorescence spectrum on the short wavelength side, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent and the horizontal axis. Here, it is preferable that the thermally activated delayed fluorescence compound is 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 and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes emission from both the excited singlet and excited triplet states, and it is difficult to distinguish which state emitted the light, but the triplet energy value is basically 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 77K This 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

[0263] 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.

[0264] (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).

[0265] 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.

[0266] (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.

[0267] (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.

[0268] [ka]

[0269] [ka]

[0270] [ka]

[0271] [ka]

[0272] [ka]

[0273]

change

[0274]

change

[0275]

change

[0276]

change

[0277]

change

[0278]

change

[0279]

change

[0280]

change

[0281]

change

[0282]

change

[0283]

change

[0284]

change

[0285]

change

[0286]

change

[0287]

change

[0288]

change

[0289]

change

[0290]

change

[0291]

change

[0292]

change

[0293]

change

[0294] [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.

[0295] In this embodiment, the fluorescent material is one or more compounds selected from the group consisting of a third compound represented by the following general formula (41).

[0296] [ka]

[0297] (In the above general formula (41), Rings a, b, and c are each independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. L 401 and L 402 These are O, S, Se, and NR, respectively, independently. 40 , C(R 41 )(R 42 ), or Si(R 43 )(R 44 ) and L 403 is B, P, or P=O, R 40 ~R 44 Each of them operates independently. It combines with the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted monoring, It bonds with the a, b, or c ring to form a substituted or unsubstituted fused ring, or The a ring and b ring and c ring do not bond, R 41 and R 42 teeth, 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 43 and R 44 teeth, 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 40 ~R 44 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R 45 teeth, Substituted or unsubstituted ring-forming aryl groups with 6 to 60 carbon atoms, A heterocyclic group with 5 to 60 substituted or unsubstituted ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, R 40 If multiple R 40 They are either identical or different from each other. R 41 If multiple R 41 They are either identical or different from each other. R 42 If multiple R42 They are either identical or different from each other. R 43 If multiple R 43 They are either identical or different from each other. R 44 If multiple R 44 They are either identical or different from each other. R 45 If multiple R 45 They are either identical or different to one another.

[0298] In this embodiment, the compound represented by the general formula (41) is preferably the compound represented by the following general formula (410).

[0299] [ka]

[0300] (In the above general formula (410), Rings a, b, and c are each independent of the others. A substituted or unsubstituted ring-forming aromatic hydrocarbon ring with 6 to 50 carbon atoms, or These are heterocycles with 5 to 50 ring-forming atoms, either substituted or unsubstituted. R 401 and R 402 Each of them operates independently. It combines with the aforementioned ring a, ring b, or ring c to form a substituted or unsubstituted monoring, It bonds with the a, b, or c ring to form a substituted or unsubstituted fused ring, or The a ring and b ring and c ring do not bond, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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.

[0301] In this embodiment, the compound represented by general formula (41) is preferably a compound selected from the group consisting of compounds represented by the following general formulas (41-1) to (41-6).

[0302] [ka]

[0303] [ka]

[0304] [ka]

[0305] (In the above general formula (41-1), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 And, R 401 and R 421 The pair, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The pair, R 402 and R 424 The pair, R 424 ~R 427 A set of two or more adjacent elements, R 427 and R 412 The pair with, and R 412 and R 411One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , and R 421 ~R 427 Each of these independently comprises a hydrogen atom or a substituent R. X And, The substituent R X Each of them operates independently. 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, -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 ) 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. 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 multiple R 901 They are either identical or different from each other, R 902 If multiple R 902 They are either identical or different from each other, R 903 If multiple R 903 They are either identical or different from each other, R 904 If multiple R 904 , either identical or different from each other, R 905 If multiple R 905 They are either identical or different from each other, R 906 If multiple R 906 They are either identical or different from each other, R 907 If multiple R 907 They are either identical or different to one another. (In the above general formula (41-2), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 And, R 401 and R 421 The pair, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The pair, R 402 and R 424 The pair, R 424 ~R 427 A set of two or more adjacent elements, R 413 and R 414 The pair with, and R 414 and R 401 One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 413 , R 414 , and R 421 ~R 427 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above.X (This is synonymous with...) (In the above general formula (41-3), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 And, R 401 and R 421 The pair, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The pair, R 415 and R 416 The pair, R 416 and R 412 The pair with, and R 412 and R 411 One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , R 415 , R416 , and R 421 ~R 423 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X It is synonymous with, R 403 If multiple R 403 They are either identical or different from each other. R 404 If multiple R 404 They are either identical or different from each other. R 405 If multiple R 405 They are either identical or different to one another. (In the above general formula (41-4), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 And, R 401 and R 421 The pair, R 421 ~R 423 A set consisting of two or more adjacent items, R 423 and R 402 The pair, R 402 and R 418 The pair, R 418 and R 417 The pair with, and R 412 and R 411 One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 411 , R 412 , R 417 , R 418 , and R 421 ~R 423 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X It is synonymous with, R 403 If multiple R 403 They are either identical or different from each other. R 404 If multiple R 404 They are either identical or different from each other. R 405 If multiple R 405 They are either identical or different to one another. (In the above general formula (41-5), Xa and Xb are independently O, S, Se, C(R) 403 )(R 404 ), or NR 405 And, R 401 and R 421 The pair, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The pair, R 402 and R 418The pair, R 418 and R 417 The pair, R 413 and R 414 The pair with, and R 414 and R 401 One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl group, 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 403 ~R 405 , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 413 , R 414 , R 417 , R 418 , and R 421 ~R 423 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X It is synonymous with, R 403 If multiple R 403 They are either identical or different from each other. R 404 If multiple R404 They are either identical or different from each other. R 405 If multiple R 405 They are either identical or different to one another. (In the above general formula (41-6), R 401 and R 421 The pair, R 421 ~R 423 A set of two or more adjacent elements, R 423 and R 402 The pair, R 402 and R 424 The pair, R 424 ~R 427 A set of two or more adjacent elements, R 427 and R 428 The pair, R 428 ~R 431 A set consisting of two or more adjacent items, and R 431 and R 401 One or more pairs are selected from the group consisting of the following pairs: 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 401 and R 402 Each of them operates independently. 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, -CR 45 =N represents the iminyl 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. R, which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring 421 ~R 431 are each independently a hydrogen atom or a substituent R X where the substituent R X is synonymous with the substituent R X in the general formula (41-1).)

