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

Abstract

To provide a compound capable of reducing the driving voltage of an organic electroluminescent element, and to provide a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element. [Solution] For example, a compound synthesized by starting with 4,6-dibromodibenzo[b,d]thiophene and proceeding through multiple intermediates.

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%. Therefore, research is being conducted to improve the performance of OLEDs.

[0003] For example, it is expected that using triplet excitons in addition to singlet excitons will make organic EL devices emit light even more efficiently. Against this backdrop, highly efficient fluorescent organic EL devices utilizing thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being researched. The TADF (Thermally Activated Delayed Fluorescence) mechanism utilizes the phenomenon where reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when using materials with a small energy difference (ΔST) between the singlet and triplet energy levels. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors," edited by Chihaya Adachi, Kodansha, published April 1, 2012, pp. 261-268. Examples of compounds that exhibit thermally activated delayed fluorescence (TADF) (hereinafter also referred to as TADF compounds) include compounds in which a donor site and an acceptor site are bound together within the molecule.

[0004] Patent Document 1 is cited as a document relating to organic EL elements and compounds used in organic EL elements. [Prior Art Document] [Patent Document]

[0005] [Patent Document 1] International Publication No. 2014 / 208698 [Summary of the Invention] [Problem to be Solved by the Invention]

[0006] In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is demanded. Examples of the performance of organic EL elements include luminance, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifetime.

[0007] An object of the present invention is to provide a compound capable of lowering the driving voltage of an organic electroluminescence element, a material for an organic electroluminescence element containing the compound, an organic electroluminescence element containing the compound, and an electronic device mounted with the organic electroluminescence element. [Means for Solving the Problem]

[0008] According to one aspect of the present invention, there is provided a compound represented by the following general formula (1).

[0009] [Chemical Formula]

[0010] (In the general formula (1), CN is a cyano group, D 11 each independently represents a group represented by the following general formulae (10a) and (10b), D12 each independently represents a group represented by the following general formula (11), (12) or (13), each R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl 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, -Si(R 901 )(R 902 )(R 903 ) a group represented by this formula, -O-(R 904 ) a group represented by this formula, -S-(R 905 ) a group represented by this formula, -N(R 906 )(R 907 ) a group represented by this formula, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 a group represented by this formula, -COOR 909 a group represented by this formula, a cyano group, a nitro group, -P(=O)(R 931 )(R 932 ) a group represented by this formula, -Ge(R 933 )(R 934 )(R 935 ) a group represented by this formula, -B(R 936 )(R 937 ) a group represented by this formula, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, provided that at least one R is a substituent, k is 1, 2 or 3, m is 0, 1 or 2, n is 1, 2, or 3. k+m+n is 4, When k is 2 or 3, multiple D 11 They are either identical or different from each other. When m is 2, multiple D 12 They are either identical or different from each other. When n is 2 or 3, multiple Rs are either identical or different from one another.

[0011] [ka]

[0012] (In the above general formula (10a), At positions a1, a2, a3, or a4, the position of b in the general formula (10b) is condensed. * indicates the bond position with the benzene ring in the general formula (1) above. In the above general formula (10b), The position of b is contracted to the positions of a1, a2, a3, or a4 in the general formula (10a), X is an oxygen atom, a sulfur atom, N(R3), or C(R4)(R5), R4 and R5 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, R3, R4 (which does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring), and R5 (which does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring) are each independently: hydrogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 911 )(R 912 )(R 913 ) a base represented by -O-(R 914 ) a base represented by -S-(R 915 A base represented by ) or -N(R 916 )(R 917 It is a base represented by ), The group represented by the general formula (10a) above is a substituent R 10a Having or not having, R 10a If multiple R 10a They are either identical or different from each other. Multiple R 10a 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, The group represented by the general formula (10b) above is a substituent R 10b Having or not having, R 10b If multiple R 10b They are either identical or different from each other. Multiple R 10b 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 10a , and R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 10b 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 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 It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0013] [ka]

[0014] (One or more sets of two or more adjacent R1 to R8 in the general formula (11) above, 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, In the above general formula (12), R 11 ~R 18 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (13), R 111 ~R 118 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R1 to R8 that do not form a substituted or unsubstituted monoring in the general formula (11) and do not form a substituted or unsubstituted fused ring, and R that do not form a substituted or unsubstituted monoring in the general formula (12) and do not form a substituted or unsubstituted fused ring. 11 ~R 18 Furthermore, R that does not form a substituted or unsubstituted monoring in the general formula (13) and does not form a substituted or unsubstituted condensed ring. 111 ~R 118 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 (12) and (13), Rings A, B, and C are each independently ring structures represented by the following general formulas (14) or (15): 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 general formulas (11) to (13) above, * indicates the bond position with the benzene ring in the general formula (1).

[0015] [ka] (In the above general formula (14), r is 0, 2, or 4, when r is 2 or 4, a plurality of R 19 are the same as or different from each other, when r is 2 or 4, a plurality of R 19 form a set which bonds to each other to form a substituted or unsubstituted monocyclic ring, bonds to each other to form a substituted or unsubstituted fused ring, or does not bond to each other, does not form a substituted or unsubstituted monocyclic ring, and does not form a substituted or unsubstituted fused ring; R 19 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl 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 group represented by -Si(R 901 )(R 902 )(R 903 ), a group represented by -O-(R 904 ), a group represented by -S-(R 905 ), a group represented by -N(R 906 )(R 907 ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by -C(=O)R 908 , a group represented by -COOR 909 , a halogen atom, a cyano group, a nitro group, a group represented by -P(=O)(R 931 )(R 932 ), -Ge(R 933 )(R 934 )(R935 a group represented by), -B(R 936 )(R 937 a group represented by), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and in the general formula (15), X1 is a sulfur atom or an oxygen atom, a plurality of R 19 are the same as or different from each other, a plurality of X1 are the same as or different from each other.) (In the general formula, 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 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, R 901 when a plurality of R 901 are the same as or different from each other, R 902 when a plurality of R 902 are the same as or different from each other, R 903 when a plurality of R 903 are the same as or different from each other, R 904 when a plurality of R904 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.

[0016] According to one aspect of the present invention, a material for an organic electroluminescent device is provided, which contains a compound according to one aspect of the present invention.

[0017] According to one aspect of the present invention, an organic electroluminescent element is provided, having an anode, a cathode, and an organic layer contained between the anode and the cathode, wherein the organic layer contains a compound according to one aspect of the present invention as compound M2.

[0018] According to one aspect of the present invention, an electronic device is provided that incorporates an organic electroluminescent element according to one aspect of the present invention. [Effects of the Invention]

[0019] According to one aspect of the present invention, a compound capable of reducing the driving voltage of an organic electroluminescent element, a material for an organic electroluminescent element containing the compound, an organic electroluminescent element containing the compound, and an electronic device equipped with the organic electroluminescent element can be provided. [Brief explanation of the drawing]

[0020] [Figure 1] This is a schematic diagram of a device for measuring transient PL (Power Level). [Figure 2] This figure shows an example of a transient PL decay curve. [Figure 3] This figure shows a schematic configuration of an example of an organic electroluminescent element according to the third embodiment of the present invention. [Figure 4] This figure shows the relationship between the energy levels and energy transfer of compounds M1 and M2 in the light-emitting layer of an example of an organic electroluminescent element according to the third embodiment of the present invention. [Figure 5] This figure shows the energy levels and energy transfer relationships of compounds M1, M2, and M3 in the light-emitting layer of an example of an organic electroluminescent element according to the fourth embodiment of the present invention. [Figure 6] This figure shows the energy levels of compound M2 and compound M3 in the light-emitting layer of an example of an organic electroluminescent element according to the fifth embodiment of the present invention, as well as the relationship between energy transfer. [Modes for carrying out the invention]

[0021] [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] "Substituents as described herein" The substituents described herein will be explained below.

[0029] 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.

[0030] • "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.

[0031] • 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).

[0032] [ka]

[0033] [ka]

[0034] • 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.

[0035] • "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-ring 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.

[0036] 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).

[0037] 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).

[0038] • 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.

[0039] • 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.

[0040] • 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).

[0041] • 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):

[0042] [ka]

[0043] [ka]

[0044] 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.

[0045] • 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.

[0046] • 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].

[0047] • 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].

[0048] • 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):

[0049] 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.

[0050] • "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.

[0051] • 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.

[0052] • Substituting alkyl groups (specific examples group G3B): Heptafluoropropyl group (including isomers), Pentafluoroethyl group, 2,2,2-trifluoroethyl group, and Trifluoromethyl group.

[0053] • "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.

[0054] • Unsubstituted alkenyl groups (specific examples group G4A): vinyl group, allyl group, 1-Butenyl group, 2-butenyl group, and 3-Butenyl group.

[0055] • 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.

[0056] • "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.

[0057] • Unsubstituted alkynyl groups (specific examples group G5A): Ethynyl group

[0058] • "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.

[0059] • 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.

[0060] • Substituting cycloalkyl groups (specific examples group G6B): 4-methylcyclohexyl group.

[0061] · "-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.

[0062] ·「-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.

[0063] · "-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.

[0064] · "-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.

[0065] • "Halogen atom" Specific examples of "halogen atoms" as described herein (Specific Examples Group G11) include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0066] • "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.

[0067] • "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.

[0068] • "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.

[0069] • "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.

[0070] • "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.

[0071] • "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.

[0072] • "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.

[0073] • "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.

[0074] 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.

[0075] 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.

[0076] In this specification, unless otherwise specified, the carbazolyl group is specifically one of the following groups:

[0077] [ka]

[0078] In this specification, unless otherwise specified, the (9-phenyl)carbazolyl group is specifically one of the following groups:

[0079] [ka]

[0080] In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bond position.

[0081] In this specification, unless otherwise specified, the dibenzofuranyl group and the dibenzothiophenyl group specifically refer to any of the following groups:

[0082] [ka]

[0083] In the general formulas (TEMP-34) to (TEMP-41) above, * represents a bond position.

[0084] Unless otherwise specified herein, the substituted or unsubstituted alkyl groups are preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, and t-butyl groups.

[0085] • "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.

[0086] • "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.

[0087] • "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.

[0088] Unless otherwise specified herein, the substituted or unsubstituted arylene groups are preferably any of the following general formulas (TEMP-42) to (TEMP-68).

[0089] [ka]

[0090] [ka]

[0091] 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.

[0092] [ka]

[0093] 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.

[0094] [ka]

[0095] 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.

[0096] 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).

[0097] [ka]

[0098] [ka]

[0099] [ka]

[0100] In the general formulas (TEMP-69) to (TEMP-82) above, Q1 to Q9 are each independently a hydrogen atom or a substituent.

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] In the general formulas (TEMP-83) to (TEMP-102) above, Q1 to Q8 are each independently a hydrogen atom or a substituent.

[0106] The above is a description of the substituents described herein.

[0107] • "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.

[0108] [ka]

[0109] For example, R921 ~R 930 In the case where "one or more pairs of adjacent groups are joined together to form a ring," the pairs of adjacent groups that make up one set are R 921 and R 922 The pair, R 922 and R 923 The pair, R 923 and R 924 The pair, R 924 and R 930 The pair, R 930 and R 925 The pair, R 925 and R 926 The pair, R 926 and R 927 The pair, R 927 and R 928 The pair, R 928 and R 929 The pair with, and R 929 and R 921 They are a pair.

[0110] The phrase "one or more pairs" above means that two or more pairs of adjacent pairs may simultaneously form a ring. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 925 and R 926 and are joined to form a ring Q B If the above general formula (TEMP-103) is formed, the anthracene compound represented by the above general formula (TEMP-104) is represented by the following general formula (TEMP-104).

[0111] [ka]

[0112] The case where "two or more adjacent elements form a ring" includes not only cases where two adjacent elements are joined, as in the example above, but also cases where three or more adjacent elements are joined. For example, R 921 and R 922 and are joined to form a ring Q A Forms R 922 and R923 and are joined to form a ring Q C It forms three adjacent (R 921 , R 922 and R 923 This refers to the case where a set consisting of ) is bonded to each other to form a ring and condenses onto the anthracene matrix skeleton, in which case the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q A and ring Q C R 922 Share.

[0113] [ka]

[0114] 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.

[0115] An "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. A "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocycle. Specific examples of aromatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G1 are terminated by hydrogen atoms. A concrete example of an aromatic heterocycle is the structure in which the aromatic heterocycle group listed as a concrete example in concrete example group G2 is terminated by a hydrogen atom. Specific examples of aliphatic hydrocarbon rings include structures in which the groups listed as examples in specific example group G6 are terminated by hydrogen atoms. "To form a ring" means to form a ring with only multiple atoms of the parent skeleton, or with multiple atoms of the parent skeleton and one or more additional arbitrary elements. For example, as shown in the general formula (TEMP-104), 921 and R 922 A ring Q is formed when these two elements are bonded together. A R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 It refers to a ring formed by the carbon atoms of the anthracene skeleton to which the R atoms are bonded, and one or more arbitrary elements. A specific example is R 921 and R 922 And the environment Q A When forming R 921 The carbon atoms of the anthracene skeleton to which R is bonded, 922 When the carbon atoms of the anthracene skeleton bonded to the four carbon atoms form a monocyclic unsaturated ring, R 921 and R 922 The ring formed by these two is a benzene ring.

[0116] 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.

[0117] 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").

[0118] • Substituents in the phrase "substituted or unsubstituted" In one embodiment described herein, the substituent referred to as "substituted or unsubstituted" (which may be referred to herein as "any substituent") is, for example, Unsubstituted alkyl groups with 1 to 50 carbon atoms, Unsubstituted alkenyl groups with 2 to 50 carbon atoms, Unsubstituted alkynyl groups with 2 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R 901 )(R 902 )(R 903 ), -O-(R 904 ), -S-(R 905 ), -N(R 906 )(R 907 ), halogen atom, cyano group, nitro group, Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, and Unsubstituted heterocyclic groups with 5 to 50 ring-forming atoms It is a base selected from the group consisting of, Here, R 901 ~R 907 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 901 If there are two or more of them, then there are two or more R 901 They are either identical or different from each other. R 902 If there are two or more of them, then there are two or more R 902 They are either identical or different from each other. 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.

[0119] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 50 carbon atoms, A ring-forming aryl group with 6 to 50 carbon atoms, and Heterocyclic groups with 5 to 50 ring-forming atoms It is a group selected from the group consisting of the following.

