Compound, light-emitting material, and light-emitting element

Abstract

According to the present invention, an organic light-emitting element using a compound represented by the following general formula has excellent characteristics. R1-R4 each represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or a donor group; at least two among R1-R4 are donor groups, and at least one thereof represents a substituted ring-fused carbazol-9-yl group; X1-X3 each represent N or C(R); R represents a hydrogen atom, a deuterium atom, or a substituent; Ar1 and Ar2 each represent an aryl group; and L1 represents a single bond or a linking group.

Description

Compound, light-emitting material and light-emitting device

[0001] The present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same.

[0002] Research into improving the luminous efficiency of light-emitting elements such as organic electroluminescence elements (organic EL elements) has been actively conducted. In particular, various efforts have been made to improve the luminous efficiency by newly developing and combining electron transport materials, hole transport materials, luminescent materials, etc. that constitute organic electroluminescence elements. Among these efforts, research into organic electroluminescence elements that utilize delayed fluorescent materials has also been seen.

[0003] Delayed fluorescent materials are materials that, in an excited state, undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and then emit fluorescence when returning from the excited singlet state to the ground state. Fluorescence via this route is observed later than fluorescence from the excited singlet state (normal fluorescence) directly generated from the ground state, and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency when only fluorescence from the directly generated excited singlet state is used. On the other hand, delayed fluorescent materials can utilize not only the excited singlet state but also the excited triplet state for fluorescence emission via the above-mentioned reverse intersystem crossing route, thereby achieving higher luminous efficiency than ordinary fluorescent materials.

[0004] Since this principle was clarified, various researches have led to the discovery of various delayed fluorescent materials. These include many compounds in which a cyanobenzene is substituted with a donor group and an acceptor group. For example, a compound in which a cyanobenzene is substituted with a benzofurocarbazolyl group, which is a donor group, and a diphenyltriazinyl group, which is an acceptor group, has been proposed. One example is a compound having the following structure (see Patent Document 1):

[0005]

[0006] WO2021 / 045623A1

[0007] Even if a material emits delayed fluorescence, one with extremely good properties and no practical problems has not yet been provided. Therefore, it would be even more useful if a delayed fluorescence material with a higher luminous efficiency than the delayed fluorescence material proposed in Patent Document 1 could be provided. However, the improvement of delayed fluorescence materials is still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful luminescent material.

[0008] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as light-emitting materials for light-emitting devices, and have conducted extensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as light-emitting materials.

[0009] As a result of intensive research to achieve the above object, the present inventors have found that a cyanobenzene compound having a structure that satisfies certain conditions is useful as a light-emitting material. The present invention has been proposed based on this finding, and specifically has the following configuration.

[0010] [1] A compound represented by the following general formula (1): [In general formula (1), R １ ~R ４ each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ ~R ４ Two or more of X are donor groups, and at least one of the two or more donor groups is a substituted ring-fused carbazol-9-yl group. １ ~X ３ Each independently represents N or C(R), but X １ ~X ３ At least one of Ar is N. R represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group. １represents a single bond or a divalent linking group.] [2] The compound according to [1], wherein the ring-fused carbazol-9-yl group is substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. [3] The compound according to [1] or [2], wherein the ring-fused carbazol-9-yl group is a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton-constituting atoms is fused. [4] X １ ~X ３ [5] The compound according to any one of [1] to [3], wherein Ar is N. １ and Ar ２ [6] The compound according to any one of [1] to [4], wherein L is an aryl group optionally substituted with a deuterium atom. １ [7] The compound according to any one of [1] to [5], wherein R is a single bond. １ [8] The compound according to any one of [1] to [6], wherein R is a hydrogen atom. ３ [9] The compound according to [7], wherein R is a phenyl group. ２ and R ４are the same substituted ring-fused carbazol-9-yl group.

[10] The compound according to any one of [1] to [9], having at least one deuterium atom.

[11] A light-emitting material comprising the compound according to any one of [1] to

[10] .

[12] A delayed fluorescent material comprising the compound according to any one of [1] to

[10] .

[13] A film comprising the compound according to any one of [1] to

[10] .

[14] An organic semiconductor device comprising the compound according to any one of [1] to

[10] .

[15] An organic light-emitting device comprising the compound according to any one of [1] to

[10] .

[16] The organic light-emitting device according to

[15] , wherein the device has a layer comprising the compound, and the layer also contains a host material.

[17] The organic light-emitting device according to

[16] , wherein the layer comprising the compound also contains a delayed fluorescent material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

[18] The organic light-emitting element according to

[16] , wherein the element has a layer containing the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.

[19] The organic light-emitting element according to any one of

[16] to

[18] , wherein the compound has the largest amount of light emission among the materials contained in the element.

[20] The organic light-emitting element according to

[18] , wherein the amount of light emission from the light-emitting material is greater than the amount of light emission from the compound.

[21] The organic light-emitting element according to any one of

[15] to

[20] , which is an organic electroluminescence element.

[22] The organic light-emitting element according to any one of

[15] to

[21] , which emits delayed fluorescence.

[0011] The compounds of the present invention are useful as light-emitting materials. The compounds of the present invention include compounds with high luminous efficiency. Furthermore, organic light-emitting devices using the compounds of the present invention include excellent devices with high luminous efficiency.

[0012] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２ In the chemical structural formulae of this specification, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to the carbon atom constituting the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom constituting the ring skeleton at the omitted position. In the chemical structural formulae of this specification, deuterium atoms are represented by D.

[0013] [Compound represented by general formula (1)]

[0014] In general formula (1), R １ ~R ４ R each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ ~R ４ In a preferred embodiment of the present invention, at least two of R ２ In a preferred embodiment of the present invention, at least R ４ is a substituted ring-fused carbazol-9-yl group. １ may be a ring-fused carbazol-9-yl group substituted with R ３ In a preferred embodiment of the present invention, R ２ and R ４ are each independently a substituted ring-fused carbazol-9-yl group, for example, R １ ~R ４ Among R２ and R ４ are each independently substituted ring-fused carbazol-9-yl groups. ２ and R ４ are preferably the same, provided that R ２ and R ４ In the present invention, R ２ and R ３ may each independently be a substituted ring-fused carbazol-9-yl group, and R ３ and R ４ may be independently substituted ring-fused carbazol-9-yl groups. １ and R ２ may each independently be a substituted ring-fused carbazol-9-yl group, and R １ and R ３ may each independently be a substituted ring-fused carbazol-9-yl group, and R １ and R ４ may be independently substituted ring-fused carbazol-9-yl groups. ２ ~R ４ may be independently substituted ring-fused carbazol-9-yl groups, and all may be the same, only one may be different, or all may be different. １ ~R ３ may each independently be a substituted ring-fused carbazol-9-yl group, and R １ , R ２ , R ４ may each independently be a substituted ring-fused carbazol-9-yl group, and R １ , R ３ , R ４ may be independently substituted ring-fused carbazol-9-yl groups. １ ~R ４ may be ring-fused carbazol-9-yl groups each independently substituted, and all may be the same, only one may be different, or all may be different.

[0015] The number of rings constituting the fused ring in the substituted ring-fused carbazole-9-yl group is preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0016] The substituted ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, or may be a ring formed by further condensation of these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In one embodiment of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from Substituent Group E, and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In one embodiment of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group to which a benzothieno structure is fused, for example, two or more carbazol-9-yl groups.

