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

Abstract

A compound represented by the following general formula is an excellent material for organic light-emitting elements. Y1 and Y2 are each an aryl group, a heteroaryl group, or the like, two or more of R1 to R5 are each a donor group bonded to a nitrogen atom, and the others are each a hydrogen atom, a deuterium atom, a non-acceptor heteroaryl group bonded to a carbon atom, an aryl group, or the like.

Description

Compounds, light-emitting materials, and organic light-emitting devices

[0001] This invention relates to compounds using compounds having a specific structure. The invention also relates to light-emitting materials and organic light-emitting devices using such compounds.

[0002] Research on organic light-emitting devices is actively being conducted. For example, there is a lot of research being done to improve the luminescence efficiency of light-emitting devices such as organic electroluminescent devices (organic EL devices). In particular, various methods are being used to improve luminescence efficiency by newly developing and combining electron transport materials, hole transport materials, and light-emitting materials that make up organic electroluminescent devices. Among these, there is also research on organic electroluminescent devices that utilize delayed fluorescence materials.

[0003] Delayed fluorescence materials are materials that, in their excited state, emit fluorescence when they return from the excited singlet state to the ground state after undergoing a reverse intersystem crossover from the excited triplet state to the excited singlet state. This fluorescence is called delayed fluorescence because it is observed later than fluorescence directly generated from the excited singlet state (normal fluorescence) from the ground state. For example, when a luminescent compound is excited by carrier injection, the probability of generating the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to improving the luminescence efficiency if only fluorescence from the directly generated excited singlet state is used. On the other hand, with delayed fluorescence materials, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission via the reverse intersystem crossover pathway described above, resulting in higher luminescence efficiency compared to normal fluorescence materials.

[0004] Since this principle was revealed, various delayed fluorescence materials have been discovered through various studies, and their application to organic light-emitting devices such as organic electroluminescent elements has been proposed. Among these are many compounds in which a benzene ring is substituted with a donor group and an acceptor group. For example, a compound has been proposed in which a benzene ring is substituted with a carbazole-9-yl group, which is a donor group, and a substituted triazinyl group, which is an acceptor group (see Patent Document 1).

[0005] WO2019 / 191665 A1

[0006] So far, no compound has been provided that exhibits extremely good performance when applied to an organic light-emitting device and has no problems in practical applications. Therefore, it would be more useful to develop a compound that can provide an organic light-emitting device with even better performance. However, the improvement of compounds is at the stage of trial and error, and it is not easy to generalize the chemical structures of useful compounds.

[0007] Under such circumstances, the present inventors have conducted extensive research aimed at providing more useful compounds for organic light-emitting devices. Then, they have intensively studied to derive and generalize the general formula of more useful compounds for organic light-emitting devices.

[0008] As a result of intensive studies to achieve the above object, the present inventors have found that compounds having a structure satisfying specific conditions have excellent light-emitting characteristics, and that an organic light-emitting device with excellent performance can be provided by using such compounds. The present invention has been proposed based on such findings, and specifically, it has the following configurations. [1] A compound represented by the following general formula (1). General formula (1) [In general formula (1), R １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a donor group bonded through a nitrogen atom, a non-acceptor heteroaryl group bonded through a carbon atom, or a substituted or unsubstituted aryl group. However, two or more of R １ ~R ５ are donor groups bonded through a nitrogen atom. Y １ and Y ２ represent a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Y １ and Y ２ are not both hydrogen atoms or deuterium atoms. ] [2] The compound according to [1], wherein three or more of R １ ~R ５ are donor groups bonded through a nitrogen atom. [3] R １ ~R ５The compound according to [1] or [2], wherein two of the groups are donor groups bonded by a nitrogen atom and have different structures from each other. [4] R １ ~R ５ The compound according to any one of [1] to [3], wherein one or more of the groups is a substituted or unsubstituted carbazole-9-yl group. [5] R １ ~R ５ The compound according to any one of [1] to [4], wherein one or more of the groups are substituted or unsubstituted ring-condensed carbazole-9-yl groups. [6] R １ ~R ５ The compound according to [5], wherein two or more of these are substituted or unsubstituted ring-condensed carbazole-9-yl groups. [7] R １ ~R ５ At least one of them is a substituted or unsubstituted ring-condensed carbazole-9-yl group, R １ ~R ５ The compound according to any one of [1] to [6], wherein at least one of the other groups is a substituted or unsubstituted carbazole-9-yl group in which the ring is not fused. [8] R １ ~R ５ A compound according to any one of [1] to [7], wherein one or two of the atoms are hydrogen atoms or deuterium atoms. [9] Y １ and Y ２ The compound according to any one of [1] to [8], wherein the compound is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[10] Y １ and Y ２A compound according to any one of [1] to [8], wherein at least one of the groups is a substituted or unsubstituted aryl group.