[0120] In one embodiment, the substituent in the case of "substituted or unsubstituted" is: Alkyl alkyl groups with 1 to 18 carbon atoms, A ring-forming aryl group with 6 to 18 carbon atoms, and Heterocyclic groups with 5 to 18 ring-forming atoms It is a group selected from the group consisting of the following.

[0121] Specific examples of each of the above-mentioned substituents are the specific examples of substituents described in the section "Substituents as described herein" above.

[0122] 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.

[0123] 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.

[0124] [First Embodiment] (compound) The compound according to this embodiment is a compound represented by the following general formula (1).

[0125] [ka]

[0126] (In the above general formula (1), CN is a cyano group, D 11 These are groups that are independently represented by the following general formulas (10a) and (10b), D 12 These are, independently, groups represented by the following general formulas (11), (12), or (13): 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. k is 1, 2, or 3. m is 0, 1, or 2. n is 1, 2, or 3. k+m+n is 4, When k is 2 or 3, multiple D 11 They are either identical or different from each other. When m is 2, multiple D 12 They are either identical or different from each other. When n is 2 or 3, multiple Rs are either identical or different from one another.

[0127] [ka]

[0128] (In the above general formula (10a), At positions a1, a2, a3, or a4, the position of b in the general formula (10b) is condensed. * indicates the bond position with the benzene ring in the general formula (1) above. In the above general formula (10b), The position of b is contracted to the positions of a1, a2, a3, or a4 in the general formula (10a), X is an oxygen atom, a sulfur atom, N(R3), or C(R4)(R5), R4 and R5 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, R3, R4 (which does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring), and R5 (which does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring) are each independently: hydrogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 911 )(R 912 )(R 913 ) a base represented by -O-(R 914 ) a base represented by -S-(R 915 A base represented by ) or -N(R 916 )(R 917 It is a base represented by ), The group represented by the general formula (10a) above is a substituent R 10aHaving or not having, R 10a If multiple R 10a They are either identical or different from each other. Multiple R 10a 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, The group represented by the general formula (10b) above is a substituent R 10b Having or not having, R 10b If multiple R 10b They are either identical or different from each other. Multiple R 10b 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 10a , and R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 10b 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 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 It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0129] [ka]

[0130] (One or more sets of two or more adjacent R1 to R8 in the general formula (11) above, 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, In the above general formula (12), R 11 ~R 18 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (13), R 111 ~R 118Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R1 to R8 that do not form a substituted or unsubstituted monoring in the general formula (11) and do not form a substituted or unsubstituted fused ring, and R that do not form a substituted or unsubstituted monoring in the general formula (12) and do not form a substituted or unsubstituted fused ring. 11 ~R 18 Furthermore, R that does not form a substituted or unsubstituted monoring in the general formula (13) and does not form a substituted or unsubstituted condensed ring. 111 ~R 118 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 (12) and (13), Rings A, B, and C are each independently ring structures represented by the following general formulas (14) or (15): 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 general formulas (11) to (13) above, * indicates the bond position with the benzene ring in the general formula (1).

[0131] [ka]

[0132] (In the above general formula (14), r is 0, 2, or 4. When r is 2 or 4, multiple R 19 They are either identical or different from each other. When r is 2 or 4, multiple R 19 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 19 teeth, 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 general formula (15) above, X1 is a sulfur atom or an oxygen atom, Multiple R19 They are either identical or different from each other. Multiple X1s are either identical or different from one another. (In the general formula, 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 R907 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.

[0133] Conventionally, in organic EL devices using TADF materials, there was a problem of high driving voltage due to the large ionization potential of the TADF material. The compound according to this embodiment has a heteroaromatic compound containing a sulfur atom, and therefore has a low ionization potential. For this reason, by using the compound according to this embodiment in the organic layer of an organic EL element, the organic EL element can be driven at a lower voltage. Furthermore, the compound according to this embodiment exhibits a different TADF property compared to conventional TADF materials, specifically k RISCIt has a large reverse intersystem crossing (RISC) rate constant. Therefore, it is also excellent as a TADF material for organic EL elements.

[0134] In the compound according to this embodiment, the benzene ring of general formula (1) to which the groups represented by general formulas (10a) and (10b), and the groups represented by general formulas (11) to (13), etc., are bonded is the benzene ring explicitly shown in general formula (1), and R, D 11 and D 12 It is not a benzene ring contained within it.

[0135] In the compound according to this embodiment, D 11 and D 12 Preferably, these groups are different from each other.

[0136] In the compound according to this embodiment, D 11 The group represented by the general formulas (10a) and (10b) is preferably a group represented by the following general formula (10A-1) or (10A-2). The group represented by the following general formula (10A-1) or (10A-2) is a group with substituent R 10a Having or not having substituent R 10b Having or not having.

[0137] [ka]

[0138] (In the above general formulas (10A-1) and (10A-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R 10a and R 10b These are the substituents R in the general formulas (10a) and (10b), respectively. 10a and R 10b (This is synonymous with...)

[0139] In the compound according to this embodiment, D 11The group represented by the general formulas (10a) and (10b) is also preferably a group represented by the following general formula (10B-1) or (10B-2). The group represented by the following general formula (10B-1) or (10B-2) is a substituent R 10a Having or not having substituent R 10b Having or not having.

[0140] [ka]

[0141] (In the above general formulas (10B-1) and (10B-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R 10a and R 10b These are the substituents R in the general formulas (10a) and (10b), respectively. 10a and R 10b (This is synonymous with...)

[0142] In the compound according to this embodiment, D 11 The group represented by the general formulas (10a) and (10b) is also preferably a group represented by the following general formula (10C-1) or (10C-2). The group represented by the following general formula (10C-1) or (10C-2) is a substituent R 10a Having or not having substituent R 10b Having or not having.

[0143] [ka]

[0144] (In the above general formulas (10C-1) and (10C-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R 10a and R 10b These are the substituents R in the general formulas (10a) and (10b), respectively. 10a and R 10b (This is synonymous with...)

[0145] In the compound according to this embodiment, D 11 The group represented by the general formulas (10a) and (10b) is also preferably a group represented by the following general formula (10D-1) or (10D-2). The group represented by the following general formula (10D-1) or (10D-2) is a substituent R 10a Having or not having substituent R 10b Having or not having.

[0146] [ka]

[0147] (In the above general formulas (10C-1) and (10C-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R 10a and R 10b These are the substituents R in the general formulas (10a) and (10b), respectively. 10a and R 10b (This is synonymous with...)

[0148] In the compound according to this embodiment, substituent R 10a If multiple R 10a It is preferable that no pairs of adjacent elements are combined with each other.

[0149] In the compound according to this embodiment, substituent R 10b If multiple R 10b It is preferable that no pairs of adjacent elements are combined with each other.

[0150] In the compound according to this embodiment, substituent R 10a and R 10bPreferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.

[0151] In the compound according to this embodiment, substituent R 10a and R 10b Each of these is more preferably a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, or an unsubstituted ring-forming C6-C50 aryl group.

[0152] The compound according to this embodiment has substituent R 10a and R 10b It is also preferable that it does not have this feature.

[0153] In the compound according to this embodiment, when X is C(R4)(R5), it is preferable that R4 and R5 do not bond to each other.

[0154] In the compound according to this embodiment, X is preferably a sulfur atom.

[0155] In the compound according to this embodiment, at least one D 12 Preferably, the group is represented by the following general formulas (121), (122), or (131).

[0156] [ka]

[0157] [ka]

[0158] [ka]

[0159] (In the above general formulas (121) and (122), R 11 ~R 18 R in the general formula (12) is 11 ~R 18 It is synonymous with, Ring A 1、 Of rings A2, A3, and A4, two are ring structures represented by the general formula (14), and the remaining two are ring structures represented by the general formula (15). In the above general formula (131), R 111 ~R 118 R in the general formula (13) is 111 ~R 118 It is synonymous with, One of ring B1 and ring B2 is a ring structure represented by the general formula (14), and the other of ring B1 and ring B2 is a ring structure represented by the general formula (15), One of ring C1 and ring C2 is a ring structure represented by the general formula (14), and the other of ring C1 and ring C2 is a ring structure represented by the general formula (15), In the general formulas (121), (122), and (131), the asterisk (*) indicates the bond position to the benzene ring in the general formula (1).

[0160] In the compound according to this embodiment, it is preferable that rings A1 and A3 are ring structures represented by the general formula (14), and rings A2 and A4 are ring structures represented by the general formula (15). In the compound according to this embodiment, it is preferable that ring B1 is a ring structure represented by the general formula (14), ring B2 is a ring structure represented by the general formula (15), ring C1 is a ring structure represented by the general formula (14), and ring C2 is a ring structure represented by the general formula (15).

[0161] In the compound according to this embodiment, at least one D 12 However, it is also preferable that the group be represented by the general formula (131) mentioned above.

[0162] In the compound according to this embodiment, at least one D 12However, it is also preferable that the group be represented by the following general formulas (123), (124), (125), or (132).

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166] [ka]

[0167] (In the above general formulas (123), (124), and (125), R 11 ~R 18 R in the general formula (12) is 11 ~R 18 It is synonymous with R 191 ~R 194 R in the general formula (13) is 19 It is synonymous with, In the above general formula (132), R 111 ~R 118 R in the general formula (14) is 111 ~R 118 It is synonymous with R 195 ~R 198 R in the general formula (13) is 19 It is synonymous with, In the above general formulas (123), (124), (125), and (132), X 11 and X 12 Each of these terms independently corresponds to X1 in the general formula (15), and * indicates the bond position with the benzene ring in the general formula (1).

[0168] In the compound according to this embodiment, R 191 ~R 194 It is preferable that no pairs of adjacent elements are combined with each other. In the compound according to this embodiment, R 195 ~R 198 It is preferable that no pairs of adjacent elements are combined with each other.

[0169] In the compound according to this embodiment, X 11 It is preferable that the atom is a sulfur atom.

[0170] In the compound according to this embodiment, X in the group represented by general formulas (123), (124), and (125) 11 It is preferable that the atom is a sulfur atom.

[0171] In the compound according to this embodiment, at least one D 12 However, it is preferable that the group is represented by the general formula (132) mentioned above. In the compound according to this embodiment, X in the group represented by general formula (132) 11 It is preferable that the X in the group represented by the general formula (132) is a sulfur atom. 11 X is a sulfur atom, 12 It is more preferable that the atom is a sulfur atom or an oxygen atom.

[0172] In the compound according to this embodiment, D 12 It is also preferable that the group is represented by the general formula (11) or the general formula (12).

[0173] In the compound according to this embodiment, D 12 It is preferable that the group is represented by the general formula (12) above.

[0174] In the compound according to this embodiment, the group represented by general formula (12) is preferably one of the groups selected from the group consisting of the following general formulas (12A), (12B), (12C), (12D), (12E), and (12F).

[0175] [ka]

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181] (In the above general formulas (12A), (12B), (12C), (12D), (12E), and (12F), R 11 ~R 18 Each of these independently corresponds to R in the general formula (12) above. 11 ~R 18 It is synonymous with, R 19 and R 20 Each of these independently corresponds to R in the general formula (14) above. 19 It is synonymous with, X1 is synonymous with X1 in the general formula (15) above, In the general formulas (12A), (12B), (12C), (12D), (12E), and (12F), the asterisk (*) indicates the bond position to the benzene ring in the general formula (1).

[0182] In the compounds according to this embodiment, the compound represented by general formula (1) is preferably represented by the following general formulas (110), (120), or (130).

[0183] [ka]

[0184] (In the above general formulas (110), (120), and (130), D 11 , D 12 , R, k, m, and n are, respectively, D in the general formula (1) above. 11 , D 12 (This is synonymous with R, k, m, and n.)

[0185] In the compound according to this embodiment, it is preferable that n in the general formula (1) is 2 or 3.

[0186] In the compound according to this embodiment, it is also preferable that n in the general formula (1) is 2.

[0187] In the compound according to this embodiment, the compound represented by general formula (1) may also be represented by the following general formula (126) or (127).

[0188] [ka]

[0189] (In the above general formulas (126) and (127), D 11 D in the general formula (1) above is 11 It is synonymous with D 12 D in the general formula (1) above is 12 It is synonymous with R 101 ~R 104Each of these terms is independently equivalent to R in the general formula (1) above, where k is 1 or 2, m is 0 or 1, and k+m is 2.

[0190] In the compound according to this embodiment, it is preferable that k is 1, m is 1, and n is 2.

[0191] In the compound according to this embodiment, the compound represented by general formula (1) may also be represented by the following general formulas (126A), (127A), or (127B).

[0192] [ka]

[0193] (In the above general formulas (126A), (127A), and (127B), D 11 D in the general formula (1) above is 11 It is synonymous with D 12 D in the general formula (1) above is 12 It is synonymous with R 101 ~R 104 Each of these terms is independently equivalent to R in the general formula (1) above.

[0194] In the compound according to this embodiment, it is also preferable that n in the general formula (1) is 3.

[0195] In the compound according to this embodiment, it is also preferable that k is 1, m is 0, and n is 3.

[0196] In the compound according to this embodiment, the compound represented by general formula (1) may also be represented by the following general formulas (111), (121), or (131).

[0197] [ka]

[0198] (In the above general formulas (111), (121), and (131), D 11 D in the general formula (1) above is 11 It is synonymous with R 101 ~R 104 Each of these terms is independently equivalent to R in the general formula (1) above.

[0199] In the compound according to this embodiment, it is preferable that at least one substituent R is bonded to the benzene ring in the general formula (1) by a carbon-carbon bond. In the compound according to this embodiment, if there are multiple Rs in the general formula (1), any pair of two or more adjacent Rs will not bond to each other. In the compound according to this embodiment, R 101 ~R 104 No two or more adjacent pairs of these pairs can be combined with each other.

[0200] In the compounds according to this embodiment, R in the general formula (1) is preferably independently a substituted or unsubstituted aryl group having 6 to 18 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring-forming atoms.

[0201] In the compound according to this embodiment, R in the general formula (1) is preferably independently a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms. In the compound according to this embodiment, R 101 ~R 104 Each of these is preferably independently a substituted or unsubstituted aryl group having 6 to 14 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms.