[0017] In the present invention, a substituted benzofuro[2,3-a]carbazol-9-yl group can be used as the substituted ring-fused carbazol-9-yl group. Alternatively, a substituted benzofuro[3,2-a]carbazol-9-yl group can also be used. Alternatively, a substituted benzofuro[2,3-b]carbazol-9-yl group can also be used. Alternatively, a substituted benzofuro[3,2-b]carbazol-9-yl group can also be used. Alternatively, a substituted benzofuro[2,3-c]carbazol-9-yl group can also be used. Alternatively, a substituted benzofuro[3,2-c]carbazol-9-yl group can also be used. A preferred substituted benzofuran-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzofuran ring is fused at the 2- and 3-positions and no other rings are fused. Specifically, it is a group having any of the following structures, in which at least one hydrogen atom in the following structure is substituted:

[0018] In the present invention, a substituted benzothieno[2,3-a]carbazol-9-yl group can be used as the substituted ring-fused carbazol-9-yl group. Alternatively, a substituted benzothieno[3,2-a]carbazol-9-yl group can also be used. Alternatively, a substituted benzothieno[2,3-b]carbazol-9-yl group can also be used. Alternatively, a substituted benzothieno[3,2-b]carbazol-9-yl group can also be used. Alternatively, a substituted benzothieno[2,3-c]carbazol-9-yl group can also be used. Alternatively, a substituted benzothieno[3,2-c]carbazol-9-yl group can also be used. A preferred substituted benzothiophene-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzothiophene ring is fused at the 2- and 3-positions and no other rings are fused. Specifically, it is a group having any of the following structures, in which at least one hydrogen atom in the following structure is substituted:

[0019] In the present invention, a substituted indolo[2,3-a]carbazol-9-yl group can be used as the substituted ring-fused carbazol-9-yl group. Alternatively, a substituted indolo[3,2-a]carbazol-9-yl group can also be used. Alternatively, a substituted indolo[2,3-b]carbazol-9-yl group can also be used. Alternatively, a substituted indolo[3,2-b]carbazol-9-yl group can also be used. Alternatively, a substituted indolo[2,3-c]carbazol-9-yl group can also be used. Alternatively, a substituted indole-fused carbazol-9-yl group can also be used. A preferred substituted indole-fused carbazol-9-yl group is a carbazol-9-yl group in which only one indole ring is fused at the 2- and 3-positions and no other rings are fused. Specifically, it is a group having any of the following structures, in which at least one hydrogen atom in the following structure is substituted. In the following structures, R' represents a hydrogen atom or a substituent. In one embodiment of the present invention, R' is a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group, preferably a substituted or unsubstituted aryl group. Substituents for the aryl group and the alkyl group may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the aryl group and the alkyl group are unsubstituted.

[0020] The substituted ring-fused carbazol-9-yl group has a structure in which a substituent is bonded to at least one of the carbon atoms constituting the ring skeleton of the ring-fused carbazol-9-yl group. The substituent of the ring-fused carbazol-9-yl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent of the ring-fused carbazol-9-yl group is selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted alkyl group, and some or all of the hydrogen atoms of these substituents may be substituted with deuterium atoms. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has no substituents other than the substituents described herein. The aryl group may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, or a substituted or unsubstituted naphthalen-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is unsubstituted. The alkyl group may be linear, branched, or cyclic. In addition, two or more of the linear, cyclic, and branched moieties may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decanyl, isodecanyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the alkyl group has one or more substituents selected from the group consisting of an aryl group and a deuterium atom. In a preferred embodiment of the present invention, the alkyl group is unsubstituted. The number of substituents substituted on the ring-fused carbazol-9-yl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0021] Specific examples of substituted ring-fused carbazol-9-yl groups that can be employed in general formula (1) are shown below. However, the substituted ring-fused carbazol-9-yl groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates a bonding position, and Ph represents a phenyl group. Methyl groups are not shown. For this reason, D200 to D223 have a methyl group.

[0022]

[0023] Compounds in which all hydrogen atoms present in the above D1 to D224 have been replaced with deuterium atoms are disclosed as D1(Da) to D224(Da). Compounds in which all hydrogen atoms present in the phenyl or alkyl groups that are substituents of the above D1 to D224 have been replaced with deuterium atoms are disclosed as D1(Db) to D224(Db). In one aspect of the present invention, the compound represented by general formula (1) has a group selected from the group consisting of D1 to D224, D1(Da) to D224(Da), and D1(Db) to D224(Db). For example, the substituted ring-fused carbazol-9-yl group has only groups selected from the group consisting of D1 to D224, D1(Da) to D224(Da), and D1(Db) to D224(Db). In a preferred embodiment of the present invention, the compound represented by general formula (1) has groups selected from the group consisting of D1 to D31, D1(Da) to D31(Da), and D1(Db) to D31(Db). For example, the substituted ring-fused carbazol-9-yl group has only groups selected from the group consisting of D1 to D31, D1(Da) to D31(Da), and D1(Db) to D31(Db). In a more preferred embodiment of the present invention, the compound represented by general formula (1) has groups selected from the group consisting of D1 to D9, D1(Da) to D9(Da), and D1(Db) to D9(Db). For example, the substituted ring-fused carbazol-9-yl group has only groups selected from the group consisting of D1 to D9, D1(Da) to D9(Da), and D1(Db) to D9(Db). In a preferred embodiment of the present invention, the compound represented by general formula (1) has groups selected from the group consisting of D10 to D31, D10(Da) to D31(Da), and D10(Db) to D31(Db). For example, the substituted ring-fused carbazol-9-yl group has only groups selected from the group consisting of D10 to D31, D10(Da) to D31(Da), and D10(Db) to D31(Db).

[0024] R in general formula (1) １ ~R ４ may be a donor group other than a substituted ring-fused carbazol-9-yl group. Here, donor groups other than a substituted ring-fused carbazol-9-yl group are referred to as "other donor groups." The donor group can be selected from groups with a negative Hammett σp value. The Hammett σp value was proposed by L. P. Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is the constant (σp) specific to the substituent in a para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of a benzene derivative without a substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative without a substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0025] R １ ~R ４ Among these, the number of other donor groups is 0 to 3, preferably 0 to 2, and more preferably 0 or 1. When there are two or more other donor groups, they may be the same or different. In one embodiment of the present invention, the number of other donor groups is 0. In one embodiment of the present invention, the number of other donor groups is 1. In one embodiment of the present invention, R １ is another donor group. In one embodiment of the present invention, R ２ is another donor group. In a preferred embodiment of the present invention, R ３ is another donor group. In one embodiment of the present invention, R ４ is another donor group. In one embodiment of the present invention, R１ is the only other donor group. ２ In a preferred embodiment of the present invention, R ３ is the only other donor group. ４ is the only other donor group.

[0026] The other donor group is preferably a substituted or unsubstituted diarylamino group, a substituted or unsubstituted dialkylamino group, or a substituted or unsubstituted alkylarylamino group, and is preferably a substituted or unsubstituted diarylamino group. The two aryl groups constituting the diarylamino group may be bonded to each other to form a cyclic structure such as a carbazole ring. For descriptions and preferred ranges of the aryl groups and alkyl groups constituting the diarylamino group, dialkylamino group, and alkylarylamino group, please refer to the descriptions and preferred ranges of the aryl groups and alkyl groups in the section on the substituted ring-fused carbazol-9-yl group above. The other donor group may also be a ring-fused indol-1-yl group. The number of rings constituting the ring-fused indol-1-yl group is 4 or more, more preferably 4 to 9, and even more preferably 4 to 7. In a preferred embodiment of the present invention, the other donor group is a substituted or unsubstituted non-fused carbazol-9-yl group. The other donor group may also be an unsubstituted ring-fused carbazol-9-yl group. In this case, the number of rings constituting the fused ring of the fused carbazol-9-yl group is 4 or more, more preferably 5 to 9, and even more preferably 5 to 7. In one embodiment of the present invention, the number of rings constituting the fused ring is 6. In one embodiment of the present invention, the number of rings constituting the fused ring is 7. In one embodiment of the present invention, the number of rings constituting the fused ring is 5. In either case, no substituent is bonded to the carbon atoms constituting the ring skeleton of the fused ring. Note that at least one of the carbon atoms constituting the ring skeleton of the two benzene rings constituting the carbazol-9-yl group may be substituted with a nitrogen atom.

[0027] Specific examples of other donor groups that can be employed in general formula (1) are shown below. However, the other donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates a bonding position, and Ph represents a phenyl group. Methyl groups are not shown. Therefore, for example, Z2 and Z3 have methyl groups.