[0306] In the compounds represented by the general formulas (41-1) to (41-5), it is also preferable that at least one set selected from the group consisting of the pair of R 412 and R 411 , the pair of R 413 and R 414 , the pair of R 415 and R 416 , and the pair of R 417 and R 418 are bonded to each other to form a substituted or unsubstituted monocyclic ring or are bonded to each other to form a substituted or unsubstituted condensed ring.

[0307] In the present embodiment, it is also preferable that the compound represented by the general formula (41) is a compound represented by the following general formula (41-7).

[0308]

Chemical formula

[0309] (In the general formula (41-7), Xa is O, S, Se, C(R 403 )(R 404 ), or NR 405 , the pair of R 401 and R 421 , the set consisting of two or more adjacent ones among R 421 ~R 423 , the pair of R 423 and R 402 , the pair of R 402 and R 424 , the set consisting of two or more adjacent ones among R 424 ~R 427 , and R 437~R 440 One or more groups selected from a group consisting of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, or bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted condensed ring, R 401 and R 402 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, 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, R 403 ~R 405 and R 421 ~R 427 and R 437 ~R 440 are each independently a hydrogen atom or a substituent R X , and the substituent R X is synonymous with the substituent R X in the general formula (41-1).)

[0310] In this embodiment, R 401 and R 402 are each independently preferably 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, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, and even more preferably a group represented by the following general formula (42).

[0311] [ka]

[0312] (In the above general formula (42), R 432 ~R 436 Of these, one or more pairs consisting of two or more adjacent items, 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 432 ~R 436 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X It is synonymous with, Multiple R 432 If multiple R 432 They are either identical or different from one another. Multiple R 433 If multiple R 433 They are either identical or different from one another. Multiple R 434 If multiple R 434 They are either identical or different from one another. Multiple R 435 If multiple R 435 They are either identical or different from one another. Multiple R 436 If multiple R 436 They are either identical or different from one another. * indicates the bond location.

[0313] In this embodiment, the compound represented by general formula (41) is also preferably the compound represented by the following general formula (42-1).

[0314] [ka] (In the above general formula (42-1), R 421 ~R 431 These are, respectively, R in the general formula (41-6) above. 421 ~R 431 It is synonymous with, R 451 ~R 455 Of these, one or more pairs consisting of two or more adjacent items, 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 456 ~R 460 Of these, one or more pairs consisting of two or more adjacent items, 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 451 ~R 455 and R 456 ~R 460 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X (This is synonymous with...)

[0315] In this embodiment, the compound represented by the general formula (41) is also preferably the compound represented by the following general formula (42-2).

[0316] [ka]

[0317] (In the above general formula (42-2), R 422 , R 426 , R 429 , R 453、and R 458 is, independently of each other, a hydrogen atom or a substituent R X where the substituent R X is synonymous with the substituent R in the general formula (41-1).)

[0318] In the present embodiment, it is also preferable that the compound represented by the general formula (41) is a compound represented by the following general formula (42-3).

[0319]

Chemical formula

[0320] (In the general formula (42-3), R 421 ~R 427 、R 437 ~R 440 and Xa are, respectively, synonymous with R 421 ~R 427 、R 437 ~R 440 、and Xa in the general formula (41-7), and R 451 ~R 455 one or more sets of two or more adjacent ones among them are bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or not bonded to each other, R 456 ~R 460 [[ID=​​​​​​​​​​​​​​​​​Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X (This is synonymous with...)