[0202] In the compound according to this embodiment, R in the general formula (1) is preferably independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group. In the compound according to this embodiment, R101 ~R 104 Preferably, each of these is independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0203] In the compound according to this embodiment, it is also preferable that R in the general formula (1) is independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group having 6 ring-forming atoms. In the compound according to this embodiment, R 101 ~R 104 These may each be independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group with 6 ring-forming atoms.

[0204] In the compound according to this embodiment, it is preferable that no pairs of adjacent R1 to R8 groups are bonded to each other. In the compound according to this embodiment, R 11 ~R 18 It is preferable that no pairs of adjacent elements are combined with each other. In the compound according to this embodiment, R 11 ~R 20 It is preferable that no pairs of adjacent elements are combined with each other. In the compound according to this embodiment, R 111 ~R 118 It is preferable that no pairs of adjacent elements are combined with each other.

[0205] In the compound according to this embodiment, R1 to R8 in the general formula (11), and R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 Furthermore, R in the general formula (14) 19Preferably, each of these is independently a hydrogen atom, a substituted or unsubstituted C1-C50 alkyl group, a substituted or unsubstituted ring-forming C3-C50 cycloalkyl group, or a substituted or unsubstituted ring-forming C6-C50 aryl group.

[0206] In the compound according to this embodiment, R1 to R8 in the general formula (11), and R in the general formula (12) 11 ~R 18 , R in the general formula (13) 111 ~R 118 Furthermore, R in the general formula (14) 19 Each of these is more preferably a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, or an unsubstituted ring-forming C6-C50 aryl group.

[0207] In the compound according to this embodiment, R 191 ~R 198 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, or a substituted or unsubstituted ring-forming C6-C50 aryl group, and more preferably a hydrogen atom, an unsubstituted C1-C50 alkyl group, an unsubstituted ring-forming C3-C50 cycloalkyl group, or an unsubstituted ring-forming C6-C50 aryl group.

[0208] The compound according to this embodiment is preferably a delayed-fluorescence compound. The compound according to this embodiment is k RISC Due to its large size, it is useful as a delayed-fluorescence compound.

[0209] • Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya Adachi, Kodansha, published April 1, 2012). In that document, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is described. 13It is explained that if the coefficient 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, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 in the said literature. It is preferable that the compound according to this embodiment is a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0210] Generally, delayed fluorescence emission can be confirmed by transient PL (photoluminescence) measurement.

[0211] 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 materials is classified into a emission component from singlet excitons generated by the initial PL excitation and a emission component from singlet excitons generated via triplet excitons. The lifetime of 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.

[0212] Figure 1 shows a schematic diagram of an exemplary apparatus for measuring transient PL. An example of a transient PL measurement method using Figure 1, and an example of delayed fluorescence behavior analysis, will be explained.

[0213] The transient PL measurement device 100 shown in Figure 1 comprises a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for containing 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 1.

[0214] 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 with a matrix material at a concentration of 12% by mass.

[0215] 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.

[0216] 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.

[0217] [ka]

[0218] 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.

[0219] Figure 2 shows the decay curves obtained from transient PL measurements for thin film sample A and thin film sample B.

[0220] [ka]

[0221] 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.

[0222] Specifically, there are two types of emission from delayed-fluorescence materials: prompt emission and delayed emission. Prompt emission is emission observed immediately after the delayed-fluorescence material is excited by pulsed light (light emitted from a pulsed laser) at a wavelength absorbed by the material. Delayed emission is emission that is not observed immediately after excitation by the pulsed light, but is observed later.

[0223] 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). Furthermore, using the amounts of prompt emission and delayed emission, and following the method described in “Chem. Phys. Lett., 644, 16, 62-67 2016” (Reference 2), k RISC It is possible to find this. Furthermore, the amount of Prompt emission and Delay emission, and k RISC The apparatus used for calculating is not limited to the apparatus described in Reference 1 or the apparatus described in Figure 1.

[0224] Furthermore, to measure the delayed fluorescence of the compound according to this embodiment, a sample prepared by the following method is used. For example, the 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.

[0225] 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 the compounds according to this embodiment is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of the compounds according to this embodiment.

[0226] ·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.

[0227] The lowest excited singlet energy S1(M2) of the compound according to this embodiment, and the energy gap T at 77[K] of the compound according to this embodiment. 77KThe difference ΔST(M2) from (M2) is preferably less than 0.3eV, more preferably less than 0.2eV, and even more preferably less than 0.1eV. That is, ΔST(M2) preferably satisfies the relationship of the following formulas (Equation 10), (Equation 11), (Equation 12), or (Equation 13). ΔST(M2)=S1(M2)-T 77K (M2)<0.3eV…(Number 10) ΔST(M2)=S1(M2)-T 77K (M2)<0.2eV …(Math. 11) ΔST(M2)=S1(M2)-T 77K (M2)<0.1eV …(Math. 12) ΔST(M2)=S1(M2)-T 77K (M2)<0.01eV…(Math 13)

[0228] • Relationship between triplet energy and the energy gap at 77 K Here, we will explain the relationship between triplet energy and the energy gap at 77[K]. In this embodiment, the energy gap at 77[K] differs from the triplet energy as it is normally defined. The triplet energy is measured as follows: First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum of this sample is measured at a low temperature (77 K) (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength). A tangent line is drawn to the rising edge of the short-wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from the wavelength value at the intersection of the tangent line and the horizontal axis using a predetermined conversion formula. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescence compound is preferably a compound with a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77[K]), and excited singlet states and excited triplet states coexist. As a result, the spectrum measured in the same manner as above includes emission from both excited singlet states and excited triplet states, and it is difficult to distinguish which state emitted the light, but basically the triplet energy value is considered to be dominant. Therefore, in this embodiment, although the measurement method is the same as that for the usual triplet energy T, in order to distinguish that it is different in a strict sense, the value measured as follows is the energy gap T 77K This method is called [method name]. The compound to be measured is dissolved in EPA (diethyl ether:isopentane:ethanol = 5:5:2 (volume ratio)) to a concentration of 10 μmol / L, and this solution is placed in a quartz cell to 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

[0229] 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.

[0230] • 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).

[0231] 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.

[0232] (Method for producing the compound according to this embodiment) The compounds according to this embodiment can be produced by following the synthesis method described in the examples below, or by using known alternative reactions and raw materials tailored to the target product, in accordance with that synthesis method.

[0233] (Specific examples of compounds according to this embodiment) Specific examples of compounds according to this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples. In this specification, deuterium atoms are denoted as D in chemical formulas, and light hydrogen atoms are denoted as H or omitted from the description.

[0234] [ka]

[0235] [ka]

[0236] [ka]

[0237] [ka]

[0238] [ka]

[0239] [ka]

[0240] [ka]

[0241] [ka]

[0242] [ka]

[0243] [ka]

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] [ka]

[0250] [ka]

[0251] [ka]

[0252] [Second Embodiment] (Materials for organic electroluminescent devices) The material for an organic electroluminescent device according to this embodiment contains the compound according to the first embodiment. One embodiment is a material for an organic electroluminescent device that contains only the compound according to the first embodiment, and another embodiment is a material for an organic electroluminescent device that contains the compound according to the first embodiment and other compounds different from the compound in the first embodiment. In the organic electroluminescent element material of this embodiment, it is preferable that the compound according to the first embodiment is the host material. In this case, the organic electroluminescent element material may include the compound according to the first embodiment as the host material and other compounds such as dopant materials. Furthermore, in the organic electroluminescent element material of this embodiment, it is preferable that the compound according to the first embodiment is a delayed fluorescence material.

[0253] [Third Embodiment] (Organic electroluminescent element) The organic EL element according to this embodiment will be described below. The organic EL element according to this 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.

[0254] In the organic EL element according to this embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL element according to this embodiment has an anode, a cathode, and an organic layer contained between the anode and the cathode, and the organic layer contains the compound according to the first embodiment as compound M2.

[0255] In the organic EL element of this embodiment, the organic layer preferably has at least one light-emitting layer, and the light-emitting layer preferably contains compound M2.

[0256] The organic layer may consist of, for example, a single light-emitting layer, or it may include layers that can be used in an organic EL device. The layers that can be used in an organic EL device 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.

[0257] In one embodiment, the light-emitting layer may contain a metal complex. In one embodiment, it is also preferable that the light-emitting layer does not contain a metal complex. In one embodiment, it is preferable that the light-emitting layer does not contain phosphorescent material (dopant material). Furthermore, in one embodiment, it is preferable that the luminescent layer does not contain heavy metal complexes and phosphorescent rare earth metal complexes. Examples of heavy metal complexes include iridium complexes, osmium complexes, and platinum complexes.

[0258] Figure 3 shows a schematic configuration of an example of an organic EL element according to this embodiment. The organic EL element 1 includes a light-transmitting 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 3.

[0259] (Emitting layer) In the organic EL element of this embodiment, the light-emitting layer contains compound M2. Preferably, compound M2 in the light-emitting layer is the compound according to the first embodiment. Furthermore, it is preferable that the light-emitting layer further contains compound M1. In this embodiment, compound M2 is preferably a host material (sometimes referred to as a matrix material), and compound M1 is also preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material). In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, it is preferable that the light-emitting layer does not contain phosphorescent metal complexes, and also preferably does not contain metal complexes other than phosphorescent metal complexes.

[0260] (Compound M2) Compound M2 is a compound according to the first embodiment. It is preferable that compound M2 in this embodiment is a thermally activated delayed fluorescence compound. The compound according to the first embodiment is k RISC Because of its large size, it is expected to improve the luminous efficiency of organic EL elements.

[0261] (Compound M1) Compound M1 is preferably a fluorescent compound. Compound M1 is preferably a compound that does not exhibit delayed fluorescence. Compound M1 in this embodiment is not a phosphorescent metal complex. It is preferable that compound M1 is not a heavy metal complex. Furthermore, it is preferable that compound M1 is not a metal complex.

[0262] As compound M1 in this embodiment, a fluorescent material can be used. Specific examples of fluorescent materials include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, bisarylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, compounds containing boron atoms, pyrometenoboron complex compounds, compounds having a pyrometene skeleton, metal complexes of compounds having a pyrometene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0263] Compound M1 is preferably a compound that exhibits emission with a maximum peak wavelength of 400 nm to 700 nm. In this specification, the maximum peak wavelength is defined as the wavelength of the compound being measured when it is 10 -6 moles / liter or more (10) -5 For toluene solutions dissolved at a concentration of mol / liter or less, this refers to the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum. The measuring instrument used is a spectrofluorometer (Hitachi High-Tech Science Corporation, F-7000).

[0264] Compound M1 preferably exhibits red or green luminescence. In this specification, red emission refers to emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 600 nm to 660 nm. If compound M1 is a red fluorescent compound, the maximum peak wavelength of compound M1 is preferably 600 nm to 660 nm, more preferably 600 nm to 640 nm, and even more preferably 610 nm to 630 nm. In this specification, green emission refers to emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 500 nm to 560 nm. If compound M1 is a green fluorescent compound, the maximum peak wavelength of compound M1 is preferably 500 nm to 560 nm, more preferably 500 nm to 540 nm, and even more preferably 510 nm to 540 nm. In this specification, blue emission refers to emission in which the maximum peak wavelength of the fluorescence spectrum is in the range of 430 nm to 480 nm. If compound M1 is a blue fluorescent compound, the maximum peak wavelength of compound M1 is preferably 430 nm to 480 nm, more preferably 440 nm to 480 nm.

[0265] 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).

[0266] (Compound represented by general formula (D1)) In this embodiment, compound M1 is also preferably a compound represented by the following general formula (D1).

[0267] [ka]

[0268] (In the above general formula (D1), Rings A, B, D, E, and F are each independent of each other. Substituted or unsubstituted aryl rings with 6 to 30 carbon atoms, and A ring structure selected from the group consisting of heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms. Either ring B or ring D exists, or both ring B and ring D exist. If both ring B and ring D exist, ring B and ring D share a bond connecting Zc and Zh. Either ring E or ring F exists, or both ring E and ring F exist. If both ring E and ring F exist, ring E and ring F share a bond connecting Zf and Zi. Za is a nitrogen atom or a carbon atom, Zb is If ring B is present, it is a nitrogen atom or a carbon atom. If ring B is absent, it consists of an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2), or Si(Rb3)(Rb4). Zc is a nitrogen atom or a carbon atom, Zd is If ring D is present, it is a nitrogen atom or a carbon atom. If ring D is not present, it is an oxygen atom, a sulfur atom, or NRd. Ze is If ring E is present, it is a nitrogen atom or a carbon atom. If ring E is not present, it is an oxygen atom, a sulfur atom, or NRe. Zf is a nitrogen atom or a carbon atom, Zg is If ring F is present, it is a nitrogen atom or a carbon atom. If ring F is absent, it is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O, or P=S. Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently a hydrogen atom or a substituent. Rb, Rb1, Rb2, Rb3, Rb4, Rd, Re, Rg, Rg1 as substituents Rg2, Rg3, Rg4, and Rh are each independent of each other. Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R 911 )(R 912 )(R 913 ) a base represented by -O-(R 914 ) a base represented by -S-(R 915 A base represented by ) or -N(R 916 )(R 917 It is a base represented by ), However, the bonds between Y and Za, Y and Zd, and Y and Ze are all single bonds.

[0269] The bonds between Y and Za, between Y and Zd, and between Y and Ze are all single bonds, and these single bonds are covalent bonds, not coordinate bonds.

[0270] In this specification, examples of heterocycles include ring structures (heterocycles) obtained by removing the bonding bonds from the "heterocycle groups" exemplified in "Substituents described herein" above. These heterocycles may have substituents or may be unsubstituted. In this specification, examples of aryl rings include ring structures (aryl rings) obtained by removing the bonding bond from the "aryl group" exemplified in "Substituents described herein" above. These aryl rings may have substituents or may be unsubstituted.

[0271] In this embodiment, compound M1 is also preferably a compound represented by the following general formula (D11).