[0028]

[0029] Z1(Da) to Z209(Da) are groups in which all hydrogen atoms present in Z1 to Z209 are replaced with deuterium atoms. In one embodiment of the present invention, the compound represented by general formula (1) has a group selected from the group consisting of Z1 to Z209 and Z1(Da) to Z209(Da). For example, the compound represented by general formula (1) has only groups selected from the group consisting of Z1 to Z209 and Z1(Da) to Z209(Da) as other donor groups. In one embodiment of the present invention, the compound represented by general formula (1) has a group selected from the group consisting of Z1 to Z6, Z195 to Z209, Z1(Da) to Z6(Da), and Z195(Da) to Z209(Da). For example, the other donor groups include only groups selected from the group consisting of Z1 to Z6, Z195 to Z209, Z1(Da) to Z6(Da), and Z195(Da) to Z209(Da). In one embodiment of the present invention, the compound represented by general formula (1) includes only groups selected from the group consisting of Z7 to Z194 and Z7(Da) to Z194(Da). For example, the other donor groups include only groups selected from the group consisting of Z7 to Z194 and Z7(Da) to Z194(Da).

[0030] R in general formula (1) １ ~R ４may be a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. For the description and preferred ranges of the aryl group and the alkyl group, please refer to the description and preferred ranges of the aryl group and the alkyl group in the section on the substituted ring-fused carbazole-9-yl group above. In one embodiment of the present invention, the hydrogen atom of the aryl group and the alkyl group may be substituted with a deuterium atom or a group selected from Substituent Group E. In one embodiment of the present invention, the aryl group and the alkyl group are unsubstituted. Specific examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, an n-propyl group, and a tert-butyl group. Specific examples of the substituted or unsubstituted aryl group include the following groups. However, the substituted or unsubstituted alkyl group and the substituted or unsubstituted aryl group that can be employed in the present invention should not be construed as being limited by these specific examples. In the following specific examples, t-Bu represents a tert-butyl group, and * indicates the bonding position.

[0031]

[0032] Ar1(Da) to Ar26(Da) are groups in which all hydrogen atoms present in the above Ar1 to Ar26 are substituted with deuterium atoms. Ar2(Db) to Ar18(Db) are groups in which all hydrogen atoms present in the alkyl or phenyl groups that are substituents of Ar2 to Ar18 are substituted with deuterium atoms.

[0033] In one aspect of the present invention, R １ ~R ４ In a preferred embodiment of the present invention, at least one of R １ ~R ４ In a preferred embodiment of the present invention, only one of R １ is a hydrogen atom or a deuterium atom. ２ is a hydrogen atom or a deuterium atom. ３ is a hydrogen atom or a deuterium atom. ４ is a hydrogen atom or a deuterium atom.１ In one aspect of the present invention, only R ２ In one aspect of the present invention, only R ３ In one aspect of the present invention, only R ４ In one aspect of the present invention, only R １ is a substituted or unsubstituted alkyl group. ２ is a substituted or unsubstituted alkyl group. ３ is a substituted or unsubstituted alkyl group. ４ is a substituted or unsubstituted alkyl group. １ is a substituted or unsubstituted aryl group. ２ is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R ３ is a substituted or unsubstituted aryl group. ４ is a substituted or unsubstituted aryl group.

[0034] In a preferred embodiment of the present invention, R １ ~R ４ Two of R are donor groups, one is a hydrogen atom or a deuterium atom, and the other is a substituted or unsubstituted aryl group. １ ~R ４ Two of R are substituted ring-fused carbazol-9-yl groups, one is a hydrogen atom or a deuterium atom, and the other is an unsubstituted aryl group. １ ~R ４ In one embodiment of the present invention, two of R are ring-fused carbazol-9-yl groups substituted with alkyl or aryl groups, one is a hydrogen atom or a deuterium atom, and the other is an unsubstituted phenyl group. １ ~R ４ In one embodiment of the present invention, three of R are donor groups and one is a hydrogen atom or a deuterium atom. １ ~R ４Three of the R are donor groups, and one is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). １ ~R ４ Three of R are ring-fused carbazol-9-yl groups substituted with alkyl or aryl groups, and one is a hydrogen atom or a deuterium atom. １ ~R ４ Three of the R are ring-fused carbazol-9-yl groups substituted with alkyl or aryl groups, and one is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). １ ~R ４ In one aspect of the present invention, all of R １ ~R ４ are ring-fused carbazol-9-yl groups substituted with an alkyl group or an aryl group.

[0035] In one aspect of the present invention, R １ and R ２ is a donor group. In one embodiment of the present invention, R １ and R ３ is a donor group. In one embodiment of the present invention, R １ and R ４ is a donor group. In one embodiment of the present invention, R ２ and R ３ is a donor group. In one embodiment of the present invention, R ３ and R ４ is a donor group. In one embodiment of the present invention, R １ and R ２ and R ３ is a donor group. In one embodiment of the present invention, R １ and R ２ and R ４ is a donor group. In one embodiment of the present invention, R １ and R ３ and R ４ is a donor group. In one embodiment of the present invention, R ２ and R ３ and R ４ is a donor group. In a preferred embodiment of the present invention, R １is a hydrogen atom or a deuterium atom, and R ２ and R ４ is a donor group (preferably a ring-fused carbazol-9-yl group substituted with an alkyl group or an aryl group), and R ３ is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group). １ is a hydrogen atom or a deuterium atom, and R ２ and R ４ is a donor group (preferably a ring-fused carbazol-9-yl group substituted with an alkyl group or an aryl group), and R ３ is a substituted or unsubstituted alkyl group (preferably an unsubstituted alkyl group). １ is a hydrogen atom or a deuterium atom, and R ２ and R ４ is a donor group (preferably a ring-fused carbazol-9-yl group substituted with an alkyl group or an aryl group), and R ３ is a hydrogen atom or a deuterium atom. １ is a substituted or unsubstituted aryl group (preferably an unsubstituted aryl group), and R ２ and R ４ is a donor group (preferably a ring-fused carbazol-9-yl group substituted with an alkyl group or an aryl group), and R ３ is a hydrogen atom or a deuterium atom. １ is a hydrogen atom or a deuterium atom, and R ２ ~R ４ is a donor group. In one embodiment of the present invention, R １ is a hydrogen atom or a deuterium atom, and R ２ ~R ４ is a ring-fused carbazol-9-yl group substituted with an alkyl or aryl group. １ is a hydrogen atom or a deuterium atom, and R ２ and R ４ is a ring-fused carbazol-9-yl group substituted with an alkyl group or an aryl group, and R ３In a preferred embodiment of the present invention, in the general formula (1) of the present invention, R １ and R ２ , R ２ and R ３ , R ３ and R ４ are not bonded to each other to form a ring structure.

[0036] X in general formula (1) １ ~X ３ Each independently represents N or C(R). １ ~X ３ At least one of the groups is N. R represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, X １ ~X ３ is N. In one aspect of the present invention, X １ and X ３ is N and X ２ is C(R). In one aspect of the present invention, X １ and X ２ is N and X ３ is C(R). In one aspect of the present invention, X １ is N and X ２ and X ３ is C(R). In one aspect of the present invention, X ２ is N and X １ and X ３ is C(R).

[0037] Ar in general formula (1) １ and Ar ２ Each of Ar independently represents a substituted or unsubstituted aryl group. For the description and preferred range of the substituted or unsubstituted aryl group, please refer to the description and preferred range of the aryl group and alkyl group in the section describing the substituted ring-fused carbazol-9-yl group above. １ and Ar ２Specific examples of Ar include Ar1 to Ar26, Ar1(Da) to Ar26(Da), and Ar1(Db) to Ar18(Db). １ and Ar ２ is an unsubstituted aryl group, more preferably an unsubstituted phenyl group.

[0038] L in general formula (1) １ represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L １ is a single bond. In one aspect of the present invention, L １ is a substituted or unsubstituted arylene group. １ is a substituted or unsubstituted heteroarylene group. For the aryl moiety constituting the arylene group, the explanation and preferred range of the aryl group and alkyl group in the section describing the substituted ring-fused carbazol-9-yl group above can be referred to. Examples of the heteroarylene group include a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is substituted with a nitrogen atom. Hereinafter, L １ However, the L that can be used in the present invention is １ is not to be construed as being limited by these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0039]

[0040] In a preferred embodiment of the present invention, X １ ~X ３ is N, and Ar １ and Ar ２ is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably a phenyl group), and L １ is a single bond.