[0321] In this embodiment, the compound represented by the general formula (41) is also preferably the compound represented by the following general formula (42-4).

[0322] [ka]

[0323] (In the above general formula (42-4), Xa is the same as Xa in the above general formula (41-6), R 422 , R 426 , R 429 , R 439 , R 453 , and R 458 Each of these independently comprises a hydrogen atom or a substituent R. X and substituent R X This refers to the substituent R in the general formula (41-1) mentioned above. X (This is synonymous with...)

[0324] In this embodiment, R in the third compound 422 , R 426 , R 429 , R 439 , R 453 , and R 458 Each of these is preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and even more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

[0325] In this embodiment, it is preferable that Xa and Xb in the third compound are independently O or S.

[0326] (Method for producing compounds represented by general formula (41)) The compound represented by the general formula (41) can be produced by known methods. Furthermore, the compound represented by the general formula (41) can also be produced by following known methods and using known alternative reactions and raw materials tailored to the target product.

[0327] (Specific examples of compounds represented by general formula (41)) Examples of compounds represented by the general formula (41) include the following compounds. In the examples below, Me represents a methyl group, tBu represents a tert-butyl group, and Ph represents a phenyl group.

[0328] [ka]

[0329] [ka]

[0330] [ka]

[0331] [ka]

[0332] [ka]

[0333] [ka]

[0334] [ka]

[0335] [ka]

[0336]

change

[0337]

change

[0338]

change

[0339]

change

[0340]

change

[0341]

change

[0342]

change

[0343]

change

[0344]

change

[0345]

change

[0346]

change

[0347]

change

[0348]

change

[0349]

change

[0350]

change

[0351]

change

[0352]

change

[0353]

change

[0354]

change

[0355]

change

[0356]

change

[0357]

change

[0358]

change

[0359]

change

[0360]

change

[0361]

change

[0362]

change

[0363]

change

[0364]

change

[0365]

change

[0366]

change

[0367]

change

[0368]

change

[0369]

change

[0370]

change

[0371]

change

[0372]

change

[0373]

change

[0374]

change

[0375]

change

[0376]

change

[0377]

change

[0378]

change

[0379]

change

[0380]

change

[0381]

change

[0382]

change

[0383]

change

[0384]

change

[0385]

change

[0386]

change

[0387]

change

[0388]

change

[0389] [ka]

[0390] [ka]

[0391] In one embodiment, the substituents in the case of "substituted or unsubstituted" in each of the above general formulas are an unsubstituted C1-C50 alkyl group, an unsubstituted C2-C50 alkenyl group, an unsubstituted C2-C50 alkynyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, and -Si(R 901a )(R 902a )(R 903a ), -O-(R 904a ), -S-(R 905a ), -N(R 906a )(R 907a ), halogen atoms, cyano groups, nitro groups, unsubstituted aryl groups with 6 to 50 ring-forming carbon atoms, or unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms, R 901a ~R 907a Each of these is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. R 901a If there are 2 or more of them, then there are 2 or more R 901a They are either identical to each other or different, R 902a If there are 2 or more of them, then there are 2 or more R 902a They are either identical to each other or different, R 903a If there are 2 or more of them, then there are 2 or more R 903a They are either identical to each other or different, R 904a If there are 2 or more of them, then there are 2 or more R 904a They are either identical to each other or different, R 905a If there are 2 or more of them, then there are 2 or more R 905a They are either identical to each other or different, R906a If there are 2 or more of them, then there are 2 or more R 906a They are either identical to each other or different, R 907a If there are 2 or more of them, then there are 2 or more R 907a They are either identical or different from one another.

[0392] In one embodiment, the substituents in the "substituted or unsubstituted" cases of each general formula are unsubstituted C1-C50 alkyl groups, unsubstituted ring-forming C6-C50 aryl groups, or unsubstituted ring-forming C5-C50 heterocyclic groups.

[0393] In one embodiment, the substituents in the "substituted or unsubstituted" cases of each general formula are unsubstituted C1-C18 alkyl groups, unsubstituted ring-forming C6-C18 aryl groups, or unsubstituted ring-forming C5-C18 heterocyclic groups.

[0394] (Maximum peak wavelength) In this embodiment, the maximum peak wavelength of the third compound as a fluorescent material is preferably 480 nm or less, and more preferably 475 nm or less. In this embodiment, the maximum peak wavelength of the third compound 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 this embodiment, the first compound 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.

[0395] (Emission spectrum half-width) In this embodiment, the emission spectral width at half maximum (FWHM) of the third compound as a fluorescent material is preferably 40 nm or less, and more preferably 30 nm or less. In this embodiment, the emission spectral width at half maximum (FWHM) of the third compound as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. FWHM is an abbreviation for full width at half maximum.