[0272] [ka]

[0273] (In the above general formula (D11), Rings A, D, and E are independent of each other. Substituted or unsubstituted aryl rings with 6 to 30 carbon atoms, and A ring structure selected from the group consisting of heterocycles with 5 to 30 substituted or unsubstituted ring-forming atoms. Za is a nitrogen atom or a carbon atom, Zb is an oxygen atom, a sulfur atom, NRb, C(Rb1)(Rb2) or Si(Rb3)(Rb4), Zc is a nitrogen atom or a carbon atom, Zd is a nitrogen atom or a carbon atom, Ze is a nitrogen atom or a carbon atom, Zf is a nitrogen atom or a carbon atom, Zg is an oxygen atom, a sulfur atom, NRg, C(Rg1)(Rg2) or Si(Rg3)(Rg4), Zh is a nitrogen atom or a carbon atom, Zi is a nitrogen atom or a carbon atom, Y is a boron atom, a phosphorus atom, SiRh, P=O, or P=S. Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4, and Rh are each independently equivalent to Rb, Rb1, Rb2, Rb3, Rb4, Rg, Rg1, Rg2, Rg3, Rg4, and Rh in the general formula (D1).

[0274] In this embodiment, compound M1 is also preferably a compound represented by the following general formula (D16).

[0275] [ka]

[0276] (In the above general formula (D16), R 161 ~R 177 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, Furthermore, R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 161 ~R 177 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups with 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 50 carbon atoms, -Si(R 961 )(R 962 )(R 963 ) a base represented by -O-(R 964 ) a base represented by -S-(R 965 ) a base represented by -N(R 966 )(R 967 ) a base represented by -C(=O)R 968 A base represented by -COOR 969 A base represented by halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 961 ~R 969 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R 961 If multiple R 961 They are either identical or different from each other. R 962 If multiple R 962 They are either identical or different from each other. R 963 If multiple R 963 They are either identical or different from one another. R 964 If multiple R 964 They are either identical or different from one another. R 965 If multiple R 965 They are either identical or different from one another. R 966 If multiple R 966 They are either identical or different from one another. R 967 If multiple R967 They are either identical or different from one another. R 968 If multiple R 968 They are either identical or different from one another. R 969 If multiple R 969 They are either identical or different to one another.

[0277] (Compound represented by general formula (20)) In this embodiment, compound M1 is also preferably a compound represented by the following general formula (20).

[0278] [ka]

[0279] In the above general formula (20), X is a nitrogen atom, or a carbon atom bonded to Y. Y is a hydrogen atom or a substituent. R 21 ~R 26 Each of these is independently either a hydrogen atom or a substituent, or R 21 and R 22 The group, R 22 and R 23 The group, R 24 and R 25 The set, and R 25 and R 26 One or more of these pairs join together to form a ring, Y and R as substituents 21 ~R 26 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, Substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted halogenated alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms, Substituted or unsubstituted ring-forming arylthio groups with 6 to 30 carbon atoms, Substituted or unsubstituted alkenyl groups with 2 to 30 carbon atoms, Substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, A heteroaryl group with 5 to 30 substituted or unsubstituted ring-forming atoms, halogen atom, Carboxy group, Substituted or unsubstituted ester groups, Substituted or unsubstituted carbamoyl groups, Substituted or unsubstituted amino groups, Nitro group, Cyano group, Substituted or unsubstituted silyl groups, and Selected from the group consisting of substituted or unsubstituted siloxanil groups, Z 21 and Z 22 Each of these is independently a substituent or Z 21 and Z 22 They bond to each other to form a ring, Z as a substituent 21 and Z 22 Each of them operates independently. halogen atom, Substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms, Substituted or unsubstituted alkyl halides with 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, Substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, Substituted or unsubstituted halogenated alkoxy groups having 1 to 30 carbon atoms, and The group is selected from those consisting of substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms in a ring-forming structure.

[0280] (Method for producing compound M1) The compounds according to this embodiment can be produced by known methods. Furthermore, the compounds according to this embodiment can also be produced by following known methods and using known alternative reactions and raw materials tailored to the target product.

[0281] (Specific example of compound M1) Specific examples of compound M1 in this embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds. Note that coordination bonds between boron atoms and nitrogen atoms in the pyromethene skeleton can be represented in various ways, such as with solid lines, dashed lines, arrows, or omitted. In this specification, they are represented with solid lines, dashed lines, or omitted entirely.

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] <Relationship between compound M1 and compound M2 in the light-emitting layer> In the organic EL element of this embodiment, it is preferable that the lowest excited singlet energy S1(M1) of compound M1 and the lowest excited singlet energy S1(M2) of compound M2 satisfy the relationship shown in the following formula (Equation 1). S1(M2)>S1(M1)…(Math 1)

[0286] Energy gap T of compound M2 at 77[K] 77K (M2) is the energy gap T of compound M1 at 77[K]. 77K It is preferable that it is greater than (M1). That is, it is preferable that the relationship shown in the following formula (Equation 5) is satisfied. T 77K (M2)>T 77K (M1) …(Math 5)

[0287] When the organic EL element of this embodiment is made to emit light, it is preferable that mainly compound M1 emits light in the light-emitting layer.

[0288] • TADF mechanism Figure 4 shows an example of the relationship between the energy levels of compound M2 and compound M1 in the light-emitting layer. In Figure 4, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1. T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2. T1(M2) represents the lowest excited triplet state of compound M2. The dashed arrow in Figure 4, pointing from S1(M2) to S1(M1), represents the Förster-type energy transfer from the lowest excited singlet state of compound M2 to compound M1. As shown in Figure 4, when a compound with a small ΔST(M2) is used as compound M2, 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 compound M2 to compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of compound M1 can be observed. It is thought that by utilizing this TADF mechanism of delayed fluorescence, the internal quantum efficiency can theoretically be increased to 100%.

[0289] The organic EL element in this embodiment preferably emits red or green light. When the organic EL element of this embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 500 nm or more and 560 nm or less. When the organic EL element of this embodiment emits red light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 600 nm or more and 660 nm or less. When the organic EL element of this embodiment emits blue light, the maximum peak wavelength of the light emitted from the organic EL element is preferably 430 nm or more and 480 nm or less.

[0290] 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 is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage is applied to the organic EL 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).

[0291] • Film thickness of the luminescent layer The thickness of the light-emitting layer in the organic EL element of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and even more preferably 10 nm to 50 nm. When the thickness of the light-emitting layer is 5 nm or more, it is easier to form the light-emitting layer and adjust the chromaticity, and when the thickness of the light-emitting layer is 50 nm or less, it is easier to suppress the rise in the driving voltage.

[0292] • Compound content in the luminescent layer The content of compound M2 and compound M1 contained in the light-emitting layer is preferably within the following ranges, for example. The content of compound M2 may be 90% by mass or more and 99.9% by mass or less, 95% by mass or more and 99.9% by mass or less, or 99% by mass or more and 99.9% by mass or less. The content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. This embodiment does not exclude the inclusion of materials other than compound M2 and compound M1 in the light-emitting layer. The light-emitting layer may contain only one type of compound M2, or two or more types. The light-emitting layer may contain only one type of compound M1, or two or more types.

[0293] (substrate) The substrate is used as a support for the organic EL element. Examples of substrates include glass, quartz, and plastic. Flexible substrates may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Inorganic vapor-deposited films can also be used.

[0294] (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). 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. 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. 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.

[0295] (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. 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. 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.

[0296] (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.

[0297] (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.

[0298] (electron transport layer) The electron transport layer is a layer containing a material with high electron transport properties. The electron transport layer can contain: 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3) polymer compounds. Specifically, low-molecular-weight organic compounds such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviated as BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ, among others, can be used. In addition to metal complexes, there are also 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as (abbreviated as TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviated as p-EtTAZ), vasophenanthroline (abbreviated as BPhen), vasocuproin (abbreviated as BCP), and 4,4'-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviated as BzOs) can also be used. The substances described here are mainly 10 -6 cm 2The material has an electron mobility of 1 / Vs or higher. However, any material with higher electron transport properties than hole transport properties may be used as the electron transport layer. Furthermore, the electron transport layer may be a single layer or a layer consisting of two or more layers of the above material stacked together. Furthermore, polymer compounds can also be used in the electron transport layer. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy) can be used.

[0299] (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.

[0300] (Layer formation method) The method for forming each layer of the organic EL element in this embodiment 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.

[0301] (film thickness) The film thickness of each organic layer in the organic EL element of this embodiment is not limited to those specifically mentioned above. However, generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and if it is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, a range of a few nanometers to 1 μm is usually preferred.

[0302] The organic EL element according to the third embodiment contains, in its light-emitting layer, the compound of the first embodiment as compound M2 and compound M1 having a lower minimum excitation singlet energy than compound M2. Since the organic EL element according to the third embodiment contains the compound of the first embodiment (compound M2), which has a small ionization potential, in its light-emitting layer, the energy barrier between the hole transport layer and the light-emitting layer is reduced, making it easier for holes to be injected from the hole transport layer to the light-emitting layer. Therefore, according to the third embodiment, a high-performance organic EL element that can be driven at a lower voltage can be provided.

[0303] [Fourth Embodiment] The configuration of the organic EL element according to the fourth embodiment will now be described. In the description of the fourth embodiment, components identical to those in the third embodiment will be given the same reference numerals and names, and their descriptions will be omitted or simplified. Furthermore, in the fourth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third embodiment.

[0304] The organic EL element according to the fourth embodiment differs from the organic EL element according to the third embodiment in that the light-emitting layer further contains compound M3. In other respects, it is the same as the third embodiment. In other words, in the fourth embodiment, the light-emitting layer includes compound M3, compound M2, and compound M1. In this embodiment, compound M2 is preferably a host material, and compound M1 is preferably a dopant material.

[0305] <Compound M3> Compound M3 in this embodiment may be a thermally activated delayed fluorescence compound or a compound that does not exhibit thermal activation delayed fluorescence, but it is preferable that it is a compound that does not exhibit thermal activation delayed fluorescence.

[0306] Compound M3 is not particularly limited, but it is preferably a compound other than an amine compound. For example, compound M3 can be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0307] In this embodiment, compound M3 is preferably a compound represented by the following general formula (3X) or (3Y).

[0308] (Compounds represented by the general formula (3X)) Compound M3 is also preferably a compound represented by the following general formula (3X).

[0309] [ka]

[0310] (In the above general formula (3X), A3 is A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. L3 is single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, Divalent heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms, A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of three groups selected from the group consisting of substituted or unsubstituted ring-forming arylene groups with 6 to 30 carbon atoms and substituted or unsubstituted divalent heterocyclic groups with 5 to 30 ring-forming atoms. R 31 ~R 38 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R38 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 Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is a group represented by the following general formula (3A).

[0311] [ka]

[0312] (In the above general formula (3A), R B teeth, 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 with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. R B When there are multiple R B They are either identical or different from one another. L 31 teeth, single bond, Substituted or unsubstituted ring-forming arylene groups having 6 to 50 carbon atoms, trivalent groups, tetravalent groups, pentavalent groups or hexavalent groups derived from said arylene groups, A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from said heterocyclic group, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms, and a trivalent, tetravalent, pentavalent, or hexavalent group derived from said divalent group. L 32 teeth, single bond, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, n3 is 1, 2, 3, 4, or 5. L 31 If it is a single bond, then n3 is 1, and L 32 This is bonded to the carbon atoms of the six-membered ring in the general formula (3X), L 32 When there are multiple L 32 They are either identical or different from one another. * represents the bonding site with the carbon atom of the six-membered ring in the general formula (3X) above.

[0313] (In compound M3, 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 937Each 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 with 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 one another. R 902 If multiple R 902 They are either identical or different from one another. R 903 If multiple R 903 They are either identical or different from one another. R 904 If multiple R 904 They are either identical or different from one another. R 905 If multiple R 905 They are either identical or different from one another. R 906 If multiple R 906 They are either identical or different from one another. R 907 If multiple R 907 They are either identical or different from one another. R 908 If multiple R 908 They are either identical or different from one another. R 909 If multiple R 909 They are either identical or different from one another. R 931 If multiple R 931 They are either identical or different from one another. R 932 If multiple R 932 They are either identical or different from one another. R 933If multiple R 933 They are either identical or different from one another. R 934 If multiple R 934 They are either identical or different from one another. R 935 If multiple R 935 They are either identical or different from one another. R 936 If multiple R 936 They are either identical or different from one another. R 937 If multiple R 937 They are either identical or different to one another.

[0314] Compound M3 is also preferably a compound represented by any of the following general formulas (31) to (36).

[0315] [ka]

[0316] [ka]

[0317] [ka]

[0318] (In the above general formulas (31) to (36), A3 and L3 are equivalent to A3 and L3 in the general formula (3X) above, respectively. R 341 ~R 350 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, X 31is a sulfur atom, oxygen atom, NR 352 or CR 353 R 354 And, R 353 and R 354 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 341 ~R 350 And, R 352 R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 353 and R 354 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, and does not form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0319] In compound M3, R 352 teeth, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0320] In compound M3, R 353 and R 354 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 353 and R 354 Each of them operates independently. Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0321] In compound M3, X 31 It is preferable that this atom is a sulfur atom or an oxygen atom.

[0322] In compound M3, A3 is preferably a group represented by any of the following general formulas (A31) to (A37).

[0323] [ka]

[0324] [ka]

[0325] (In the above general formulas (A31) to (A37), Multiple R 300 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 300 , and R 333 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 It is synonymous with, In the general formulas (A31) to (A37) above, the asterisks (*) indicate the bonding position of compound M3 to L3, respectively.

[0326] In compound M3, A3 is also preferably a group represented by the general formula (A34), (A35), or (A37).

[0327] Compound M3 is also preferably a compound represented by any of the following general formulas (311) to (316).

[0328] [ka]

[0329] [ka]

[0330] [ka]

[0331] [ka]

[0332] [ka]

[0333] [ka]

[0334] (In the above general formulas (311) to (316), L3 is synonymous with L3 in the general formula (3X) above, Multiple R 300 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 341 ~R350 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 300 Furthermore, R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 341 ~R 350 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0335] Compound M3 is also preferably a compound represented by the following general formula (321).

[0336] [ka]

[0337] (In the above general formula (321), L3 is synonymous with L3 in the general formula (3X) above, R 31 ~R 38 , and R 301 ~R 308 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0338] In compound M3, L3 is preferably a single-bonded, substituted, or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms.

[0339] In compound M3, L3 is single bond, Substituted or unsubstituted phenylene groups, A substituted or unsubstituted biphenylene group, It is preferable that the terphenylene group is substituted or unsubstituted.

[0340] In compound M3, L3 is preferably a group represented by the following general formula (317).

[0341] [ka]

[0342] (In the above general formula (317), R 310 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 This is synonymous with *, and each * independently indicates a binding position.