[0041] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing no hydrogen atoms but containing deuterium atoms.

[0042] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl ... It means one group or a combination of two or more groups selected from the group consisting of a heteroarylthio group (for example, having 5 to 30 atoms constituting the ring skeleton), an acyl group (for example, having 1 to 40 carbon atoms), an alkenyl group (for example, having 1 to 40 carbon atoms), an alkynyl group (for example, having 1 to 40 carbon atoms), an alkoxycarbonyl group (for example, having 1 to 40 carbon atoms), an aryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group. In the present specification, "substituent group B" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring atoms), heteroaryloxy groups (e.g., having 5 to 30 ring atoms), and diarylamino groups (e.g., having 0 to 20 carbon atoms). In the present specification, "substituent group C" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). As used herein, "substituent group D" means one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms) and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0043] Specific examples of the compound represented by general formula (1) are shown in Tables 1 and 2 below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Tables 1 and 2, R １ ~R ４ The structures of compounds 1 to 1700384 are individually shown by specifying each compound. １ and Ar ２ is a phenyl group (Ar1), and X １ ~X ３ is a nitrogen atom (N), and L １ is a single bond, and R １ ~R ４ The structures in which is a group specified in Tables 1 and 2 are shown individually as the structures of Compounds 1 to 1700384.

[0044] In Table 2, each row contains R １ ~R ４ For example, in the column of compounds 1 to 224 in Table 2, R １ is a hydrogen atom (H), R ３ is fixed to the phenyl group (Ph), and R ２ and R ４ The compounds in which both are D1 to D224 are designated as compounds 1 to 224, respectively. ２ and R ４In other words, the column of compounds 1 to 224 in Table 2 collectively displays compounds 1 to 224 specified in Table 1. Similarly, in the column of compounds 225 to 448 in Table 2, R １ is a hydrogen atom (H), R ３ is fixed to the methyl group (Me), and R ２ and R ４ Compounds 225 to 448 are identified in the same manner as compounds 449 to 12096 in Table 2. Compounds 12097 to 14784 in Table 2 are identified in the same manner as compounds 225 to 448. １ ~R ４ Three of the R １ ~R ４ The compounds 15009 to 858696 in Table 2 are all the same and are specified as any of D1 to D224. １ ~R ４ One of the following is any one of D1 to D224, and R １ ~R ４ The other one of the two is one of Z1 to Z209. Here, first, D1 to D224 are fixed to one value, and Z1 to Z209 are sequentially changed to identify the compound. Then, D1 to D224 are fixed to the next value, and Z1 to Z209 are sequentially changed to identify the compound. For this reason, R １ is a hydrogen atom (H), R ３ is fixed to the phenyl group (Ph), and R ２ is D1 and R ４ are compounds 15009 to 15232 in order, and R ２ is D2 and R ４ are compounds 15233 to 15456 in the order Z1 to Z209, and R ３ is D3 and R ４ The compounds are numbered in the order of Z1 to Z209, with compounds 15457 to 15680, and R ３ is D224, and R ４Compounds 61601 to 61824 are identified in the same manner as compounds 61825 to 857696 in Table 2. Compounds 857697 to 1700384 in Table 2 are identified in the same manner as compounds 61601 to 61824. １ ~R ４ Two of the same are any of D1 to D224, and R １ ~R ４ and the other one of R is any one of Z1 to Z209. １ ~R ４ One of the following is any one of D1 to D224, and R １ ~R ４ The other two are the same and the structure is identified as one of Z1 to Z209. Here too, first D1 to D224 are fixed to one and Z1 to Z209 are changed in order to identify the compound, then D1 to D224 are fixed to the next one and Z1 to Z209 are changed in order to identify the compound. In this manner, compounds 1 to 1700384 are identified.

[0045] Compounds 1(Da) to 1700384(Da) are compounds obtained by substituting all hydrogen atoms present in the molecules of the above compounds 1 to 1700384 with deuterium atoms. Compounds 1(Db) to 1700384(Db) are compounds obtained by substituting all hydrogen atoms bonded to two phenyl groups substituted on triazine rings present in the molecules of the above compounds 1 to 1700384 with deuterium atoms. Compounds 1(Dc) to 1700384(Dc) are compounds obtained by substituting all hydrogen atoms of phenyl groups or alkyl groups bonded to benzene rings of D1 to D224 present in the molecules of the above compounds 1 to 1700384 with deuterium atoms. The above compounds 1 to 224, 673 to 1568, 2017 to 2240, 2689 to 3584, 4033 to 4256, 4705 to 5600, 6049 to 6272, 6721 to 7616, 8065 to 8288, 8737 to 9632, 10081 to 10304, 10753 to 11648, 12097 to 12320, 12769 to 12992, 13441 to 13664, 14113 to 14336, 15009 to 61824, 155457 to 342720, 436353 to 483168, 576801 to 764064, 857697 to 904512, 998145 to 1044960, 1138593 to 1185408, 1279041 to 1325856, 1419489 to 1466304, 1559937 to 1606752 (hereinafter, these groups of compounds are referred to as "compound group a") １ ~R ４All hydrogen atoms bonded to the phenyl group present in one of the above compounds are replaced with deuterium atoms, and these compounds are designated as compounds 1(Dd) to 224(Dd), 673(Dd) to 1568(Dd), 2017(Dd) to 2240(Dd), 2689(Dd) to 3584(Dd), 4033(Dd) to 4256(Dd), and 4705(Dd) to 5 600 (Dd), 6049 (Dd) ~ 6272 (Dd), 6721 (Dd) ~ 7616 (Dd), 8065 (Dd) ~ 8288 (Dd), 8737 (Dd) ~ 9 632 (Dd), 10081 (Dd) to 10304 (Dd), 10753 (Dd) to 11648 (Dd), 12097 (Dd) to 12320 (Dd), 12769 (Dd) ~ 12992 (Dd), 13441 (Dd) ~ 13664 (Dd), 14113 (Dd) ~ 14336 (Dd), 15009 (Dd) ~ 61824 (D d), 155457 (Dd) ~ 342720 (Dd), 436353 (Dd) ~ 483168 (Dd), 576801 (Dd) ~ 764064 (Dd), 857 697(Dd) to 904512(Dd), 998145(Dd) to 1044960(Dd), 1138593(Dd) to 1185408(Dd), 1279041(Dd) to 1325856(Dd), 1419489(Dd) to 1466304(Dd), and 1559937(Dd) to 1606752(Dd). １ ~R ４All hydrogen atoms bonded to the phenyl group present in one of the molecules D1 to D224 are replaced with deuterium atoms, and all hydrogen atoms of the phenyl group or alkyl group bonded to the benzene rings D1 to D224 present in the molecule are replaced with deuterium atoms. These compounds are named compounds 1(De) to 224(De), 673(De) to 1568(De), 2017(De) to 2240(De), 2 689 (De) ~ 3584 (De), 4033 (De) ~ 4256 (De), 4705 (De) ~ 5600 (De), 6049 (De) ~ 6272 (De), 6721 (De) ~ 7616 (De), 8065 (De) ~ 8288 (De), 8737 (De) ~ 9632 (De), 10081 (De) ~ 10304 (De), 10753 (De) ~ 11648 (De), 12097 (De) ~ 12320 (De), 12769 (De) ~ 12992 (De), 13441 (De) ~ 13664 (De), 14113 (De) ~ 1433 6 (De), 15009 (De) ~ 61824 (De), 155457 (De) ~ 342720 (De), 436353 (De) ~ 483168 (De), 576801 (De) to 764064 (De), 857697 (De) to 904512 (De), 998145 (De) to 1044960 (De), 1138593 (De) to 1185408 (De), 1279041 (De) to 1325856 (De), 1419489 (De) to 1466304 (De), and 1559937 (De) to 1606752 (De). １ ~R ４All hydrogen atoms bonded to the phenyl group present in one of the molecules D1 to D224 are replaced with deuterium atoms, all hydrogen atoms of the phenyl group or alkyl group bonded to the benzene ring of D1 to D224 present in the molecule are replaced with deuterium atoms, and all hydrogen atoms bonded to the two phenyl groups substituted on the triazine ring present in the molecule are replaced with deuterium atoms, and these compounds are called Compounds 1(Df) to 224 ( Df), 673 (Df) ~ 1568 (Df), 2017 (Df) ~ 2240 (Df), 2689 (Df) ~ 3584 (Df), 4033 (Df) ~ 4256 (Df), 4705 (Df) ~ 56 00 (Df), 6049 (Df) ~ 6272 (Df), 6721 (Df) ~ 7616 (Df), 8065 (Df) ~ 8288 (Df), 8737 (Df) ~ 9632 (Df), 10081 (Df) ) ~ 10304 (Df), 10753 (Df) ~ 11648 (Df), 12097 (Df) ~ 12320 (Df), 12769 (Df) ~ 12992 (Df), 13441 (Df) ~ 1366 4 (Df), 14113 (Df) ~ 14336 (Df), 15009 (Df) ~ 61824 (Df), 155457 (Df) ~ 342720 (Df), 436353 (Df) ~ 483168 (D f), 576801(Df) to 764064(Df), 857697(Df) to 904512(Df), 998145(Df) to 1044960(Df), 1138593(Df) to 1185408(Df), 1279041(Df) to 1325856(Df), 1419489(Df) to 1466304(Df), and 1559937(Df) to 1606752(Df). R of compound group a １ ~R ４All hydrogen atoms bonded to the phenyl group present in one of the compounds were replaced with deuterium atoms, and all hydrogen atoms bonded to the two phenyl groups substituted on the triazine rings present in the molecule were replaced with deuterium atoms. These compounds were designated as compounds 1(Dg) to 224(Dg), 673(Dg) to 1568(Dg), 2017(Dg) to 2240(Dg), and 2689(Dg). g) ~ 3584 (Dg), 4033 (Dg) ~ 4256 (Dg), 4705 (Dg) ~ 5600 (Dg), 6049 (Dg) ~ 6272 (Dg), 6721 (Dg) ~ 7616 (Dg), 8065 (Dg) ~ 8288 (Dg), 8737 (Dg) ~ 9632 (Dg), 10081 (Dg) ~ 10304 (Dg), 10753 (Dg) ~ 11648 (Dg) ), 12097 (Dg) ~ 12320 (Dg), 12769 (Dg) ~ 12992 (Dg), 13441 (Dg) ~ 13664 (Dg), 14113 (Dg) ~ 14336 (D g), 15009 (Dg) ~ 61824 (Dg), 155457 (Dg) ~ 342720 (Dg), 436353 (Dg) ~ 483168 (Dg), 576801 (Dg) ~ 7 64064 (Dg), 857697 (Dg) to 904512 (Dg), 998145 (Dg) to 1044960 (Dg), 1138593 (Dg) to 1185408 (Dg), 1279041 (Dg) to 1325856 (Dg), 1419489 (Dg) to 1466304 (Dg), and 1559937 (Dg) to 1606752 (Dg). All compounds identified by the above numbers are considered to be individually disclosed. Note that, when rotamers exist among the above specific compound examples, both the mixture of rotamers and each separated rotamer are considered to be disclosed in the present specification.