[0396] In this specification, the maximum fluorescence emission peak wavelength is defined as the wavelength at which the compound being measured is 10 -6 moles / liter or more, 10 -5 For a toluene solution dissolved at a concentration of mol / liter or less, the fluorescence spectrum measured is defined as the wavelength at which the emission intensity is maximized. The emission spectrum half-width (FWHM) is the full width at half-width at the peak of the fluorescence spectrum. A fluorescence spectrum analyzer can be used to measure the fluorescence spectrum. For example, a fluorescence spectrum analyzer manufactured by JASCO Corporation (model name: FP-8300) can be used. However, the fluorescence spectrum analyzer is not limited to the example given here.

[0397] (Stokes shift) In this embodiment, the Stokes shift of the third compound 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 as a fluorescent material is preferably 5 nm or more, and more preferably 10 nm or more. The third compound has a Stokes shift of 20 nm or less, which allows for a reduction in excitation energy. The third compound's Stokes shift is greater than 10 nm, 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. -5Prepare 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 -6 Prepare 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.

[0398] (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 necessarily contain the phosphorescent metal complex.

[0399] Figure 4 shows an example of the relationship between the energy levels of the host material (first compound), the delayed-fluorescence compound (second compound) as a sensitizer, and the fluorescent material (third compound) in the light-emitting layer. In Figure 4, 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 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%.

[0400] In one embodiment, the energy gap T of the host material at 77[K] 77K (H1) and the energy gap T at 77[K] in the sensitizing material. 77K It is preferable that (G2) and the following equation (Equation 1) satisfy the relationship. T 77K (H1)>T 77K (G2) …(Number 1)

[0401] In one embodiment, it is also preferable that the lowest excited singlet energy S1(GT2) of the delayed-fluorescence compound and the lowest excited singlet energy S1(D) of the fluorescence-emitting material satisfy the relationship shown in the following formula (Equation 4). S1(GT2)>S1(D) …(Math 4)

[0402] In one embodiment, it is also preferable that the lowest excited singlet energy S1(H1) of the host material and the lowest excited singlet energy S1(GT2) of the delayed fluorescence compound satisfy the relationship shown in the following formula (Equation 4A). S1(H1)>S1(GT2) …(Math 4A)

[0403] In one embodiment, it is also preferable that the lowest excitation singlet energy S1 of the host material, the delayed fluorescence compound, and the fluorescence-emitting material satisfy the following relationship (Equation 4B). S1(H1)>S1(GT2)>S1(D)…(Number 4B)

[0404] In this embodiment, when the sensitizing material is a delayed-fluorescence compound, the above formula (Equation 1) is expressed by the following formula (Equation 6). T 77K (H1)>T 77K (GT2) …(Math 6)

[0405] In one embodiment, the energy gap T of a delayed-fluorescence compound at 77[K] 77K (GT2) and the energy gap T at 77[K] of the fluorescent material 77K It is also preferable that (D) and satisfy the following equation (Equation 6A). T 77K (GT2)>T 77K (D) …(Math 6A)

[0406] In one embodiment, the energy gap T at 77[K] of the host material, the delayed fluorescence compound, and the fluorescent material is 77K It is also preferable that the following equation (Mathematics 6B) satisfies the relationship. T 77K (H1)>T 77K (GT2)>T77K (D) …(Number 6B)

[0407] When the organic EL element of this embodiment is made to emit light, it is preferable that the light-emitting layer mainly emits light from a fluorescent compound.

[0408] The maximum peak wavelength of light emitted from an organic EL element is measured as follows. Current density is 10 mA / cm² 2 The 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. In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is measured and defined as the maximum peak wavelength (unit: nm).

[0409] (Compound content in the luminescent layer) The content of the host material (first compound), sensitizing material (second compound), and fluorescent material (third compound) contained in the light-emitting layer is preferably within the following ranges, for example.

[0410] The content of the host material (first compound) 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 (first compound) in the light-emitting layer is preferably 95% by mass or less, and more preferably 90% by mass or less.

[0411] When the sensitizing material (second compound) is a delayed-fluorescence compound, the content of the delayed-fluorescence compound in the light-emitting layer is preferably 5% by mass or more, and more preferably 10% by mass or more. The content of the delayed fluorescence compound in the luminescent layer is preferably 50% by mass or less, and more preferably 30% by mass or less.

[0412] The content of the fluorescent material (third compound) 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 (third compound) 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 (first compound), sensitizing material (second compound), and fluorescent material (third compound) 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.

[0413] (film thickness of the light-emitting layer) The film thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If it is 5 nm or more, it is easier to form the light-emitting layer and adjust the chromaticity, and if it is 50 nm or less, it is easier to suppress the rise in the driving voltage.

[0414] Let's further explain the configuration of the organic EL element.

[0415] (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.

[0416] (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).

[0417] 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.

[0418] 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.

[0419] 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.

[0420] 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.

[0421] 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.

[0422] (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.

[0423] 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.

[0424] 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.

[0425] 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.

[0426] 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.

[0427] 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.

[0428] (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.

[0429] (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.

[0430] (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.

[0431] (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 2 The 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.

[0432] (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.

[0433] (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.

