Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device

Abstract

Provided are compounds represented by any of formulas (11) to (13). R1 to R4 are each independently a group D1 represented by formula (1-1), etc., or a group D2 represented by formula (2-1), etc.; at least one of R1 to R4 is the group D1 and at least one of R1 to R4 is the group D2; with reference to formulas (1-1) and (2-1), X1 is an O atom or S atom and R101 to R110 and R161 to R168 are each independently an H atom or a substituent, etc., wherein in at least one group D1, at least one of R101 to R110 is a group represented by formula (110) or formula (120); Z1 is a C atom, etc.; the ring (B) is an aromatic hydrocarbon ring, etc.; Y12 to Y14 are each independently CR10A, etc.; Y21 to Y24 are each independently CR20A, etc.; Z2 is an aryl group, etc.; and * represents a bonding site.

Description

[Technical field]

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

[0002] When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an "organic EL element"), 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 electroluminescence (EL) elements that use light emitted from singlet excitons are being applied to full-color displays of 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 organic EL elements.

[0003] It is expected that organic EL elements will emit light more efficiently by utilizing triplet excitons in addition to singlet excitons. In this context, highly efficient fluorescent organic EL elements using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as "delayed fluorescence") have been proposed and are being researched. For example, the TADF (Thermally Activated Delayed Fluorescence) mechanism has been studied. The TADF mechanism utilizes the phenomenon in which reverse intersystem crossing from triplet excitons to singlet excitons occurs thermally when a material with a small energy difference (ΔST) between the singlet and triplet levels is used. Thermally activated delayed fluorescence is described, for example, in "Device Properties of Organic Semiconductors" edited by Adachi Chinaya, Kodansha, published April 1, 2012, pp. 261-268. Known examples of compounds that exhibit thermally activated delayed fluorescence (TADF) include compounds in which a donor moiety and an acceptor moiety are bound within the molecule. For example, Patent Document 1 discloses compounds in which dicyanobenzene is substituted with carbazole or the like, benzofurocarbazole, benzothienocarbazole, or the like. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2020 / 022378 Summary of the Invention [Problem to be solved by the invention]

[0005] In order to improve the performance of electronic devices such as displays, there is a demand for further improvement in the performance of organic EL elements. The performance of an organic EL element includes luminous efficiency, and a factor for improving the luminous efficiency is the use of a compound with a high photoluminescence quantum yield (PLQY).

[0006] The present invention aims to provide a compound capable of providing a high-performance organic electroluminescence device. In particular, the present invention aims to provide a compound having a high PLQY. The present invention also aims to provide a material for an organic electroluminescence device containing a compound having a high PLQY, an organic electroluminescence device, and an electronic device equipped with the organic electroluminescence device. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided a compound represented by any one of the following general formulas (11) to (13).

[0008] [ka]

[0009] (In the general formulas (11) to (13), R1 to R4 each independently represent A group D1 represented by any one of the following general formulas (1-1) to (1-6), or A group D2 represented by any one of the following general formulas (2-1) to (2-4): At least one of R1 to R4 is a group D1; At least one of R1 to R4 is a group D2; When a plurality of groups D1 are present, the plurality of groups D1 are the same or different from each other, When a plurality of groups D2 are present, the plurality of groups D2 are the same or different from each other.

[0010] [ka]

[0011] [ka]

[0012] [ka]

[0013] (In the general formulas (1-1) to (1-6), X1 to X6 each independently represent an oxygen atom or a sulfur atom, R 101 ~R 160 each independently represents a hydrogen atom, a substituent, a group represented by the general formula (110), or a group represented by the general formula (120), However, in at least one group D1, R 101 ~R 160 At least one of the above is a group represented by general formula (110) or a group represented by general formula (120), In the general formula (110), Z1 is a constituent atom of ring (B) and is a carbon atom or a nitrogen atom. The ring (B) containing Z1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 30 ring carbon atoms, Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and R 10A are each independently a hydrogen atom or a substituent, or a plurality of R 10A or one or more pairs of adjacent two or more of R are bonded to each other to form a ring, or ring (B) and one R adjacent to ring (B) 10A and R are bonded to each other to form a ring, or a ring (B) and a plurality of R 10A one or more pairs of adjacent two or more of In the general formula (120), The Z2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Y 21 ~Y 24 each independently represents a nitrogen atom or CR 20A and R 20A each independently represents a hydrogen atom or a substituent, Multiple R 20A one or more of adjacent pairs of two or more of Multiple R 10A are the same or different, Multiple R 20A are the same or different, In the general formulae (2-1) to (2-4), R 161 ~R 168 and R 171 ~R 200 are each independently a hydrogen atom or a substituent, R as a substituent other than the group represented by the general formula (110) and the group represented by the general formula (120) in the general formulae (1-1) to (1-6) 101 ~R 160 R as a substituent in the general formula (110) 10A R as a substituent in the general formula (120) 20A and R as a substituent in the general formulae (2-1) to (2-4) 161 ~R 168 and R 171 ~R 200 are each independently Halogen atoms, Cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxy groups, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A group represented by -N(Rz)2, Thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, substituted germanium groups, Substituted phosphine oxide groups, Nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Two Rz in -N(Rz)2 are the same or different, In the general formulae (1-1) to (1-6), * each independently represents a bonding position to a carbon atom of the 6-membered ring in the general formulae (11) to (13), In the general formula (110), * represents a bonding position to a carbon atom of a six-membered ring in the general formulae (1-1) to (1-6), In the general formula (120), * represents a bonding position to a carbon atom of a six-membered ring in the general formulae (1-1) to (1-6), In the general formulae (2-1) to (2-4), * each independently represents a bonding position to a carbon atom of the six-membered ring in the general formulae (11) to (13).

[0014] According to one aspect of the present invention, there is provided a material for an organic electroluminescence device, comprising the compound according to the above-described aspect of the present invention.

[0015] According to one aspect of the present invention, An anode; A cathode; a first organic layer comprised between the anode and the cathode; having the first organic layer comprises a first compound; The first compound is a compound according to one aspect of the present invention. An organic electroluminescent device is provided.

[0016] According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence element according to the above-described aspect of the present invention.

[0017] According to one aspect of the present invention, a compound capable of providing a high-performance organic electroluminescence device can be provided. In particular, a compound having a high PLQY can be provided. According to another aspect of the present invention, a material for an organic electroluminescence device or an organic electroluminescence device containing a compound having a high PLQY can be provided. According to another aspect of the present invention, an electronic device equipped with the organic electroluminescence device can be provided. [Brief description of the drawings]

[0018] FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Figure 1] FIG. 4 is a diagram showing a schematic configuration of an example of an organic electroluminescence element according to a third embodiment of the present invention. [Diagram 2] FIG. 1 is a schematic diagram of an apparatus for measuring transient PL. [Diagram 3] FIG. 13 is a diagram showing an example of an attenuation curve of a transient PL. [Figure 4] FIG. 11 is a diagram showing the energy levels of a first compound and a second compound in an emitting layer of an example of an organic electroluminescence element according to a third embodiment of the present invention, and the relationship of energy transfer. [Diagram 5] FIG. 13 is a diagram showing the energy levels of a first compound, a second compound, and a third compound in an emitting layer of an example of an organic electroluminescence element according to a fourth embodiment of the present invention, and a relationship between energy transfer. [Figure 6] FIG. 13 is a diagram showing the energy levels of a first compound and a fourth compound in an example of an emitting layer of an organic electroluminescence element according to a fifth embodiment of the present invention, and a relationship between energy transfer. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] First Embodiment [Compound] The compound according to this embodiment is a compound represented by any one of the following general formulas (11) to (13).

[0020] [ka]

[0021] (In the general formulas (11) to (13), R1 to R4 each independently represent A group D1 represented by any one of the following general formulas (1-1) to (1-6), or A group D2 represented by any one of the following general formulas (2-1) to (2-4): At least one of R1 to R4 is a group D1; At least one of R1 to R4 is a group D2; When a plurality of groups D1 are present, the plurality of groups D1 are the same or different from each other, When a plurality of groups D2 are present, the plurality of groups D2 are the same or different from each other.

[0022] [ka]

[0023] [ka]

[0024] [ka]

[0025] (In the general formulas (1-1) to (1-6), X1 to X6 each independently represent an oxygen atom or a sulfur atom, R 101 ~R 160 each independently represents a hydrogen atom, a substituent, a group represented by the general formula (110), or a group represented by the general formula (120), However, in at least one group D1, R 101 ~R 160At least one of the above is a group represented by general formula (110) or a group represented by general formula (120), In the general formula (110), Z1 is a constituent atom of ring (B) and is a carbon atom or a nitrogen atom. The ring (B) containing Z1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 30 ring carbon atoms, Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and R 10A are each independently a hydrogen atom or a substituent, or a plurality of R 10A or one or more pairs of adjacent two or more of R are bonded to each other to form a ring, or ring (B) and one R adjacent to ring (B) 10A and R are bonded to each other to form a ring, or a ring (B) and a plurality of R 10A one or more pairs of adjacent two or more of In the general formula (120), The Z2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Y 21 ~Y 24 each independently represents a nitrogen atom or CR 20A and R 20A each independently represents a hydrogen atom or a substituent, Multiple R 20A one or more of adjacent pairs of two or more of Multiple R 10A are the same or different, Multiple R 20A are the same or different, In the general formulae (2-1) to (2-4), R 161 ~R 168 and R 171 ~R200 are each independently a hydrogen atom or a substituent, R as a substituent other than the group represented by the general formula (110) and the group represented by the general formula (120) in the general formulae (1-1) to (1-6) 101 ~R 160 R as a substituent in the general formula (110) 10A R as a substituent in the general formula (120) 20A and R as a substituent in the general formulae (2-1) to (2-4) 161 ~R 168 and R 171 ~R 200 are each independently Halogen atoms, Cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms; a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxy groups, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A group represented by -N(Rz)2, Thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, substituted germanium groups, Substituted phosphine oxide groups, Nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Two Rz in -N(Rz)2 are the same or different, In the general formulae (1-1) to (1-6), * each independently represents a bonding position to a carbon atom of the 6-membered ring in the general formulae (11) to (13), In the general formula (110), * represents a bonding position to a carbon atom of a six-membered ring in the general formulae (1-1) to (1-6), In the general formula (120), * represents a bonding position to a carbon atom of a six-membered ring in the general formulae (1-1) to (1-6), In the general formulae (2-1) to (2-4), * each independently represents a bonding position to a carbon atom of the six-membered ring in the general formulae (11) to (13).

[0026] The present inventors have found that, like the compounds represented by the general formulae (11) to (13), a compound having a high PLQY can be obtained by introducing a specific substituent (a group represented by the general formula (110) or (120)) into the group D1 represented by the general formulae (1-1) to (1-6) substituted on dicyanobenzene. The reason for this will be explained by taking as an example the case where the group D1 in the compound of this embodiment is a group represented by the following general formulas (1-4A) to (1-4C). The general formulas (1-4A) to (1-4C) are examples of the general formula (1-4). The groups represented by the general formulas (1-4A) to (1-4C) are groups in which a specific substituent (the group represented by the general formula (110) or (120)) has been introduced into benzothienocarbazole. The group represented by the general formula (1-4A) is a structure in which a phenyl group is bonded to the ortho position (**) of the benzene ring of the "benzothienocarbazole-benzene structure." In such a structure, the specific substituent (1,1'-biphenyl-2-yl group) introduced into the group D1 is twisted with respect to the benzothienocarbazole plane. In the group represented by the general formula (1-4B), a carbon atom is located at the ortho position (**) of the benzene ring of the "benzothienocarbazole-benzene structure", and the carbon atom is one of the constituent atoms of the naphthalene ring. In such a structure, a specific substituent (1-naphthyl group) introduced into the group D1 is twisted with respect to the benzothienocarbazole plane. In the group represented by the general formula (1-4C), a carbon atom is located at the ortho position (**) of the benzene ring of the "benzothienocarbazole-benzene structure", and the carbon atom is one of the constituent atoms of the dibenzofuran ring. In such a structure, a specific substituent (1-dibenzofuranyl group) introduced into the group D1 is twisted with respect to the benzothienocarbazole plane. These twisted structures are believed to arise due to steric hindrance.

[0027] [ka]

[0028] On the other hand, the groups represented by the following general formulae (1-R1) to (1-R3) are groups in which a group not corresponding to the specific substituent (the group represented by the general formula (110) or (120)) has been introduced into benzothienocarbazole. The compounds having groups represented by the general formulae (1-R1) to (1-R3) correspond to Comparative Examples 4 to 6, respectively, which will be described later. The group represented by general formula (1-R1) has a structure in which a phenyl group is bonded to the meta position of the benzene ring of a "benzothienocarbazole-benzene structure." Therefore, the group bonded to benzothienocarbazole (1,1'-biphenyl-3-yl group) has small steric hindrance and is not easily twisted relative to the benzothienocarbazole plane. The group represented by general formula (1-R2) has a structure in which a phenyl group is bonded to the para position of the benzene ring of a "benzothienocarbazole-benzene structure." Therefore, the group bonded to benzothienocarbazole (1,1'-biphenyl-4-yl group) has small steric hindrance and is not easily twisted relative to the benzothienocarbazole plane. In the group represented by the general formula (1-R3), an oxygen atom is located at the ortho position of the benzene ring of the "benzothienocarbazole-benzene structure", and the oxygen atom is one of the constituent atoms of the dibenzofuran ring. In such a structure, since there is no hydrogen atom or substituent on the oxygen atom (on the oxygen atom located at the ortho position of the benzene ring) in the group (4-dibenzofuranyl group) bonded to benzothienocarbazole, the 4-dibenzofuranyl group is unlikely to twist with respect to the benzothienocarbazole plane.

[0029] [ka]

[0030] Thus, in the compound of this embodiment, the introduction of a specific substituent (a group represented by the general formula (110) or (120)) into the group D1 leads to a twisted structure of the specific substituent, which is believed to reduce the intermolecular interaction between the compounds represented by the general formulas (11) to (13). In addition, the presence of the specific substituent is believed to facilitate an increase in the intermolecular distance. As a result, it is believed that concentration quenching is suppressed, and a compound with a high PLQY can be obtained. Therefore, according to this embodiment, it is possible to provide a compound that can provide a high-performance organic EL device, and in particular, it is possible to provide a compound that has a high PLQY. High performance means that one or more of the light emitting efficiency, device life, driving voltage, and brightness are improved.

[0031] In the compound of this embodiment, "at least one group D1 is R 101 ~R 160At least one of is a group represented by general formula (110) or a group represented by general formula (120)" includes, for example, the following embodiments. One of R1 to R4 is a group D1, and R in the one group D1 101 ~R 160 At least one of R1 to R4 is a group represented by general formula (110) or general formula (120). Two of R1 to R4 are groups D1, and R in one of the two groups D1 is 101 ~R 160 At least one of R in the other group D1 is a group represented by the general formula (110) or the general formula (120). 101 ~R 160 At least one of the above is a group represented by general formula (110) or general formula (120).

[0032] In the general formula (110), “ring (B) and one R adjacent to ring (B)” 10A and bond to each other to form a ring" is, for example, the following embodiment 1.

[0033] (Aspect 1) In the general formula (110), the ring (B) and Y 12 R in 10A (One R adjacent to ring (B) 10A ) are bonded to each other to form a ring (C), and the ring (C) is condensed to the six-membered ring in the general formula (110). In this case, the group represented by the general formula (110) is represented by the following general formula (110-1). In the following general formula (110-1), Y 12 R in 10A "One R adjacent to ring (B) 10A " is equivalent to

[0034] [ka]

[0035] (In the general formula (110-1), the ring (B), Z1 and Y 13 ~Y 14each independently represents the ring (B), Z1, and Y in the general formula (110). 13 ~Y 14 Z3 is a constituent atom of ring (B) and ring (C) and represents a carbon atom, a nitrogen atom, a silicon atom, or a germanium atom. Ring (C) is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 30 ring carbon atoms. In general formula (110-1), ring (B) and ring (C) share Z3. * represents the bonding position to the carbon atom of the six-membered ring in general formulae (1-1) to (1-6).

[0036] Examples of the group represented by the general formula (110-1) include groups represented by the following general formulae (110-1A) and (110-1B).

[0037] [ka]

[0038] (In the general formula (110-1A) and the general formula (110-1B), Y 13 ~Y 14 each independently represents Y in the general formula (110) 13 ~Y 14 and (B) to (C) correspond to ring (B) to ring (C) in general formula (110-1) above. In the general formula (110-1), Z1 and Z3 are carbon atoms in the general formulas (110-1A) and (110-1B). * represents the bonding position with the carbon atom of the six-membered ring in the general formulas (1-1) to (1-6).

[0039] In the general formula (110), "ring (B) and a plurality of R 10A An example of the embodiment in which one or more pairs of adjacent two or more of the groups are bonded to each other to form a ring is embodiment 2 below.

[0040] (Aspect 2) In the general formula (110), the ring (B) and Y12 R in 10A and are bonded to each other to form a ring (C), and Y 12 R in 10A And, Y 13 R in 10A and are bonded to each other to form a ring (D), and the ring (C) and the ring (D) are condensed to the six-membered ring in the general formula (110). In this case, the group represented by the general formula (110) is represented by the following general formula (110-2). In the following general formula (110-2), Y 12 R in 10A and Y 13 R in 10A "Multiple R 10A (Y 12 ~Y 14 The three R's in 10A ) adjacent pair.

[0041] [ka]

[0042] (In the general formula (110-2), ring (B), ring (C), Z1, Z3 and Y 14 each independently represents ring (B), ring (C), Z1, Z3, and Y in the general formula (110-1). 14 The ring (B) and the ring (C) share Z3, and the ring (C) and the ring (D) share Z4. In the general formula (110-2), the ring (B) and Y 12 R in 10A and Y 13 R in 10A and are bonded to each other to form ring (B), ring (C) and ring (D). * represents the bonding position to the carbon atom of the six-membered ring in the general formulae (1-1) to (1-6).

[0043] In the compound of this embodiment, when a plurality of groups (group D1) represented by the general formula (1-1) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (1-1) are the same groups including the substituents, When a plurality of groups (group D1) represented by the general formula (1-2) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (1-2) are the same groups including the substituents, When a plurality of groups (group D1) represented by the general formula (1-3) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (1-3) are the same groups including the substituents, When a plurality of groups (group D1) represented by the general formula (1-4) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (1-4) are the same groups including the substituents, When a plurality of groups (group D1) represented by the general formula (1-5) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (1-5) are the same groups including the substituents, When a plurality of groups (group D1) represented by general formula (1-6) are present as groups R1 to R4, it is preferable that the plurality of groups represented by general formula (1-6) are the same groups including the substituents.

[0044] In the compound according to this embodiment, when two groups D1 are selected as groups of R1 to R4, it is preferable that the two selected groups D1 are all represented by one of the general formulas (1-1) to (1-6) and are the same groups including the substituents. For example, when two groups represented by general formula (1-1) (group D1) are selected as the groups R1 and R2, it is preferable that the two groups represented by general formula (1-1) (groups R1 and R2) are the same groups including the substituents. In the compound according to this embodiment, when three groups D1 are selected as groups R1 to R4, it is preferable that all of the selected three groups D1 are represented by one of the general formulas (1-1) to (1-6) and are identical to each other, including the substituents. For example, when three groups (group D1) represented by general formula (1-1) are selected as groups R1 to R3, it is preferable that the three groups (groups R1 to R3) represented by general formula (1-1) are the same groups including the substituents.