[0343] In compound M3, L3 may also preferably contain a divalent group represented by the following general formula (318) or general formula (319). In compound M3, L3 is also preferably a divalent group represented by the following general formula (318) or general formula (319).

[0344] Compound M3 is also preferably a compound represented by the following general formula (322) or general formula (323).

[0345] [ka]

[0346] [ka]

[0347] (In the above general formulas (322) and (323), L 31 teeth, Substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, A substituted or unsubstituted divalent heterocyclic group with 5 to 50 ring-forming atoms, or A divalent group formed by the bonding of two groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, and a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms. However, L 31 It includes a divalent group represented by the following general formula (318) or general formula (319), R 31 ~R 38 , R 300 , and R 321 ~R 328 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0348] [ka]

[0349] (In the above general formula (319), Multiple R 304 Two adjacent pairs of these combine to form a ring represented by the general formula (320), In the above general formula (320), 1* and 2* are each independently of R 304 This shows the bond position with the ring to which it is bonded. In the above general formula (318), R 302 , R in the general formula (319) 303 , R that does not form a ring represented by the general formula (320) 304 , and R in the general formula (320) 305 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 It is synonymous with, In the general formulas (318) to (320) above, * indicates the bond position, respectively.

[0350] In compound M3, L3 or L 31 The group represented by the general formula (319) is, for example, the group represented by the following general formula (319A).

[0351] [ka]

[0352] (In the above general formula (319A), R 303 , R 304 and R 305 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 This is synonymous with the above general formula (319A), where * indicates the bond position.

[0353] Compound M3 is a compound represented by the general formula (322), L 31 It is also preferable that the group is represented by the general formula (318).

[0354] Compound M3 is also preferably a compound represented by the following general formula (324).

[0355] [ka]

[0356] (In the above general formula (324), R 31 ~R 38 , R 300 , and R 302 Each of these independently does not form the aforementioned substituted or unsubstituted monoring, nor does it form the aforementioned substituted or unsubstituted condensed ring. 31 ~R 38 (This is synonymous with...)

[0357] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or The group is represented by the general formula (3A) above, In the above general formula (3A), R B teeth, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is preferable that the heterocyclic group has 5 to 50 substituted or unsubstituted ring-forming atoms.

[0358] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or The group is represented by the general formula (3A) above, In the above general formula (3A), R B It is preferable that the ring-forming aryl group has 6 to 50 carbon atoms and is either substituted or unsubstituted.

[0359] R that does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted condensed ring 31 ~R 38 Each of them operates independently. hydrogen atom, A substituted or unsubstituted phenyl group, The group is represented by the general formula (3A) above, In the above general formula (3A), R B It is preferable that this is a substituted or unsubstituted phenyl group.

[0360] Compound M3 is also preferably a compound that does not have a pyridine ring, a pyrimidine ring, or a triazine ring.

[0361] (Compounds represented by the general formula (3Y)) Compound M3 is also preferably a compound represented by the following general formula (3Y).

[0362] [ka]

[0363] (In the above general formula (3Y), Y 31 ~Y 36 Each of these is independently either a CR3 atom or a nitrogen atom. However, Y 31 ~Y 36 Two or more of them are nitrogen atoms, If there are multiple R3s, then one or more pairs of adjacent R3s 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, R3, which does not form the aforementioned substituted or unsubstituted monoring and does not form the aforementioned substituted or unsubstituted fused ring, is 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 Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is a group represented by the following general formula (3B).

[0364] [ka]

[0365] (In the above general formula (3B), R B , L 31 , L 32 and n3 are, independently, R in the general formula (3A) B , L 31 , L 32 And is synonymous with n3, R B When there are multiple R B They are either identical or different from one another. L 31 If it is a single bond, then n3 is 1, and L 32 This is bonded to the carbon atoms of the six-membered ring in the general formula (3Y), L 32 When there are multiple L 32 They are either identical or different from one another. * represents the bonding site with the carbon atom of the six-membered ring in the general formula (3Y).

[0366] Compound M3 preferably does not contain a pyridine ring in its molecule.

[0367] Compound M3 is also preferably a compound represented by the following general formula (31a) or general formula (32a).

[0368] [ka]

[0369] (In the above general formula (32a), R 35 ~R 37 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (31a), R 31 ~R 33 , and R in the general formula (32a) 34 and R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring. 35 ~R 37 Each of these terms is independently equivalent to R3 in the general formula (3Y) mentioned above.

[0370] Compound M3 is also preferably a compound represented by the general formula (31a).

[0371] In the above general formula (3Y), R3 is determined independently of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, A heterocyclic group with 5 to 50 substituted or unsubstituted ring-forming atoms, or It is preferable that the group is represented by the general formula (3B) mentioned above.

[0372] In the above general formula (3Y), R3 is determined independently of each other. hydrogen atom, Substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is preferable that the group is represented by the general formula (3B) mentioned above.

[0373] The compound M3 represented by the general formula (3Y) preferably has at least one group selected from the group consisting of groups represented by the following general formulas (B31) to (B44) in its molecule.

[0374] [ka]

[0375] [ka]

[0376] (In the above general formulas (B31) to (B38), Multiple R 300 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R 331 and R 332 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 300 , R 331 and R 332 , and R 333 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, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or These are heterocyclic groups with 5 to 50 substituted or unsubstituted ring-forming atoms. In the general formulas (B31) to (B38) above, the asterisks (*) indicate the bonding positions of the compound M3 with other atoms within the molecule.

[0377] [ka]

[0378] [ka]

[0379] [ka]

[0380] (In the above general formulas (B39) to (B44), R 341 ~R 350 Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, However, R 341 ~R 351 At least one of these indicates the bonding position with other atoms in the molecule of compound M3, X 31 is a sulfur atom, oxygen atom, NR 352 or CR 353 R 354 And, R 353 and R 354 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 is not a bond position with other atoms in the molecule of compound M3, but does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. 341 ~R 351 And, R 352 R that does not form the substituted or unsubstituted monoring and does not form the substituted or unsubstituted condensed ring 353 and R 354 These are, independently 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 halogen atom, Cyano group, Nitro group, A substituted or unsubstituted ring-forming aryl group with 6 to 50 carbon atoms, or It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted.

[0381] The compound M3 represented by the general formula (3Y) preferably has at least one group selected from the group consisting of groups represented by the general formulas (B38) to (B44) in its molecule.

[0382] In the above general formula (3Y), Y 31 ~Y 36 At least one of them is CR3, At least one R3 is a group represented by the general formula (3B), and R B It is preferable that the group is one of the groups represented by the general formulas (B31) to (B44) above.

[0383] In the above general formula (3Y), Y 31 ~Y 36At least one of them is CR3, At least one R3 is a group represented by the general formula (3B), and R B It is preferable that the group is one of the groups represented by the general formulas (B38) to (B44) above.

[0384] In the above general formulas (3A) and (3B), L 31 teeth, single bond, A substituted or unsubstituted ring-forming arylene group having 6 to 50 carbon atoms, a trivalent group, a tetravalent group, a pentavalent group or a hexavalent group derived from the arylene group, or A divalent group formed by the bonding of two groups selected from the group consisting of substituted or unsubstituted ring-forming arylene groups with 6 to 50 carbon atoms, and a trivalent, tetravalent, pentavalent, or hexavalent group derived from said divalent group. L 32 Each of them operates independently. Single bond, or It is preferable that the ring-forming arylene group has 6 to 50 carbon atoms and is either substituted or unsubstituted.

[0385] In the above general formulas (3A) and (3B), L 31 teeth, Single bond, or A substituted or unsubstituted ring-forming arylene group with 6 to 50 carbon atoms, n3 is 1, L 32 teeth, Single bond, or It is preferable that the ring-forming arylene group has 6 to 50 carbon atoms and is either substituted or unsubstituted.

[0386] In the above general formulas (3A) and (3B), L 31 teeth, single bond, Substituted or unsubstituted phenylene groups, A substituted or unsubstituted biphenylene group, a divalent group formed by bonding two groups selected from the group consisting of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, a trivalent group, a tetravalent group, a pentavalent group, or a hexavalent group derived from said divalent group, n3 is 1, L 32 is preferably a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0387] In the compounds represented by general formulas (3X) and (3Y), R 352 is preferably a substituted or unsubstituted alkyl group having 1 to 50 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.

[0388] In the compounds represented by general formulas (3X) and (3Y), the pair consisting of R 353 and R 354 either: bond to each other to form a substituted or unsubstituted monocyclic ring, bond to each other to form a substituted or unsubstituted fused ring, or do not bond to each other, do not bond to each other, do not form a substituted or unsubstituted monocyclic ring, and do not form a substituted or unsubstituted fused ring; and R 353 and R 354 are each independently preferably a substituted or unsubstituted alkyl group having 1 to 50 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.

[0389] In the compounds represented by general formulas (3X) and (3Y), when the term "substituted or unsubstituted" is used, the substituent is an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted alkenyl group having 2 to 25 carbon atoms, an unsubstituted alkynyl group having 2 to 25 carbon atoms, an unsubstituted cycloalkyl group having 3 to 25 ring-forming carbon atoms, -Si(R 901 )(R 902 )(R 903 ) a group represented by, -O-(R 904 ) a group represented by, -S-(R 905 ) a group represented by, -N(R 906 )(R 907 ) a group represented by, an unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R 908 a group represented by, -COOR 909 a group represented by, -P(=O)(R 931 )(R 932 ) a group represented by, -Ge(R 933 )(R 934 )(R 935 ) a group represented by, -B(R 936 )(R 937 ) a group represented by, -S(=O)2R 938 a group represented by, a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms, R 901 to R 909 , and R 931 to R 938 are each independently, a hydrogen atom, an unsubstituted alkyl group having 1 to 25 carbon atoms, an unsubstituted aryl group having 6 to 25 ring-forming carbon atoms, or preferably an unsubstituted heterocyclic group having 5 to 25 ring-forming atoms.

[0390] In the compounds represented by the general formulas (3X) and (3Y) mentioned above, the substituents in the phrase "substituted or unsubstituted" are: halogen 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.

[0391] In the compounds represented by the general formulas (3X) and (3Y) mentioned above, the substituents in the phrase "substituted or unsubstituted" are: Unsubstituted alkyl groups having 1 to 10 carbon atoms, Unsubstituted ring-forming aryl groups with 6 to 12 carbon atoms, or It is preferable that the heterocyclic group is unsubstituted and has 5 to 12 ring-forming atoms.

[0392] In the compounds represented by the general formulas (3X) and (3Y) mentioned above, it is also preferable that the groups described as "substituted or unsubstituted" are both "unsubstituted" groups.

[0393] (Method for producing compound M3) Compound M3 according to this embodiment can be produced by known methods.

[0394] (Specific example of compound M3) Specific examples of compound M3 in this embodiment include, for example, the following compounds. However, the present invention is not limited to these specific examples of compounds.

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398]

change

[0399]

change

[0400]

change

[0401]

change

[0402]

change

[0403]

change

[0404]

change

[0405]

change

[0406]

change

[0407]

change

[0408] [ka]

[0409] [ka]

[0410] [ka]

[0411] <Relationship between compounds M3, M2, and M1 in the light-emitting layer> In the organic EL element of this embodiment, it is preferable that the lowest excited singlet energy S1(M2) of compound M2 and the lowest excited singlet energy S1(M1) of compound M1 satisfy the relationship shown in the following formula (Equation 1). S1(M2)>S1(M1)…(Math 1)

[0412] In the organic EL element of this embodiment, it is preferable that the lowest excited singlet energy S1(M2) of compound M2 and the lowest excited singlet energy S1(M3) of compound M3 satisfy the following relationship (Equation 2). S1(M3)>S1(M2)…(Math 2)

[0413] Furthermore, it is preferable that the lowest excited singlet energy S1(M3) of compound M3 is greater than the lowest excited singlet energy S1(M1) of compound M1. S1(M3)>S1(M1)…(Number 2A)

[0414] It is preferable that the lowest excited singlet energy S1(M3) of compound M3, the lowest excited singlet energy S1(M2) of compound M2, and the lowest excited singlet energy S1(M1) of compound M1 satisfy the following equation (Equation 2B). S1(M3)>S1(M2)>S1(M1)…(Number 2B)

[0415] In the organic EL element of this embodiment, the energy gap T of compound M3 at 77[K] 77K (M3) is the energy gap T of compound M2 at 77[K]. 77K It is preferable that it be greater than (M2).

[0416] In the organic EL element of this embodiment, the energy gap T of compound M2 at 77[K] 77K (M2) is the energy gap T of compound M1 at 77[K]. 77K It is preferable that it be greater than (M1).

[0417] In the organic EL element of this embodiment, it is preferable that compound M3, compound M2, and compound M1 satisfy the relationship shown in the following formula (Equation 5A). T 77K (M3)>T 77K (M2)>T 77K (M1) …(Number 5A)

[0418] 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 the fluorescent compound M1. The organic EL element in this embodiment preferably emits red or green light.

[0419] • Compound content in the luminescent layer The content of compounds M3, M2, and M1 contained in the light-emitting layer is preferably within the following ranges, for example. The content of compound M3 is preferably 10% by mass or more and 80% by mass or less. The content of compound M2 is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of compound M1 is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and even more preferably 0.01% by mass or more and 1% by mass or less. The upper limit of the total content of compound M3, compound M2, and compound M1 in the light-emitting layer is 100% by mass. This embodiment does not exclude the inclusion of materials other than compound M3, compound M2, and compound M1 in the light-emitting layer. The light-emitting layer may contain only one type of compound M3, or two or more types. The light-emitting layer may contain only one type of compound M2, or two or more types. The light-emitting layer may contain only one type of compound M1, or two or more types.

[0420] Figure 5 shows an example of the relationship between the energy levels of compounds M3, M2, and M1 in the light-emitting layer. In Figure 5, S0 represents the ground state. S1(M1) represents the lowest excited singlet state of compound M1, and T1(M1) represents the lowest excited triplet state of compound M1. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. The dashed arrow from S1(M2) to S1(M1) in Figure 5 represents the Förster-type energy transfer from the lowest excited singlet state of compound M2 to the lowest excited singlet state of compound M1. As shown in Figure 5, when a compound with a small ΔST(M2) is used as compound M2, 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 compound M2 to compound M1, generating the lowest excited singlet state S1(M1). As a result, fluorescence emission from the lowest excited singlet state S1(M1) of compound M1 can be observed. It is thought that by utilizing this TADF mechanism of delayed fluorescence, the internal quantum efficiency can theoretically be increased to 100%.