[0434] (film thickness) The film thickness of each organic layer in the organic EL element according to this 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.

[0435] The organic EL element according to this embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0436] According to the third embodiment, high efficiency of organic EL elements can be achieved. The organic EL element according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0437] [Fourth Embodiment] (electronic equipment) The electronic device according to this embodiment is equipped with an organic EL element according to any of the embodiments described above. 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. The light-emitting device can also be used in a display device, for example, as a backlight for a display device.

[0438] The display device as an electronic device according to this 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.

[0439] [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 compound according to the first embodiment as a host material and a phosphorescent metal complex 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 compound according to the first embodiment as a host material, a phosphorescent metal complex as a sensitizing material, and a fluorescent material (third compound) as a dopant material.

[0440] According to other embodiments, high efficiency of organic EL elements can be achieved. Organic EL elements according to other embodiments can be used in electronic devices such as display devices and light-emitting devices.

[0441] [Changes to 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.

[0442] 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.

[0443] 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. An organic EL element according to one embodiment includes an anode, a cathode, a light-emitting layer disposed between the anode and the cathode, and an electron barrier layer between the anode and the light-emitting layer. The electron barrier layer may contain the compound according to the first embodiment (the compound represented by the general formula (1)). It is preferable that the electron barrier layer is in direct contact with the light-emitting layer.

[0444] 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]

[0445] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0446] <Compound> The structures of the compounds represented by general formula (1) used in the manufacture of the organic EL elements in Examples 1 to 4 are shown below.

[0447] [ka]

[0448] The structures of the compounds used in the manufacture of the organic EL elements in Comparative Examples 1 and 2 are shown below.

[0449] [ka]

[0450] The structures of the other compounds used in the manufacture of the organic EL elements in Examples 1-4 and Comparative Examples 1-2 are shown below.

[0451] [ka]

[0452] [ka]

[0453] <Fabrication of Organic EL Devices (1)> Organic EL elements were fabricated and evaluated as follows.

[0454] (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-1 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 set to 97% by mass, and the proportion of compound HA-1 was set to 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 (the first compound) as a host material, compound STZ-1 (the second compound) as a sensitizing material, and compound BD-1 (the third compound) as a fluorescent material were co-deposited onto 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 shown schematically as follows. ITO(130) / HT-1:HA-1(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 (in nm). Similarly, in the above device configuration, the percentages in parentheses (97%:3%) indicate the proportion (mass%) of compound HT-1 and compound HA-1 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. The same notation will be used hereafter.

[0455] (Examples 2-4) The organic EL elements of Examples 2 to 4 were fabricated in the same manner as in Example 1, except that the compound Host-1 used as the host material in the light-emitting layer of Example 1 was replaced with one of the compounds listed in Table 1.

[0456] (Comparative Examples 1-2) The organic EL elements of Comparative Examples 1 and 2 were fabricated in the same manner as in Example 1, except that the compound Host-1 used as the host material in the light-emitting layer of Example 1 was replaced with one of the compounds listed in Table 1.

[0457] <Evaluation of Organic EL Devices> The fabricated organic EL elements were evaluated as follows. The evaluation results are shown in Table 1. In addition, the lowest excited singlet energy S1 and energy gap T of the compounds used in the light-emitting layer of each example were obtained. 77K This is also shown in Table 1.

[0458] (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 was performed. Based on the measured values ​​of EQE for each example, and the following formula (Equation 1X), the "EQE (relative value)" (unit: %) was calculated. EQE (relative value) = (EQE of each example / EQE of comparison example 1) × 100 ... (Equation 1 x)

[0459] [Table 1]

[0460] As shown in Table 1, the organic EL elements of Examples 1 to 4 contained a host material represented by general formula (1), a sensitizing material, and a fluorescent material in the light-emitting layer, and emitted light with higher efficiency compared to the organic EL elements of Comparative Examples 1 and 2.

[0461] <Evaluation of Compounds> The following evaluations were performed on the compound.

[0462] (Lowest excitation singlet energy S1) The lowest excited singlet energy S1 of the target compound was measured using the solution method described above.

[0463] (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.

[0464] (Energy gap T) 77K ) Energy gap T of the compound being measured 77K This refers to the energy gap T described in the aforementioned "Relationship between triplet energy and the energy gap at 77[K]". 77K The measurement was performed using the specified measurement method.

[0465] (Fluorescence emission maximum peak wavelength λ FL (and emission spectrum half-width FWHM) The compound to be measured is dissolved in toluene, and 5.0 × 10⁻⁶ -6 A mol / L solution was prepared. The obtained solution was placed in a quartz cell (optical path length 1.0 cm), and the peak fluorescence wavelength λ when excited at 400 nm was measured using a fluorescence spectrum analyzer, "Spectrofluorometer FP-8300" (manufactured by JASCO Corporation). FL The emission spectrum (in nm) and half-width at half maximum (FWHM) (in nm) were measured.