[11] A compound according to any one of [1] to

[10] , comprising at least one deuterium atom in the molecule.

[12] A light-emitting material comprising a compound according to any one of [1] to

[11] .

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

[11] .

[14] An organic light-emitting element comprising a compound according to any one of [1] to

[11] .

[15] An organic light-emitting element according to

[14] , which is an organic electroluminescent element.

[16] An organic light-emitting element according to

[15] , wherein the organic electroluminescent element has a layer comprising the compound, and the layer also comprises a host material.

[17] An organic light-emitting element according to

[15] or

[16] , wherein the organic electroluminescent element has a layer comprising the compound, and the layer also comprises a light-emitting material having a structure outside the range of the general formula (1).

[18] The organic light-emitting device according to

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

[0009] Compounds represented by general formula (1) exhibit excellent luminescence performance. They can also be used in organic light-emitting devices.

[0010] The contents of the present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention are deuterium atoms ( ２It can be substituted with H (deuterium D). In the chemical structural formulas herein, hydrogen atoms are either represented as H or omitted. For example, when the representation of an atom bonded to a carbon atom in the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom in the ring skeleton where the representation is omitted. In this specification, the term "substituent" means an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that the hydrogen atom may be substituted with a deuterium atom or a substituent.

[0011] [Compounds represented by general formula (1)] The compound represented by the general formula (1) below will be explained. General formula (1)

[0012] R in general formula (1) １ ~R ５ Two or more of these are donor groups bonded by nitrogen atoms. "Donor groups" can be selected from groups with a negative Hammett σp value. "Acceptor groups" can be selected from groups with a positive Hammett σp value. The Hammett σp value was proposed by L. P. Hammett and quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is a constant (σp) specific to the substituent in the following equation that holds between the substituent and the reaction rate constant or equilibrium constant in a para-substituted benzene derivative: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of the unsubstituted benzene derivative, k is the rate constant of the substituted benzene derivative, K0 is the equilibrium constant of the unsubstituted benzene derivative, K is the equilibrium constant of the substituted benzene derivative, and ρ is the reaction constant determined by the type and conditions of the reaction. For an explanation of "Hammett's σp value" in this invention and the numerical values ​​of each substituent, refer to the description of σp value in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991).

[0013] R １ ~R ５The donor group bonded by the nitrogen atom that can be adopted preferably has a σp of -0.3 or less, more preferably -0.5 or less, and even more preferably -0.7 or less. For example, it may be selected from the range of -0.9 or less, or from the range of -1.1 or less.

[0014] In the present invention, the donor group bonded to the nitrogen atom is preferably a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0015] R １ ~R ５ The donor group bonded by the nitrogen atom that can be adopted is preferably a group represented by the following general formula (a). General formula (a)

[0016] In general formula (a), Z １ CR １４ Or it represents N, Z ２ CR １５ Or it represents N, Z ３ CR １６ Or it represents N, Z ４ CR １７ Or it represents N. Z ５ represents C or N, and Ar ５ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring. １４ and R １５ , R １５ and R １６ , R １６ and R １７They may be joined together to form a ring structure.