[0045] In the compound of this embodiment, when two of R1 to R4 are selected from the groups (group D1) represented by the general formulas (1-1) to (1-6) and the remaining two are selected from the groups (group D2) represented by the general formulas (2-1) to (2-4), it is preferable that the two groups represented by the general formulas (1-1) to (1-6) are both represented by one of the general formulas (1-1) to (1-6) and are the same groups including the substituents. Furthermore, when three of R1 to R4 are selected from the groups (group D1) represented by the general formulas (1-1) to (1-6) and the remaining one is selected from the groups (group D2) represented by the general formulas (2-1) to (2-4), it is preferable that the three groups represented by the general formulas (1-1) to (1-6) are all represented by one of the general formulas (1-1) to (1-6) and are the same groups including substituents. For example, when three groups (group D1) represented by general formula (1-1) are selected as groups R1 to R4, it is preferable that the three selected groups are groups represented by general formula (1-1) and are the same groups including the substituents.

[0046] In the compound of this embodiment, when a plurality of groups (group D2) represented by the general formula (2-1) are present as groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (2-1) are the same groups including the substituents, When a plurality of groups (group D2) represented by the general formula (2-2) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (2-2) are the same groups including the substituents, When a plurality of groups (group D2) represented by the general formula (2-3) are present as the groups of R1 to R4, it is preferable that the plurality of groups represented by the general formula (2-3) are the same groups including the substituents, When a plurality of groups (group D2) represented by general formula (2-4) are present as groups R1 to R4, it is preferable that the plurality of groups represented by general formula (2-4) are the same groups including the substituents.

[0047] In the compound according to this embodiment, when two groups D2 are selected as groups of R1 to R4, it is preferable that the two selected groups D2 are all represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents. For example, when two groups represented by the general formula (2-1) (group D2) are selected as the groups R1 and R2, it is preferable that the two groups represented by the general formula (2-1) (groups R1 and R2) are the same groups including the substituents. In the compound according to this embodiment, when three groups D2 are selected as groups of R1 to R4, it is preferable that all of the selected three groups D2 are represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents. For example, when three groups (group D2) represented by general formula (2-1) are selected as groups R1 to R3, it is preferable that the three groups (groups R1 to R3) represented by general formula (2-1) are the same groups including the substituents.

[0048] In the compound of this embodiment, when two of R1 to R4 are selected from the groups (group D2) represented by the general formulas (2-1) to (2-4) and the remaining two are selected from the groups (group D1) represented by the general formulas (1-1) to (1-6), it is preferable that the two groups represented by the general formulas (2-1) to (2-4) are both represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents. Furthermore, when three of R1 to R4 are selected from the groups (group D2) represented by the general formulas (2-1) to (2-4) and the remaining one is selected from the groups (group D1) represented by the general formulas (1-1) to (1-6), it is preferable that all of the three groups represented by the general formulas (2-1) to (2-4) are represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents. For example, when three groups (group D2) represented by general formula (2-1) are selected as groups R1 to R4, it is preferable that the three selected groups are groups represented by general formula (2-1) and are the same groups including the substituents.

[0049] The compound according to this embodiment is preferably a compound represented by any one of the following general formulas (1001) to (1023).

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] (In the general formulae (1001) to (1023), D1 is each independently defined as the group D1 represented by any one of the general formulae (1-1) to (1-6), and D2 is each independently defined as the group D2 represented by any one of the general formulae (2-1) to (2-4).)

[0054] In the compound according to this embodiment, the group D2 is preferably a group represented by the general formula (2-1).

[0055] In the compound according to this embodiment, the group D1 is preferably a group represented by the general formula (1-4) or (1-5).

[0056] In the compound according to this embodiment, when one of R1 to R4 is a group D1, in one group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (110) or a group represented by the general formula (120). In the compound according to this embodiment, when two of R1 to R4 are group D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (110) or a group represented by the general formula (120). In the compound according to this embodiment, when three of R1 to R4 are groups D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (110) or a group represented by the general formula (120).

[0057] In the compound according to this embodiment, R 107 ~R 110 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-2) 116 ~R 119 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-3) 126 ~R 129 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-4) 135 ~R 138 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-5) 145 ~R 148 is a group represented by the general formula (110) or a group represented by the general formula (120), or R in the general formula (1-6) 157 ~R 160 It is preferable that any one of the above is a group represented by general formula (110) or a group represented by general formula (120).

[0058] In the compound according to this embodiment, R 108 ~R 110 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-2) 117 ~R 119 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-3) 127 ~R 129 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-4) 136 ~R 138 is a group represented by general formula (110) or a group represented by general formula (120), R in the general formula (1-5) 146 ~R 148 is a group represented by the general formula (110) or a group represented by the general formula (120), or R in the general formula (1-6) 157~R 160 It is more preferable that any one of the above is a group represented by general formula (110) or a group represented by general formula (120).

[0059] In the compound according to this embodiment, it is preferable that only one of R1 to R4 is the group D1. That is, the compound according to this embodiment is preferably represented by any one of the following general formulas (1003), (1007), (1008), (1012), (1018), and (1021).

[0060] [ka]

[0061] (In the general formulae (1003), (1007), (1008), (1012), (1018), and (1021), D1 has the same meaning as the group D1 represented by any one of the general formulae (1-1) to (1-6), and D2 each independently has the same meaning as the group D2 represented by any one of the general formulae (2-1) to (2-4).)

[0062] The compound according to this embodiment is preferably a compound represented by any one of the following general formulas (1003A), (1007A), (1008A), (1012A), (1018A), and (1021A).

[0063] [ka]

[0064] [ka]

[0065] (In the general formulae (1003A), (1007A), (1008A), (1012A), (1018A), and (1021A), D1 has the same meaning as the group D1 represented by any one of the general formulae (1-1) to (1-6), R 161 ~R 168 each independently represents R in the general formula (2-1) 161 ~R 168 is equivalent to

[0066] In the compound according to this embodiment, it is preferable that only two of R1 to R4 are the group D1. That is, the compound according to this embodiment is preferably represented by any one of the following general formulas (1001), (1002), (1005), (1010), (0111), (1014) to (1017), (1022), and (1023).

[0067] [ka]

[0068] (In the general formulae (1001), (1002), (1005), (1010), (1011), (1014) to (1017), (1022) and (1023), D1 is each independently defined as the group D1 represented by any one of the general formulae (1-1) to (1-6), and D2 is each independently defined as the group D2 represented by any one of the general formulae (2-1) to (2-4).)

[0069] In the compounds of this embodiment, at least one group D1 is R 101 ~R 160 At least one of them is preferably a group represented by the general formula (110).

[0070] In the compound of this embodiment, when one of R1 to R4 is a group D1, in one group D1, R 101 ~R 160It is preferable that only one of them is a group represented by the general formula (110). In the compound of this embodiment, when two of R1 to R4 are group D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (110). In the compound of this embodiment, when three of R1 to R4 are group D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (110).

[0071] In the compound of this embodiment, Z1 in the general formula (110) is preferably a carbon atom.

[0072] In the compound of this embodiment, the group represented by the general formula (110) is preferably a group represented by any one of the following general formulae (111) to (117).

[0073] [ka]

[0074] (In the general formula (111), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 11 and Y 31 ~Y 33 each independently represents a nitrogen atom or CR 30A and R 10A and R 30A are each independently a hydrogen atom or a substituent, or one or more R 30A and one or more R 10A one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent30A R as a substituent in the general formula (110) 10A is equivalent to (In the general formula (112), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 11 and Y 31 each independently represents a nitrogen atom or CR 30A and Y 34 and Y 35 are each independently, NR 30B , oxygen atom, sulfur atom, or CR 30C R 30D and R 10A , R 30A , R 30B , R 30C and R 30D are each independently a hydrogen atom or a substituent, or one or more R 10A , one or more R 30A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30A , R 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A is equivalent to (In the general formula (113), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 12 is NR 30B or CR 30C R 30D and Y 38 is NR30B , oxygen atom, sulfur atom, or CR 30C R 30D and Y 36 and Y 37 each independently represents a nitrogen atom or CR 30A and R 10A , R 30A , R 30B , R 30C and R 30D are each independently a hydrogen atom or a substituent, or one or more R 10A , one or more R 30A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30A , R 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A is equivalent to (In the general formula (114), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 12 is NR 30B or CR 30C R 30D and Y 39 is NR 30B , oxygen atom, sulfur atom, or CR 30C R 30D and Y 32 and Y 33 each independently represents a nitrogen atom or CR 30A and R 10A , R 30A , R 30B , R 30C and R 30Dare each independently a hydrogen atom or a substituent, or one or more R 10A , one or more R 30A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30A , R 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A is equivalent to In the general formulae (111) to (114), the term "adjacent" in the "group of two or more adjacent" means, in the case of the general formula (111), Z 11 and Y 31 , Y 31 and Y 32 , Y 32 and Y 33 , Y 12 and Y 13 , and Y 13 and Y 14 Not only Y 12 and Y 33 Similarly, in the case of the general formula (112), Y 12 and Y 35 In the case of the general formula (113), Y 12 and Y 38 In the case of the general formula (114), Y 12 and Y 33 are also considered to be adjacent.

[0075] [ka]

[0076] (In the general formula (115), Y 12 ~Y 14 each independently represents a nitrogen atom or CR10A and Z 13 is NR 30B or CR 30C R 30D and Y 42 and Y 43 each independently represents a nitrogen atom or CR 30A and R 10A , R 30A , R 30B , R 30C and R 30D are each independently a hydrogen atom or a substituent, or one or more R 10A , one or more R 30A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30A , R 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A is equivalent to (In the general formula (116), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 13 is NR 30B or CR 30C R 30D and Y 48 and Y 49 are each independently, NR 30B , oxygen atom, sulfur atom, or CR 30C R 30D and R 10A , R 30B , R 30C and R 30D are each independently a hydrogen atom or a substituent, or one or more R10A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A (In the general formula (117), Y 12 ~Y 14 each independently represents a nitrogen atom or CR 10A and Z 14 and Y 45 each independently represents a nitrogen atom or CR 30A and Y 46 is NR 30B , oxygen atom, sulfur atom, or CR 30C R 30D and R 10A , R 30A , R 30B , R 30C and R 30D are each independently a hydrogen atom or a substituent, or one or more R 10A , one or more R 30A , one or more R 30B , one or more R 30C and one or more R 30D one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent 10A and R as a substituent 30A , R 30B , R 30C and R 30D R as a substituent in the general formula (110) 10A is equivalent to (In the general formulae (111) to (117), a plurality of R 10AIf multiple R 10A are the same or different, and multiple R 30A If multiple R 30A are the same or different, and multiple R 30B If there are multiple R 30B are the same or different, and multiple R 30C If there are multiple R 30C are the same or different, and multiple R 30D If there are multiple R 30D are either identical or different.) In the general formulae (115) to (117), the term "adjacent" in the "group of two or more adjacent" means, in the case of the general formula (115), Z 13 and Y 42 , Y 42 and Y 43 , Y 12 and Y 13 , and Y 13 and Y 14 Not only Y 12 and Y 43 Similarly, in the case of the general formula (116), Y 12 and Y 49 In the case of the general formula (117), Y 12 and Y 46 are also considered to be adjacent.

[0077] In the compound of this embodiment, the group represented by the general formula (110) is preferably a group represented by any one of the general formulae (111), (115), and (117).

[0078] In the compound of this embodiment, Y in the general formula (110) 12 ~Y 14 CR 10A It is preferable that: In the compound of this embodiment, Y in the general formula (120) 21 ~Y 24 CR 20A It is preferable that:

[0079] In the compound of this embodiment, the group represented by the general formula (110) is preferably a group represented by any one of the following general formulae (b1) to (b14).

[0080] [ka]

[0081] [ka]

[0082] (In the general formulae (b1) to (b14), Ra is a hydrogen atom or a substituent, or one or more pairs of adjacent Ra are bonded to each other to form a ring; The multiple Ra are the same or different, Rb is a hydrogen atom or a substituent; Rc and Rd each independently represent a hydrogen atom or a substituent, or a pair consisting of Rc and Rd combine with each other to form a ring; The substituents Ra, Rb, Rc and Rd are each independently R 10A is equivalent to

[0083] In the general formulae (b1) to (b14), Ra is preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom. In the general formulae (b10) and (b12), Rc and Rd each independently represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a pair consisting of Rc and Rd bonded to each other to form a ring. In the general formulae (b9) and (b11), Rb is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0084] In the general formulae (b1) to (b14), it is preferable that one or more pairs of adjacent Ra groups do not bond with each other to form a ring. In the general formulae (b1) to (b14), it is preferable that a pair consisting of Rc and Rd do not combine with each other to form a ring.

[0085] In the compound of this embodiment, the group represented by the general formula (110) is preferably a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group.

[0086] In the compounds of this embodiment, at least one group D1 is R 101 ~R 160 At least one of them is preferably a group represented by the general formula (120).

[0087] In the compound of this embodiment, when one of R1 to R4 is a group D1, in one group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (120). In the compound of this embodiment, when two of R1 to R4 are group D1, in each group D1, R 101 ~R 160It is preferable that only one of them is a group represented by the general formula (120). In the compound of this embodiment, when three of R1 to R4 are group D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the general formula (120).

[0088] In the compound of this embodiment, Z2 in the general formula (120) is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted benzoanthryl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9-dimethylphenyl group, a substituted or unsubstituted ... Preferred are a substituted or unsubstituted ethylfluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

[0089] In the compound of this embodiment, Z2 in the general formula (120) is preferably a group represented by any one of the following general formulae (Z21) to (Z31).

[0090] [ka]

[0091] [ka]

[0092] (In the general formulae (Z-21) to (Z-31), Re is a hydrogen atom or a substituent, or one or more pairs of adjacent Re are bonded to each other to form a ring, and the multiple Re are the same or different, Re1 and Re2 each independently represent a hydrogen atom or a substituent, or a pair consisting of Re1 and Re2 bond to each other to form a ring; Re3 is a hydrogen atom or a substituent; Re, Re1, Re2 and Re3 as substituents each independently represent R 20A Each * independently represents a bonding position to a carbon atom of the six-membered ring in the general formula (120).

[0093] In the general formulae (Z-21) to (Z-31), Re is preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom. In the general formulae (Z-28) to (Z-29), Re1 and Re2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a pair consisting of Re1 and Re2 are preferably bonded to each other to form a ring. In the general formula (Z-30), Re3 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0094] In the compound of this embodiment, the group represented by the general formula (120) is preferably a group represented by any one of the following general formulae (c1) to (c8).

[0095] [ka]

[0096] (In the general formulae (c1) to (c8), Re is a hydrogen atom or a substituent, The multiple Re are the same or different, Re as a substituent is R 20A is equivalent to

[0097] In the general formulas (c1) to (c8), Re is preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom.

[0098] In the compound of this embodiment, X1 to X6 in the group D1 are preferably oxygen atoms. In the compound of this embodiment, X1 to X6 in the group D1 are preferably sulfur atoms.

[0099] The compound of this embodiment is preferably a compound represented by the general formula (11). The compound of this embodiment is preferably a compound represented by the general formula (12). The compound of this embodiment is preferably a compound represented by the general formula (13).

[0100] In the compound of this embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , R 10A and R 20Aeach independently represents a hydrogen atom, a halogen atom, a cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 30 carbon atoms, an unsubstituted alkynyl group having 2 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted ring Preferred are an arylphosphoryl group having 6 to 60 carbon atoms, a hydroxy group, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a group represented by -N(Rz)2, a thiol group, an unsubstituted alkylthio group having 1 to 30 carbon atoms, an unsubstituted aralkyl group having 7 to 30 ring carbon atoms, a substituted germanium group, a substituted phosphine oxide group, a nitro group, a substituted boryl group, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms. In the compound of this embodiment, Rz in -N(Rz)2 is preferably an unsubstituted aryl group having 6 to 30 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 30 ring atoms, or an unsubstituted alkyl group having 1 to 30 carbon atoms.

[0101] In the compound of this embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , R 10A and R 20A are each independently preferably a hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a group represented by -N(Rz)2, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0102] In the compound of this embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , R 10A and R 20A are preferably each independently a hydrogen atom, a halogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0103] In the compound of this embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , R 10A and R 20A are preferably each independently a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0104] In the compound of this embodiment, R 10A and R 20A is preferably a hydrogen atom, the ring (B) is an unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or an unsubstituted heterocyclic ring having 5 to 30 ring carbon atoms, and Z2 is preferably an unsubstituted aryl group having 6 to 30 ring carbon atoms or an unsubstituted heterocyclic group having 5 to 30 ring atoms.

[0105] In the compound of this embodiment, it is also preferable that one or more of the hydrogen atoms in the molecule is a deuterium atom.

[0106] In the compound of this embodiment, R in the group D1101 ~R 160 It is also preferred that one or more of the hydrogen atoms are hydrogen atoms and all of the hydrogen atoms are deuterium atoms. In the compound of this embodiment, R in the group D1 101 ~R 160 It is also preferred that one or more of the hydrogen atoms be hydrogen atoms and that all of the hydrogen atoms be proton atoms. In the compound of this embodiment, R in the group D1 101 ~R 160 is preferably a hydrogen atom other than the group represented by the general formula (110) or the group represented by the general formula (120), and the hydrogen atom is preferably a deuterium atom. In the compound of this embodiment, R in the group D1 101 ~R 160 is a substituent (including a group represented by the general formula (110) or a group represented by the general formula (120)) and the substituent has one or more hydrogen atoms, it is preferable that all of the hydrogen atoms are protium atoms, any one or more of the hydrogen atoms are deuterium atoms, or all of the hydrogen atoms are deuterium atoms.

[0107] In the compound of this embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 It is also preferred that one or more of the hydrogen atoms are hydrogen atoms and all of the hydrogen atoms are deuterium atoms. In the compound of this embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 It is also preferred that one or more of the hydrogen atoms be hydrogen atoms and that all of the hydrogen atoms be proton atoms. In the compound of this embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 is a hydrogen atom, and it is also preferred that the hydrogen atom is a deuterium atom. In the compound of this embodiment, R in the group D2161 ~R 168 and R 171 ~R 200 When any one or more of the above is a substituent having one or more hydrogen atoms, it is preferable that all of the hydrogen atoms are protium atoms, any one or more of the hydrogen atoms are deuterium atoms, or all of the hydrogen atoms are deuterium atoms.

[0108] In the compound of this embodiment, R 101 ~R 160 is a hydrogen atom other than the group represented by the general formula (110) and the group represented by the general formula (120), and R 161 ~R 168 and R 171 ~R 200 is preferably a hydrogen atom. In the compound of this embodiment, R 101 ~R 160 is a hydrogen atom other than the group represented by the general formula (110) and the group represented by the general formula (120), and the hydrogen atom is a deuterium atom, and R 161 ~R 168 and R 171 ~R 200 is a hydrogen atom, and it is also preferred that the hydrogen atom is a deuterium atom.

[0109] In the compound of this embodiment (the compound represented by any one of the general formulas (11) to (13)), the substituents in the case of being “substituted or unsubstituted” are each independently: Halogen atoms, Cyano group, an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted heterocyclic group having 5 to 30 ring atoms, an unsubstituted alkyl group having 1 to 30 carbon atoms; an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; an unsubstituted alkenyl group having 2 to 30 carbon atoms, an unsubstituted alkynyl group having 2 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, an unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxy groups, an unsubstituted alkoxy group having 1 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, A group represented by -N(Rz)2, Thiol groups, an unsubstituted alkylthio group having 1 to 30 carbon atoms, an unsubstituted aralkyl group having 7 to 30 ring carbon atoms, substituted germanium groups, Substituted phosphine oxide groups, Nitro group, a substituted boryl group, or an unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is an unsubstituted aryl group having 6 to 30 ring carbon atoms; an unsubstituted heterocyclic group having 5 to 30 ring atoms, or An unsubstituted alkyl group having 1 to 30 carbon atoms is preferred. The two Rz in -N(Rz)2 are the same or different.

[0110] Method for producing the compound of this embodiment The compound of this embodiment can be produced, for example, by the method described in the Examples below. The compound of this embodiment can be produced by following the reactions described in the Examples below and using known alternative reactions and raw materials suited to the target product.