[0421] The organic EL element according to the fourth embodiment contains, in its light-emitting layer, the compound of the first embodiment as compound M2, compound M1 having a lower minimum excitation singlet energy than compound M2, and compound M3 having a higher minimum excitation singlet energy than compound M2. Since the organic EL element according to the fourth embodiment contains the compound of the first embodiment (compound M2) which has a small ionization potential, hole injection from the hole transport layer side is improved. Therefore, according to the fourth embodiment, a high-performance organic EL element that can be driven at a lower voltage can be provided.

[0422] [Fifth Embodiment] The configuration of the organic EL element according to the fifth embodiment will now be described. In the description of the fifth embodiment, components identical to those in the third or fourth embodiment will be given the same reference numerals or names, and their descriptions will be omitted or simplified. Furthermore, in the fifth embodiment, materials and compounds not specifically mentioned can be the same as those described in the third or fourth embodiment.

[0423] The organic EL element according to the fifth embodiment differs from the organic EL element according to the third or fourth embodiment in that the light-emitting layer includes compounds M2 and M3, but does not include compound M1. In other respects, it is the same as the third or fourth embodiment. In other words, in the fifth embodiment, the light-emitting layer includes compound M2 and compound M3. In this embodiment, compound M3 is preferably a host material, and compound M2 is preferably a dopant material. In this embodiment, when the light-emitting layer contains the compound according to the first embodiment, it is preferable that the light-emitting layer does not contain phosphorescent metal complexes, and also preferably does not contain metal complexes other than phosphorescent metal complexes.

[0424] <Compound M2> Compound M2 is a compound according to the first embodiment. Compound M2 is preferably a delayed-fluorescence compound. The compound according to the first embodiment is kRISC Because of its large size, it is expected to improve the luminous efficiency of organic EL elements.

[0425] <Compound M3> Compound M3 is the same as compound M3 described in the fourth embodiment.

[0426] <Relationship between compound M2 and compound M3 in the light-emitting layer> In the organic EL element of this embodiment, it is preferable that the lowest excited singlet energy S1(M2) of compound M2 and the lowest excited singlet energy S1(M3) of compound M3 satisfy the following relationship (Equation 2). S1(M3)>S1(M2)…(Math 2)

[0427] Energy gap T of compound M3 at 77[K] 77K (M3) is the energy gap T of compound M2 at 77[K]. 77K It is preferable that it be greater than (M2).

[0428] Figure 6 is a diagram illustrating the principle of light emission according to an embodiment of the present invention. In Figure 6, S0 represents the ground state. S1(M2) represents the lowest excited singlet state of compound M2, and T1(M2) represents the lowest excited triplet state of compound M2. S1(M3) represents the lowest excited singlet state of compound M3, and T1(M3) represents the lowest excited triplet state of compound M3. As shown in Figure 6, when a compound with a small ΔST(M2) is used as compound M2, the lowest excited triplet state T1(M2) of compound M2 can undergo reverse intersystem crossing to the lowest excited singlet state S1(M2) due to thermal energy. By utilizing the reverse intersystem crossing that occurs in compound M2, luminescence such as that shown in (i) or (ii) below can be observed. (i) If the luminescent layer does not contain a fluorescent dopant for the lowest excited singlet state S1(M2) of compound M2, then emission from the lowest excited singlet state S1(M2) of compound M2 can be observed. (ii) If the light-emitting layer contains a fluorescent dopant (fluorescent compound M1 in the third or fourth embodiment) in which the lowest excited singlet state S1 (M2) of compound M2 is smaller than the lowest excited singlet state S1 of compound M2, then light emission from the fluorescent dopant can be observed. Furthermore, in the organic EL element of this embodiment, the light emission shown in (i) above can be observed. In the organic EL element of the third or fourth embodiment described above, the light emission shown in (ii) above can be observed.

[0429] • Compound content in the luminescent layer The content of compounds M2 and M3 contained in the light-emitting layer is preferably within the following ranges, for example. The content of compound M2 is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, even more preferably 10% by mass or more and 60% by mass or less, and even more preferably 20% by mass or more and 60% by mass or less. The content of compound M3 is preferably 10% by mass or more and 90% by mass or less. The upper limit for the total content of compound M2 and compound M3 in the light-emitting layer is 100% by mass. The light-emitting layer may contain only one type of compound M2, or two or more types. The light-emitting layer may contain only one type of compound M3, or two or more types.

[0430] The organic EL element according to the fifth embodiment contains, in its light-emitting layer, the compound of the first embodiment as compound M2 and compound M3 having a lower minimum excitation singlet energy greater than that of compound M2. Since the organic EL element according to the fifth embodiment contains the compound of the first embodiment (compound M2) which has a small ionization potential, hole injection from the hole transport layer side is improved. Therefore, according to the fifth embodiment, a high-performance organic EL element that can be driven at a lower voltage can be provided.

[0431] [Sixth 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.

[0432] [Variations of the Embodiment] Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that can achieve the objectives of the present invention are included in the present invention.

[0433] 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.

[0434] 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 barrier layer prevents excitons generated in the light-emitting layer from moving to layers closer to the electrodes (for example, electron transport layers and hole transport layers). It is preferable that the light-emitting layer and the barrier layer are bonded together.

[0435] 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]

[0436] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples.

[0437] <Compound> The structure of the compound represented by general formula (1) used in the manufacture of the organic EL element according to Example 1, and the structure of the compound represented by general formula (1) according to the synthesis example are shown below.

[0438] [ka]

[0439] The structures of the comparative compounds used in the manufacture of the organic EL elements related to Comparative Examples 1 to 3 are shown below.

[0440] [ka]

[0441] The structures of other compounds used in the organic EL elements in Example 1 and Comparative Examples 1-3 are shown below.

[0442] [ka]

[0443] <Fabrication of Organic EL Devices (1)> Organic EL elements were fabricated and evaluated as follows.

[0444] [Example 1] A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25mm x 75mm x 1.1mm thick ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 1 minute. The film thickness of the ITO transparent electrode was set to 130 nm. After cleaning, the glass substrate with transparent electrode lines was mounted in the substrate holder of the vacuum deposition apparatus. First, compound HT-1 and compound HI were co-deposited onto the surface on which the transparent electrode lines were formed, covering the transparent electrodes, 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 HI was set to 3% by mass. Next, compound HT-1 was deposited onto this hole injection layer to form a first hole transport layer with a thickness of 90 nm. Next, compound HT-2 was deposited onto this first hole transport layer to form a second hole transport layer with a thickness of 30 nm. Next, compound M3-1 (as compound M3) and compound A-1 (as compound M2) were co-deposited onto this second hole transport layer to form a light-emitting layer with a thickness of 25 nm. The proportion of compound M3-1 in the light-emitting layer was set to 75% by mass, and the proportion of compound A-1 was set to 25% by mass. Next, compound ET-1 was deposited onto this light-emitting layer to form a hole barrier layer with a thickness of 5 nm. Next, compound ET-2 and Liq were co-deposited onto this hole barrier layer to form an electron transport layer with a thickness of 50 nm. The proportion of compound ET-2 in the electron transport layer was set to 50% by mass, and the proportion of Liq was set to 50% by mass. Liq is an abbreviation for (8-Quinolinolato)lithium. Next, metallic ytterbium (Yb) was deposited onto this electron transport layer to form an electron injection layer with a thickness of 1 nm. Then, metallic aluminum (Al) was deposited onto this electron injection layer to form a metallic Al cathode with a film thickness of 80 nm. In this manner, the organic EL element according to Example 1 was fabricated.

[0445] The element configuration of Example 1 is schematically shown below. ITO(130) / HT-1:HI(10,97%:3%) / HT-1(90) / HT-2(30) / M3-1:A-1(25,75%:25%) / ET-1(5) / ET-2:Liq(50,50%:50%) / Yb(1) / Al(80) The numbers in parentheses indicate the film thickness (in nm). Similarly, within the parentheses, the percentage figures (97%:3%) represent the proportion (mass%) of compound HT-1 and compound HI in the hole injection layer, the percentage figures (75%:25%) represent the proportion (mass%) of compound M3-1 and compound A-1 in the light-emitting layer, and the percentage figures (50%:50%) represent the proportion (mass%) of compound ET-2 and Liq in the electron transport layer.

[0446] [Comparative Examples 1-3] The organic EL elements of Comparative Examples 1 to 3 were prepared in the same manner as in Example 1, except that compound A-1, which was used as compound M2 in the light-emitting layer of Example 1, was replaced with one of the compounds M2 listed in Table 1.

[0447] <Evaluation of Organic EL Devices> The organic EL elements fabricated in Example 1 and Comparative Examples 1-3 were evaluated as follows. The evaluation results are shown in Table 1. Note that the comparative compounds used in Comparative Examples 1-3 (Ref-1-Ref-3) do not correspond to compound M2, but for convenience, they are listed in the same column as compound M2.

[0448] (Drive voltage) Current density is 10 mA / cm² 2 The voltage (in volts) was measured when current was passed between the anode and cathode in such a manner.

[0449] (CIE1931 chromaticity) The current density of the organic EL element is 10.00 mA / cm². 2 The CIE1931 chromaticity coordinates (x, y) were measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied to the element in such a manner.

[0450] (External quantum efficiency EQE) The fabricated organic EL element has a current density of 10.00 mA / cm². 2 The spectral radiance spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) when a voltage was applied in such a manner. From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that lambassian emission occurred. Furthermore, the "EQE (relative value)" (unit: %) was calculated based on the measured values ​​of EQE for each example, as well as the following formula (Equation 2X). EQE (relative value) = (EQE of each example / EQE of comparison example 2) × 100 ... (Equation 2 ×)

[0451] (Maximum peak wavelength λ) EL (and emission half-width FWHM) The current density of the organic EL element is 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 to the element in such a manner. From the obtained spectral radiance spectrum, the maximum peak wavelength λ was determined. EL The emission width at half maximum (FWHM) was calculated (in nm). FWHM is an abbreviation for Full Width at Half Maximum.

[0452] [Table 1]

[0453] As shown in Table 1, the organic EL element of Example 1 contains a compound represented by general formula (1) in its light-emitting layer, and it was confirmed that it can be driven at a lower voltage compared to the organic EL elements of Comparative Examples 1 to 3.

[0454] <Evaluation of Compounds> The following evaluations were performed on compound A-1 and comparative compounds Ref-1 to Ref-3 used in the light-emitting layer of each example of an organic EL device.

[0455] (Maximum peak wavelength of the compound) The maximum peak wavelength λ of the compound was measured by the following method. The evaluation results are shown in Table 2. A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell. The emission spectrum of this sample (vertical axis: emission intensity, horizontal axis: wavelength) was measured at room temperature (300 K). In this example, the emission spectrum was measured using a spectrofluorometer (instrument name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here. In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity was defined as the maximum peak wavelength λ.

[0456] (Ionization potential Ip) The ionization potential Ip of the compound to be measured was calculated using the following formula (equation Y1). The evaluation results are shown in Tables 1 and 2. (Number Y1):Ip=-1.40×(Eox-Efc)-4.60eV In the formula (Equation Y1), Eox and Efc are as follows: Eox: First oxidation potential (DPV, positive scan) of the object being measured. Efc: First oxidation potential (DPV, positive scan) of ferrocene (approx. +0.55V vs Ag / AgCl) The oxidation-reduction potential was measured using differential pulsed voltammetry (DPV) with an electrochemical analyzer (ALS CH1852D). The sample solution used for the measurement was prepared by dissolving the substance to be measured in N,N-dimethylformamide (DMF) as the solvent to a concentration of 1.0 mmol / L, and then dissolving tetrabutylammonium hexafluorophosphate (TBHP) as the supporting electrolyte to a concentration of 100 mmol / L. A glassy carbon electrode was used as the working electrode, and a platinum (Pt) electrode was used as the counter electrode.

[0457] (Delayed fluorescence of compounds) Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in Figure 1. Compound A-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. After compound A-1 is excited by pulsed light (light irradiated from a pulsed laser) at a wavelength absorbed by the compound, there are two types of emission: prompt emission (immediate emission) which is observed immediately from the excited state, and delayed 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 delayed 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. Comparative compounds Ref-1 to Ref-3 were measured in the same manner as compound A-1. For compound A-1 and comparative compounds Ref-1 to Ref-3, it was confirmed that the amount of delayed emission was 5% or more of the amount of prompt emission. Specifically, for compound A-1 and comparative compounds Ref-1 to Ref-3, X D / X P The value was 0.05 or higher.

[0458] (Lowest excitation singlet energy S1) The lowest excited singlet energy S1 of the target compound was measured using the solution method described above. The evaluation results are shown in Tables 1 and 2.

[0459] (Energy gap T) 77K and ΔST) 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. For compound A-1 and comparative compounds Ref-1 to Ref-3, the energy gap T 77K ΔST was determined from the value of and the value of the lowest excitation singlet energy S1 mentioned above. The evaluation results are shown in Table 2. In the table, "<0.01" indicates that ΔST is less than 0.01 eV.

[0460] (k RISC ) Using the measured amounts of Prompt emission and Delay emission as described above, the k of the target compound was measured according to the method described in “Chem. Phys. Lett., 644, 16, 62-67 2016” (Reference 2). RISC The calculation was performed. The results are shown in Table 2.

[0461] [Table 2]

[0462] As shown in Table 2, compound A-1 in Example 1 is a compound represented by general formula (1), and compared to comparative compounds Ref-1 to Ref-3 in Comparative Examples 1 to 3, k RISC It improved.

[0463] <Examples of synthesis> [Synthesis Example 1: Synthesis of Compound A-1] Compound A-1 was synthesized using the following synthetic route.