[0466] (Stokes shift) The compound to be measured is 2.0 × 10 -5The sample for measurement was prepared by dissolving the compound in toluene at a concentration of mol / L. The sample was placed in a quartz cell and irradiated with continuous ultraviolet-visible light at room temperature (300K), and the absorption spectrum (vertical axis: absorbance, horizontal axis: wavelength) was measured. A Hitachi High-Tech Science U-3900 / 3900H spectrophotometer was used for the absorption spectrum measurement. The compound to be measured was measured in 4.9 × 10⁻⁶ units. -6 Samples for measurement were prepared by dissolving the substance in toluene at a concentration of mol / L. The sample was placed in a quartz cell and irradiated with excitation light at room temperature (300K), and the fluorescence spectrum (vertical axis: fluorescence intensity, horizontal axis: wavelength) was measured. A Hitachi High-Tech Science F-7000 spectrofluorometer was used for fluorescence spectrum measurement. From these absorption and fluorescence spectra, the difference between the absorption maximum wavelength and the fluorescence maximum wavelength was calculated to determine the Stokes shift (SS). The unit of the Stokes shift SS was nm.

[0467] The maximum peak wavelength λ of compound BD-1 FL The wavelength was 455 nm, the emission spectrum half-width (FWHM) was 23 nm, and the Stokes shift was 14 nm.

[0468] <Example of synthesis> (1) Synthesis of compound Host-1

[0469] [ka]

[0470] (1-1) Synthesis of Compounds 1-3 Under an argon atmosphere, compound 1-1 (5.00 g, 20.3 mmol), compound 1-2 (4.02 g, 20.3 mmol), tetrakistriphenylphosphine palladium (1.17 g, 1.02 mmol), 2M aqueous sodium carbonate solution (30 mL), and 1,2-dimethoxyethane (150 mL) were added, and the mixture was heated and stirred at 80°C for 20 hours. After the reaction was complete, water and toluene 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 (4.86 g, yield 75%). The obtained solid was the target compound 1-3, and mass spectral analysis showed a molecular weight of 319 and a m / e ratio of 319.

[0471] (1-2) Synthesis of compound Host-1 Under an argon atmosphere, compounds 1-3 (4.00 g, 12.5 mmol), 1-4 (4.03 g, 12.5 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.343 g, 0.375 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.435 g, 1.50 mmol), sodium-tert-butoxide (3.60 g, 37.5 mmol), and toluene (130 mL) were added and the mixture was heated and stirred at 110 °C for 5 hours. After the reaction was complete, the reaction product was filtered to obtain the crude product. The crude product was purified by column chromatography to obtain a white solid (5.12 g, yield 73%). The obtained solid was the target compound Host-1, and mass spectral analysis showed a molecular weight of 560 and a m / e ratio of 560.

[0472] (2) Synthesis of compound Host-2

[0473] [ka]

[0474] (2-1) Synthesis of Compounds 2-3 Under an argon atmosphere, compound 2-1 (3.50 g, 14.2 mmol), compound 2-2 (2.89 g, 14.2 mmol), tetrakistriphenylphosphine palladium (0.820 g, 0.710 mmol), 2M aqueous sodium carbonate solution (20 mL), and 1,2-dimethoxyethane (100 mL) were added, and the mixture was heated and stirred at 80°C for 22 hours. After the reaction was complete, water and toluene 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 (3.18 g, yield 69%). The obtained solid was the target compound 2-3, and mass spectral analysis showed a molecular weight of 324 and a m / e ratio of 324.

[0475] (2-2) Synthesis of compound Host-2 Under an argon atmosphere, compounds 2-3 (3.00 g, 9.25 mmol), compounds 1-4 (2.98 g, 9.25 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.254 g, 0.278 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.323 g, 1.11 mmol), sodium-tert-butoxide (2.67 g, 27.8 mmol), and toluene (100 mL) were added and the mixture was heated and stirred at 110 °C for 7 hours. After the reaction was complete, the reaction product was filtered to obtain the crude product. The obtained crude product was purified by column chromatography to obtain a white solid (4.08 g, yield 78%). The obtained solid was the target compound Host-2, and mass spectral analysis showed a molecular weight of 565 and a m / e ratio of 565.

[0476] (3) Synthesis of compound Host-3

[0477] [ka]

[0478] (3-1) Synthesis of compound 3-2 Under an argon atmosphere, compound 3-1 (4.00 g, 16.3 mmol), compound 1-2 (3.22 g, 16.3 mmol), tetrakistriphenylphosphine palladium (0.942 g, 0.815 mmol), 2M aqueous sodium carbonate solution (25 mL), and 1,2-dimethoxyethane (125 mL) were added, and the mixture was heated and stirred at 80°C for 24 hours. After the reaction was complete, water and toluene 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 (3.28 g, yield 63%). The obtained solid was the target compound 3-2, and mass spectral analysis showed a molecular weight of 319 and a m / e ratio of 319.