[0111] Specific examples of the compound of this embodiment Specific examples of the compound of this embodiment include the following compounds, however, the present invention is not limited to these specific examples of compounds.

[0112] [ka]

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[0165] Second Embodiment [Materials for organic EL devices] The material for an organic EL device according to the second embodiment includes the compound of the first embodiment (at least any of the compounds represented by any of general formulas (11) to (13)). One aspect of the material for an organic EL device includes only the compound of the first embodiment, and another aspect of the material for an organic EL device includes the compound of the first embodiment and another compound different from the compound of the first embodiment. In the organic EL device material of this embodiment, the compound of the first embodiment is preferably a host material. In this case, the material for an organic EL device may contain the compound of the first embodiment as a host material and other compounds such as a dopant material. In the material for an organic EL device of this embodiment, the compound of the first embodiment is preferably a delayed fluorescent material. The material for an organic EL device according to the second embodiment contains a compound (the compound of the first embodiment) capable of providing a high-performance organic EL device, in particular, a compound of the first embodiment having a high PLQY. Therefore, according to the second embodiment, a material for an organic EL device capable of providing a high-performance organic EL device can be provided. The material for an organic EL device according to the second embodiment may further contain other compounds. When the material for an organic EL device according to the second embodiment further contains other compounds, the other compounds may be solid or liquid.

[0166] Third Embodiment [Organic EL element] The configuration of the organic EL element according to the third embodiment will be described below.

[0167] The organic EL element includes an organic layer between an anode and a cathode. This organic layer is usually formed by laminating a plurality of layers each composed of an organic compound. The organic layer may further include an inorganic compound. The organic EL element of this embodiment includes a first organic layer between the anode and the cathode. The first organic layer includes at least one of the compounds according to the first embodiment (at least one of the compounds represented by any one of general formulas (11) to (13)). The first organic layer may be, for example, at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

[0168] The first organic layer is preferably an emissive layer. In the organic EL device of this embodiment, the first organic layer is the light-emitting layer. In the present embodiment, the organic layer may be composed of only an emitting layer as a first organic layer, or may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, and the like.

[0169] FIG. 1 shows a schematic configuration of one example of the 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 configured by laminating, in this order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an emitting layer 5 as a first organic layer, an electron transport layer 8, and an electron injection layer 9.

[0170] In the organic EL device 1 of the present embodiment, the light-emitting layer 5 contains a first compound. The first compound is a compound according to the first embodiment (at least any of the compounds represented by any of general formulas (11) to (13)). The light-emitting layer 5 preferably does not contain a phosphorescent material (dopant material). It is preferable that the light-emitting layer 5 does not contain a heavy metal complex or a phosphorescent rare earth metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex. It is also preferable that the light-emitting layer 5 does not contain a metal complex.

[0171] In the organic EL device 1 of the present embodiment, the light-emitting layer 5 contains a first compound (at least one of the compounds represented by any of general formulas (11) to (13)) and further contains a second compound. In this embodiment, the first compound is preferably a host material (sometimes referred to as a matrix material), and the second compound is preferably a dopant material (sometimes referred to as a guest material, emitter, or light-emitting material).

[0172] <First compound> The first compound is a compound according to a first embodiment. The first compound is preferably a delayed fluorescent compound.

[0173] Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Adachi Chihaya, published by Kodansha). In that paper, the energy difference ΔE between the excited singlet state and the excited triplet state of a fluorescent material is 13 It is explained that if it is possible to reduce the energy transfer rate, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. Furthermore, the mechanism of delayed fluorescence generation is explained in Figure 10.38 of the document. The first compound in this embodiment is preferably a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

[0174] In general, delayed fluorescence can be confirmed by transient PL (Photo Luminescence) measurement.

[0175] The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from transient PL measurements. Transient PL measurements are a method of exciting a sample with a pulsed laser and measuring the decay behavior (transient characteristics) of PL emission after the irradiation is stopped. PL emission in TADF materials is classified into emission components from singlet excitons generated during the first PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated during the first PL excitation is on the order of nanoseconds, which is very short. Therefore, the emission from the singlet excitons decays quickly after irradiation with a pulsed laser. On the other hand, delayed fluorescence decays slowly because it is emitted from singlet excitons generated via triplet excitons, which have a long life span. Thus, there is a large 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, it is possible to obtain the emission intensity derived from delayed fluorescence.

[0176] A schematic diagram of an exemplary apparatus for measuring transient PL is shown in Fig. 2. An example of a method for measuring transient PL using Fig. 2 and an analysis of the behavior of delayed fluorescence will be described.

[0177] 2 includes a pulsed laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 for accommodating a measurement sample, a spectroscope 103 for dispersing 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 FIG. 2.

[0178] The sample accommodated in the sample chamber 102 is obtained by forming a thin film, in which a doping material is doped at a concentration of 12 mass % relative to a matrix material, on a quartz substrate.

[0179] A pulsed laser is irradiated from a pulsed laser unit 101 to a thin film sample accommodated in a sample chamber 102 to excite the doping material. Emission light is extracted in a direction at 90 degrees to the irradiation direction of the excitation light, and the extracted light is dispersed by a spectrometer 103 to form a two-dimensional image in a streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and bright spots correspond to emission intensity. By cutting out this two-dimensional image at a predetermined time axis, an emission spectrum can be obtained in which the vertical axis is emission intensity and the horizontal axis is wavelength. Furthermore, by cutting out the two-dimensional image at the wavelength axis, a decay curve (transient PL) can be obtained in which the vertical axis is the logarithm of emission intensity and the horizontal axis is time.

[0180] For example, the following reference compound H1 was used as the matrix material, and the following reference compound D1 was used as the doping material to prepare thin film sample A as described above, and transient PL measurement was performed.

[0181] [ka]

[0182] Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. Thin film sample B was prepared as described above using the following reference compound H2 as a matrix material and the above-mentioned reference compound D1 as a doping material.

[0183] FIG. 3 shows the decay curves obtained from the transient PL measured for thin film sample A and thin film sample B.

[0184] [ka]

[0185] As described above, the transient PL measurement can provide an emission decay curve with the emission intensity on the vertical axis and the time on the horizontal axis. Based on this emission decay curve, the fluorescence intensity ratio between the fluorescence emitted from the singlet excited state generated by photoexcitation and the delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state can be estimated. In delayed fluorescent materials, the ratio of the intensity of the delayed fluorescence that decays slowly to the intensity of the fluorescence that decays quickly is somewhat large.

[0186] Specifically, there are two types of luminescence from delayed fluorescent materials: prompt luminescence and delayed luminescence. Prompt luminescence is luminescence that is observed immediately from the excited state after being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength that the delayed fluorescent material absorbs. Delay luminescence is luminescence that is not observed immediately after excitation by the pulsed light, but is observed later.

[0187] The amount and ratio of prompt luminescence and delayed luminescence can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2.

[0188] In addition, in this specification, a sample prepared by the following method is used to measure the delayed fluorescence of the first compound. For example, the first compound is dissolved in toluene to prepare a dilute solution with an absorbance of 0.05 or less at the excitation wavelength in order to eliminate the contribution of self-absorption. In addition, in order to prevent quenching due to oxygen, the sample solution is frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon. The fluorescence spectrum of the above sample solution is measured using a spectrofluorometer FP-8600 (manufactured by JASCO Corporation), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is also measured under the same conditions. The total fluorescence quantum yield is calculated using the fluorescence area intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969.

[0189] The amount and ratio of prompt luminescence and delayed luminescence can be determined by a method similar to that described in "Nature 492, 234-238, 2012" (Reference 1). Note that the device used to calculate the amount of prompt luminescence and delayed luminescence is not limited to the device described in Reference 1 or the device shown in FIG. 2. In this embodiment, the amount of prompt luminescence (prompt luminescence) of the compound to be measured (first compound) is calculated as X P and the amount of delay light emission is X D When X D / X P It is preferable that the value is 0.05 or more. In this specification, the amounts and ratio of prompt luminescence and delayed luminescence of compounds other than the first compound are measured in the same manner as the amounts and ratio of prompt luminescence and delayed luminescence of the first compound.

[0190] <Second Compound> The second compound of the present embodiment is preferably a fluorescent compound. The second compound may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermally activated delayed fluorescent properties. The second compound of this embodiment is preferably a compound that does not exhibit thermally activated delayed fluorescence. The second compound of this embodiment is not a phosphorescent metal complex. The second compound of this embodiment is preferably not a heavy metal complex. In addition, the second compound of this embodiment is preferably not a metal complex.

[0191] The second compound according to the present embodiment may be a fluorescent material.Specific examples of the fluorescent material 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, pyrromethene boron complex compounds, compounds having a pyrromethene skeleton, metal complexes of compounds having a pyrromethene skeleton, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

[0192] A compound represented by the general formula (20) In this embodiment, the second compound is preferably a compound represented by the following general formula (20).

[0193] [ka]

[0194] In the 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 are each independently a hydrogen atom or a substituent, or R 21 and R 22 Group R 22 and R 23 Group R 24 and R 25 and R 25 and R 26 any one or more of the pairs of Y and R as Substituents 21 ~R 26 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; Halogen atoms, Carboxy group, a substituted or unsubstituted ester group; a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted amino group, Nitro group, Cyano group, a substituted or unsubstituted silyl group, and selected from the group consisting of substituted or unsubstituted siloxanyl groups; Z 21 and Z 22 are each independently a substituent or Z 21 and Z 22 are bonded together to form a ring, Z as a Substituent 21 and Z 22 are each independently Halogen atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and The aryloxy group is selected from the group consisting of substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.

[0195] When the second compound is a fluorescent compound, the second compound preferably exhibits emission having a maximum peak wavelength of 400 nm or more and 700 nm or less. In this specification, the maximum peak wavelength is the wavelength at which the compound to be measured -6 Moles / L > 10 -5 This refers to the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum in the fluorescence spectrum measured for a toluene solution in which the compound is dissolved at a concentration of mol / L or less. The measurement device used is a spectrofluorophotometer (Hitachi High-Tech Science, F-7000).

[0196] The second compound preferably exhibits red or green emission. In this specification, red emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 600 nm or more and 660 nm or less. When the second compound is a red fluorescent compound, the maximum peak wavelength of the second compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and further preferably 610 nm or more and 630 nm or less. In this specification, green emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 500 nm or more and 560 nm or less. When the second compound is a green fluorescent compound, the maximum peak wavelength of the second compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and even more preferably 510 nm or more and 540 nm or less. In this specification, blue emission refers to emission having a maximum peak wavelength in the fluorescence spectrum within the range of 430 nm or more and 480 nm or less. When the second compound is a blue fluorescent compound, the maximum peak wavelength of the second compound is preferably 430 nm or more and 480 nm or less, more preferably 440 nm or more and 480 nm or less.

[0197] The maximum peak wavelength of the light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2 A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0198] Method for producing the second compound The second compound can be prepared by a known method.

[0199] Method for producing the second compound The second compound can be prepared by a known method.

[0200] Specific examples of the second compound Specific examples of the second compound of this embodiment (the compound represented by formula (20)) are shown below. However, the present invention is not limited to these specific examples of the compound. The coordinate bond between the boron atom and the nitrogen atom in the pyrromethene skeleton can be represented in various ways, such as a solid line, a dashed line, an arrow, or omitted. In this specification, it is represented by a solid line, a dashed line, or omitted.

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[0224] <Relationship between the first compound and the second compound in the light-emitting layer> In the organic EL device 1 of the present embodiment, it is preferable that the singlet energy S1 (Mat1) of the first compound and the singlet energy S1 (Mat2) of the second compound satisfy the relationship of the following mathematical formula (Math 1). S1(Mat1)>S1(Mat2) ...(Number 1)

[0225] Energy gap T at 77[K] of the first compound 77K (Mat1) is the energy gap T at 77[K] of the second compound 77K It is preferable that the value is larger than (Mat2). In other words, it is preferable that the relationship of the following formula (Math. 4) is satisfied. T 77K (Mat1)>T 77K (Mat2) ...(Number 4)

[0226] When the organic EL device 1 of the present embodiment is caused to emit light, it is preferable that the second compound in the light-emitting layer 5 mainly emits light.

[0227] Relationship between triplet energy and energy gap at 77[K] Here, a relationship between the triplet energy and the energy gap at 77 [K] will be described. In this embodiment, the energy gap at 77 [K] is different from the triplet energy that is usually defined. The triplet energy is measured as follows. First, a sample is prepared by dissolving the compound to be measured in an appropriate solvent and sealing the solution in a quartz glass tube. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this sample is measured at low temperature (77[K]). ) is measured, a tangent line is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the triplet energy is calculated from a predetermined conversion formula based on the wavelength value at the intersection of the tangent line and the horizontal axis. Here, among the compounds according to this embodiment, the thermally activated delayed fluorescent compound is preferably a compound with a small ΔST. If ΔST is small, intersystem crossing and reverse intersystem crossing are likely to occur even at low temperatures (77 [K]), and the excited singlet state and the excited triplet state are mixed. As a result, the spectrum measured in the same manner as above contains light emission from both the excited singlet state and the excited triplet state, and it is difficult to clearly distinguish which state the light emission is from, but it is basically considered that the triplet energy value is dominant. Therefore, in this embodiment, although the measurement method is the same as that of the normal triplet energy T, in order to distinguish the difference in the strict sense, the value measured as follows is referred to as the energy gap T 77K 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 prepare a measurement sample. The phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) of this measurement sample is measured at low temperature (77 [K]), a tangent is drawn to the rising edge on the short wavelength side of this phosphorescence spectrum, and the wavelength value λ at the intersection of the tangent and the horizontal axis is determined. edge Based on [nm], the amount of energy calculated from the following conversion formula (F1) is the energy gap T at 77[K]. 77K Let us assume that. Conversion formula (F1):T 77K [eV]=1239.85 / λ edge

[0228] The tangent to the rising edge 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 maximum of the spectral maxima, 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 is at its maximum (i.e., the tangent at the inflection point) is the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side. Note that a maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is regarded as the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum. Phosphorescence can be measured using a spectrofluorometer body, model F-4500, manufactured by Hitachi High-Technologies Corp. However, the measuring device is not limited to this, and measurements may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

[0229] Singlet energy S1 The following method can be used to measure the singlet energy S1 using a solution (sometimes referred to as a solution method). Prepare a 10 μmol / L toluene solution of the compound to be measured and place it in a quartz cell, then measure the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample at room temperature (300 K). Draw a tangent to the falling edge on the long wavelength side of this absorption spectrum, and substitute the wavelength value λedge [nm] at the intersection of the tangent and the horizontal axis into the following conversion formula (F2) to calculate the singlet energy. Conversion formula (F2): S1[eV]=1239.85 / λedge An example of an absorption spectrum measuring device is a spectrophotometer manufactured by Hitachi (device name: U3310), but is not limited to this.

[0230] The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving along the spectral curve from the maximum value on the longest wavelength side among the maximum values ​​of the absorption spectrum in the direction towards longer wavelengths, consider the tangent at each point on the curve. 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 slope is at its minimum value on the longest wavelength side (excluding cases where the absorbance is 0.1 or less) is regarded as the tangent to the falling edge on the long wavelength side of the absorption spectrum. Note that maximum points with absorbance values ​​of 0.2 or less are not included in the maximum value on the longest wavelength side.

[0231] In this embodiment, the singlet energy S1 and the energy gap T at 77 [K] 77K Difference between (S1-T 77K ) is defined as ΔST.

[0232] In this embodiment, the singlet energy S1(Mat1) of the first compound and the energy gap T 77K The difference ΔST(Mat1) from (Mat1) is preferably less than 0.3 eV, more preferably less than 0.2 eV, and further preferably less than 0.1 eV. That is, ΔST(Mat1) preferably satisfies any one of the relationships of the following formulas (Math 1A) to (Math 1C). ΔST(Mat1)=S1(Mat1)-T 77K (Mat1)<0.3eV(Math1A)ΔST(Mat1)=S1(Mat1)-T 77K (Mat1)<0.2 eV (Math 1B) ΔST(Mat1)=S1(Mat1)-T 77K (Mat1)<0.1eV(Math 1C)

[0233] The organic EL element 1 of the present embodiment preferably emits red or green light. When the organic EL element 1 of the present embodiment emits green light, the maximum peak wavelength of the light emitted from the organic EL element 1 is preferably 500 nm or more and 560 nm or less. When the organic EL element 1 of the present embodiment emits red light, the maximum peak wavelength of the light emitted from the organic EL element 1 is preferably 600 nm or more and 660 nm or less. When the organic EL element 1 of the present embodiment emits blue light, the maximum peak wavelength of the light emitted from the organic EL element 1 is preferably 430 nm or more and 480 nm or less.

[0234] The maximum peak wavelength of the light emitted from the organic EL element is measured as follows. Current density is 10mA / cm 2A voltage is applied to the organic EL element so that the spectral radiance spectrum is measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta). In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum where the emission intensity is maximum is measured, and this is defined as the maximum peak wavelength (unit: nm).

[0235] Thickness of the light-emitting layer The thickness of the light-emitting layer 5 in the organic EL device 1 of this embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. When the thickness is 5 nm or more, the formation of the light-emitting layer and the adjustment of the chromaticity are easily facilitated, and when the thickness is 50 nm or less, an increase in the driving voltage is easily suppressed.

[0236] Compound content in the light-emitting layer The contents of the first compound and the second compound in the light-emitting layer 5 are preferably within the following ranges, for example. The content of the first compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass. The content of the second compound is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass. In this embodiment, the light-emitting layer 5 may contain materials other than the first compound and the second compound. The light-emitting layer 5 may contain only one type of the first compound or may contain two or more types of the second compound. The light-emitting layer 5 may contain only one type of the second compound or may contain two or more types of the second compound.

[0237] TADF mechanism FIG. 4 is a diagram showing an example of the relationship between the energy levels of the first compound and the second compound in the light-emitting layer. In FIG. 4, S0 represents the ground state. S1(Mat1) represents the lowest excited singlet state of the first compound. T1(Mat1) represents the lowest excited triplet state of the first compound. S1(Mat2) represents the lowest excited singlet state of the second compound. T1(Mat2) represents the lowest excited triplet state of the second compound. The dashed arrow from S1(Mat1) to S1(Mat2) in FIG. 4 represents a Forster type energy transfer from the lowest excited singlet state of the first compound to the second compound. As shown in Figure 4, when a compound with a small ΔST(Mat1) is used as the first compound, the lowest excited triplet state T1(Mat1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(Mat1) by thermal energy. Then, Förster type energy transfer occurs from the lowest excited singlet state S1(Mat1) of the first compound to the second compound, generating the lowest excited singlet state S1(Mat2). As a result, fluorescence emission from the lowest excited singlet state S1(Mat2) of the second compound can be observed. It is believed that the internal efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0238] The organic EL device 1 according to the third embodiment contains, in the light-emitting layer 5, the compound of the first embodiment as a first compound (at least any of the compounds represented by general formulas (11) to (13)) and a second compound having a lower singlet energy than the first compound. The organic EL element according to the third embodiment contains a compound (the compound of the first embodiment) capable of providing a high-performance organic EL element, in particular, a compound of the first embodiment having a high PLQY. Therefore, according to the third embodiment, a high-performance organic EL element can be provided. The organic EL element 1 according to the third embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0239] The following is a further explanation of the configuration of the organic EL element 1. Hereinafter, reference numerals may be omitted.

[0240] (substrate) The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, etc. can be used as the substrate. A flexible substrate may also be used. A flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate. Examples of materials for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. An inorganic deposition film can also be used.

[0241] (anode) For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, graphene, and the like. 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 metal materials (e.g., titanium nitride), and the like.