[0046] In one aspect of the present invention, a compound is selected from compounds 1 to 12096. In one aspect of the present invention, a compound is selected from compounds 1 to 2016. In one aspect of the present invention, a compound is selected from compounds 2017 to 4032. In one aspect of the present invention, a compound is selected from compounds 4033 to 6048. In one aspect of the present invention, a compound is selected from compounds 6049 to 8064. In one aspect of the present invention, a compound is selected from compounds 8065 to 10080. In one aspect of the present invention, a compound is selected from compounds 10081 to 12096. In one aspect of the present invention, a compound is selected from compounds 1 to 224, 1121 to 1344, 2017 to 2240, 3137 to 3360, 4033 to 4256, 5153 to 5376, 6049 to 6272, 7169 to 7392, 8065 to 8288, 9185 to 9008, 10081 to 10304, and 11201 to 11424. In one aspect of the present invention, a compound is selected from compounds 673 to 896, 2689 to 2912, 4705 to 4928, 6721 to 6944, 8737 to 8960, and 10753 to 10976. In one aspect of the present invention, a compound is selected from compounds 12097 to 14784. In one aspect of the present invention, a compound is selected from compounds 12097 to 12768. In one aspect of the present invention, a compound is selected from compounds 12769 to 13440. In one aspect of the present invention, a compound is selected from compounds 13441 to 14112. In one aspect of the present invention, a compound is selected from compounds 14113 to 14784. In one aspect of the present invention, a compound is selected from compounds 12097 to 12320, 12769 to 12992, 13441 to 13664, and 14113 to 14336. In one aspect of the present invention, a compound is selected from compounds 14785 to 15008. In one aspect of the present invention, a compound is selected from compounds 15009 to 857696. In one aspect of the present invention, a compound is selected from compounds 15009 to 155456. In one aspect of the present invention, a compound is selected from compounds 155457 to 295904. In one embodiment of the present invention, the compound is selected from compounds 295905-436352, 436353-576800, 576801-717248, and 717249-857696.In one embodiment of the present invention, a compound is selected from compounds 15009 to 61824 and 436353 to 483168. In one embodiment of the present invention, a compound is selected from compounds 857697 to 1700384. In one embodiment of the present invention, a compound is selected from compounds 857697 to 998144. In one embodiment of the present invention, a compound is selected from compounds 998145 to 1138592. In one embodiment of the present invention, a compound is selected from compounds 1138593 to 1279040. In one embodiment of the present invention, a compound is selected from compounds 1279041 to 1419488. In one embodiment of the present invention, a compound is selected from compounds 1419489 to 1559936. In one embodiment of the present invention, a compound is selected from compounds 1559937 to 1700384. In one aspect of the present invention, the compound is selected from compounds 857697 to 904512, 998145 to 1044960, 1138593 to 1185408, 1279041 to 1325856, 1419489 to 1466304, and 1559937 to 1606752. In one aspect of the present invention, the compound is selected from compounds 951329 to 998144, 1091777 to 1138592, 1232225 to 1279040, 1372673 to 1419488, 1513121 to 1559936, and 1653569 to 1700384.

[0047] In the above, Ar in general formula (1) １ and Ar ２ is a phenyl group (Ar1), and X １ ~X ３ is a nitrogen atom (N), and L １ is a single bond, and R １ ~R ４ The structures of Compounds 1 to 1700384 were identified as those in which Ar is a group specified in Tables 1 and 2. Table 3 shows the structures of Compounds 1 to 1700384, respectively. １ and Ar ２ The compounds in which the Ar of Compound 1 is changed as shown in Table 3 are listed in order in a table format. In Table 3, compounds 1 to 1700384 are also listed to make the correspondence easier to understand. For example, Compound 1a is Compound 1 with Ar １ and Ar ２Compound 2a is a compound having a structure in which Ar is substituted with Ar. １ and Ar ２ Compound 1700384a is a compound having a structure in which Ar is substituted with Ar. １ and Ar ２ The compounds 1b to 1700384b and subsequent compounds are identified in the same manner. １ ~X ３ are all nitrogen atoms (N), and L １ is a single bond.

[0048] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds: the compound may be selected from Group 1, Group 2, Group 3, Group 4, Group 5, Group 6, Group 7, Group 8, Group 9, Group 10, Group 11, Group 12, Group 13, or Group 14.

[0049] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0050] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0051] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0052] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４ each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0053] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0054] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group.

[0055] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0056] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the ultraviolet region of the spectrum (e.g., 280-400 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the infrared region of the spectrum (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can be used to fabricate organic semiconductor devices. The organic semiconductor element referred to here may be an organic optical element in which light is mediated, or an organic element in which light is not mediated.The organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element that causes energy transfer by light within the element. In some embodiments of the present disclosure, an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present disclosure, a CMOS (complementary metal oxide semiconductor) or the like can be fabricated using a compound represented by general formula (1).