[0464] [ka]

[0465] (Synthesis of intermediate MA) Under a nitrogen atmosphere, 4,6-dibromodibenzo[b,d]thiophene (22 g, 64.3 mmol) and THF (tetrahydrofuran) (643 mL) were placed in a 1000 mL three-necked flask. The materials in the three-necked flask were cooled to -78°C using a dry ice / acetone bath, and then n-butyllithium solution (2.7 M hexane solution) (24.47 mL, 67.5 mmol) was added dropwise. The mixture was stirred at -78°C for 2 hours, and then iodine (I2) (19.59 g, 77 mmol) was added, and the mixture was slowly returned to room temperature while stirring. After adding sodium bisulfite aqueous solution (100 mL), the organic layer was extracted with ethyl acetate, the organic layer was recovered and dried over magnesium sulfate, and the organic solvent was removed under reduced pressure using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain a white solid (23 g, yield 92%). ASAP-MS analysis (mass spectrometry using an atmospheric pressure solid sample probe) identified the white solid as the intermediate MA. ASAP-MS is an abbreviation for Atmospheric Pressure Solid Analysis Probe Mass Spectrometry.

[0466] (Synthesis of intermediate MB) Under a nitrogen atmosphere, a 500 mL three-necked flask was filled with intermediate MA (22.5 g, 57.8 mmol), (2-(methylthio)phenylboronic acid (9.72 g, 57.8 mmol), tripotassium phosphate (30.7 g, 145 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.406 g, 1.735 mmol), 1,4-dioxane (116 mL), and deionized water (50 mL). The mixture was stirred at room temperature for 4 hours. After stirring, the organic layer was collected using a separatory funnel. The organic solvent was then removed under reduced pressure using a rotary evaporator. The resulting compound was purified by silica gel column chromatography to obtain a white solid (20 g, 90% yield). ASAP-MS analysis identified the white solid as intermediate MB.

[0467] (Synthesis of intermediate MC) Under a nitrogen atmosphere, intermediate MB (18.75 g, 48.7 mmol) and dichloromethane (97 mL) were placed in a 300 mL three-necked flask and cooled to 0°C using an ice bath. Then, metachloroperbenzoic acid (30% aqueous) (12.00 g, 48.7 mmol) was added and the mixture was stirred at 0°C for 4 hours. After stirring, 50 mL of aqueous sodium bicarbonate solution was added and the organic layer was separated. The organic layer was collected and removed under reduced pressure using a rotary evaporator to obtain a white solid (19 g, yield 97%). The white solid was identified as intermediate MC by ASAP-MS analysis.

[0468] (Synthesis of intermediate MD) Under a nitrogen atmosphere, intermediate MC (19 g, 47.4 mmol) and CH2Cl2 (415 mL) were placed in a 1000 mL three-necked flask and cooled to 0°C using an ice bath. Then, trifluoromethanesulfonic anhydride (16.74 mL, 100 mmol) was added and the mixture was stirred at 0°C for 2 hours. After stirring, 50 mL of aqueous sodium hydroxide solution was added, the temperature was raised to 40°C, and the mixture was heated and stirred for 3 hours. The organic layer was collected and removed under reduced pressure using a rotary evaporator to obtain a white solid (13 g, yield 71%). The white solid was identified as intermediate MD by ASAP-MS analysis.

[0469] (Synthesis of intermediate ME) Under a nitrogen atmosphere, intermediate MD (13.1 g, 35.5 mmol), t-butyl carbamate (4.99 g, 42.6 mmol), palladium(II) diacetate (0.239 g, 1.064 mmol), XPhos (1.015 g, 2.128 mmol), cesium carbonate (16.18 g, 49.7 mmol), and 1,4-dioxane (118 mL) were added to a 300 mL three-necked flask and heated, stirred, and refluxed for 8 hours. After cooling to room temperature, the organic layer was extracted with ethyl acetate and recovered. The organic solvent was then removed under reduced pressure using a rotary evaporator. 100 mL of THF and 50 mL of hydrochloric acid were added to the obtained compound and heated and stirred. The THF layer was recovered, and the organic solvent was removed under reduced pressure again using a rotary evaporator to obtain a white solid (9 g, yield 83%). ASAP-MS analysis identified the white solid as the intermediate ME.

[0470] (Synthesis of intermediate MF) Under a nitrogen atmosphere, 3-bromo-4-iododibenzo[b,d]thiophene (11 g, 28.3 mmol), intermediate ME (8.64 g, 28.3 mmol), Pd2(dba)3 (0.388 g, 0.424 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(triphenyl-14-phosphane) (0.622 g, 0.848 mmol), sodium t-butoxide (4.08 g, 42.4 mmol), and toluene (94 mL) were added to a 200 mL three-necked flask and heated and stirred at 100 °C for 8 hours. After cooling to room temperature (25 °C), the precipitated solid was filtered and washed with 200 mL of toluene to obtain a white solid (15 g, yield 94%). By ASAP-MS analysis, the white solid was identified as intermediate MF.

[0471] (Synthesis of intermediate MG) Under a nitrogen atmosphere, intermediate MF (14 g, 24.71 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.420 g, 0.988 mmol), palladium(II) acetate (0.111 g, 0.494 mmol), potassium carbonate (7.51 g, 54.4 mmol), and DMAc (N,N-dimethylacetamide) (82 mL) were added to a 300 mL three-necked flask and stirred at 150 °C for 4 hours. After cooling to room temperature (25 °C), the precipitated solid was filtered and washed with methanol and toluene to obtain a white solid (12 g, yield 80%). ASAP-MS analysis identified the white solid as intermediate MG.

[0472] (Synthesis of intermediate MH) Under a nitrogen atmosphere, 3',5'-difluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitride (6.50 g, 20.54 mmol), intermediate MG (9.5 g, 19.56 mmol), cesium fluoride (8.91 g, 58.7 mmol), and DMF (N,N-dimethylformamide) (65.2 mL) were placed in a 300 mL round-bottom flask and stirred at room temperature for 12 hours. 200 mL of deionized water was added to the reaction solution, and the precipitated solid was filtered off. Purification by silica gel column chromatography yielded a yellow solid (11 g, yield 72%). ASAP-MS analysis identified the yellow solid as intermediate MH.

[0473] (Synthesis of compound A-1) Under a nitrogen atmosphere, intermediate MH (3 g, 3.84 mmol), cesium fluoride (1.457 g, 9.59 mmol), 9H-carbazole (1.155 g, 6.91 mmol), and DMF (77 mL) were placed in a 300 mL round-bottom flask and stirred at 40°C for 6 hours. 200 mL of deionized water was added to the reaction solution, and the precipitated solid was filtered off. Purification by silica gel column chromatography yielded a yellow solid (3.1 g, yield 87%). ASAP-MS analysis identified the yellow solid as compound A-1.

[0474] [Synthesis Example 2: Synthesis of Compound A-2] Compound A-2 was synthesized using the following synthetic route.

[0475] [ka]

[0476] (Synthesis of intermediate MI) Under a nitrogen atmosphere, 1-bromodibenzo[b,d]furan-4-amine (50 g, 191 mmol) and hydrochloric acid (10%) (118 mL, 382 mmol) were placed in a 500 mL three-necked flask and stirred at 0°C for 30 minutes using an ice bath. Then, while maintaining 0°C, sodium nitrite (13.16 g, 191 mmol) was added and stirred at 0°C for 2 hours. Next, potassium iodide (38.0 g, 229 mmol) was added and the mixture was slowly returned to room temperature. The precipitated solid was filtered and washed with deionized water. The resulting compound was purified by silica gel column chromatography to obtain a white solid (62 g, yield 87%). By ASAP-MS analysis, the white solid was identified as the intermediate MI.

[0477] (Synthesis of intermediate MJ) Under a nitrogen atmosphere, a 500 mL three-necked flask was filled with intermediate MI (35 g, 94 mmol), (2-(methylthio)phenyl)boronic acid (16.55 g, 99 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (1.521 g, 1.877 mmol), tripotassium phosphate (43.8 g, 206 mmol), 1,4-dioxane (156 mL), and deionized water (80 mL), and the mixture was stirred at room temperature for 4 hours. After stirring, the organic layer was collected using a separatory funnel. The organic solvent was then removed under reduced pressure using a rotary evaporator. The resulting compound was purified by silica gel column chromatography to obtain a white solid (33 g, 95% yield). ASAP-MS analysis identified the white solid as intermediate MJ.

[0478] (Synthesis of intermediate MK) Under a nitrogen atmosphere, intermediate MJ (33 g, 89 mmol) and dichloromethane (97 mL) were placed in a 300 mL three-necked flask and cooled to 0°C using an ice bath. Then, metachloroperbenzoic acid (30% aqueous) (22 g, 127 mmol) was added and the mixture was stirred at 0°C for 4 hours. After stirring, 50 mL of aqueous sodium bicarbonate solution was added and the organic layer was separated. The organic layer was collected and removed under reduced pressure using a rotary evaporator to obtain a white solid (32 g, yield 93%). By ASAP-MS analysis, the white solid was identified as intermediate MK.

[0479] (Synthesis of intermediate ML) Under a nitrogen atmosphere, intermediate MK (32 g, 83 mmol) and dichloromethane (400 mL) were placed in a 1000 mL three-necked flask and cooled to 0°C using an ice bath. Then, trifluoromethanesulfonic anhydride (16.74 mL, 100 mmol) was added and the mixture was stirred at 0°C for 2 hours. After stirring, 50 mL of aqueous sodium hydroxide solution was added, the temperature was raised to 40°C, and the mixture was heated and stirred for 3 hours. The organic layer was collected and removed under reduced pressure using a rotary evaporator to obtain a white solid (24 g, yield 82%). By ASAP-MS analysis, the white solid was identified as intermediate ML.

[0480] (Synthesis of intermediate MM) Under a nitrogen atmosphere, intermediate ML (21 g, 60 mmol), chlorotrimethylsilane (15.2 mL, 120 mmol), and THF (120 mL) were placed in a 500 mL three-necked flask. The materials in the three-necked flask were cooled to -78°C using a dry ice / acetone bath, and then 45 mL of lithium diisopropylamide (2 M, THF solution) was added dropwise. The mixture was stirred at -78°C for 2 hours, then returned to room temperature and stirred for another 2 hours. After stirring, water (100 mL) was added to the three-necked flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline solution, dried over magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, followed by the dropwise addition of iodine monochloride (25 g, 150 mmol) at 0°C, and the mixture was stirred at room temperature for 6 hours. A saturated sodium bisulfite aqueous solution (100 mL) was added, and the precipitated solid was filtered off. The resulting compound was purified by silica gel column chromatography to obtain a white solid (19 g, yield 67%). By ASAP-MS analysis, the white solid was identified as intermediate MM.

[0481] (Synthesis of intermediate MN) Under a nitrogen atmosphere, dibenzo[b,d]thiophene-4-amine (0.915 g, 4.59 mmol), intermediate MM (2.2 g, 4.59 mmol), Pd2(dba)3 (0.126 g, 0.138 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(triphenyl-14-phosphane) (0.202 g, 0.275 mmol), and sodium t-butoxide (0.662 g, 6.89 mmol) were added to a 100 mL three-necked flask and heated and stirred at 100 °C for 8 hours. After cooling to room temperature (25 °C), the precipitated solid was filtered and washed with 200 mL of toluene to obtain a white solid (2.2 g, yield 87%). By ASAP-MS analysis, the white solid was identified as intermediate MN.

[0482] (Synthesis of intermediate MO) Under a nitrogen atmosphere, intermediate MN (2.2 g, 4.00 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.051 g, 0.120 mmol), palladium(II) acetate (0.013 g, 0.060 mmol), potassium carbonate (1.160 g, 8.39 mmol), and DMAc (13.32 mL) were added to a 300 mL three-necked flask and stirred at 150 °C for 4 hours. After cooling to room temperature (25 °C), the precipitated solid was filtered and washed with methanol and toluene to obtain a white solid (1 g, yield 53%). ASAP-MS analysis identified the white solid as intermediate MO.

[0483] (Synthesis of intermediate MP) Under a nitrogen atmosphere, intermediate MO (0.9 g, 1.917 mmol), 3',5'-difluoro-[1,1':4',1''-terphenyl]-2',6'-dicarbonitric acid (0.637 g, 2.012 mmol), and cesium fluoride (0.873 g, 5.75 mmol) were placed in a 50 mL three-necked flask and stirred at room temperature for 12 hours. 20 mL of deionized water was added to the reaction solution, and the precipitated solid was filtered off. Purification by silica gel column chromatography yielded a yellow solid (1.2 g, yield 82%). ASAP-MS analysis identified the yellow solid as intermediate MP.

[0484] (Synthesis of compound A-2) Under a nitrogen atmosphere, intermediate MP (3 g, 3.84 mmol), cesium fluoride (1.457 g, 9.59 mmol), 9H-carbazole (1.155 g, 6.91 mmol), and DMF (77 mL) were placed in a 300 mL round-bottom flask and stirred at 40°C for 6 hours. 200 mL of deionized water was added to the reaction solution, and the precipitated solid was filtered off. Purification by silica gel column chromatography yielded a yellow solid (3.1 g, yield 87%). ASAP-MS analysis identified the yellow solid as compound A-2.

[0485] [Comparative Synthesis Example 1: Synthesis of Compound Ref-1] The intermediate Mb was synthesized using the following synthetic route.

[0486] [ka]

[0487] (Synthesis of intermediate Ma) Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (165 g, 607 mmol), cyanocopper(I) (120 g, 1335 mmol), and NMP (N-methyl-2-pyrrolidone) (800 mL) were placed in a 2 L three-necked flask and stirred at 150 °C for 5 hours. 1 L of methylene chloride was added to the reaction mixture, filtered through Celite, and the filtrate was concentrated using an evaporator. The resulting solid was purified by silica gel chromatography to obtain a white solid (58 g, yield 58%). The obtained white solid was identified as the intermediate Ma by GC-MS analysis (mass spectrometry using gas chromatography). GC-MS is an abbreviation for Gas Chromatograph Mass Spectometer.

[0488] (Synthesis of intermediate Mb) Under a nitrogen atmosphere, intermediate Ma (20 g, 122 mmol), potassium carbonate (33.7 g, 244 mmol), palladium(II) diacetate (1.368 g, 6.09 mmol), tricyclohexylphosphine (5.13 g, 18.28 mmol), bromobenzene (31.9 mL, 305 mmol), 2-ethylhexanoic acid (7.81 mL, 48.7 mmol), and xylene (250 mL) were placed in a 500 mL three-necked flask and stirred at 100 °C for 5 hours. 200 mL of methylene chloride was added to the reaction solution and passed through Celite. Methylene chloride was removed from the resulting solution, and the precipitated solid was filtered. The obtained solid was purified by silica gel column chromatography to obtain a white solid (12 g, yield 31%). By GC-MS analysis, the white solid was identified as intermediate Mb.