[0242] These materials are usually formed into a film by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added to indium oxide at 1 mass % or more and 10 mass % or less. In addition, indium oxide containing tungsten oxide and zinc oxide can be formed by a sputtering method by using a target in which tungsten oxide is added to indium oxide at 0.5 mass % or more and 5 mass % or less and zinc oxide is added to indium oxide at 0.1 mass % or more and 1 mass % or less. In addition, it may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method, or the like.

[0243] 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 easily injects holes regardless of the work function of the anode, so that materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures of these, as well as other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

[0244] Materials with small work functions, such as elements belonging to Group 1 or 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), 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), as well as alloys containing these, can also be used. When alkali metals, alkaline earth metals, and alloys containing these are used to form the anode, vacuum deposition and sputtering methods can be used. Furthermore, when silver paste or the like is used, coating methods, inkjet methods, and the like can be used.

[0245] (cathode) For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof, each having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or 2 of the periodic table, i.e., 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.

[0246] When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.

[0247] By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

[0248] (Hole injection layer) The hole injection layer is a layer containing a substance with high hole injection properties, such as molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.

[0249] In addition, examples of materials with high hole injection properties include low-molecular-weight organic compounds such as 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), and 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DNTPD). [N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and other aromatic amine compounds, as well as dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) are also included.

[0250] In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can be used. For example, polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino)phenyl]phenyl-N'-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Poly-TPD) can be used. In addition, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene) / poly(styrenesulfonic acid) (PEDOT / PSS) or polyaniline / poly(styrenesulfonic acid) (PAni / PSS) can be used.

[0251] (Hole transport layer) The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation: BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: NPB), Examples of aromatic amine compounds that can be used include 4,4',4''-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The substances mentioned here are mainly 10 -6 cm 2 / (V s) or higher.

[0252] The hole transport layer may be made of carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA), or anthracene derivatives such as t-BuDNA, DNA, and DPAnth. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) may also be used.

[0253] However, other substances may be used as long as they have a higher hole transporting property than an electron transporting property. Note that the layer containing the substance having a high hole transporting property may be a single layer or a stack of two or more layers made of the above substances.

[0254] When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap closer to the light emitting layer. An example of such a material is HT-2, which is used in the examples described later.

[0255] (electron transport layer) The electron transport layer is a layer containing a substance with high electron transport properties. For the electron transport layer, 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 can be used. Specifically, metal complexes such as Alq, tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO, and ZnBTZ can be used as low molecular weight organic compounds. In addition to metal complexes, 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(pt-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: Heteroaromatic compounds such as 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, benzimidazole compounds can be preferably used. The substances mentioned here are mainly 10 -6 cm 2 / (V·s) or more. Note that any other substance may be used as the electron transport layer as long as it has a higher electron transporting property than a hole transporting property. The electron transport layer may be formed of a single layer or may be formed of two or more layers of the above substances.

[0256] The electron transport layer can also be made of a polymer compound, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

[0257] (electron injection layer) The electron injection layer is a layer containing a substance with high electron injection properties. For the electron injection layer, alkali metals, alkaline earth metals, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), or compounds thereof can be used. In addition, a substance having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, magnesium (Mg) in Alq, may be used. In this case, electron injection from the cathode can be performed more efficiently.

[0258] Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has 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 in transporting the generated electrons, and specifically, for example, the above-mentioned substances constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any substance that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Furthermore, alkali metal oxides and alkaline earth metal oxides are preferred, and examples thereof include lithium oxide, calcium oxide, and barium oxide. Furthermore, a Lewis base such as magnesium oxide can also be used. Furthermore, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used. (Layer formation method) The method for forming each layer of the organic EL element of this embodiment is not limited to those specifically mentioned above, but may be any known method such as a dry film formation method such as a vacuum deposition method, a sputtering method, a plasma method, or an ion plating method, or a wet film formation method such as a spin coating method, a dipping method, a flow coating method, or an inkjet method.

[0259] (Film thickness) The film thickness of each organic layer in the organic EL element of the present embodiment is not limited except as specifically mentioned above. In general, however, if the film thickness is too thin, defects such as pinholes are likely to occur, whereas if the film thickness is too thick, a high applied voltage is required, resulting in poor efficiency. Therefore, the film thickness is usually preferably in the range of several nm to 1 μm.

[0260] Fourth Embodiment The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those in the third embodiment will be given the same reference numerals or names, and the description will be omitted or simplified. In the fourth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third embodiment can be used.

[0261] The organic EL device according to the fourth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer further contains a third compound, but other points are the same as those of the third embodiment. That is, in the fourth embodiment, the light-emitting layer serving as the first organic layer contains a first compound, a second compound, and a third compound. In this embodiment, the first compound is preferably a host material, the second compound is preferably a dopant material, and the third compound is preferably a host material. One of the first compound and the third compound may be referred to as a first host material, and the other may be referred to as a second host material.

[0262] <Third compound> The third compound may be a compound exhibiting delayed fluorescence or a compound not exhibiting delayed fluorescence.

[0263] The third compound is not particularly limited, but is preferably a compound other than an amine compound. For example, the third compound may be a carbazole derivative, a dibenzofuran derivative, or a dibenzothiophene derivative, but is not limited to these derivatives.

[0264] It is also preferable that the third compound is a compound containing at least one of a partial structure represented by the following general formula (31), a partial structure represented by the following general formula (32), a partial structure represented by the following general formula (33), and a partial structure represented by the following general formula (34) in one molecule.

[0265] [ka]

[0266] In the general formula (31), Y 31 ~Y 36 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, However, Y 31 ~Y 36 at least one of the carbon atoms is bonded to another atom in the molecule of the third compound, In the general formula (32), Y 41 ~Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, However, Y 41 ~Y 48 at least one of the carbon atoms is bonded to another atom in the molecule of the third compound, X 30 is a nitrogen atom, or an oxygen atom, or a sulfur atom that is bonded to another atom in the molecule of the third compound. In the general formulae (33) and (34), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0267] In the general formula (32), Y 41 ~Y 48 It is also preferred that at least two of the carbon atoms are carbon atoms bonded to other atoms in the molecule of the third compound, and a ring structure containing the carbon atoms is constructed. For example, the partial structure represented by the general formula (32) is preferably any partial structure selected from the group consisting of partial structures represented by the following general formulae (321), (322), (323), (324), (325), and (326).

[0268] [ka]

[0269] [ka]

[0270] [ka]

[0271] In the general formulae (321) to (326), X 30 are each independently a nitrogen atom, an oxygen atom, or a sulfur atom bonded to another atom in a molecule of a third compound, Y 41 ~Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound, X 31 are each independently a nitrogen atom, an oxygen atom, a sulfur atom, or a carbon atom that is bonded to another atom in the molecule of the third compound, Y 61 ~Y 64 are each independently a nitrogen atom or a carbon atom that is bonded to another atom in the molecule of the third compound. In this embodiment, the third compound preferably has a partial structure represented by the general formula (323) among the general formulae (321) to (326).

[0272] The partial structure represented by the general formula (31) is preferably contained in the third compound as at least one group selected from the group consisting of a group represented by the following general formula (33) and a group represented by the following general formula (34): It is also preferable that the third compound has at least one of the partial structures represented by the following general formula (33) and the following general formula (34). Since the bonding sites are located in the meta positions as in the partial structures represented by the following general formula (33) and the following general formula (34), the energy gap T 77K(Mat3) can be kept high.

[0273] [ka]

[0274] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 each independently represents a nitrogen atom or CR 31 It is. In the general formula (34), Y 32 , Y 34 , and Y 36 each independently represents a nitrogen atom or CR 31 It is. In the general formulae (33) and (34), R 31 are each independently a hydrogen atom or a substituent, R as a Substituent 31 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, Halogen atoms, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of: However, the above R 31The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the above formula (I) is preferably a non-condensed ring. In the general formula (33) and the general formula (34), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0275] In the general formula (33), Y 31 , Y 32 , Y 34 , and Y 36 are each independently 31 Preferably, R 31 are either identical to or different from each other. In addition, in the general formula (34), Y 32 , Y 34 , and Y 36 are each independently 31 Preferably, R 31 are either identical to or different from each other.

[0276] The substituted germanium group is -Ge(R 301 )3. 301 are each independently a substituent. 301 is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. 301 are the same or different from each other.

[0277] The partial structure represented by the general formula (32) is preferably contained in the third compound as at least any one group selected from the group consisting of groups represented by the following general formulae (35) to (39) and the following general formula (30a):

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] In the general formula (35), Y 41 or Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formulas (36) and (37), Y 41 ~Y 45 , Y 47 , and Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (38), Y 41 , Y 42 , Y 44 , Y 45 , Y 47 , and Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (39), Y 42 ~Y 48 each independently represents a nitrogen atom or CR 32 It is. In the general formula (30a), Y 42 ~Y 47 each independently represents a nitrogen atom or CR 32 It is. In the general formulae (35) to (39) and (30a), R 32 are each independently a hydrogen atom or a substituent, R as a Substituent 32 teeth, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, Halogen atoms, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of Multiple R 32 are the same or different from each other. In the general formulae (37) to (39) and (30a), X 30 is NR 33 , an oxygen atom, or a sulfur atom; R 33 teeth, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; a substituted or unsubstituted silyl group, substituted germanium groups, Substituted phosphine oxide groups, fluorine atom, Cyano group, Nitro groups, and Substituted or unsubstituted carboxyl group is selected from the group consisting of Multiple R 33 are the same or different from each other. However, the above R 33 The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the above formula (I) is preferably a non-condensed ring. In the general formulae (35) to (39) and (30a), * each independently represents a bonding site to another atom or another structure in the molecule of the third compound.

[0282] In the general formula (35), Y 41 ~Y 48 are each independently 32 In the general formula (36) and the general formula (37), Y 41 ~Y 45 ,Y 47 , and Y 48 are each independently 32 In the general formula (38), Y 41 ,Y 42 ,Y 44 ,Y 45 ,Y 47 , and Y 48 are each independently 32 In the general formula (39), Y 42 ~Y 48 are each independently 32 In the general formula (30a), Y 42 ~Y 47 are each independently 32 Preferably, R 32 are the same or different from each other.

[0283] In the third compound, X 30 is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

[0284] In the third compound, R 31 , and R 32 are each independently a hydrogen atom or a substituent, and R 31 and R as a substituent 32R is preferably any group selected from the group consisting of a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. 31 , and R 32 is more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. 31 and R as a substituent 32 When is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group is preferably a non-condensed ring.

[0285] The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

[0286] Method for producing the third compound The third compound can be produced by, for example, the methods described in International Publication No. 2012 / 153780 and International Publication No. 2013 / 038650, etc. In addition, the third compound can be produced by, for example, using a known alternative reaction and raw materials suited to the target product.

[0287] Examples of the substituent in the third compound are as follows, but the present invention is not limited to these examples.

[0288] Specific examples of aryl groups (sometimes referred to as aromatic hydrocarbon groups) include phenyl groups, tolyl groups, xylyl groups, naphthyl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, benzo[c]phenanthryl groups, benzo[g]chrysenyl groups, benzanthryl groups, triphenylenyl groups, fluorenyl groups, 9,9-dimethylfluorenyl groups, benzofluorenyl groups, dibenzofluorenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, and fluoranthenyl groups, and preferred examples include phenyl groups, biphenyl groups, terphenyl groups, quaterphenyl groups, naphthyl groups, triphenylenyl groups, and fluorenyl groups. Examples of the aryl group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group. As the specific examples indicate, aryl groups include both fused and non-fused aryl groups. The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a triphenylenyl group, or a fluorenyl group.

[0289] Specific examples of heteroaryl groups (which may be referred to as heterocyclic groups, heteroaromatic ring groups, or aromatic heterocyclic groups) include a pyrrolyl group, a pyrazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a pyridyl group, a triazinyl group, an indolyl group, an isoindolyl group, an imidazolyl group, a benzimidazolyl group, an indazolyl group, an imidazo[1,2-a]pyridinyl group, a furyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, an azadibenzofuranyl group, a thiophenyl group, a benzothienyl group, a dibenzothienyl group, an azadibenzothienyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinol ... Examples of such groups include a nazolinyl group, a naphthyridinyl group, a carbazolyl group, an azacarbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, an oxazolyl group, an oxadiazolyl group, a furazanyl group, a benzoxazolyl group, a thienyl group, a thiazolyl group, a thiadiazolyl group, a benzthiazolyl group, a triazolyl group, and a tetrazolyl group. Preferred examples of such groups include a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothienyl group. The heteroaryl group is preferably a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, or an azadibenzothienyl group, and more preferably a dibenzofuranyl group, a dibenzothienyl group, an azadibenzofuranyl group, or an azadibenzothienyl group.

[0290] In the third compound, the substituted silyl group is also preferably selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group. Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group. Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group. Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tritolylsilyl group.

[0291] In the third compound, the substituted phosphine oxide group is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of the substituted or unsubstituted diarylphosphine oxide group include a diphenylphosphine oxide group and a ditolylphosphine oxide group.

[0292] In the third compound, an example of the substituted carboxy group is a benzoyloxy group.

[0293] Specific examples of the third compound according to this embodiment are shown below. Note that the third compound in the present invention is not limited to these specific examples.

[0294] [ka]

[0295] [ka]

[0296] [ka]

[0297] <Relationship between the first compound, the second compound, and the third compound in the light-emitting layer> In the organic EL device of the present embodiment, it is preferable that the singlet energy S1 (Mat1) of the first compound and the singlet energy S1 (Mat3) of the third compound satisfy the relationship of the following mathematical formula (Math 2). S1(Mat3)>S1(Mat1) (Number 2)

[0298] Energy gap T at 77[K] for the third compound 77K (Mat3) is the energy gap T of the first compound at 77[K] 77K It is preferable that it is larger than (Mat1). Energy gap T at 77[K] for the third compound 77K (Mat3) is the energy gap T at 77[K] of the second compound 77K It is preferable that it is larger than (Mat2).

[0299] It is preferable that the singlet energy S1(Mat1) of the first compound, the singlet energy S1(Mat2) of the second compound, and the singlet energy S1(Mat3) of the third compound satisfy the relationship of the following mathematical formula (Math 2A). S1(Mat3)>S1(Mat1)>S1(Mat2)…(Math 2A)

[0300] Energy gap T at 77[K] of the first compound 77K (Mat1) and the energy gap T at 77[K] of the second compound 77K (Mat2) and the energy gap T at 77[K] of the third compound 77K It is preferable that (Mat3) satisfies the relationship of the following mathematical formula (Math 2B). T 77K (Mat3)>T 77K (Mat1)>T 77K (Mat2) ... (Math 2B)

[0301] When the organic EL device of this embodiment is caused to emit light, it is preferable that the fluorescent compound mainly emits light in the light-emitting layer. The organic EL element of this embodiment preferably emits red or green light, similarly to the organic EL element of the third embodiment. The maximum peak wavelength of the light emitted from the organic EL element can be measured in the same manner as in the organic EL element of the third embodiment.

[0302] Compound content in the light-emitting layer The contents of the first compound, the second compound, and the third compound in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass. The content of the second compound is preferably from 0.01% by mass to 10% by mass, more preferably from 0.01% by mass to 5% by mass, and further preferably from 0.01% by mass to 1% by mass. The content of the third compound is preferably 10% by mass or more and 80% by mass or less. The upper limit of the total content of the first compound, the second compound, and the third compound in the light-emitting layer is 100 mass %. Note that this embodiment does not exclude the light-emitting layer containing materials other than the first compound, the second compound, and the third compound. The light-emitting layer may contain only one type of the first compound or may contain two or more types. The light-emitting layer may contain only one type of the second compound or may contain two or more types. The light-emitting layer may contain only one type of the third compound or may contain two or more types.

[0303] FIG. 5 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light-emitting layer. In FIG. 5, S0 represents the ground state. S1(Mat1) represents the lowest excited singlet state of the first compound, and T1(Mat1) represents the lowest excited triplet state of the first compound. S1(Mat2) represents the lowest excited singlet state of the second compound, and T1(Mat2) represents the lowest excited triplet state of the second compound. S1(Mat3) represents the lowest excited singlet state of the third compound, and T1(Mat3) represents the lowest excited triplet state of the third compound. The dashed arrow from 1(Mat1) to S1(Mat2) in FIG. 5 represents the Förster type energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound. As shown in Figure 5, when a compound with a small ΔST(Mat1) is used as the first compound, the lowest excited triplet state T1(Mat1) can undergo reverse intersystem crossing to the lowest excited singlet state S1(Mat1) by thermal energy. Then, Förster type energy transfer occurs from the lowest excited singlet state S1(Mat1) of the first compound to the second compound, generating the lowest excited singlet state S1(Mat2). As a result, fluorescence emission from the lowest excited singlet state S1(Mat2) of the second compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

[0304] The organic EL device according to the fourth embodiment includes, in an emission layer, the compound of the first embodiment (at least any one of the compounds represented by any one of general formulas (11) to (13)) as a first compound, a second compound having a singlet energy smaller than that of the first compound, and a third compound having a singlet energy larger than that of the first compound. The organic EL element according to the fourth embodiment contains a compound (the compound of the first embodiment) capable of providing a high-performance organic EL element, in particular, a compound of the first embodiment having a high PLQY. Therefore, according to the fourth embodiment, a high-performance organic EL element can be provided. The organic EL element according to the fourth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0305] Fifth Embodiment The configuration of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those in the third and fourth embodiments will be given the same reference numerals and names, and the description will be omitted or simplified. In the fifth embodiment, for materials and compounds not specifically mentioned, the same materials and compounds as those described in the third and fourth embodiments can be used.

[0306] The organic EL device according to the fifth embodiment differs from the organic EL device according to the third embodiment in that the light-emitting layer contains a fourth compound instead of the second compound, but is otherwise similar to the organic EL device according to the third embodiment. In a fifth embodiment, the light-emitting layer includes a first compound and a fourth compound. In this embodiment, the first compound is preferably a dopant material (also referred to as a guest material, emitter, or luminescent material), and the fourth compound is preferably a host material (also referred to as a matrix material). The fourth compound may be a compound exhibiting delayed fluorescence or a compound not exhibiting delayed fluorescence. The fourth compound is not particularly limited, and for example, the third compound described in the fourth embodiment can be used.

[0307] <Relationship between the first compound and the fourth compound in the light-emitting layer> In the organic EL device 1 of the present embodiment, it is preferable that the singlet energy S1 (Mat1) of the first compound and the singlet energy S1 (Mat4) of the fourth compound satisfy the relationship of the following mathematical formula (Math 3). S1(Mat4)>S1(Mat1) (Number 3)

[0308] Energy gap T at 77[K] for the fourth compound 77K (Mat4) is the energy gap T of the first compound at 77[K] 77K It is preferable that the value is larger than (Mat1). In other words, it is preferable that the relationship of the following formula (Formula 5) is satisfied. T 77K (Mat4)>T 77K (Mat1) ...(Number 5)

[0309] When the organic EL device of the present embodiment is caused to emit light, it is preferable that the first compound mainly emits light in the light-emitting layer.

[0310] Compound content in the light-emitting layer The contents of the first compound and the fourth compound contained in the light-emitting layer are preferably within the following ranges, for example. The content of the first compound is preferably from 10% by mass to 80% by mass, more preferably from 10% by mass to 60% by mass, and further preferably from 20% by mass to 60% by mass. The content of the fourth compound is preferably from 20% by mass to 90% by mass, more preferably from 40% by mass to 90% by mass, and further preferably from 40% by mass to 80% by mass. In this embodiment, the light emitting layer may contain materials other than the first compound and the fourth compound. The light-emitting layer may contain only one type of the first compound or two or more types thereof.The light-emitting layer may contain only one type of the fourth compound or two or more types thereof.