[0017] Z １ ~Z ４ Of these, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one aspect of the present invention, Z １ ~Z ４ Of these, the number of those that are N is 1. In one aspect of the present invention, Z １ ~Z ４ Of these, the number of those that are N is 0. １４ ~R １７ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. Here, the deuterium atom or substituent may be selected from, for example, group A, group B, group C, group D, group E, or from any multiple of groups A through E. １４ ~R １７ When two or more of these represent deuterium atoms or substituents, those two or more deuterium atoms or substituents may be the same or different. １４ ~R １７ The number of substituents among them is preferably 0 to 2, for example R １４ ~R １７ The number of substituents among them may be one, or R １４ ~R １７ The number of substituents among them is 0 (R １４ ~R １７ (This may be a hydrogen atom or a deuterium atom.) １４ and R １５ , R １５ and R １６ , R １６ and R １７These elements may be bonded to each other to form a cyclic structure. The cyclic structure may be an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or a ring formed by the fusion of these elements. Preferably, it is an aromatic ring or a heteroaromatic ring. As an aromatic ring, a substituted or unsubstituted benzene ring can be given. The benzene ring may be further fused with other benzene rings, or with a heterocycle such as a pyridine ring. A heteroaromatic ring means an aromatic ring that contains heteroatoms as constituent atoms of the ring skeleton, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be used. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be used as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure 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 benzofuran, benzothiophene, and indole referred to herein may be unsubstituted or substituted with a deuterium atom or substituent. The deuterium atom or substituent referred to herein may be selected from group A, group B, group C, group D, group E, or from any of the groups A to E. It is preferable that a substituted or unsubstituted aryl group is bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of deuterium atoms or substituents that can be substituted to the aryl group include those selected from any of the groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one embodiment of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７ One pair within is joined to each other to form a ring structure. In one aspect of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７None of them are bonded to each other to form a cyclic structure.

[0018] In the general formula (a), Z ５ represents C or N, and Ar ５ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z ５ is C, and Ar ５ is a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. Ar ５ The aromatic ring that Ar can take can include a benzene ring. Another benzene ring may be further condensed with the benzene ring, or a heterocyclic ring such as a pyridine ring may be condensed. Ar ５ The heteroaromatic ring that Ar can take is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the heteroaromatic ring. In one aspect of the present invention, Z ５ is C, and the heteroaromatic ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, a pyridine ring of substituted or unsubstituted quinoline, or a pyridine ring of substituted or unsubstituted isoquinoline. In one aspect of the present invention, Z ５ is N, and the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole or an imidazole ring of substituted or unsubstituted benzimidazole. Here, benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole may be unsubstituted or may be substituted with a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from group A described below, may be selected from group B described below, may be selected from group C described below, may be selected from group D described below, may be selected from group E described below, or may be selected from each of a plurality of groups A to E.

[0019] Z in general formula (a) ５ When C is present, it is preferable that the group is represented by the following general formula (b). General formula (b)

[0020] In general formula (b), Z １ CR １４ Or it represents N, Z ２ CR １５ Or it represents N, Z ３ CR １６ Or it represents N, Z ４ CR １７ Or it represents N, Z ６ CR １８ Or it represents N, Z ７ CR １９ Or it represents N, Z ８ CR ２０ Or it represents N, Z ９ CR ２１ Or it represents N. １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ They may be bonded to each other to form a ring structure. Z in general formula (b) １ ~Z ４ , R １４ ~R １７ For this, refer to the corresponding explanation in general formula (a). Z in general formula (b) ６ ~Z ９ , R １８ ~R ２１ This is Z of general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order, and for these contents, Z of general formula (a) １ ~Z ４ , R １４ ~R １７ You can refer to the explanation. In one aspect of the present invention, Z１ ~Z ４ Z ６ ~Z ９ The number of N is preferably 0 to 2, and preferably 0 or 1. In one aspect of the present invention, Z １ ~Z ４ Z ６ ~Z ９ Of these, the number of those that are N is 1. In a preferred embodiment of the present invention, Z １ ~Z ４ Z ６ ~Z ９ The number of Ns among them is 0. When it is 0, it represents a substituted or unsubstituted carbazole-9-yl group.