[0057] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴThe quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0058] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, a compound of general formula (1) substituted with a substituted ring-fused carbazole-9-yl group can be synthesized by reacting a cyanobenzene having a substituted or unsubstituted aryl group (e.g., a phenyl group) and a halogen atom with a substituted ring-fused carbazole. For details of the reaction conditions, please refer to the synthesis examples described below.

[0059] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0060] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture of the individual compounds may be used by heating, melting, and cooling. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

[0061] [Examples of Use of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferably used in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of compounds represented by general formula (1) of the present invention as light-emitting materials for organic light-emitting devices. In some embodiments, compounds represented by general formula (1) of the present invention can be effectively used as light-emitting materials in the light-emitting layer of organic light-emitting devices. In some embodiments, compounds represented by general formula (1) include delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of compounds represented by general formula (1) as delayed fluorescent materials. In some embodiments, the present invention can be used as a host material and can be used together with one or more light-emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF. In some embodiments, the compounds represented by general formula (1) can also be used as hole-transporting materials. In some embodiments, the compounds represented by general formula (1) can be used as electron-transporting materials. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves the light extraction efficiency from the emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound represented by general formula (1) as an emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device).In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic light-emitting device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole-transporting layer, a hole-injecting layer, an electron-blocking layer, a hole-blocking layer, an electron-injecting layer, an electron-transporting layer, and an exciton-blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0062] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0063] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[0064]

[0065] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0066] Further preferred light-emitting materials include compounds represented by the following general formula (2).

[0067] In general formula (2), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of the C-R groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0068] In one aspect of the present invention, X ２ When is O or NR, R ７ is an acceptor group, or R ６ and R ７are bonded to each other to form an acceptor group, or R ７ and R ８ In one embodiment of the present invention, X ３ When is O or NR, R １０ is an acceptor group, or R ９ and R １０ are bonded to each other to form an acceptor group, or R １０ and R １１ In one embodiment of the present invention, X ４ When is O or NR, R １５ is an acceptor group, or R １４ and R １５ are bonded to each other to form an acceptor group, or R １５ and R １６ In one embodiment of the present invention, X ２ is NR, R is a substituted or unsubstituted phenyl group, and R ８ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ３ is NR, R is a substituted or unsubstituted phenyl group, and R ９ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ４ is NR, R is a substituted or unsubstituted phenyl group, and R １６ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. １ is NR, R is a substituted or unsubstituted phenyl group, and R １In one embodiment of the present invention, the compound is represented by the following general formula (2a):

[0069] In general formula (2a), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of Ar is O or NR, and the remaining may be O or NR or may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ Each of C-R in general formula (1) independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ , C-R ３ , C-R ６ , C-R ７ , C-R ８, C-R ９ , C-R １０ , C-R １１ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0070] Further preferred light-emitting materials include compounds represented by the following general formula (3).

[0071] In general formula (3), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0072] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. ３ and R １０ are each independently a substituted amino group. １ and R ３ , and R ２ and R １０ In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0073] Further preferred light-emitting materials include compounds represented by the following general formula (4).

[0074] In general formula (4), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; １ ~R ９ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R１ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding to each other is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0075] In one aspect of the present invention, Z １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. １ ~R ９ are each independently a substituted or unsubstituted aryl group or an acceptor group, or R １ and R ２ are bonded to each other to form a ring, R ２ and R ３are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. ８ is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, a benzothiophene ring, and an indole ring.

[0076] Further preferred light-emitting materials include compounds having a fused ring structure A (in which a hydrogen atom may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring.

[0077] In the structure α, X １ and X ２ each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent; Z and X ２ In the fused ring structure A, the structure fused to b and X may be bonded to each other to form a cyclic structure. １ , b and Z, Z and X ２may be bonded to each other to form a cyclic structure.

[0078] Further preferred light-emitting materials include compounds represented by the following general formula (5).

[0079] In general formula (5), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0080] Further preferred light-emitting materials include compounds represented by the following general formula (6).

[0081] In the general formula (6), X ３ represents an oxygen atom or a sulfur atom; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; １ and R ４ ~R ７represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0082] Further preferred light-emitting materials include compounds represented by the following general formula (7).

[0083] In the general formula (7), X ４ represents an oxygen atom or a sulfur atom; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; １ and R ４ａ ~R ７ａ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ａ and R ５ａ , R ５ａ and R ６ａ , R ６ａ and R ７ａ , R ７ａ and R１ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0084] Further preferred light-emitting materials include compounds represented by the following general formula (8).

[0085] In the general formula (8), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ８ ~R １４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0086] Further preferred light-emitting materials include compounds represented by the following general formula (9).

[0087] In the general formula (9), Z １ and Z４ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R １５ ~R １７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , Z ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0088] Further preferred light-emitting materials include compounds represented by the following general formula (10).

[0089] In the general formula (10), Z １ and Z ５ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0090] Further preferred light-emitting materials include compounds represented by the following general formula (11).

[0091] In the general formula (11), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２１ ~R ２７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ , R ２６ and R ２７ may be bonded to each other to form a cyclic structure.

[0092] Further preferred light-emitting materials include compounds represented by the following general formula (12).

[0093] In the general formula (12), Z１ and Z ６ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２８ ~R ３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ may be bonded to each other to form a cyclic structure.

[0094] Further preferred light-emitting materials include compounds represented by the following general formula (13).

[0095] In the general formula (13), Z １ and Z ７ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２and Z ７ , Z ７ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.)

[0096] Further preferred light-emitting materials include compounds represented by the following general formula (14).

[0097] In the general formula (14), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ３１ ~R ４４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R ３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ , R ３７ and R ３８ , R ３８ and R ３９ , R ３９ and R ４０ , R ４０ and R ４１ , R ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ may be bonded to each other to form a cyclic structure.

[0098] Further preferred light-emitting materials include compounds represented by the following general formula (15).

[0099] In the general formula (15), Z １ and Z ８ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ５１ ~R ６０ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , R ５１ and R ５２ , R ５２ and R ５３ , R ５３ and R ５４ , R ５４ and R ５５ , R ５５ and R ５６ , R ５６ and R ５７ , R ５７ and R ５８ , R ５８ and R ５９ , R ５９ and R ６０ , R ６０ and Z ８ may be bonded to each other to form a cyclic structure.

[0100] Further preferred light-emitting materials include compounds represented by the following general formula (16).

[0101] In the general formula (16), Z １ , Z ８ and Z ９ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent.１ and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８ may be bonded to each other to form a cyclic structure.

[0102] Further preferred light-emitting materials include compounds represented by the following general formula (17).

[0103] In the general formula (17), Z １ , Z ９ and Z １０ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６７ ~R ６９ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７０ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , Z ９ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ , R ６９ and Z １０ , Z １０ and R ７０ may be bonded to each other to form a cyclic structure.

[0104] Further preferred light-emitting materials include compounds represented by the following general formula (18).

[0105] (In the general formula (18), Z １ , Z１１ and Z １２ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0106] Further preferred light-emitting materials include compounds represented by the following general formula (19).

[0107] In the general formula (19), Z １ and Z １１ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７６ ~R ８２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R ７５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R７８ , R ７８ and R ７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0108] Further preferred light-emitting materials include compounds represented by the following general formula (20).

[0109] In the general formula (20), X ５ represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R １０１ ~R １３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １０１ and R １０２ , R １０２ and R １０３ , R １０３ and R １０４ , R １０４ and R １０５ , R １０５ and R １０６ , R １０６ and R １０７ , R １０７ and R １０８ , R １０８ and R １０９ , R １０９ and R １１０ , R １１０ and R １１１ , R １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , R １１４ and R １１５ , R １１５ and R １１６ , R １１６ and R １１７ , R １１７ and R １１８ , R １１８ and R １１９ , R １１９ and R １２０ , R １２０and R １２１ , R １２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R １２５ , R １２５ and R １２６ , R １２６ and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R １３０ and R １０１ may be bonded to each other to form a cyclic structure.