[0311] FIG. 6 is a diagram showing an example of the relationship between the energy levels of the first compound and the fourth compound in the light-emitting layer. In FIG. 6, S0 represents the ground state. S1(Mat1) represents the lowest excited singlet state of the first compound, and T1(Mat1) represents the lowest excited triplet state of the first compound. S1(Mat4) represents the lowest excited singlet state of the fourth compound, and T1(Mat4) represents the lowest excited triplet state of the fourth compound. As shown in FIG. 6, when a material with a small ΔST(Mat1) is used as the first compound, the lowest excited triplet state T1 of the first compound can undergo reverse intersystem crossing to the lowest excited singlet state S1 by thermal energy. By utilizing the reverse intersystem crossing that occurs in this first compound, when the light-emitting layer does not contain a fluorescent dopant with a lowest excited singlet state S1 smaller than the lowest excited singlet state S1(Mat1) of the first compound, it is possible to observe light emission from the lowest excited singlet state S1(Mat1) of the first compound. It is believed that the use of delayed fluorescence due to this TADF mechanism can theoretically increase the internal efficiency to 100%.

[0312] The organic EL device according to the fifth embodiment includes, in an emission layer, the compound of the first embodiment as a first compound (at least any of the compounds represented by general formulas (11) to (13)) and a fourth compound having a higher singlet energy than the first compound. The organic EL element according to the fifth embodiment contains a compound (the compound of the first embodiment) capable of providing a high-performance organic EL element, in particular, a compound of the first embodiment having a high PLQY. Therefore, according to the fifth embodiment, a high-performance organic EL element can be provided. The organic EL element according to the fifth embodiment can be used in electronic devices such as display devices and light-emitting devices.

[0313] Sixth Embodiment [Compound] The compound of the sixth embodiment is a compound in which the group represented by the general formula (110) or (120) in the compound of the first embodiment (a compound represented by any one of the general formulas (11) to (13)) is replaced with a group represented by the following general formula (120C). That is, the compound of the sixth embodiment is different from the compound of the first embodiment. Specifically, the compound of the sixth embodiment is a compound represented by the general formulas (1-1) to (1-6) of the first embodiment, 101 ~R 160 are each independently a hydrogen atom, a substituent, a group represented by the general formula (110), or a group represented by the general formula (120), provided that in at least one group D1, R 101 ~R 160 is a group represented by the general formula (110) or a group represented by the general formula (120)" is changed to "R 101 ~R 160 are each independently a hydrogen atom, a substituent, or a group represented by the general formula (120C), provided that in at least one group D1, R 101 ~R 160 is a group represented by general formula (120C)." Therefore, in the sixth embodiment, the explanation will be centered on "a group represented by the following general formula (120C)" which is different from the first embodiment, and the description of the same contents as those in the first embodiment will be simplified or omitted.

[0314] [ka]

[0315] (In the general formula (120C), Z 200 teeth, a substituted or unsubstituted alkyl group having 2 to 30 carbon atoms; a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted trialkylsilyl group having 3 to 30 carbon atoms, Y 21 ~Y 24 each independently represents Y in the general formula (120) 21 ~Y 24 Synonymous with "R" except that multiple R 20A At least one pair of adjacent pairs of R 20A are the same or different from each other. In the general formula (120C), * represents the bonding position to the carbon atom of the six-membered ring in the general formulae (1-1) to (1-6).

[0316] Preferred aspects of the compound of the sixth embodiment A preferred embodiment of the compound of the sixth embodiment is the same as that of the compound of the first embodiment, except that the group represented by the general formula (120) in the compound of the first embodiment is replaced with a group represented by the general formula (120C). For example, the following preferred embodiments can be mentioned. In the compound of the sixth embodiment, when three groups D1 are selected as groups of R1 to R4, it is preferable that all of the selected three groups D1 are represented by one of the general formulas (1-1) to (1-6) and are the same groups including the substituents. In the compound of the sixth embodiment, when two groups D1 are selected as groups of R1 to R4, it is preferable that the two selected groups D1 are all represented by one of the general formulas (1-1) to (1-6) and are the same groups including the substituents.

[0317] In the compound of the sixth embodiment, when two groups D2 are selected as groups of R1 to R4, it is preferable that the two selected groups D2 are all represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents. In the compound of the sixth embodiment, when three groups D2 are selected as groups of R1 to R4, it is preferable that all of the selected three groups D2 are represented by one of the general formulas (2-1) to (2-4) and are the same groups including the substituents.

[0318] In the compound of the sixth embodiment, the group D2 is preferably a group represented by the general formula (2-1). In the compound of the sixth embodiment, the group D1 is preferably a group represented by the general formula (1-4) or (1-5).

[0319] In the compound of the sixth embodiment, when one of R1 to R4 is a group D1, in one group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the above general formula (120C). In the compound of the sixth embodiment, when two of R1 to R4 are groups D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the above general formula (120C). In the compound of the sixth embodiment, when three of R1 to R4 are group D1, in each group D1, R 101 ~R 160 It is preferable that only one of them is a group represented by the above general formula (120C).

[0320] In the compound of the sixth embodiment, R in the general formula (1-1) 107 ~R 110 is a group represented by general formula (120C), R in the general formula (1-2) 116 ~R 119 is a group represented by general formula (120C), R in the general formula (1-3) 126 ~R 129 is a group represented by general formula (120C), R in the general formula (1-4) 135 ~R 138 is a group represented by general formula (120C), R in the general formula (1-5) 145 ~R 148 is a group represented by general formula (120C), or R in the general formula (1-6) 157 ~R 160 It is preferable that any one of the above is a group represented by general formula (120C).

[0321] In the compound of the sixth embodiment, it is preferable that only one of R1 to R4 is the group D1.

[0322] The compound of the sixth embodiment is preferably a compound represented by any one of the general formulae (1003A), (1007A), (1008A), (1012A), (1018A) and (1021A). However, in the general formulae (1003A), (1007A), (1008A), (1012A), (1018A) and (1021A), at least one group D1 is R 101 ~R 160 At least one of the above is a group represented by general formula (120C).

[0323] In the compound of the sixth embodiment, it is preferable that only two of R1 to R4 are the group D1.

[0324] In the compound of the sixth embodiment, Y in the general formula (120C) 21 ~Y 24 CR 20A It is preferable that:

[0325] In the compound of the sixth embodiment, Z in the general formula (120C) 200 teeth, Substituted or unsubstituted ethyl group, substituted or unsubstituted n-propyl group, substituted or unsubstituted isopropyl group, substituted or unsubstituted n-butyl group, substituted or unsubstituted s-butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted t-butyl group, substituted or unsubstituted n-pentyl group, substituted or unsubstituted n-hexyl group, substituted or unsubstituted n-heptyl group, substituted or unsubstituted n-octyl group, substituted or unsubstituted n-nonyl group, substituted or unsubstituted n-decyl group, substituted or unsubstituted n-undecyl group, substituted or unsubstituted n-dodecyl group, substituted or unsubstituted n-tridecyl group a substituted or unsubstituted n-tetradecyl group, a substituted or unsubstituted n-pentadecyl group, a substituted or unsubstituted n-hexadecyl group, a substituted or unsubstituted n-heptadecyl group, a substituted or unsubstituted n-octadecyl group, a substituted or unsubstituted neopentyl group, a substituted or unsubstituted amyl group, a substituted or unsubstituted isoamyl group, a substituted or unsubstituted 1-methylpentyl group, a substituted or unsubstituted 2-methylpentyl group, a substituted or unsubstituted 1-pentylhexyl group, a substituted or unsubstituted 1-butylpentyl group, a substituted or unsubstituted 1-heptyloctyl group, a substituted or unsubstituted 3-methylpentyl group, A fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, a pentafluoroethyl group, It is preferably a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted triethylsilyl group, a substituted or unsubstituted tri-n-butylsilyl group, a substituted or unsubstituted tri-n-octylsilyl group, a substituted or unsubstituted triisobutylsilyl group, a substituted or unsubstituted dimethylethylsilyl group, a substituted or unsubstituted dimethylisopropylsilyl group, a substituted or unsubstituted dimethyl-n-propylsilyl group, a substituted or unsubstituted dimethyl-n-butylsilyl group, a substituted or unsubstituted dimethyl-t-butylsilyl group, a substituted or unsubstituted diethylisopropylsilyl group, a substituted or unsubstituted vinyldimethylsilyl group, a substituted or unsubstituted propyldimethylsilyl group, or a substituted or unsubstituted triisopropylsilyl group.

[0326] In the compound of the sixth embodiment, X1 to X6 in the group D1 are preferably oxygen atoms. In the compound of the sixth embodiment, X1 to X6 in the group D1 are preferably a sulfur atom.

[0327] The compound of the sixth embodiment is preferably a compound represented by the general formula (11). The compound of the sixth embodiment is preferably a compound represented by the general formula (12). The compound of the sixth embodiment is preferably a compound represented by the general formula (13).

[0328] In the compound of the sixth embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , and R 20Aare each independently preferably a hydrogen atom, a halogen atom, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, a group represented by -N(Rz)2, a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0329] In the compound of the sixth embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , and R 20A are preferably each independently a hydrogen atom, a halogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or an unsubstituted arylthio group having 6 to 14 ring carbon atoms.

[0330] In the compound of the sixth embodiment, R 101 ~R 160 , R 161 ~R 168 , R 171 ~R 200 , and R 20A are preferably each independently a hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, or an unsubstituted alkyl group having 1 to 6 carbon atoms.

[0331] In the compound of the sixth embodiment, R 20Ais preferably a hydrogen atom. In the compound of the sixth embodiment, it is also preferable that one or more of the hydrogen atoms in the molecule is a deuterium atom. In the compound of the sixth embodiment, R in the group D1 101 ~R 160 It is also preferred that one or more of the hydrogen atoms are hydrogen atoms and all of the hydrogen atoms are deuterium atoms. In the compound of this embodiment, R in the group D1 101 ~R 160 It is also preferred that one or more of the hydrogen atoms be hydrogen atoms and that all of the hydrogen atoms be proton atoms. In the compound of the sixth embodiment, R in the group D1 101 ~R 160 is preferably a hydrogen atom other than the group represented by general formula (120C), and the hydrogen atom is preferably a deuterium atom. In the compound of the sixth embodiment, R in the group D1 101 ~R 160 When any one or more of the above is a substituent (including a group represented by general formula (120C)) and the substituent has one or more hydrogen atoms, it is preferable that all of the hydrogen atoms are protium atoms, any one or more of the hydrogen atoms are deuterium atoms, or all of the hydrogen atoms are deuterium atoms.

[0332] In the compound of the sixth embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 It is also preferred that one or more of the hydrogen atoms are hydrogen atoms and all of the hydrogen atoms are deuterium atoms. In the compound of the sixth embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 It is also preferred that one or more of the hydrogen atoms be hydrogen atoms and that all of the hydrogen atoms be proton atoms. In the compound of the sixth embodiment, R in the group D2 161 ~R 168 and R 171~R 200 is a hydrogen atom, and it is also preferred that the hydrogen atom is a deuterium atom. In the compound of the sixth embodiment, R in the group D2 161 ~R 168 and R 171 ~R 200 When any one or more of the above is a substituent having one or more hydrogen atoms, it is preferable that all of the hydrogen atoms are protium atoms, any one or more of the hydrogen atoms are deuterium atoms, or all of the hydrogen atoms are deuterium atoms.

[0333] In the compound of the sixth embodiment, R 101 ~R 160 is a hydrogen atom other than the group represented by the general formula (120C), and R 161 ~R 168 and R 171 ~R 200 is preferably a hydrogen atom. In the compound of the sixth embodiment, R 101 ~R 160 is a hydrogen atom other than the group represented by the general formula (120C), and the hydrogen atom is a deuterium atom, and R 161 ~R 168 and R 171 ~R 200 is a hydrogen atom, and it is also preferred that the hydrogen atom is a deuterium atom.

[0334] In the compound of the sixth embodiment, the substituents in the case of "substituted or unsubstituted" are each independently the same as the substituents in the case of "substituted or unsubstituted" in the compound of the first embodiment.

[0335] Method for producing the compound of the sixth embodiment The compound of the sixth embodiment can be produced by a known method.

[0336] Specific examples of the compound of the sixth embodiment Specific examples of the compound of the sixth embodiment include the following compounds. However, the present invention is not limited to these specific examples of compounds.

[0337] [ka]

[0338] [ka]

[0339] [ka]

[0340] Seventh Embodiment [Organic EL element] An organic EL device according to one aspect of the seventh embodiment includes an anode, a cathode, and a first organic layer between the anode and the cathode, the first organic layer including a first compound C, The first compound C is a compound of the sixth embodiment.

[0341] The organic EL element according to the seventh embodiment is an organic EL element in which the first compound in any one of the third, fourth, and fifth embodiments is replaced with the first compound C (the compound in the sixth embodiment). That is, the organic EL element according to the seventh embodiment is different from the organic EL elements according to the third, fourth, and fifth embodiments.

[0342] Preferred aspects of the organic EL element according to the seventh embodiment Preferred aspects of the organic EL element according to the seventh embodiment are the same as those of the organic EL elements according to the third, fourth and fifth embodiments. For example, the following preferred aspects can be mentioned.

[0343] In the organic EL element of the seventh embodiment, the first organic layer is preferably a light-emitting layer. In the organic EL element of the seventh embodiment, the first organic layer contains a first compound C (the compound of the sixth embodiment) and further a second compound, and the second compound is preferably a fluorescent compound.

[0344] In the organic EL element of the seventh embodiment, it is preferable that the singlet energy S1(Mat1') of the first compound C and the singlet energy S1(Mat2) of the second compound satisfy the relationship of the following mathematical formula (Math 1'). S1(Mat1')>S1(Mat2) (Number 1')

[0345] In the organic EL device of the seventh embodiment, the first organic layer contains the first compound C (the compound of the sixth embodiment) and the second compound, and further contains a third compound, It is preferable that the singlet energy S1(Mat1') of the first compound C and the singlet energy S1(Mat3) of the third compound satisfy the relationship of the following mathematical formula (Math 2'). S1(Mat3)>S1(Mat1') (Number 2')

[0346] In the organic EL device of the seventh embodiment, the first organic layer contains the first compound C (the compound of the sixth embodiment) and the second compound, and further contains a third compound, It is preferable that the compound further includes a fourth compound in addition to the first compound C, and that the singlet energy S1(Mat1') of the first compound C and the singlet energy S1(Mat4) of the fourth compound satisfy the relationship of the following mathematical formula (Math 3'). S1(Mat4)>S1(Mat1') (Number 3')

[0347] In the organic EL element of the seventh embodiment, it is preferable that the first organic layer does not contain a metal complex. In the organic EL element of the seventh embodiment, the organic EL element includes the first compound C (the compound of the sixth embodiment) and the second compound, and further includes a third compound, and the first compound C is preferably a delayed fluorescent compound.

[0348] Specific examples of the second compound, the third compound, and the fourth compound in the seventh embodiment are shown in the specific examples of the second compound, the third compound, and the fourth compound described in the third embodiment.

[0349] Eighth embodiment [Electronic equipment] The electronic device according to the present embodiment is equipped with any of the organic EL elements according to the above-mentioned embodiments. Examples of the electronic device include display devices and light-emitting devices. Examples of the display device include display components (e.g., organic EL panel modules), televisions, mobile phones, tablets, and personal computers. Examples of the light-emitting device include lighting and vehicle lamps.

[0350] [Modifications of the embodiment] The present invention is not limited to the above-described embodiment, and any modifications and improvements that can achieve the object of the present invention are included in the present invention.

[0351] For example, the light-emitting layer is not limited to one layer, and multiple light-emitting layers may be laminated. When the organic EL element has multiple light-emitting layers, at least one of the light-emitting layers may satisfy 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 by electron transition from a triplet excited state directly to a ground state. Furthermore, when the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or the organic EL element may be a so-called tandem type organic EL element in which a plurality of light-emitting units are stacked via an intermediate layer.

[0352] In addition, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer and blocks at least one of holes, electrons, and excitons. For example, when a blocking layer is disposed in contact with the light-emitting layer on the cathode side, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) on the cathode side of the blocking layer. When the organic EL device includes an electron transport layer, it is preferable to include the blocking layer between the light-emitting layer and the electron transport layer. In addition, when a blocking layer is disposed in contact with the light-emitting layer on the anode side, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) on the anode side of the blocking layer. When the organic EL device includes a hole transport layer, it is preferable to include the blocking layer between the light-emitting layer and the hole transport layer. A barrier layer may be provided adjacent to the light-emitting layer to prevent the excitation energy from leaking from the light-emitting layer to the surrounding layers, and prevents excitons generated in the light-emitting layer from migrating to layers on the electrode side of the barrier layer (e.g., the electron transport layer and the hole transport layer, etc.). The light emitting layer and the barrier layer are preferably in contact with each other.

[0353] In addition, the specific structure and shape in carrying out the present invention may be other structures and shapes within the scope of the invention in which the object of the present invention can be achieved.

[0354] In this specification, a numerical range expressed using "to" means a range that includes the numerical value before "to" as the lower limit and the numerical value after "to" as the upper limit.

[0355] In this specification, Rx and Ry are bonded to each other to form a ring means, for example, that Rx and Ry contain a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom, and an atom contained in Rx (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom) and an atom contained in Ry (a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom) are bonded via a single bond, a double bond, a triple bond, or a divalent linking group to form a ring having 5 or more ring-forming atoms (specifically, a heterocyclic ring or an aromatic hydrocarbon ring). x is a number, a letter, or a combination of a number and a letter. y is a number, a letter, or a combination of a number and a letter. The divalent linking group is not particularly limited, and examples thereof include -O-, -CO-, -CO2-, -S-, -SO-, -SO2-, -NH-, -NRa-, and groups formed by combining two or more of these linking groups. Specific examples of the heterocycle include the ring structures (heterocycles) obtained by removing a bond from the "heteroaryl group Sub2" exemplified in the "Explanation of each substituent in the general formula" described below. These heterocycles may have a substituent. Specific examples of the aromatic hydrocarbon ring include the ring structures (aromatic hydrocarbon rings) obtained by removing a bond from the "aryl group Sub1" exemplified in the "Explanation of each substituent in the general formula" described below. These aromatic hydrocarbon rings may have a substituent. Examples of Ra include a substituted or unsubstituted alkyl group Sub3 having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group Sub1 having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group Sub2 having 5 to 30 ring atoms, which are exemplified in the "Explanation of each substituent in the general formula" described later. For example, when Rx and Ry are bonded to each other to form a ring, it means that in the molecular structure represented by the following general formula (E1), an atom included in Rx1 and an atom included in Ry1 form a ring (ring structure) E represented by general formula (E2); in the molecular structure represented by general formula (F1), an atom included in Rx1 and an atom included in Ry1 form a ring F represented by general formula (F2); in the molecular structure represented by general formula (G1), an atom included in Rx1 and an atom included in Ry1 form a ring G represented by general formula (G2); in the molecular structure represented by general formula (H1), an atom included in Rx1 and an atom included in Ry1 form a ring H represented by general formula (H2); in the molecular structure represented by general formula (I1), an atom included in Rx1 and an atom included in Ry1 form a ring I represented by general formula (I2). In the general formulae (E1) to (I1), * each independently represents a bonding position with other atoms in one molecule. The two * in the general formula (E1) correspond to the two * in the general formula (E2), the two * in the general formula (F1) correspond to the two * in the general formula (F2), the two * in the general formula (G1) correspond to the two * in the general formula (G2), the two * in the general formula (H1) correspond to the two * in the general formula (H2), and the two * in the general formula (I1) correspond to the two * in the general formula (I2).

[0356] [ka]

[0357] [ka]

[0358] In the molecular structures represented by the general formulae (E2) to (I2), E to I each represent a ring structure (a ring having 5 or more ring atoms). In the general formulae (E2) to (I2), * each independently represents a bonding position to other atoms in one molecule. The two * in the general formula (E2) correspond to the two * in the general formula (E1), respectively. Similarly, the two * in the general formulae (F2) to (I2) correspond to the two * in the general formulae (F1) to (I1), respectively.