[0479] (3-2) Synthesis of compound Host-3 Under an argon atmosphere, compound 3-2 (3.00 g, 9.39 mmol), compound 3-3 (3.87 g, 9.39 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.258 g, 0.282 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.327 g, 1.13 mmol), sodium-tert-butoxide (2.71 g, 28.2 mmol), and toluene (100 mL) were added, and the mixture was heated and stirred at 110 °C for 8 hours. After the reaction was complete, the reaction product was filtered to obtain the crude product. The obtained crude product was purified by column chromatography to obtain a white solid (4.39 g, yield 72%). The obtained solid was the target compound Host-3, and mass spectral analysis showed a molecular weight of 650 and a m / e ratio of 650.

[0480] (4) Synthesis of compound Host-4

[0481] [ka]

[0482] (4-1) Synthesis of compound 4-1 Under an argon atmosphere, compound 2-1 (4.00 g, 16.3 mmol), compound 1-2 (3.22 g, 16.3 mmol), tetrakistriphenylphosphine palladium (0.942 g, 0.815 mmol), 2M aqueous sodium carbonate solution (25 mL), and 1,2-dimethoxyethane (125 mL) were added, and the mixture was heated and stirred at 80°C for 20 hours. After the reaction was complete, water and toluene 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 (3.79 g, yield 73%). The obtained solid was the target compound 4-1, and mass spectral analysis showed a molecular weight of 319 and a m / e ratio of 319.

[0483] (4-2) Synthesis of compound Host-4

[0484] Under an argon atmosphere, compound 4-1 (3.00 g, 9.39 mmol), compound 4-2 (3.07 g, 9.39 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.258 g, 0.282 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.327 g, 1.13 mmol), sodium-tert-butoxide (2.67 g, 27.8 mmol), and toluene (100 mL) were added and the mixture was heated and stirred at 110 °C for 7 hours. After the reaction was complete, the reaction product was filtered to obtain the crude product. The obtained crude product was purified by column chromatography to obtain a white solid (4.20 g, yield 79%). The obtained solid was the target compound Host-4, and mass spectral analysis showed a molecular weight of 565 and a m / e ratio of 565. [Explanation of symbols]

[0485] 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 (1). 【Chemistry 1】 【Chemistry 2】 (In the above general formula (1), Ar １ is a group represented by the general formula (11) or (12), R １ ~R ４ A set consisting of two or more adjacent items, and R ６ and R ７ One or more of the groups 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 ８ ~R １１ a set consisting of two or more adjacent ones among them, and １２ ~R １５ one or more sets consisting of two or more adjacent ones among them 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, The compound represented by the general formula (1) satisfies either condition i or condition ii. (Condition i): R １ ~R ４ A set consisting of two or more adjacent elements, R ６ and R ７ Group R ８ ~R １１ A set consisting of two or more adjacent items, and R １２ ~R １５ When one or more pairs of adjacent rings combine with each other, the substituted or unsubstituted monorings and the substituted or unsubstituted fused rings formed are, independently of each other, The ring is represented by the general formula (14) above, or A substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, R ５ , and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring １ ~R ４ and R ６ ~R １５ Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, In the above general formula (14), Y １ is an oxygen atom or a sulfur atom, R １６ ~R １９ Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R ４１ ) (Caution ４２ ) (Caution ４３ A base represented by ) or -Ge(R) ４４ ) (Caution ４５ ) (Caution ４６ It is a base represented by ), The two asterisks indicate the bonding positions with the carbazole ring in the general formula (1) above. However, R １ ~R １９ Of these, at least one is a group represented by the general formula (13), and if there are multiple groups represented by the general formula (13), the multiple groups represented by the general formula (13) are either identical or different from each other, and if there are multiple rings represented by the general formula (14), the multiple rings represented by the general formula (14) are either identical or different from each other. (Condition ii): R １ ~R ４ A set consisting of two or more adjacent elements, R ６ and R ７ Group R ８ ~R １１ A set consisting of two or more adjacent items, and R １２ ~R １５ If any of the pairs of adjacent elements do not combine with each other, R １ ~R １５ Each of them operates independently. hydrogen atom, The group represented by the general formula (13) above, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 20 carbon atoms, However, R １ ~R １５ Of these, at least one is a group represented by the general formula (13), and if there are multiple groups represented by the general formula (13), the multiple groups represented by the general formula (13) are either identical or different from each other. (In the above general formulas (11) and (12), R ２１ ~R ２５ Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, or They do not bind to each other, R ２６ ~R ２９ Of these, one or more pairs consisting of two or more adjacent items, They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, or They do not bind to each other, Multiple R ３０ Of the sets of two or more adjacent items, one or more sets are They bond to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms, or They do not bind to each other, R that does not form a ring-forming aliphatic hydrocarbon ring with 3 to 20 carbon atoms, whether substituted or unsubstituted. ２１ ~R ３０ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R ４１ ) (Caution ４２ ) (Caution ４３ A base represented by ) or -Ge(R) ４４ ) (Caution ４５ ) (Caution ４６ It is a base represented by ), Multiple R ３０ They are either identical to each other or different to each other. X １ is an oxygen atom, a sulfur atom, C(R) ５１ ) (Caution ５２ ), or Si (R ５３ ) (Caution ５４ ) and R ５１ and R ５２ 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 bind to each other, R ５３ and R ５４ 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 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 ５１ ~R ５４ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 60 carbon atoms, or These are heterocyclic groups with 5 to 60 substituted or unsubstituted ring-forming atoms. In the general formula (11), * is the same as Ar in the general formula (1). １ This is the bonding position with the nitrogen atom to which it is bonded. * in the above general formula (12) is equivalent to Ar in the above general formula (1). １ (This indicates the bonding position with the nitrogen atom to which it is bonded.) (In the above general formula (13), R ３１ ~R ３９ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 20 carbon atoms, -Si(R ４１ ) (Caution ４２ ) (Caution ４３ A base represented by ) or -Ge(R) ４４ ) (Caution ４５ ) (Caution ４６ It is a base represented by ), * indicates the bonding position. (In the compound represented by the general formula (1) above, R ４１ ~R ４３ One of the pairs of adjacent items is 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 ４４ ~R ４６ One of the pairs of adjacent items is 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 ４１ ~R ４６ Each of them operates independently. Substituted or unsubstituted ring-forming aryl groups with 6 to 60 carbon atoms, A heterocyclic group with 5 to 60 substituted or unsubstituted ring-forming atoms, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, (These are substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms forming a ring.)