[0021] R １ ~R ５ The donor group bonded by the nitrogen atom that can be adopted is preferably a substituted or unsubstituted carbazole-9-yl group. The carbazole-9-yl group referred to here may be unsubstituted, or it may be substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to here may be selected from group A, group B, group C, group D, group E, or any of the groups A to E described below. For example, it may be substituted with at least a deuterium atom. For example, it may be substituted with at least a cyano group. For example, it may be substituted with at least a deuterium atom or an alkyl group or an aryl group or an aryl group. For example, it may be substituted with at least an alkyl group or an alkyl group or an alkyl group. Furthermore, one or more rings may be fused to the two benzene rings constituting the carbazole-9-yl group. In one preferred embodiment of the present invention, R １ ~R ５The nitrogen atom bonded donor group that can be adopted is a carbazole-9-yl group, which may be substituted with a deuterium atom or substituent selected from group E, and may have one or more rings fused together. If a compound with a short emission wavelength is desired, it is preferable to use a carbazole-9-yl group that is substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group or an aryl group. When a carbazole-9-yl group that does not have a fused ring is substituted, the substitution position is not particularly limited, but is preferably at least one position between 2 and 7, more preferably at least one position between 3 and 6, and even more preferably two positions between 3 and 6.

[0022] In one aspect of the present invention, R １ ~R ５ The nitrogen atom-bonded donor group that can be formed is a carbazole-9-yl group in which one or more rings are fused, and hereafter this will be referred to as the "ring-fused carbazole-9-yl group". １ ~R ５ The ring-condensed carbazole-9-yl group that can be formed may be unsubstituted or substituted with a deuterium atom or substituent. The deuterium atom or substituent referred to here may be selected from group A, group B, group C, group D, group E, or any of the groups A to E described below. Preferably, it is unsubstituted or substituted with a deuterium atom or substituent selected from group E. In one embodiment of the present invention, the ring-condensed carbazole-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-condensed carbazole-9-yl group is substituted with an aryl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of deuterium atoms, alkyl groups, and aryl groups.

[0023] The total number of fused rings in the ring-condensed carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In one preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. The number of rings referred to here includes the number of rings of the carbazole being condensed (i.e., 3).

[0024] The ring-condensed carbazole-9-yl group is a group bonded to the nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is condensed to at least one of the two benzene rings constituting carbazole. The condensed ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or it may be a ring formed by further condensation of these. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocycle. As an aromatic hydrocarbon ring, a substituted or unsubstituted benzene ring can be given. The benzene ring may be further condensed to another benzene ring, or a heterocycle such as a pyridine ring may be condensed. An aromatic heterocycle means an aromatic ring that contains a heteroatom as a constituent atom of the ring skeleton, and is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring can be used. In one aspect of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be used as the aromatic heterocycle. In one aspect of the present invention, the fused ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. Preferably, the nitrogen atom of the pyrrole ring is bonded to a deuterium atom or substituent (except in cases where only a deuterium atom is present) selected from group E described below, and more preferably, an aryl group which may be substituted with an alkyl group or an aryl group is bonded to it. In the present invention, it is preferable to use a carbazole-9-yl group in which a ring having one or more atoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms as ring skeleton constituent atoms is fused. In particular, a carbazole-9-yl group in which a benzofuro structure is fused, a carbazole-9-yl group in which a benzothieno structure is fused, or a carbazole-9-yl group in which an indole structure is fused can be preferably used. In one aspect of the present invention, there is at least one carbazole-9-yl group in which a benzofuro structure is fused, for example, there are two or more. In one aspect of the present invention, the material has at least one carbazole-9-yl group formed by the condensation of a benzothieno structure, for example, two or more such groups.