[0359] For example, in general formula (E1), when Rx1 and Ry1 are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted benzene ring, the molecular structure represented by general formula (E1) becomes a molecular structure represented by the following general formula (E3), where the two * in general formula (E3) each independently correspond to the two * in general formula (E2) and general formula (E1). For example, in general formula (E1), when Rx1 and Ry1 are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted pyrrole ring, the molecular structure represented by general formula (E1) becomes a molecular structure represented by the following general formula (E4). Here, the two * in general formula (E4) each independently correspond to the two * in general formula (E2) and general formula (E1). In general formulas (E3) and (E4), * each independently represent a bonding position to another atom in one molecule.

[0360] [ka]

[0361] In this specification, the number of ring carbon atoms represents the number of carbon atoms among the atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbon atoms. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridinyl group has 5 ring carbon atoms, and a furanyl group has 4 ring carbon atoms. In addition, when a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring carbon atoms. In addition, when a fluorene ring is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring carbon atoms.

[0362] In this specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, a heterocyclic compound). Atoms that do not constitute a ring, and atoms contained in the substituent when the ring is substituted with a substituent, are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, a pyridine ring has 6 ring-forming atoms, a quinazoline ring has 10 ring-forming atoms, and a furan ring has 5 ring-forming atoms. The hydrogen atoms and atoms constituting the substituents bonded to the carbon atoms of the pyridine ring and the quinazoline ring are not included in the number of ring-forming atoms. In addition, when a fluorene ring is bonded to a fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

[0363] Explanation of each substituent in the general formula in this specification (Explanation of each substituent) An aryl group (sometimes referred to as an aromatic hydrocarbon group) in this specification is, for example, an aryl group Sub1. The aryl group Sub1 preferably has 6 to 30 ring carbon atoms, more preferably 6 to 20 ring carbon atoms, further preferably 6 to 14 ring carbon atoms, and even more preferably 6 to 12 ring carbon atoms. The aryl group Sub1 in this specification is, for example, at least one group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, a benzo[a]anthryl group, a benzo[c]phenanthryl group, a triphenylenyl group, a benzo[k]fluoranthenyl group, a benzo[g]chrysenyl group, a benzo[b]triphenylenyl group, a picenyl group, and a perylenyl group.

[0364] Among the above aryl groups Sub1, phenyl, biphenyl, naphthyl, phenanthryl, terphenyl and fluorenyl groups are preferred. As for the 1-fluorenyl, 2-fluorenyl, 3-fluorenyl and 4-fluorenyl groups, it is preferred that the carbon atom at the 9th position is substituted with a substituted or unsubstituted alkyl group Sub3 or a substituted or unsubstituted aryl group Sub1 as described later in this specification.

[0365] The heteroaryl group (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) in this specification is, for example, a heterocyclic group Sub2. The heterocyclic group Sub2 is a group containing, as a heteroatom, at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, a selenium atom, and a germanium atom. The heterocyclic group Sub2 is preferably a group containing, as a heteroatom, at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen. The heterocyclic group Sub2 preferably has 5 to 30 ring atoms, more preferably 5 to 20, and even more preferably 5 to 14 ring atoms.

[0366] In the present specification, the heterocyclic group Sub2 is, for example, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolinyl group, a naphthyridinyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an indolyl group, a benzimidazolyl group, an indazolyl group, an imidazopyridinyl group, a benztriazolyl group, a carbazolyl group, a furyl group, a thienyl group, an oxy group, At least one group selected from the group consisting of an azolyl group, a thiazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzofuranyl group, a benzothienyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoisoxazolyl group, a benzoisothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a piperidinyl group, a pyrrolidinyl group, a piperazinyl group, a morpholyl group, a phenazinyl group, a phenothiazinyl group, and a phenoxazinyl group.

[0367] Among the heterocyclic groups Sub2, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, and 9-carbazolyl are even more preferred. In the 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, and 4-carbazolyl groups, the nitrogen atom at the 9-position is preferably substituted with a substituted or unsubstituted aryl group Sub1 or a substituted or unsubstituted heterocyclic group Sub2 as defined herein.

[0368] In addition, in this specification, the heterocyclic group Sub2 may be, for example, a group derived from a partial structure represented by the following general formulae (XY-1) to (XY-18).

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] In the general formulae (XY-1) to (XY-18), X A and Y A are each independently a heteroatom, and are preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. The partial structures represented by the general formulae (XY-1) to (XY-18) have a bond at any position to form a heterocyclic group, and this heterocyclic group may have a substituent.

[0373] In this specification, the heterocyclic group Sub2 may be, for example, a group represented by the following general formulae (XY-19) to (XY-22). The position of the bond may also be changed appropriately.

[0374] [ka]

[0375] In this specification, the alkyl group may be any of a straight chain alkyl group, a branched chain alkyl group, and a cyclic alkyl group. An alkyl group herein is, for example, the alkyl group Sub3. The linear alkyl group in this specification is, for example, the linear alkyl group Sub 31 It is. In the present specification, the branched alkyl group is, for example, the branched alkyl group Sub 32 It is. The cyclic alkyl group in this specification is, for example, the cyclic alkyl group Sub 33 (Cycloalkyl group Sub33 (also called). The alkyl group Sub3 may be, for example, a straight-chain alkyl group Sub 31 , branched alkyl group Sub 32 , and the cyclic alkyl group Sub 33 and at least one group selected from the group consisting of: The linear alkyl group Sub 31 or a branched alkyl group Sub 32 The number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, even more preferably 1 to 10, and even more preferably 1 to 6. The cycloalkyl groups Sub 33 The number of ring carbon atoms is preferably 3 to 30, more preferably 3 to 20, even more preferably 3 to 10, and even more preferably 5 to 8.

[0376] The linear alkyl group Sub 31 or a branched alkyl group Sub 32 is, for example, at least one group selected from the group consisting of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl group, an amyl group, an isoamyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 1-pentylhexyl group, a 1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl group.

[0377] The above straight chain alkyl group Sub 31 or a branched alkyl group Sub 32As the alkyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an amyl group, an isoamyl group, and a neopentyl group are even more preferred.

[0378] The cycloalkyl groups Sub 33 is, for example, at least one group selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. 33 Among these, a cyclopentyl group and a cyclohexyl group are even more preferred.

[0379] A halogenated alkyl group in this specification is, for example, a halogenated alkyl group Sub4, which is, for example, an alkyl group Sub3 substituted with one or more halogen atoms, preferably fluorine atoms.

[0380] In this specification, the halogenated alkyl group Sub4 is, for example, at least one group selected from the group consisting of a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.

[0381] The substituted silyl group in this specification is, for example, a substituted silyl group Sub5, and the substituted silyl group Sub5 is, for example, an alkylsilyl group Sub 51 and the arylsilyl group Sub 52 and at least one group selected from the group consisting of:

[0382] The alkylsilyl group Sub 51 is, for example, a trialkylsilyl group Sub having the above alkyl group Sub3. 511 It is. Trialkylsilyl group Sub 511is, for example, at least one group selected from the group consisting of a trimethylsilyl group, a triethylsilyl group, a tri-n-butylsilyl group, a tri-n-octylsilyl group, a triisobutylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, a dimethyl-n-propylsilyl group, a dimethyl-n-butylsilyl group, a dimethyl-t-butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. 511 The three alkyl groups Sub3 in the formula may be the same or different.

[0383] The arylsilyl group Sub 52 is, for example, a dialkylarylsilyl group Sub 521 , alkyldiarylsilyl group Sub 522 , and the triarylsilyl group Sub 523 and at least one group selected from the group consisting of:

[0384] Dialkylarylsilyl group Sub 521 is, for example, a dialkylarylsilyl group having two of the above alkyl groups Sub3 and one of the above aryl groups Sub1. 521 The number of carbon atoms is preferably 8 to 30.

[0385] Alkyldiarylsilyl group Sub 522 is, for example, an alkyldiarylsilyl group having one of the above alkyl groups Sub3 and two of the above aryl groups Sub1. 522 The number of carbon atoms is preferably 13 to 30.

[0386] Triarylsilyl group Sub 523 is, for example, a triarylsilyl group having three of the above aryl groups Sub1. 523 The number of carbon atoms is preferably 18 to 30.

[0387] The substituted or unsubstituted alkylsulfonyl group in this specification is, for example, an alkylsulfonyl group Sub6, and the alkylsulfonyl group Sub6 is -SO2R w It is expressed as -SO2R w R in w represents the above-mentioned substituted or unsubstituted alkyl group Sub3.

[0388] An aralkyl group (sometimes referred to as an arylalkyl group) in this specification is, for example, an aralkyl group Sub7. The aryl group in the aralkyl group Sub7 includes, for example, at least one of the above aryl group Sub1 and the above heteroaryl group Sub2.

[0389] In the present specification, the aralkyl group Sub7 is preferably a group having an aryl group Sub1, and is represented as -Z3-Z4. Z3 is, for example, an alkylene group corresponding to the above alkyl group Sub3. Z4 is, for example, the above aryl group Sub1. In the aralkyl group Sub7, the aryl portion preferably has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl portion preferably has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, and even more preferably 1 to 6). This aralkyl group Sub7 is, for example, at least one group selected from the group consisting of benzyl group, 2-phenylpropan-2-yl 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.

[0390] The alkoxy group in this specification is, for example, an alkoxy group Sub8, which is represented as -OZ1. This Z1 is, for example, the above-mentioned alkyl group Sub3. The number of carbon atoms in the alkoxy group Sub8 is preferably 1 to 30, and more preferably 1 to 20. The alkoxy group Sub8 is, for example, at least any one group selected from the group consisting of a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.

[0391] A halogenated alkoxy group in this specification is, for example, a halogenated alkoxy group Sub9, which is, for example, an alkoxy group in which the above alkoxy group Sub8 is substituted with one or more halogen atoms, preferably fluorine atoms.

[0392] The aryloxy group (sometimes referred to as an arylalkoxy group) in this specification is, for example, an arylalkoxy group Sub 10 The arylalkoxy group Sub 10 The aryl group in the formula (I) includes at least one of an aryl group Sub1 and a heteroaryl group Sub2.

[0393] The arylalkoxy group Sub 10 is represented as -OZ2. Z2 is, for example, an aryl group Sub1 or a heteroaryl group Sub2. An arylalkoxy group Sub 10 The number of ring carbon atoms of this arylalkoxy group Sub is preferably 6 to 30, and more preferably 6 to 20. 10 Examples of the aryl group include a phenoxy group.

[0394] The substituted amino group in this specification is, for example, the substituted amino group Sub 11 and the substituted amino group Sub 11 is, for example, an arylamino group Sub 111 and alkylamino groups Sub 112 and at least one group selected from the group consisting of: Arylamino GroupsSub 111 -NHR V1 , or -N(R V1 )2. This R V1 is, for example, an aryl group Sub1. V1 )2 in two R V1 are the same or different. Alkylamino group Sub 112 -NHR V2 , or -N(R V2 )2. This R V2 is, for example, the alkyl group Sub3. V2 )2 in two R V2 are the same or different.

[0395] The alkenyl group in this specification is, for example, the alkenyl group Sub 12 and the alkenyl group Sub 12 is either a straight chain or a branched chain, and is, for example, at least one group selected from the group consisting of a vinyl group, a propenyl group, a butenyl group, an oleyl group, an eicosapentaenyl group, a docosahexaenyl group, a styryl group, a 2,2-diphenylvinyl group, a 1,2,2-triphenylvinyl group, and a 2-phenyl-2-propenyl group.

[0396] The alkynyl group in this specification is, for example, the alkynyl group Sub 13 and the alkynyl group Sub 13 may be either a straight chain or a branched chain, and is, for example, at least one group selected from the group consisting of ethynyl, propynyl, and 2-phenylethynyl.

[0397] The alkylthio group in this specification is, for example, the alkylthio group Sub 14 It is. Alkylthio group Sub 14 -SR V3 This R V3 is, for example, the alkyl group Sub3. 14The carbon number of the group is preferably 1 to 30, and more preferably 1 to 20. The arylthio group in this specification is, for example, the arylthio group Sub 15 It is. Arylthio group Sub 15 -SR V4 This R V4 is, for example, an aryl group Sub1. 15 The ring-forming carbon atoms are preferably 6 to 30, and more preferably 6 to 20.

[0398] In this specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom being preferred.

[0399] The substituted phosphino group in this specification is, for example, the substituted phosphino group Sub 16 and the substituted phosphino group Sub 16 is, for example, a phenylphosphanyl group.

[0400] The arylcarbonyl group in this specification is, for example, the arylcarbonyl group Sub 17 and the arylcarbonyl group Sub 17 is represented as -COY'. This Y' is, for example, an aryl group Sub1. In the present specification, the arylcarbonyl group Sub 17 is, for example, at least one group selected from the group consisting of a phenylcarbonyl group, a diphenylcarbonyl group, a naphthylcarbonyl group, and a triphenylcarbonyl group.

[0401] The acyl group in this specification is, for example, the acyl group Sub 18 and the acyl group Sub 18 is represented as -COR'. This R' is, for example, an alkyl group Sub3. In this specification, the acyl group Sub 18 is, for example, at least one group selected from the group consisting of an acetyl group and a propionyl group.

[0402] Substituted phosphoryl groups herein include, for example, the substituted phosphoryl group Sub 19 and a substituted phosphoryl group Sub 19 is represented by the following general formula (P).

[0403] [ka]

[0404] In the general formula (P), Ar P1 and Ar P2 is any substituent selected from the group consisting of the alkyl group Sub3 and the aryl group Sub1.

[0405] The ester group in this specification is, for example, the ester group Sub 20 and the ester group Sub 20 is, for example, at least one group selected from the group consisting of an alkyl ester group and an aryl ester group. The alkyl ester group in this specification is, for example, the alkyl ester group Sub 201 and the alkyl ester group Sub 201 is -C(=O)OR E It is expressed as R E is, for example, the above-mentioned substituted or unsubstituted alkyl group Sub3. The aryl ester group in this specification is, for example, the aryl ester group Sub 202 and the aryl ester group Sub 202 is -C(=O)OR Ar It is expressed as R Ar is, for example, the above substituted or unsubstituted aryl group Sub1.

[0406] The siloxanyl group in this specification is, for example, the siloxanyl group Sub 21 and the siloxanyl group Sub 21 is a silicon compound group via an ether bond. 21 is, for example, a trimethylsiloxanyl group.

[0407] In this specification, a carbamoyl group is represented by -CONH2. The substituted carbamoyl group in this specification is, for example, the carbamoyl group Sub 22 and the carbamoyl group Sub 22 -CONH-Ar C , or -CONH-R C It is expressed as Ar C is, for example, at least one group selected from the group consisting of the substituted or unsubstituted aryl group Sub1 (preferably having 6 to 10 ring carbon atoms) and the heteroaryl group Sub2 (preferably having 5 to 14 ring atoms). C may be a group formed by bonding an aryl group Sub1 and a heteroaryl group Sub2. R C is, for example, the above-mentioned substituted or unsubstituted alkyl group Sub3 (preferably having 1 to 6 carbon atoms).

[0408] In the present specification, the term "ring carbon atom" refers to a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. The term "ring atom" refers to a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

[0409] In addition, in this specification, hydrogen atom includes isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium. In the present specification, in a chemical structural formula, a hydrogen atom, i.e., a protium atom, a deuterium atom, or a tritium atom is assumed to be bonded to a possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom.

[0410] Hereinafter, the alkyl group Sub3 is the straight-chain alkyl group Sub described in "Description of each substituent". 31 , branched alkyl group Sub 32 , and the cyclic alkyl group Sub 33 The term "group" means any one or more of the groups represented by the formula: Similarly, the substituted silyl group Sub5 is an alkylsilyl group Sub 51 and the arylsilyl group Sub 52 The term "group" means any one or more of the groups represented by the formula: Similarly, the substituted amino group Sub 11 The arylamino group Sub 111 and alkylamino groups Sub 112 The term "group" means any one or more of the groups represented by the formula:

[0411] In the present specification, examples of the substituent in the case of "substituted or unsubstituted" include the substituent R F1 and the substituent R F1 are aryl groups Sub1, heteroaryl groups Sub2, alkyl groups Sub3, halogenated alkyl groups Sub4, substituted silyl groups Sub5, alkylsulfonyl groups Sub6, aralkyl groups Sub7, alkoxy groups Sub8, halogenated alkoxy groups Sub9, arylalkoxy groups Sub 10 , substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16 , arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 , a carbamoyl group Sub 22 , an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxy group, a nitro group, and a carboxy group.

[0412] In the present specification, the substituent R in the case of "substituted or unsubstituted" F1 is a diarylboron group (Ar B1 Ar B2 B-) may be used. B1 and Ar B2Examples of Ar include the aryl group Sub1 described above. B1 Ar B2 B-Ar B1 and Ar B2 are the same or different.

[0413] Substituent R F1 Specific examples and preferred groups of the substituents are those in the "Description of Each Substituent" (e.g., aryl group Sub1, heteroaryl group Sub2, alkyl group Sub3, halogenated alkyl group Sub4, substituted silyl group Sub5, alkylsulfonyl group Sub6, aralkyl group Sub7, alkoxy group Sub8, halogenated alkoxy group Sub9, arylalkoxy group Sub 10 , substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16 , arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 and the carbamoyl group Sub 22 Specific examples and preferred groups of the same as those of the above-mentioned aryl group are mentioned.

[0414] Substituent R in the case of "substituted or unsubstituted" F1 are aryl groups Sub1, heteroaryl groups Sub2, alkyl groups Sub3, halogenated alkyl groups Sub4, substituted silyl groups Sub5, alkylsulfonyl groups Sub6, aralkyl groups Sub7, alkoxy groups Sub8, halogenated alkoxy groups Sub9, arylalkoxy groups Sub 10 , substituted amino group Sub 11 , alkenyl group Sub 12 , an alkynyl group Sub 13 , an alkylthio group Sub 14 , an arylthio group Sub 15 , substituted phosphino group Sub 16, arylcarbonyl group Sub 17 , acyl group Sub 18 , substituted phosphoryl group Sub 19 , ester group Sub 20 , siloxanyl group Sub 21 , a carbamoyl group Sub 22 , at least one group selected from the group consisting of an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxy group, a nitro group, and a carboxy group (hereinafter, the substituent R F2 These substituents R F2 may be bonded to each other to form a ring.

[0415] In the case of "substituted or unsubstituted", "unsubstituted" means the above-mentioned substituent R F1 This means that the ring is not substituted with a hydrogen atom and has a hydrogen atom bonded thereto.

[0416] In the present specification, the "number of carbon atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having a carbon number of XX to YY" represents the number of carbon atoms when the ZZ group is unsubstituted, and represents the number of carbon atoms when the ZZ group is substituted. F1 The carbon number is not included.

[0417] In the present specification, the "number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having the number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and the number of substituents R F1 The number of atoms is not included.

[0418] The same applies to the term "substituted or unsubstituted" in the compounds or partial structures thereof described in this specification.

[0419] In this specification, when substituents are bonded to each other to form a ring, the ring structure is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.

[0420] In this specification, examples of the aromatic hydrocarbon group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-mentioned monovalent aryl group Sub1. In this specification, examples of the heterocyclic group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-mentioned monovalent heteroaryl group Sub2. EXAMPLES

[0421] <Compound> The structures of the compounds according to Examples 1 to 3 are shown below. The compounds according to Examples 1 to 3 were synthesized according to Synthesis Examples 1 to 3. Compounds TADF1 and TADF3 were used in the preparation of the organic EL devices of Example 1A and Example 2A, respectively.

[0422] [ka]

[0423] The structures of the compounds synthesized according to Synthesis Examples 4 and 5 are shown below.