[0489] The intermediate Me was synthesized using the following synthesis route.

[0490] [ka]

[0491] (Synthesis of intermediate Mc) Under a nitrogen atmosphere, 26.3 g, 100 mmol of 3-bromodibenzothiophene, 33 g, 300 mmol of chlorotrimethylsilane, and 150 mL of THF were placed in a 500 mL three-necked flask. The materials in the three-necked flask were cooled to -78°C using a dry ice / acetone bath, and then 125 mL of lithium diisopropylamide (2 M THF solution) was added dropwise. The mixture was stirred at -78°C for 2 hours, then allowed to return to room temperature and stirred for another 2 hours. After stirring, 100 mL of water was added to the three-necked flask, and the organic layer was extracted with ethyl acetate. The extracted organic layer was washed with water and saline solution, dried with magnesium sulfate, and the solvent was removed under reduced pressure using a rotary evaporator. 200 mL of dichloromethane was added to the resulting liquid, followed by the dropwise addition of 49 g, 300 mmol of iodine monochloride at 0°C, and the mixture was stirred at 40°C for 6 hours. The mixture was allowed to return to room temperature, and 100 mL of saturated sodium bisulfite aqueous solution was added. The organic layer was extracted with dichloromethane, washed with water and saline solution, dried over magnesium sulfate, and concentrated using a rotary evaporator. The compound obtained after concentration was purified by silica gel column chromatography to obtain a white solid (28 g, 72 mmol, yield 72%). By GC-MS analysis, the white solid was identified as the intermediate Mc.

[0492] (Synthesis of intermediate Md) Under a nitrogen atmosphere, intermediate Mc (24.5 g, 63.0 mmol), dibenzo[b,d]thiophene-4-amine (12.55 g, 63.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.865 g, 0.945 mmol), Xantphos (1.385 g, 1.889 mmol), sodium t-butoxide (9.08 g, 94 mmol), and 210 mL of toluene were added to a 500 mL three-necked flask. The mixture was heated and stirred at 60 °C for 8 hours, then cooled to room temperature (25 °C). The precipitated solid was filtered and washed with 200 mL of toluene to obtain a white solid (25 g, yield 86%). GC-MS analysis identified the white solid as intermediate Md.

[0493] (Synthesis of intermediate Me) Under a nitrogen atmosphere, intermediate Md (9.5 g, 20.7 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.36 g, 0.82 mmol), palladium(II) acetate (0.093 g, 0.41 mmol), potassium carbonate (5.8 g, 42 mmol), and 60 mL of DMAc were added to a 200 mL three-necked flask. The mixture was stirred at 160 °C for 10 hours and then cooled to room temperature (25 °C). The precipitated solid was filtered and washed with acetone to obtain a white solid (6.9 g, yield 86%). ASAP-MS analysis identified the white solid as intermediate Me.

[0494] Compound Ref-1 was synthesized using the following synthetic route.

[0495] [ka]

[0496] (Synthesis of intermediate Mf) Under a nitrogen atmosphere, intermediate Mb (3.0 g, 9.48 mmol), intermediate Me (3.6 g, 9.5 mmol), potassium carbonate (2.6 g, 19 mmol), and 50 mL of DMF were placed in a 200 mL three-necked flask and stirred at 100 °C for 4 hours. 100 mL of deionized water was added to the reaction solution, and the precipitated solid was filtered off. The filtered solid was purified by silica gel column chromatography to obtain a yellow solid (4.1 g, yield 64%). By ASAP-MS analysis, the yellow solid was identified as intermediate Mf.

[0497] (Synthesis of compound Ref-1) Under a nitrogen atmosphere, 9H-carbazole (0.809 g, 2.96 mmol), sodium hydride (containing 40% by mass oil) (0.14 g, 3.55 mmol), and 15 mL of DMF were placed in a 100 mL three-necked flask and stirred at 0°C for 30 minutes. Next, intermediate Mf (2 g, 2.96 mmol) was added to the reaction mixture and stirred at room temperature for 2 hours. 50 mL of water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain a yellow solid (1.6 g, yield 58%). By ASAP-MS analysis, the yellow solid was identified as compound Ref-1. [Explanation of Symbols]

[0498] 1...Organic EL element, 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】 (In the above general formula (1), CN is a cyano group, D １１ These are groups that are independently represented by the following general formulas (10a) and (10b), D １２ These are, independently, groups represented by the following general formulas (11), (12), or (13): R is independent of each other, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution 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 group 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 ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, However, at least one R is a substituent. k is 1, 2, or 3. m is 0, 1, or 2. n is 1, 2, or 3. k + m + n is 4, When k is 2 or 3, multiple D １１ They are either identical or different from each other. When m is 2, multiple D １２ They are either identical or different from each other. When n is 2 or 3, multiple Rs are either identical or different from one another. 【Chemistry 2】 (In the above general formula (10a), At positions a1, a2, a3, or a4, the position of b in the general formula (10b) is contracted. * indicates the bond position with the benzene ring in the general formula (1) above. In the above general formula (10b), The position of b is contracted to the positions of a1, a2, a3, or a4 in the general formula (10a), X is an oxygen atom, a sulfur atom, N(R) ３ ), or C (R ４ ) (Caution ５ ) and R ４ and R ５ That 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 ３ R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted condensed ring. ４ , and R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted condensed ring ５ Each of them operates independently. hydrogen atom, Substituted or unsubstituted ring-forming aryl groups with 6 to 30 carbon atoms, A heterocyclic group with 5 to 30 substituted or unsubstituted ring-forming atoms, Substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, -Si(R ９１１ ) (Caution ９１２ ) (Caution ９１３ ) a base represented by -O-(R ９１４ ) a base represented by -S-(R ９１５ A base represented by ) or -N(R) ９１６ ) (Caution ９１７ It is a base represented by ), The group represented by the general formula (10a) is a substituent R １０ａ Having or not having, R １０ａ If multiple R １０ａ They are either identical or different from each other. Multiple R １０ａ 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, The group represented by the general formula (10b) is a substituent R １０ｂ Having or not having, R １０ｂ If multiple R １０ｂ They are either identical or different from each other. Multiple R １０ｂ 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. １０ａ , and R that does not form a substituted or unsubstituted monoring and does not form a substituted or unsubstituted condensed ring １０ｂ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution 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 ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, It is a heterocyclic group with 5 to 50 ring-forming atoms, either substituted or unsubstituted. 【Transformation 3】 (R in the general formula (11) above) １ ~R ８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (12), R １１ ~R １８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, In the above general formula (13), R １１１ ~R １１８ Of the sets of two or more adjacent items, one or more sets are They combine with each other to form a monoring, either substituted or unsubstituted, They bond to each other to form substituted or unsubstituted fused rings, or They do not bind to each other, R does not form a substituted or unsubstituted monoring in the general formula (11) and does not form a substituted or unsubstituted fused ring. １ ~R ８ R that does not form a substituted or unsubstituted monoring in the general formula (12) and does not form a substituted or unsubstituted condensed ring. １１ ~R １８ Furthermore, R that does not form a substituted or unsubstituted monoring in the general formula (13) and does not form a substituted or unsubstituted condensed ring. １１１ ~R １１８ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ) a base represented by -N(R) ９０６ ) (Caution 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 ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, In the above general formula (12) and the above general formula (13), Rings A, B, and C are each independently ring structures represented by the following general formula (14) or (15): Rings A, B, and C condense with adjacent rings at any position. p, px, and py are each independently 1, 2, 3, or 4. When p is 2, 3, or 4, the multiple rings A are either identical or different from each other. If px is 2, 3, or 4, the multiple rings B are either identical or different from each other. If py is 2, 3, or 4, the multiple rings C are either identical or different from one another. In the above general formulas (11) to (13), the asterisk (*) indicates the bond position with the benzene ring in the above general formula (1). 【Chemistry 4】 (In the above general formula (14), r is 0, 2, or 4. When r is 2 or 4, a plurality of R １９ are the same as or different from each other, When r is 2 or 4, multiple R １９ 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 a substituted or unsubstituted monoring and does not form a substituted or unsubstituted fused ring. １９ teeth, hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, Substituted or unsubstituted haloalkyl groups with 1 to 50 carbon atoms, Substituted or unsubstituted alkenyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted alkynyl groups having 2 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, -Si(R ９０１ ) (Caution ９０２ ) (Caution ９０３ ) a base represented by -O-(R ９０４ ) a base represented by -S-(R ９０５ ), a group represented by -N(R) ９０６ ) (Caution 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 ) (Caution ９３２ ) a base represented by -Ge(R) ９３３ ) (Caution ９３４ ) (Caution ９３５ ) a base represented by -B(R) ９３６ ) (Caution ９３７ ) a base represented by A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, In the above general formula (15), X １ is a sulfur atom or an oxygen atom, Multiple R １９ They are either identical or different from each other. Multiple X １ They are either identical or different to one another. (In the general formula, 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 having 1 to 50 carbon atoms, Substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, A heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms, R 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.

2. The groups represented by the general formulas (10a) and (10b) are the groups represented by the following general formulas (10A-1) or (10A-2), The group represented by the general formula (10A-1) or (10A-2) is Substituent R １０ａ Having or not having, Substituent R １０ｂ Having or not having The compound according to claim 1. 【Transformation 5】 (In the above general formulas (10A-1) and (10A-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R １０ａ and R １０ｂ These are the substituents R in the general formulas (10a) and (10b), respectively. １０ａ and R １０ｂ (This is synonymous with...)

3. The groups represented by the general formulas (10a) and (10b) are the groups represented by the following general formulas (10B-1) or (10B-2), The group represented by the general formula (10B-1) or (10B-2) is Substituent R １０ａ Having or not having, Substituent R １０ｂ Having or not having The compound according to claim 1. 【Transformation 6】 (In the above general formulas (10B-1) and (10B-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R １０ａ and R １０ｂ These are the substituents R in the general formulas (10a) and (10b), respectively. １０ａ and R １０ｂ (This is synonymous with...)

4. The groups represented by the general formulas (10a) and (10b) are the groups represented by the following general formulas (10C-1) or (10C-2): The group represented by the general formula (10C-1) or (10C-2) is Substituent R １０ａ Having or not having, Substituent R １０ｂ Having or not having The compound according to claim 1. 【Transformation 7】 (In the above general formulas (10C-1) and (10C-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R １０ａ and R １０ｂ These are the substituents R in the general formulas (10a) and (10b), respectively. １０ａ and R １０ｂ (This is synonymous with...)

5. The groups represented by the general formulas (10a) and (10b) are the groups represented by the following general formulas (10D-1) or (10D-2): The group represented by the general formula (10D-1) or (10D-2) is Substituent R １０ａ Having or not having, Substituent R １０ｂ Having or not having The compound according to claim 1. 【Transformation 8】 (In the above general formulas (10C-1) and (10C-2), * is equivalent to * in the above general formula (10a), X is equivalent to X in the above general formula (10b), and substituent R １０ａ and R １０ｂ These are the substituents R in the general formulas (10a) and (10b), respectively. １０ａ and R １０ｂ (This is synonymous with...)

6. R is independent of each other, A substituted or unsubstituted ring-forming aryl group having 6 to 18 carbon atoms, or These are heterocyclic groups with 5 to 18 substituted or unsubstituted ring-forming atoms. The compound according to any one of claims 1 to 5.

7. R is independent of each other, A substituted or unsubstituted phenyl group, A substituted or unsubstituted carbazolyl group, The compound according to any one of claims 1 to 6.

8. X is a sulfur atom. The compound according to any one of claims 1 to 7.

9. The compound represented by the general formula (1) is represented by the following general formulas (110), (120), or (130): The compound according to any one of claims 1 to 8. 【Chemistry 9】 (In the above general formulas (110), (120), and (130), D １１ , D １２ R, k, m, and n are, respectively, D in the general formula (1) １１ , D １２ (This is synonymous with R, k, m, and n.)

10. k is 1, m is 1, and n is 2. The compound according to any one of claims 1 to 9.

11. The compound represented by the general formula (1) is represented by the following general formulas (126A), (127A), or (127B): The compound according to any one of claims 1 to 10. 【Chemistry 10】 (In the above general formulas (126A), (127A), and (127B), D １１ D in the general formula (1) is １１ It is synonymous with D １２ D in the general formula (1) is １２ It is synonymous with R １０１ ~R １０４ Each of these terms independently has the same meaning as R in the general formula (1) above.

12. R in the above general formula (11) １ ~R ８ , R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ Furthermore, R in the general formula (14) １９ Each of them operates independently. hydrogen atom, Substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, A substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, or A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms. The compound according to any one of claims 1 to 11.

13. R in the above general formula (11) １ ~R ８ , R in the general formula (12) １１ ~R １８ , R in the general formula (13) １１１ ~R １１８ Furthermore, R in the general formula (14) １９ Each of them operates independently. hydrogen atom, Unsubstituted alkyl groups having 1 to 50 carbon atoms, Unsubstituted ring-forming cycloalkyl groups with 3 to 50 carbon atoms, or Unsubstituted ring-forming aryl groups with 6 to 50 carbon atoms, The compound according to any one of claims 1 to 12.

14. A compound containing the compound described in any one of claims 1 to 13, Materials for organic electroluminescent devices.

15. Anode and, Cathode and, The anode and the cathode are interposed in an organic layer, The organic layer contains a compound according to any one of claims 1 to 13 as compound M2. Organic electroluminescent element.

16. The organic layer has at least one light-emitting layer, The light-emitting layer contains the compound M2. The organic electroluminescent element according to claim 15.

17. The light-emitting layer further comprises compound M1, The lowest singlet excitation energy S of compound M1 １ (M1) and the lowest excitation singlet energy S of compound M2. １ (M2) and satisfy the following relationship (Equation 1): The organic electroluminescent element according to claim 16. S １ (M2) > S １ (M1)…(Number 1)

18. The light-emitting layer further comprises compound M3, The lowest singlet excitation energy S of compound M2 １ (M2) and the lowest excitation singlet energy S of compound M3. １ (M3) and satisfy the following relationship (Equation 2): The organic electroluminescent element according to claim 16 or claim 17. S １ (M3) > S １ (M2) … (Number 2)

19. An electronic device equipped with an organic electroluminescent element according to any one of claims 15 to 18.

Images