[0110] Further preferred light-emitting materials include compounds represented by the following general formula (21).

[0111] In general formula (21), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R２ , R ２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １ may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0112] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. １ and Z １ are bonded to each other to form a ring structure. １ and Z １ are bonded to each other to form a pyrrole ring.

[0113] Further preferred light-emitting materials include compounds represented by the following general formula (22).

[0114] In the general formula (22), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １is a nitrogen atom, R １７ and R １８ are bonded to each other to form a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0115] In one aspect of the present invention, R ３ and R ６ In one embodiment of the present invention, at least one of R ３ and R ６ are both substituents. In one aspect of the present invention, R ３ and R ６ is one group selected from the group consisting of alkyl groups and aryl groups, or a group in which two or more groups are combined. ８ and R １２ In one embodiment of the present invention, the compound is represented by the following general formula (1a).

[0116] In the general formula (22a), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ４１and R ４２ each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represents an integer of 0 to 5, n1 and n3 each independently represents an integer of 0 to 4, and n2 and n4 each independently represents an integer of 0 to 3. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent.

[0117] In one aspect of the present invention, A １ and A ２ are each independently a group having a Hammett σp value of greater than 0.2. １ and A ２ In one embodiment of the present invention, A １ and A ２ are both halogen atoms. In one embodiment of the present invention, the structure has a rotational symmetry.

[0118] Preferred specific examples of the compound having the fused ring structure A and the compound represented by any one of general formulas (5) to (22) are given below.

[0119] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0120] In some embodiments, the host material is selected from the group consisting of: In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of the present invention may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0121] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0122] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0123] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0124] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0125] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0126]

[0127] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0128] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0129] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0130]

[0131] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0132]

[0133] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0134] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0135]

[0136] Electron Transport Layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0137]

[0138] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0139]

[0140] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0141] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0142] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0143] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0144] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0145] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0146] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0147] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0148] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0149] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0150] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0151] The features of the present invention will be explained in more detail below with reference to synthesis examples and examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the synthesis examples below, compounds represented by general formula (1) were synthesized.

[0152] (Synthesis Example 1) Synthesis of Compound 1

[0153] Under a nitrogen stream, compound a (0.56 g, 1.25 mmol) was added to a dimethylformamide solution (25 mL) of 2-phenyl-5H-benzofuro[3,2-c]carbazole (1.05 g, 3.1 mmol) and potassium carbonate (0.86 g, 3.76 mmol), and the mixture was stirred at 100°C for 15 hours. The mixture was returned to room temperature and quenched by adding methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to obtain compound 1 (1.10 g, 1.02 mmol, yield 81.9%). 1 H NMR (400 MHz, CDCl3) δ 9.06 (s, 1H), 8.65 (dd, J = 4.4, 0.8 Hz, 1H), 8.45 (d, J = 2.0 Hz, 1H), 8.00-7.94 (m, 6H), 7.91 (d, J = 7.6 Hz, 1H), 7.86 (dd, J = 8.4, 0.8 Hz, 1H), 7.80-7.60 (m, 8H), 7.54-7.30 (m, 12H), 7.24-7.16 (m, 8H), 6.78-6.76 (m, 2H), 6.54-6.45 (m, 3H), ASAP mass spectrum analysis: theoretical value 1072.4, Observed value 1072.8

[0154] (Synthesis Example 2) Synthesis of Compound 1 (Db)

[0155] A solution of compound b (0.75 g, 1.64 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (1.09 g, 3.28 mmol), and potassium carbonate (0.56 g, 4.10 mmol) in dimethylformamide (32 mL) was stirred at room temperature for 14 hours under a nitrogen stream. Water was added and the mixture was washed with methanol, filtered, and then dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene:hexane = 1:1) and recrystallized from toluene to obtain 0.75 g (0.69 mmol, yield 42.1%) of compound 1 (Db) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.05 (s, 1H), 8.66(d, J= 5.2 Hz, 1H) 8.44 (s, 1H),7.99-7.59 (m, 12H), 7.52-7.17 (m, 16H), 6.77 (d, J= 7.2 Hz,2H), 6.49 (dd, J= 21.2 Hz, 7.2 Hz, 2H) ASAP MS spectrum analysis: C 76 H 34 D 10 N6O2: Calculated 1082.42, Observed 1083.50

[0156] (Synthesis Example 3) Synthesis of Compound 1 (Dg)

[0157] A solution of compound c (2.0 g, 4.33 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (2.89 g, 8.66 mmol), and potassium carbonate (1.5 g, 10.83 mmol) in dimethylformamide (85 mL) was stirred at room temperature for 20 hours under a nitrogen stream. Water was added, and the mixture was washed with methanol, filtered, and then dried. The solvent was distilled off, and the residue was purified by silica gel column chromatography (toluene:hexane:chloroform=4:5:1) and then recrystallized from toluene to obtain 2.5 g (2.29 mmol, 53.0% yield) of compound 1 (Dg) as a yellow solid. 1 H NMR (400 MHz, CDCl3): δ 9.06 (s, 1H), 8.66 (dd, J= 1.6 Hz, 4.5 Hz,1H) 8.45 (d, J= 1.6 Hz, 1H), 8.00-7.90 (m, 3H), 7.86 (dd, J= 8.4 Hz, 6.4 Hz, 1H), 7.80-7.77 (m, 2H), 7.75-7.66 (m,4H), 7.65-7.60 (m, 2H), 7.54-7.46 (m, 6H), 7.44-7.30 (m, 6H), 7.22-7.19 (m, 2H) ASAP MS spectral analysis: C 76 H 29 D 15 N6O2: Calculated 1087.45, Observed 1088.42

[0158] (Synthesis Example 4) Synthesis of Compound 3

[0159] Compound d: Under a nitrogen stream, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (5.43 g, 7.40 mmol) was added to a solution of 6-bromo-2-phenyldibenzofuran (60.7 g, 185 mmol), bis(pinacolato)diborane (70.5 g, 278 mmol), and potassium acetate (54.5 g, 555 mmol) in 1,4-dioxane (800 mL), and the mixture was stirred at 110°C for 20 hours. The reaction solution was returned to room temperature, and potassium carbonate (51.1 g, 370 mmol), 2-bromo-4-chloro-nitrobenzene (52.5 g, 222 mmol), tetrakis(triphenylphosphine)palladium(0) (10.7 g, 9.25 mmol), and deionized water (100 mL) were added, followed by stirring at 80°C for 12 hours. The reaction solution was returned to room temperature and filtered through Celite. The crude product was purified by silica gel column chromatography (tetrahydrofuran) to obtain 33.3 g (83.3 mmol, yield 45%) of compound d as a yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.16 (s, 1H), 8.09 (d, J = 8.7 Hz, 1H), 8.06 (dd, J = 8.7 Hz, 1.8 Hz, 1H), 7.69-7.64 (m, 4H), 7.59-7.64 (m, 2H), 7.51-7.44 (m, 4H), 7.38 (t, J = 8.7 Hz, 1H). ASAP MS spectral analysis: C 24 H 14 ClNO3 theoretical value 399.07 observed value 400.16

[0160] Compound e: Under a nitrogen stream, tris(dibenzylideneacetone)dipalladium(0) (1.57 g, 1.71 mmol) was added to a mixed solution of compound d (34.3 g, 85.7 mmol), phenylboronic acid (12.5 g, 103 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.41 g, 3.43 mmol), and tripotassium phosphate (36.4 g, 171 mmol) in 1,4-dioxane / water (210 / 70 mL), and the mixture was stirred at 110°C for 12 hours. The reaction solution was returned to room temperature and washed with water. The aqueous layer was extracted with chloroform and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane:dichloromethane=3:2) to obtain 33.1 g (0.85 mmol, 88% yield) of compound e as a yellow solid. 1 H NMR (400 MHz, CDCl3: δ 8.23 ​​(d, J= 8.2 Hz, 1H), 8.17 (s, 1H), 8.06 (d, J = 8.2 Hz, 1H), 7.84-7.79 (m, 2H), 7.69-7.66 (m, 5H), 7.57-7.43 (m, 8H), 7.38 (t, J = 8.2 Hz, 1H). ASAP MS spectral analysis: C 30 H 19 NO3 theoretical value 441.14 observed value 442.33