[0424] [ka]

[0425] The structures of the compounds according to Comparative Examples 1 to 6 are shown below: Compound Ref-3 was used in the production of the organic EL device of Comparative Example 1B.

[0426] [ka]

[0427] [ka]

[0428] [ka]

[0429] The structures of other compounds used in the production of the organic EL devices of Examples 1A to 2A and Comparative Example 1B are shown below.

[0430] [ka]

[0431] [ka]

[0432] [ka]

[0433] [ka]

[0434] <Fabrication of organic EL elements> An organic EL device was prepared as follows and evaluated.

[0435] Example 1A A 25mm x 75mm x 1.1mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 1 minute. The ITO film thickness was 130nm. The glass substrate with the transparent electrode lines after cleaning was mounted on a substrate holder of a vacuum deposition apparatus, and the compound HT1 and the compound HA were co-deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer with a thickness of 10 nm. The concentration of the compound HT1 in the hole injection layer was 97% by mass, and the concentration of the compound HA was 3% by mass. Next, the compound HT1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 200 nm on the hole injection layer. Next, the compound HT2 was deposited on the first hole transport layer to form a second hole transport layer (sometimes referred to as an electron blocking layer) having a thickness of 10 nm. Next, a compound TADF1 as a first compound, a compound RD as a second compound, and a compound HOST as a third compound were co-deposited on the second hole transport layer to form a light-emitting layer having a thickness of 25 nm. The concentration of the compound TADF1 in the light-emitting layer was 25 mass %, the concentration of the compound RD was 1 mass %, and the concentration of the compound HOST was 74 mass %. Next, the compound ET1 was evaporated onto this light-emitting layer to form a first electron transporting layer (sometimes referred to as a hole blocking layer) having a thickness of 10 nm. Next, the compound ET2 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 30 nm. Next, lithium fluoride (LiF) was deposited on this second electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm. Then, metallic aluminum (Al) was vapor-deposited on this electron injecting electrode to form a metallic Al cathode with a film thickness of 80 nm. The device configuration of the organic EL device according to Example 1A is shown in schematic form as follows. ITO(130) / HT1:HA(10,97%:3%) / HT1(200) / HT2(10) / HOST:TADF1:RD(25,74%:25%:1%) / ET1(10) / ET2(30) / LiF(1) / Al(80) The numbers in parentheses indicate the film thickness (unit: nm). Also in parentheses, the figures expressed as percentages (97%:3%) indicate the proportions (mass%) of compound HT1 and compound HA in the hole injection layer, and the figures expressed as percentages (74%:25%:1%) indicate the proportions (mass%) of compound HOST, compound TADF1, and compound RD in the light-emitting layer.

[0436] [Example 2A and Comparative Example 1B] The organic EL devices of Example 2A and Comparative Example 1B were prepared in the same manner as in Example 1A, except that the compound TADF1 in the emitting layer of Example 1A was replaced with the compounds shown in Table 1.

[0437] <Evaluation of organic EL elements> The organic EL devices prepared in Examples 1A to 2A and Comparative Example 1B were evaluated as follows. The results are shown in Table 1. Although the compound Ref-3 used in Comparative Example 1B does not correspond to the general formula of the first compound, it is conveniently shown in the same column as the compound TADF1 in Example 1A.

[0438] External quantum efficiency (EQE) Current density is 0.1mA / cm 2 , or 10mA / cm 2 The spectral radiance spectrum when a voltage was applied to the element so that the spectral radiance was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.) From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit: %) was calculated assuming that Lambertian radiation was performed. Below a current density of 0.1 mA / cm 2 The external quantum efficiency EQE (%) at a current density of 10 mA / cm is referred to as the "EQE (%) at low current." 2 The external quantum efficiency EQE (%) at this time is referred to as "EQE (%) at high current."

[0439] Using the following formula (number 100), the "EQE (%) at low current" of each example was calculated as "EQE (relative value: %) at low current" when the "EQE (%) at low current" of Comparative Example 1B was set to 100. EQE (relative value:%) at low current for each example = (EQE (%) at low current for each example / EQE (%) at low current for Comparative Example 1B) × 100 (number 100)

[0440] Using the following formula (Equation 101), the "EQE (%) at high current" of each example was calculated as the "EQE (relative value: %) at high current" when the "EQE (%) at high current" of Comparative Example 1B was set to 100. EQE (relative value:%) at high current for each example = (EQE (%) at high current for each example / EQE (%) at high current for Comparative Example 1B) × 100 (equation 101)

[0441] Chromaticity CIEx, CIEy, and maximum peak wavelength λp Using a spectroradiometer CS-2000 (Konica Minolta, Inc.), a current density of 10 mA / cm 2 The spectral radiance spectrum was measured when a voltage was applied to the element so that the spectral radiance spectrum was as follows: Chromaticity CIEx, CIEy, and maximum peak wavelength λp (unit: nm) were calculated from the obtained spectral radiance spectrum.

[0442] [Table 1]

[0443] The organic EL elements of Examples 1A to 2A exhibited a higher luminance at low currents (current densities of 0.1 mA / cm2) than the organic EL element of Comparative Example 1B. 2 Even at high currents (current densities of 10 mA / cm 2 The external quantum efficiency EQE was also improved when

[0444] <Compound evaluation>

[0445] (Preparation of toluene solution) The compound TADF1 was dissolved in toluene to a concentration of 5 μmol / L to prepare a toluene solution of the compound TADF1. After that, the prepared solution was bubbled with nitrogen for 5 minutes and sealed to prevent mixing with outside air. For each of the compounds TADF2 to TADF3 and Ref-1 to Ref-6, a toluene solution was prepared in the same manner as for the compound TADF1. Then, the prepared solution was bubbled with nitrogen for 5 minutes and sealed to prevent mixing with outside air.

[0446] (Measurement of fluorescence quantum yield (PLQY)) For each of the toluene solutions of the prepared compounds TADF1 to TADF3 and Ref-1 to Ref-6, the PLQY was measured using an absolute PL (photoluminescence) quantum yield measurement device Quantaurus-QY (manufactured by Hamamatsu Photonics KK). The measurement results are shown in Table 2.

[0447] (Maximum peak wavelength of compound) A 5 μmol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the fluorescence spectrum (vertical axis: fluorescence emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300K). In this example, the fluorescence spectrum was measured using a Hitachi spectrophotometer (device name: F-7000). Note that the fluorescence spectrum measuring device is not limited to the device used here. In the fluorescence spectrum, the peak wavelength of the fluorescence spectrum at which the emission intensity is maximum was taken as the maximum peak wavelength. The measurement results are shown in Table 2.

[0448] (Thermal activated delayed fluorescence) Delayed fluorescence of compound TADF1 The delayed fluorescence was confirmed by measuring the transient PL using the apparatus shown in Figure 2. The compound TADF1 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. To prevent quenching by oxygen, the sample solution was frozen and degassed, and then sealed in a cell with a lid under an argon atmosphere to prepare an oxygen-free sample solution saturated with argon. 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 intensity of both spectra according to formula (1) in Morris et al. J. Phys. Chem. 80 (1976) 969. After being excited by pulsed light (light irradiated from a pulsed laser) having a wavelength absorbed by the compound TADF1, there are prompt luminescence (instantaneous luminescence) that is observed immediately from the excited state, and delayed luminescence (delayed luminescence) that is not observed immediately after the excitation and is observed later. In this embodiment, delayed fluorescent luminescence means that the amount of delayed luminescence (delayed luminescence) is 5% or more relative to the amount of prompt luminescence (instantaneous luminescence). Specifically, when the amount of prompt luminescence (instantaneous luminescence) is X P and the amount of delay light emission is X D When X D / X P This means that the value is 0.05 or more. The amount and ratio of prompt and delay luminescence are calculated using a method similar to that described in “Nature 492, 234-238, 2012” (Reference 1). The device used to calculate the amount of prompt light emission and delayed light emission is not limited to the device described in Reference 1 or the device shown in FIG. It was confirmed that the amount of delayed luminescence (delayed luminescence) of the compound TADF1 was 5% or more relative to the amount of prompt luminescence (prompt luminescence). Specifically, for compound TADF1, X D / X P It was confirmed that the value was 0.05 or higher.

[0449] Delayed fluorescence of compounds TADF2-3 and comparison compounds Ref-1-Ref-6 The delayed fluorescence properties of the compounds TADF2 to 3 and the comparative compounds Ref-1 to Ref-6 were confirmed in the same manner as above, except that the compounds TADF2 to 3 and the comparative compounds Ref-1 to Ref-6 were used instead of the compound TADF1, respectively. For compounds TADF2-3 and comparative compounds Ref-1-Ref-6, X D / X P The values ​​were all above 0.05.

[0450] (Singlet energy S1) The singlet energies S1 of the compounds TADF2 to 3 and the comparative compounds Ref-1 to Ref-6 were measured by the above-mentioned solution method. The measurement results are shown in Table 2.

[0451] (ΔST) T of compounds TADF2-3 and comparison compounds Ref-1-Ref-6 77K was measured, and ΔST was confirmed from the results and the value of the singlet energy S1 mentioned above. T of compounds TADF2-3 and comparison compounds Ref-1-Ref-6 77Kis the energy gap T 77K The measurement was performed according to the method described above. The measurement results are shown in Table 2.

[0452] [Table 2]

[0453] Explanation in the table "<0.01" indicates less than 0.01 eV.

[0454] As shown in Table 2, the compounds TADF1 to TADF3 of Examples 1 to 3 showed improved PLQY compared to the comparative compounds Ref-1 to Ref-6. The only difference between compounds TADF1 to TADF3 of Examples 1 to 3 and compounds Ref-1 to Ref-6 of Comparative Examples 1 to 6 is the presence or absence of a group represented by general formula (110) or (120). It is therefore understood that the presence of a group represented by general formula (110) or (120) improves the PLQY. In particular, a comparison between Example 1 and Comparative Examples 4 and 5 reveals that, compared to the compound TADF1 having the general formula (120), the compounds Ref-4 and Ref-5, which are similar to the general formula (120) but have a different bonding position of Z2, have inferior PLQY. In particular, a comparison between Example 3 and Comparative Example 6 reveals that, compared to compound TADF3 having a 1-dibenzofuranyl group as general formula (110), compound Ref-6 having a 4-dibenzofuranyl group that does not correspond to general formula (110) despite being the same dibenzofuranyl group, has an inferior PLQY.

[0455] <Synthesis of Compounds>

[0456] Synthesis Example 1 The method for synthesizing the compound TADF1 is described below.

[0457] [ka]

[0458] In a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 2-biphenylboronic acid (9.7 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 6 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 13.3 g of a white solid. The compound was identified as Ma by GC-MS (Gas Chromatograph Mass Spectometer) analysis (yield 97%).

[0459] [ka]

[0460] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Ma (11 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 16 g of a white solid. It was identified as compound Mb by GC-MS analysis (yield 91%).

[0461] In a nitrogen atmosphere, compound Mb (16 g, 35 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.30 g, 0.70 mmol), palladium(II) acetate (Pd(OAc)2) (78 mg, 0.35 mmol), potassium carbonate (9.7 g, 70 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 10.6 g of a white solid. It was identified as compound Mc by GC-MS analysis (yield 72%).

[0462] [ka]

[0463] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mc (2.4 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 4.2 g of a red solid. It was identified as TADF1 by ASAP-MS (Atmospheric Pressure Solid Analysis Probe Mass Spectrometry) analysis (yield 88%).

[0464] Synthesis Example 2 The method for synthesizing the compound TADF2 is described below.

[0465] [ka]

[0466] Under a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 1-naphthylboronic acid (8.4 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 6 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 9.6 g of a white solid. The compound was identified as Md by GC-MS analysis (yield 77%).

[0467] [ka]

[0468] Under a nitrogen atmosphere, 4-bromodibenzothiophene (9.2 g, 35 mmol), compound Md (9.6 g, 35 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.32 g, 0.35 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.41 g, 1.4 mmol), sodium tert-butoxide (NaOtBu) (5.0 g, 53 mmol) and 100 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 14 g of a white solid. It was identified as compound Me by GC-MS analysis (yield 94%).

[0469] In a nitrogen atmosphere, compound Me (14 g, 33 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.30 g, 0.70 mmol), palladium(II) acetate (Pd(OAc)2) (78 mg, 0.35 mmol), potassium carbonate (9.7 g, 70 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 11.2 g of a white solid. It was identified as compound Mf by GC-MS analysis (yield 85%).

[0470] [ka]

[0471] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mf (2.2 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.8 g of a red solid. It was identified as TADF2 by ASAP-MS analysis (yield 80%).

[0472] Synthesis Example 3 The method for synthesizing the compound TADF3 is described below.

[0473] [ka]

[0474] In a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 1-dibenzofuranylboronic acid (10.4 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 8 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 13.7 g of a white solid. The compound was identified as Mg by GC-MS analysis (yield 95%).

[0475] [ka]

[0476] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Mg (11.2 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 17.7 g of a white solid. It was identified as compound Mh by GC-MS analysis (yield 98%).

[0477] In a nitrogen atmosphere, compound Mh (17.7 g, 37.2 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.32 g, 0.74 mmol), palladium(II) acetate (Pd(OAc)2) (84 mg, 0.37 mmol), potassium carbonate (10.2 g, 74 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 14.4 g of a white solid. The compound was identified as compound Mi by GC-MS analysis (yield 88%).

[0478] [ka]

[0479] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mi (2.4 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.5 g of a red solid. It was identified as TADF3 by ASAP-MS analysis (yield 71%).

[0480] Synthesis Example 4 The method for synthesizing the compound TADF4 is described below.

[0481] [ka]

[0482] In a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 9-phenanthrenylboronic acid (10.8 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 6 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 13.4 g of a white solid. The compound was identified as Mj by GC-MS analysis (yield 90%).

[0483] [ka]

[0484] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Mj (11.6 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 16.4 g of a white solid. It was identified as compound Mk by GC-MS analysis (yield 89%).

[0485] In a nitrogen atmosphere, compound Mk (16.4 g, 33.8 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.29 g, 0.68 mmol), palladium(II) acetate (Pd(OAc)2) (77 mg, 0.34 mmol), potassium carbonate (9.4 g, 68 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 10.5 g of a white solid. It was identified as compound Ml by GC-MS analysis (yield 69%).

[0486] [ka]

[0487] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Ml (2.5 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 4.1 g of a red solid. It was identified as TADF4 by ASAP-MS analysis (yield 84%).

[0488] Synthesis Example 5 The synthesis method of the compound TADF5 is described below.

[0489] [ka]

[0490] Under a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 3-fluoranthene boronic acid (12 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 6 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 13.7 g of a white solid. The compound was identified as Mm by GC-MS analysis (yield 85%).

[0491] [ka]

[0492] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Mm (12.5 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 16.9 g of a yellow solid. It was identified as compound Mn by GC-MS analysis (yield 87%).

[0493] In a nitrogen atmosphere, compound Mn (16.9 g, 33.1 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.28 g, 0.66 mmol), palladium(II) acetate (Pd(OAc)2) (74 mg, 0.33 mmol), potassium carbonate (9.1 g, 66 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 14.3 g of a yellow solid. The compound was identified as compound M-о by GC-MS analysis (yield 91%).

[0494] [ka]

[0495] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0g, 4.6mmol), compound M-о (2.6g, 5.5mmol), potassium carbonate (1.1g, 8.2mmol) and 20mL of DMF were placed in a 50mL three-neck flask and stirred at 120℃ for 4 hours. 10mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.0g of a red solid. It was identified as TADF5 by ASAP-MS analysis (yield 66%).

[0496] [Comparative Synthesis Example 1] Comparative compound Ref-1 was synthesized according to Synthesis Example 21 described in WO2020 / 022378A1.

[0497] [Comparative Synthesis Example 2] Comparative compound Ref-2 was synthesized according to Synthesis Example 22 described in WO2020 / 022378A1.

[0498] [Comparative Synthesis Example 3] The synthesis method of the comparative compound Ref-3 is described below.

[0499] [ka]

[0500] Under a nitrogen atmosphere, 5-bromo-2-chloro-aniline (50 g, 242 mmol), phenylboronic acid (32.5 g, 266 mmol), palladium acetate (1.4 g, 6.2 mmol), sodium carbonate (50 g, 484 mmol) and 250 mL of methanol were placed in a 500 mL three-neck flask and stirred at 80°C for 6 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 39.5 g of a white solid. The compound was identified as M-E1 by GC-MS analysis (yield 80%).

[0501] [ka]

[0502] Under a nitrogen atmosphere, 4-bromodibenzothiophene (12.9 g, 49.1 mmol), compound M-E1 (10 g, 49.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.67 g, 0.74 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.85 g, 2.95 mmol), sodium tert-butoxide (NaOtBu) (7.1 g, 73.7 mmol) and 130 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 7 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 18 g of a white solid. It was identified as compound M-E2 by GC-MS analysis (yield 93%).

[0503] In a nitrogen atmosphere, compound M-E2 (10 g, 26 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.22 g, 0.52 mmol), palladium(II) acetate (Pd(OAc)2) (58 mg, 0.26 mmol), potassium carbonate (7.1 g, 52 mmol) and 90 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 7.9 g of a white solid. The product was identified as compound M-E3 by GC-MS analysis (yield 87%).

[0504] [ka]

[0505] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound M-E3 (1.9 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 11 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.3 g of a red solid. It was identified as comparative compound Ref-3 by ASAP-MS analysis (yield 52%).

[0506] Comparative Synthesis Example 4 The synthesis method of the comparative compound Ref-4 is described below.

[0507] [ka]

[0508] In a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 3-biphenylboronic acid (9.7 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 7 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 13.0 g of a white solid. The compound was identified as Mp by GC-MS analysis (yield 95%).

[0509] [ka]

[0510] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Mp (11 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 15.6 g of a white solid. It was identified as compound Mq by GC-MS analysis (yield 89%).

[0511] In a nitrogen atmosphere, compound Mq (15 g, 32 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.27 g, 0.64 mmol), palladium(II) acetate (Pd(OAc)2) (72 mg, 0.32 mmol), potassium carbonate (8.8 g, 64 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 12.8 g of a white solid. The compound was identified as Mr by GC-MS analysis (yield 94%).

[0512] [ka]

[0513] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mr (2.4 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.7 g of a red solid. It was identified as comparative compound Ref-4 by ASAP-MS analysis (yield 77%).

[0514] [Comparative Synthesis Example 5] The synthesis method of the comparative compound Ref-5 is described below.

[0515] [ka]

[0516] Under a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 4-biphenylboronic acid (9.7 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80°C for 7 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 12.3 g of a white solid. The compound was identified as Ms by GC-MS analysis (yield 90%).

[0517] [ka]

[0518] Under a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Ms (11 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 4 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 12.4 g of a white solid. It was identified as compound Mt by GC-MS analysis (yield 71%).

[0519] In a nitrogen atmosphere, compound Mt (12 g, 26 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.22 g, 0.52 mmol), palladium(II) acetate (Pd(OAc)2) (59 mg, 0.26 mmol), potassium carbonate (7.2 g, 52 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 9.4 g of a white solid. The compound was identified as Mu by GC-MS analysis (yield 85%).

[0520] [ka]

[0521] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mu (2.4 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 2.6 g of a red solid. It was identified as comparative compound Ref-5 by ASAP-MS analysis (yield 55%).

[0522] Comparative Synthesis Example 6 The synthesis method of the comparative compound Ref-6 is described below.

[0523] [ka]

[0524] In a nitrogen atmosphere, 5-bromo-2-chloro-aniline (10 g, 49 mmol), 4-dibenzofuranylboronic acid (10.4 g, 49 mmol), palladium acetate (0.11 g, 0.5 mmol), sodium carbonate (10 g, 98 mmol) and 100 mL of methanol were placed in a 300 mL three-neck flask and stirred at 80° C. for 7 hours. 100 mL of ion-exchanged water was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 12.7 g of a white solid. The compound was identified as Mv by GC-MS analysis (yield 88%).