2. The compound represented by the general formula (1) is the compound represented by the general formula (10) below. The compound according to claim 1. 【Transformation 3】 (In the above general formula (10), R １ ~R １５ each independently has the same meaning as R in the general formula (1), １ ~R １５ and is synonymous with, R ２１ ~R ２５ Each of these independently corresponds to R in the general formula (11) ２１ ~R ２５ (This is synonymous with...)

3. R １ to R ４ a set consisting of two or more adjacent ones among them, R ６ and R ７ a set of R ８ to R １１ a set consisting of two or more adjacent ones among them, and R １２ to R １５ a set consisting of two or more adjacent ones among them are all not connected to each other The compound according to claim 1 or claim 2.

4. R １ ~R １５ One of these is the group represented by the general formula (13), The compound according to claim 3.

5. R １ ~R ４ A set consisting of two or more adjacent elements, R ６ and R ７ Group R ８ ~R １１ A set consisting of two or more adjacent items, and R １２ ~R １５ One or more pairs of adjacent elements combine to form a substituted or unsubstituted monoring, or combine to form a substituted or unsubstituted fused ring. The compound according to claim 1 or claim 2.

6. R １ ~R １９ One of these is the group represented by the general formula (13), The compound according to claim 5.

7. The compound represented by the general formula (1) is a compound represented by the following general formulas (1A), (1B), (1C), or (1D): The compound according to claim 5 or claim 6. 【Chemistry 4】 (In the above general formulas (1A), (1B), (1C), and (1D), Ar １ This is Ar in the general formula (1) mentioned above. １ It is synonymous with, R １ ~R １５ Each of these independently corresponds to R in the general formula (1) above. １ ~R １５ It is synonymous with, Y １ and R １６ ~R １９ Each of these independently corresponds to Y in the general formula (14) １ and R １６ ~R １９ (This is synonymous with...)

8. R １０ , R １１ , R １６ or R １８ The group is represented by the general formula (13) above. The compound according to claim 7.

9. R １０ or R １１ The group is represented by the general formula (13) above. The compound according to any one of claims 1 to 8.

10. R ３１ ~R ３９ Each of them operates independently. hydrogen atom, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, The compound according to any one of claims 1 to 9.

11. A compound containing the compound described in any one of claims 1 to 10, Materials for organic electroluminescent devices.

12. Anode and, Cathode and, It includes a light-emitting layer disposed between the anode and the cathode, The light-emitting layer contains a host material, a sensitizing material, and a fluorescent material. The host material is a compound according to any one of claims 1 to 10. The sensitizing material, the host material, and the fluorescent material are all different compounds. Organic electroluminescent element.

13. The sensitizing material is a delayed-fluorescence compound. The organic electroluminescent element according to claim 12.

14. The sensitizing material, the host material, and the fluorescent material are contained in a single layer. The organic electroluminescent element according to claim 12 or claim 13.

15. A hole transport layer is disposed between the anode and the light-emitting layer. An organic electroluminescent element according to any one of claims 12 to 14.

16. An electron barrier layer is disposed between the anode and the light-emitting layer. An organic electroluminescent element according to any one of claims 12 to 15.

17. The electron barrier layer is in direct contact with the light-emitting layer. The organic electroluminescent element according to claim 16.

18. An electron transport layer is disposed between the cathode and the light-emitting layer. An organic electroluminescent element according to any one of claims 12 to 17.

19. An electronic device equipped with an organic electroluminescent element according to any one of claims 12 to 18.

Images