[0161] Compound f: Under a nitrogen stream, compound e (733.1 g, 32.7 mmol) was added to a solution of triphenylphosphine (58.2 g, 222 mmol) in o-dichlorobenzene (74.0 mL), and the mixture was stirred at 170°C for 18 hours. The reaction mixture was returned to room temperature, water was added, and the precipitate was filtered off. The crude product was purified by silica gel column chromatography (hexane:dichloromethane=2:1) ​​and then recrystallized from toluene to obtain 21.5 g (52.6 mmol, yield 71%) of compound f as a brown solid. 1H-NMR (400 MHz, CDCl3): δ 8.73 (s, 1H), 7.38 (s, 1H), 8.18 (s, 1H), 8.02 (d, J= 8.2 Hz, 2H), 7.81-7.71 (m, 6H), 7.66 (d, J = 8.2 Hz, 1H), 7.59 (d, J= 8.2 Hz, 1H), 7.55-7.47 (m, 5H), 7.38 (s, 2H). ASAP MS spectral analysis: C 30 H 19 NO: Theoretical value 409.15, Observed value 410.15

[0162] Compound 3

[0163] A solution of compound a (0.8 g, 1.79 mmol), compound f (1.32 g, 3.22 mmol), and potassium carbonate (0.57 g, 4.12 mmol) in dimethylformamide (36 mL) was stirred at room temperature for 14 hours under a nitrogen stream. Water was added, and the mixture was washed with methanol, filtered, and dried. The solvent was evaporated, and the residue was purified by silica gel column chromatography (toluene:hexane:chloroform=10:9:1) and then recrystallized from toluene to obtain 0.9 g (0.73 mmol, yield 41.0%) of compound 3 as a yellow solid. 1 H NMR (400 MHz, CDCl3): δ 9.06 (s, 1H), 8.66(dd, J=4.8 Hz,1.2 Hz, 1H), 8.45 (d, J=1.6 Hz, 1H), 8.15 (dd, J= 6.0 Hz,2.0 Hz, 1H), 8.09 (d, J= 2.0 Hz, 1H), 8.02-7.95 (m, 5H), 7.88 (dd, J= 8.4 Hz, 2.4 Hz,1H), 7.80-7.60 (m, 14H), 7.53-7.30 (m, 16H), 7.26-7.13 (m, 6H), 6.78 (d, J= 6.4Hz, 2H), 6.56-6.44 (m, 3H) ASAP MS Spectral Analysis: C 88 H 52 N6O2: Calculated 1225.42, Observed 1225.51

[0164] (Example 1) Preparation and evaluation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Compound 1 was evaporated under conditions of less than 1×10 Pa to form a neat thin film of Compound 1 with a thickness of 100 nm. Separately, a neat thin film of Compound 1 was evaporated on a quartz substrate by vacuum evaporation under conditions of less than 1×10 Pa. －３ Compound 1 and mCBP were evaporated from different evaporation sources under conditions of less than 10 Pa, and a doped thin film with a concentration of 20 wt % of Compound 1 was formed to a thickness of 100 nm. Neat thin films and doped thin films were similarly formed using Compound 1 (Db), Compound 1 (Dg), Compound 3, and Comparative Compound 1, respectively, instead of Compound 1. The maximum emission wavelength (λmax) and photoluminescence quantum yield (PLQY) were measured when each doped thin film was irradiated with 300 nm excitation light. The HOMO energy (E HOMO ) and the LUMO energy (E LUMO The results are shown in Table 4.

[0165] (Example 2) Fabrication and Evaluation of Organic Electroluminescence Device Each thin film was deposited by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed, at a vacuum degree of 5.0×10 －５The layers were laminated at 100 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 35 nm, and PTCz was further formed thereon to a thickness of 10 nm. Next, H1 and Compound 1 were co-deposited from different evaporation sources to form a 40 nm thick layer as an emitting layer. The concentration of Compound 1 in the emitting layer was 30 mass%. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 20 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 mass% and 70 mass%, respectively. Liq was further formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, resulting in an organic electroluminescence device. Each organic electroluminescence device was fabricated by the same procedure using Compound 1 (Db), Compound 1 (Dg), Compound 3, and Comparative Compound 1 instead of Compound 1. The external quantum efficiency (EQE) and driving voltage (V init ), delayed fluorescence lifetime (τ), 12.6 mA / cm ２ The time (LT95) elapsed until the luminescence intensity reached 95% of that at the start of the test was measured, and the results are shown in Table 4. LT95 is expressed as a relative value when the LT95 of the element using Comparative Compound 1 is set to 1.

[0166]

[0167] It has been confirmed that the use of the compound represented by general formula (1) can improve the luminous efficiency and shorten the delayed fluorescence lifetime. It has also been confirmed that the use of the compound represented by general formula (1) can extend the device lifetime and improve durability.

[0168] Example 3: Preparation and Evaluation of Organic Electroluminescence Device Using Compound 1 as an Assist Dopant An organic electroluminescence device was prepared using the same procedure as in Example 2, except that instead of the emitting layer in Example 2, H1, Compound 1, and the emitting material EM1 were deposited from different deposition sources in concentrations of 69.5 wt %, 30.0 wt %, and 0.5 wt %, respectively, to form a 40 nm thick emitting layer. The maximum emission wavelength (λmax) of the prepared organic electroluminescence device was 528 nm, and the external quantum efficiency (EQE) at 6.3 mA was 20.9%. The durability of the device was also good. From the above, it was confirmed that an organic electroluminescence device with high luminous efficiency and good durability can be provided even when the compound represented by general formula (1) is used as an assist dopant.

[0169] By using the compound represented by general formula (1), an excellent organic light-emitting device with high luminous efficiency can be provided, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 [In general formula (1), R １ , R 2 and R ４ R 3 represents a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ ~R ４ Two or more of X are donor groups, and at least one of the two or more donor groups is a substituted ring-fused carbazol-9-yl group. １ ~X ３ Each independently represents N or C(R), but X １ ~X ３ At least one of Ar is N. R represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group. １ represents a single bond or a divalent linking group.

2. The compound according to claim 1, wherein the ring-fused carbazol-9-yl group is substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

3. The compound according to claim 1, wherein the ring-fused carbazol-9-yl group is a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton-constituting atoms is fused.

4. X １ ~X ３ The compound of claim 1 , wherein is N.

5. Ar １ and Ar ２ The compound according to claim 1 , wherein is an aryl group optionally substituted with a deuterium atom.

6. L １ The compound of claim 1 , wherein is a single bond.

7. R １ The compound according to claim 1 , wherein is a hydrogen atom.

8. R ３ The compound of claim 7, wherein is a phenyl group.

9. R ２ and R ４ The compound of claim 8, wherein are the same substituted ring-fused carbazol-9-yl group.

10. The compound of claim 1 having at least one deuterium atom.

11. A light-emitting material comprising the compound according to any one of claims 1 to 10.

12. A delayed fluorescent material comprising the compound according to any one of claims 1 to 10.

13. A film comprising the compound according to any one of claims 1 to 10.

14. An organic semiconductor device comprising the compound according to any one of claims 1 to 10.

15. An organic light-emitting device comprising the compound according to any one of claims 1 to 10.

16. 16. The organic light-emitting device of claim 15, wherein the device has a layer comprising the compound, the layer also comprising a host material.

17. 17. The organic light-emitting element according to claim 16, wherein the layer containing the compound also contains a delayed fluorescent material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

18. 17. The organic light-emitting device of claim 16, wherein the device has a layer comprising the compound, the layer also comprising a light-emitting material having a structure different from that of the compound.

19. The organic light-emitting device according to claim 16 , wherein the compound emits the greatest amount of light among the materials contained in the device.

20. The organic light-emitting device of claim 18 , wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

21. The organic light-emitting device according to claim 15, which is an organic electroluminescence device.

22. The organic light-emitting device according to claim 15, which emits delayed fluorescence.

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