[0525] [ka]

[0526] In a nitrogen atmosphere, 4-bromodibenzothiophene (10 g, 38 mmol), compound Mv (11.2 g, 38 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.35 g, 0.38 mmol), tri-tert-butylphosphonium tetrafluoroborate (P(t-Bu)3HBF4) (0.44 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (5.5 g, 57 mmol) and 120 mL of toluene were added to a 200 mL three-neck flask, heated and stirred at 60 ° C for 7 hours, and then cooled to room temperature (25 ° C). The reaction solution was purified by silica gel column chromatography to obtain 13.2 g of a white solid. It was identified as compound Mw by GC-MS analysis (yield 73%).

[0527] In a nitrogen atmosphere, compound Mw (13 g, 27 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPrHCl) (0.23 g, 0.54 mmol), palladium(II) acetate (Pd(OAc)2) (61 mg, 0.27 mmol), potassium carbonate (7.5 g, 54 mmol) and 100 mL of N,N-dimethylacetamide (DMAc) were added to a 200 mL three-neck flask, stirred at 160°C for 3 hours, and then cooled to room temperature (25°C). The reaction solution was purified by silica gel column chromatography to obtain 8.2 g of a white solid. The compound was identified as compound Mx by GC-MS analysis (yield 69%).

[0528] [ka]

[0529] In a nitrogen atmosphere, 1,4-benzenedicarbonitrile,2,3,5-tri-9H-carbazol-9-yl-6-chloro-(3.0 g, 4.6 mmol), compound Mx (2.4 g, 5.5 mmol), potassium carbonate (1.1 g, 8.2 mmol) and 20 mL of DMF were placed in a 50 mL three-neck flask and stirred at 120°C for 4 hours. 10 mL of saturated aqueous ammonium chloride solution was added to the reaction mixture, and the precipitated solid was purified by silica gel column chromatography to obtain 3.6 g of a red solid. It was identified as comparative compound Ref-6 by ASAP-MS analysis (yield 74%). [Explanation of symbols]

[0530] Reference Signs List 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 any one of the following general formulas (11) to (13): 【Chemistry 1】 (In the general formulas (11) to (13), R １ ~R ４ are each independently A group D represented by any one of the following general formulas (1-1) to (1-6): １ or A group D represented by any one of the following general formulas (2-1) to (2-4): ２ and R １ ~R ４ At least one of the groups D １ and R １ ~R ４ At least one of the groups D ２ and Base D １ When a plurality of groups are present, a plurality of groups D １ are the same or different, Base D ２ When a plurality of groups are present, a plurality of groups D ２ are the same or different.) 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 (In the above general formulas (1-1) to (1-6), X １ ~X ６ are each independently an oxygen atom or a sulfur atom, R １０１ ~R １６０ each independently represents a hydrogen atom, a substituent, a group represented by the general formula (110), or a group represented by the general formula (120), However, at least one group D １ In the above, R １０１ ~R １６０ At least one of the above is a group represented by general formula (110) or a group represented by general formula (120), In the general formula (110), Z １ is a constituent atom of ring (B) and is a carbon atom or a nitrogen atom, Z １ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 30 ring carbon atoms, Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and R １０Ａ are each independently a hydrogen atom or a substituent, or a plurality of R １０Ａ one or more pairs of adjacent two or more of R １０Ａ and R are bonded to each other to form a ring, or a ring (B) and a plurality of R １０Ａ one or more pairs of adjacent two or more of In the general formula (120), Z ２ teeth, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Y ２１ ~Y ２４ each independently represents a nitrogen atom or CR ２０Ａ and R ２０Ａ each independently represents a hydrogen atom or a substituent, Multiple R ２０Ａ one or more of adjacent pairs of two or more of Multiple R １０Ａ are the same or different, Multiple R ２０Ａ are the same or different, In the general formulae (2-1) to (2-4), R １６１ ~R １６８ and R １７１ ~R ２００ are each independently a hydrogen atom or a substituent, R as a substituent other than the group represented by the general formula (110) and the group represented by the general formula (120) in the general formulas (1-1) to (1-6) １０１ ~R １６０ R as a substituent in the general formula (110) １０Ａ R as a substituent in the general formula (120) ２０Ａ and R as a substituent in the general formulae (2-1) to (2-4) １６１ ~R １６８ and R １７１ ~R ２００ are each independently Halogen atoms, Cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 ring carbon atoms, Hydroxy groups, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, -N(Rz) ２ A group represented by Thiol groups, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, substituted germanium groups, Substituted phosphine oxide groups, Nitro group, a substituted boryl group, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, Rz is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; -N(Rz) ２ Two Rz's are the same or different, In the general formulae (1-1) to (1-6), * each independently represents a bonding position to a carbon atom of a 6-membered ring in the general formulae (11) to (13), In the general formula (110), * represents a bonding position to a carbon atom of a six-membered ring in the general formulae (1-1) to (1-6), In the general formula (120), * represents a bonding position to a carbon atom of a 6-membered ring in the general formulae (1-1) to (1-6), In the general formulae (2-1) to (2-4), * each independently represents a bonding position to a carbon atom of a six-membered ring in the general formulae (11) to (13).

2. In the compound according to claim 1 , R １ ~R ４ As the group, three groups D １ When is selected, the three selected groups D １ are all represented by one of the general formulae (1-1) to (1-6) and are the same group including the substituents, R １ ~R ４ As the group, two groups D １ When is selected, the two selected groups D １ are all represented by one of the general formulae (1-1) to (1-6) and are the same group including the substituents. compound.

3. In the compound according to claim 1 or 2, R １ ~R ４ As the group, three groups D ２ When is selected, the three selected groups D ２ are all represented by one of the general formulae (2-1) to (2-4) and are the same group including the substituents, R １ ~R ４ As the group, two groups D ２ When is selected, the two selected groups D ２ are all represented by one of the general formulae (2-1) to (2-4) and are the same group including the substituents. compound.

4. In the compound according to any one of claims 1 to 3, R in the general formula (1-1) １０７ ~R １１０ is a group represented by the general formula (110) or a group represented by the general formula (120), R in the general formula (1-2) １１６ ~R １１９ is a group represented by the general formula (110) or a group represented by the general formula (120), R in the general formula (1-3) １２６ ~R １２９ is a group represented by the general formula (110) or a group represented by the general formula (120), R in the general formula (1-4) １３５ ~R １３８ is a group represented by the general formula (110) or a group represented by the general formula (120), R in the general formula (1-5) １４５ ~R １４８ is a group represented by the general formula (110) or a group represented by the general formula (120), or R in the general formula (1-6) １５７ ~R １６０ Any one of the above is a group represented by general formula (110) or a group represented by general formula (120), compound.

5. In the compound according to any one of claims 1 to 4, The group D ２ is a group represented by the general formula (2-1). compound.

6. In the compound according to any one of claims 1 to 5, R １ ~R ４ Only one of the groups D １ That is, compound.

7. In the compound according to any one of claims 1 to 5, R １ ~R ４ Only two of the groups D １ That is, compound.

8. In the compound according to any one of claims 1 to 6, The compound is represented by any one of the following general formulas (1003A), (1007A), (1008A), (1012A), (1018A), and (1021A): compound. 【Chemistry 5】 【Chemistry 6】 (In the general formulae (1003A), (1007A), (1008A), (1012A), (1018A) and (1021A), D １ represents a group D represented by any one of the general formulas (1-1) to (1-6) １ is synonymous with R １６１ ~R １６８ each independently represents R in the general formula (2-1). １６１ ~R １６８ (Same meaning as above.)

9. In the compound according to any one of claims 1 to 8, The group D １ is a group represented by the general formula (1-4) or (1-5), compound.

10. In the compound according to any one of claims 1 to 9, The group D ２ R in １６１ ~R １６８ and R １７１ ~R ２００ is a hydrogen atom, compound.

11. In the compound according to any one of claims 1 to 10, R １ ~R ４ Of these, one is group D １ If １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110) or a group represented by general formula (120), R １ ~R ４ Of these, two are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110) or a group represented by general formula (120), R １ ~R ４ Of these, three are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110) or a group represented by general formula (120), compound.

12. In the compound according to any one of claims 1 to 11, At least one group D １ In the above, R １０１ ~R １６０ At least one of the above is a group represented by general formula (110). compound.

13. In a compound according to any one of claims 1 to 12, R １ ~R ４ Of these, one is group D １ If １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110), R １ ~R ４ Of these, two are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110), R １ ~R ４ Of these, three are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (110). compound.

14. In a compound according to any one of claims 1 to 13, Z in the general formula (110) １ is a carbon atom, compound.

15. In a compound according to any one of claims 1 to 14, The group represented by the general formula (110) is a group represented by any one of the following general formulas (111) to (117): compound. 【Chemistry 7】 (In the general formula (111), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １１ and Y ３１ ~Y ３３ each independently represents a nitrogen atom or CR ３０Ａ and R １０Ａ and R ３０Ａ are each independently a hydrogen atom or a substituent, or one or more R ３０Ａ and one or more R １０Ａ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) (In the general formula (112), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １１ and Y ３１ each independently represents a nitrogen atom or CR ３０Ａ and Y ３４ and Y ３５ Each independently represents NR ３０Ｂ , an oxygen atom, a sulfur atom, or CR ３０Ｃ R ３０Ｄ and R １０Ａ , R ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) (In the general formula (113), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １２ is N.R. ３０Ｂ Or CR ３０Ｃ R ３０Ｄ and Y ３８ is N.R. ３０Ｂ , an oxygen atom, a sulfur atom, or CR ３０Ｃ R ３０Ｄ and Y ３６ and Y ３７ each independently represents a nitrogen atom or CR ３０Ａ and R １０Ａ , R ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) (In the general formula (114), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １２ is N.R. ３０Ｂ Or CR ３０Ｃ R ３０Ｄ and Y ３９ is N.R. ３０Ｂ , an oxygen atom, a sulfur atom, or CR ３０Ｃ R ３０Ｄ and Y ３２ and Y ３３ each independently represents a nitrogen atom or CR ３０Ａ and R １０Ａ , R ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) 【Chemistry 8】 (In the general formula (115), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １３ is N.R. ３０Ｂ Or CR ３０Ｃ R ３０Ｄ and Y ４２ and Y ４３ each independently represents a nitrogen atom or CR ３０Ａ and R １０Ａ , R ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) (In the general formula (116), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １３ is N.R. ３０Ｂ Or CR ３０Ｃ R ３０Ｄ and Y ４８ and Y ４９ Each independently represents NR ３０Ｂ , an oxygen atom, a sulfur atom, or CR ３０Ｃ R ３０Ｄ and R １０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (In the general formula (117), Y １２ ~Y １４ each independently represents a nitrogen atom or CR １０Ａ and Z １４ and Y ４５ each independently represents a nitrogen atom or CR ３０Ａ and Y ４６ is N.R. ３０Ｂ , an oxygen atom, a sulfur atom, or CR ３０Ｃ R ３０Ｄ and R １０Ａ , R ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ are each independently a hydrogen atom or a substituent, or one or more R １０Ａ , one or more R ３０Ａ , one or more R ３０Ｂ , one or more R ３０Ｃ and one or more R ３０Ｄ one or more pairs of adjacent two or more groups selected from the group consisting of R as a Substituent １０Ａ and R as a substituent ３０Ａ , R ３０Ｂ , R ３０Ｃ and R ３０Ｄ each independently represents R as a substituent in the general formula (110). １０Ａ (Same meaning as above.) (In the above general formulae (111) to (117), a plurality of R １０Ａ If there are multiple R １０Ａ are the same or different, and multiple R ３０Ａ If there are multiple R ３０Ａ are the same or different, and multiple R ３０Ｂ If there are multiple R ３０Ｂ are the same or different, and multiple R ３０Ｃ If there are multiple R ３０Ｃ are the same or different, and multiple R ３０Ｄ If there are multiple R ３０Ｄ are the same or different from each other.)

16. In a compound according to any one of claims 1 to 15, Y in the general formula (110) １２ ~Y １４ is CR １０Ａ and Y in the general formula (120) ２１ ~Y ２４ is CR ２０Ａ That is, compound.

17. In a compound according to any one of claims 1 to 16, The group represented by the general formula (110) is a group represented by any one of the following general formulas (b1) to (b14): compound. 【Chemistry 9】 【Chemistry 10】 (In the general formulae (b1) to (b14), Ra is a hydrogen atom or a substituent, or one or more pairs of adjacent Ra are bonded to each other to form a ring, A plurality of Ra's are the same or different, Rb is a hydrogen atom or a substituent; Rc and Rd each independently represent a hydrogen atom or a substituent, or a pair consisting of Rc and Rd combine with each other to form a ring; The substituents Ra, Rb, Rc and Rd are each independently R １０Ａ (Same meaning as above.)

18. In the compound according to claim 17, one or more pairs of adjacent pairs of Ra are not bonded to each other to form a ring, a pair consisting of Rc and Rd does not combine with each other to form a ring; compound.

19. In a compound according to any one of claims 1 to 18, The group represented by the general formula (110) is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, Substituted or unsubstituted fluoranthenyl groups a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group; compound.

20. In the compound according to any one of claims 1 to 11, At least one group D １ In the above, R １０１ ~R １６０ At least one of the above is a group represented by general formula (120). compound.

21. 21. The compound according to claim 20, R １ ~R ４ Of these, one is group D １ If １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (120), R １ ~R ４ Of these, two are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (120), R １ ~R ４ Of these, three are group D. １ When each group D １ In the above, R １０１ ~R １６０ Only one of the above is a group represented by general formula (120). compound.

22. In the compound according to claim 20 or 21, Z in the general formula (120) ２ teeth, a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group; a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted benzanthryl group; a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofluorenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; Substituted or unsubstituted fluoranthenyl groups a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, Substituted or unsubstituted carbazolyl group a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group; compound.

23. 23. The compound according to any one of claims 20 to 22, Z in the general formula (120) ２ is a group represented by any one of the following general formulas (Z21) to (Z31): compound. 【Chemistry 11】 【Chemistry 12】 In the general formulae (Z-21) to (Z-31), Re is a hydrogen atom or a substituent, or one or more pairs of adjacent Re are bonded to each other to form a ring, and the multiple Re are the same or different, R １ and Re ２ are each independently a hydrogen atom or a substituent, or Re １ and Re ２ are bonded to each other to form a ring, R ３ is a hydrogen atom or a substituent, Re and Re as Substituents １ , R ２ and Re ３ each independently represents R as a substituent in the general formula (120). ２０Ａ Each * independently represents a bonding position to a carbon atom of the six-membered ring in the general formula (120).

24. In a compound according to any one of claims 20 to 23, In the compound according to claim 21 or 22, The group represented by the general formula (120) is a group represented by any one of the following general formulas (c1) to (c8): compound. 【Chemistry 13】 (In the general formulae (c1) to (c8), Re is a hydrogen atom or a substituent, A plurality of Re are the same or different, Re as a substituent is R ２０Ａ (Same meaning as above.)

25. 25. The compound according to any one of claims 1 to 24, The group D １ X in １ ~X ６ is an oxygen atom, compound.

26. 25. The compound according to any one of claims 1 to 24, The group D １ X in １ ~X ６ is a sulfur atom, compound.

27. 27. The compound according to any one of claims 1 to 26, The compound is a compound represented by the general formula (11): compound.

28. 27. The compound according to any one of claims 1 to 26, The compound is a compound represented by the general formula (12): compound.

29. 27. The compound according to any one of claims 1 to 26, The compound is a compound represented by the general formula (13): compound.

30. 30. The compound according to any one of claims 1 to 29, R １０１ ~R １６０ , R １６１ ~R １６８ , R １７１ ~R ２００ , R １０Ａ and R ２０Ａ are each independently Hydrogen atom, Halogen atoms, a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 14 ring carbon atoms, -N(Rz) ２ A group represented by a substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 14 ring carbon atoms; compound.

31. 31. The compound according to any one of claims 1 to 30, R １０１ ~R １６０ , R １６１ ~R １６８ , R １７１ ~R ２００ , R １０Ａ and R ２０Ａ are each independently Hydrogen atom, Halogen atoms, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, an unsubstituted alkyl group having 1 to 6 carbon atoms; an unsubstituted halogenated alkyl group having 1 to 30 carbon atoms; an unsubstituted alkylsilyl group having 3 to 6 carbon atoms, an unsubstituted alkoxy group having 1 to 6 carbon atoms, an unsubstituted aryloxy group having 6 to 14 ring carbon atoms, an unsubstituted alkylamino group having 2 to 12 carbon atoms, an unsubstituted alkylthio group having 1 to 6 carbon atoms, or It is an unsubstituted arylthio group having 6 to 14 ring carbon atoms. compound.

32. 32. The compound according to any one of claims 1 to 31, R １０１ ~R １６０ , R １６１ ~R １６８ , R １７１ ~R ２００ , R １０Ａ and R ２０Ａ are each independently Hydrogen atom, an unsubstituted aryl group having 6 to 14 ring carbon atoms, an unsubstituted heterocyclic group having 5 to 14 ring atoms, or An unsubstituted alkyl group having 1 to 6 carbon atoms. compound.

33. 33. The compound according to any one of claims 1 to 32, R １０１ ~R １６０ is a hydrogen atom other than the group represented by the general formula (110) and the group represented by the general formula (120), R １６１ ~R １６８ and R １７１ ~R ２００ is a hydrogen atom, compound.

34. 34. The compound according to any one of claims 1 to 33, R １０Ａ and R ２０Ａ is a hydrogen atom, the ring (B) is an unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or an unsubstituted heterocycle having 5 to 30 ring carbon atoms, Z ２ represents an unsubstituted aryl group having 6 to 30 ring carbon atoms or an unsubstituted heterocyclic group having 5 to 30 ring atoms; compound.

35. A material for an organic electroluminescence device, comprising the compound according to any one of claims 1 to 34.

36. An anode; A cathode; a first organic layer comprised between the anode and the cathode; having the first organic layer comprises a first compound; The first compound is a compound according to any one of claims 1 to 34. Organic electroluminescent element.

37. 37. The organic electroluminescence device according to claim 36, The first organic layer is an emitting layer. Organic electroluminescent element.

38. The organic electroluminescence device according to claim 36 or 37, the first organic layer comprises the first compound and further comprises a second compound; the second compound is a fluorescent compound; Organic electroluminescent element.

39. 39. The organic electroluminescence device according to claim 38, The singlet energy S of the first compound １ (Mat1) and the singlet energy S １ (Mat2) satisfies the relationship of the following formula (Formula 1), Organic electroluminescent element. S １ (Mat1)>S １ (Mat2) (Equation 1) Organic electroluminescent element.

40. The organic electroluminescence device according to claim 38 or 39, the first organic layer comprises the first compound, the second compound, and further comprises a third compound; The singlet energy S of the first compound １ (Mat1) and the singlet energy S of the third compound １ (Mat3) satisfies the relationship of the following formula (Math 2), Organic electroluminescent element. S １ (Mat3)>S １ (Mat1) (Mat2)

41. The organic electroluminescence device according to claim 36 or 37, the first organic layer comprises the first compound and further comprises a fourth compound; The singlet energy S of the first compound １ (Mat1) and the singlet energy S of the fourth compound １ (Mat4) satisfies the relationship of the following formula (Math 3), Organic electroluminescent element. S １ (Mat4)>S １ (Mat1) (Equation 3)

42. The organic electroluminescence device according to any one of claims 36 to 41, The first organic layer does not contain a metal complex. Organic electroluminescent element.

43. The organic electroluminescence device according to any one of claims 36 to 42, The first compound is a delayed fluorescent compound. Organic electroluminescent element.

44. 44. An electronic device comprising the organic electroluminescence device according to claim 36.

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