[0025] As the ring-condensed carbazole-9-yl group, a substituted or unsubstituted benzoflo[2,3-a]carbazole-12-yl group, a substituted or unsubstituted benzoflo[3,2-a]carbazole-12-yl group, a substituted or unsubstituted benzoflo[2,3-b]carbazole-7-yl group, a substituted or unsubstituted benzoflo[3,2-b]carbazole-11-yl group, a substituted or unsubstituted benzoflo[2,3-c]carbazole-8-yl group, or a substituted or unsubstituted benzoflo[3,2-c]carbazole-5-yl group can be used. Furthermore, as the ring-condensed carbazole-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazole-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazole-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazole-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazole-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazole-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazole-5-yl group can also be used. Furthermore, as the ring-condensed carbazole-9-yl group, a substituted or unsubstituted 11-phenylindoro[2,3-a]carbazole-12-yl group, a substituted or unsubstituted 5-phenylindoro[3,2-a]carbazole-12-yl group, a substituted or unsubstituted 5-phenylindoro[2,3-b]carbazole-7-yl group, a substituted or unsubstituted 5-phenylindoro[3,2-b]carbazole-11-yl group, a substituted or unsubstituted 5-phenylindoro[2,3-c]carbazole-8-yl group, or a substituted or unsubstituted 12-phenylindoro[3,2-a]carbazole-5-yl group can also be used.

[0026] The number of substituents when the ring-condensed carbazole-9-yl group is substituted is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and may be, for example, 1 or 2. In one preferred embodiment of the present invention, either the 3-position or the 6-position of the ring-condensed carbazole-9-yl group is substituted. In one preferred embodiment of the present invention, there is at least one substituent at the para position of the benzene ring with respect to the heteroatom present in the ring-condensed carbazole-9-yl group. In one preferred embodiment of the present invention, there is at least one substituent only at the para position of the benzene ring with respect to the heteroatom present in the ring-condensed carbazole-9-yl group. In one preferred embodiment of the present invention, substituents are present at all of the substituted para positions of the benzene ring with respect to the heteroatom present in the ring-condensed carbazole-9-yl group.

[0027] In the following, R in general formula (1) １ ~R ５ The following are specific examples of nitrogen-bonded donor groups that can be adopted. The specific examples shown here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may have further ring condensation), but the nitrogen-bonded donor groups that can be adopted in the present invention are not limited to the following specific examples. In the following specific examples, Ph is a phenyl group (C ６ H ５ The symbols indicate the bond position. Methyl groups are omitted from the notation; for example, D2 has one methyl group. However, deuterated methyl groups are represented as CD. ３ It is written as follows. Also, C ６ D ５ The symbol (D) represents a phenyl group in which all hydrogen atoms have been replaced with deuterium (a hyperhydrogenated phenyl group). D represents a deuterium atom.

[0028] In the above-mentioned D1 to D459, all hydrogen atoms are replaced with deuterium atoms, and these are disclosed as D722 to D1180.

[0029] R １ ~R ５ The following are specific examples of nitrogen-bonded donor groups that are not substituted or unsubstituted carbazole-9-yl groups. However, the nitrogen-bonded donor groups that can be used in this invention are not limited to the following specific examples.

[0030] In the above D1181 to D1208, all hydrogen atoms are replaced with deuterium atoms, and these are disclosed as D1233 to D1260. In one aspect of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D1 to D1260. In one aspect of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D1 to D1180. In one aspect of the present invention, R １ ~R ５The donor groups that can be adopted are selected from the group consisting of D17-D76, D83-D118, D185-D298, D359-D453, D472-D519, D526-D653, and D704-D710. In one embodiment of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D77-D82, D119-D184, D299-D358, D455-D459, D520-D525, D654-D703, and D712-D721. In one embodiment of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D460 to D1180 and D1214 to D1260. In one embodiment of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D460 to D1180. In one preferred embodiment of the present invention, R １ ~R ５ The donor groups that can be obtained are D1-D13, D17-D22, D37, D47-D52, D77-D82, D119-D131, D134, D137, D140, D146, D149, D152, D155, D158, D161, D164, D167, D170, D173, D176, D179, D182, D198, D454, D466-D471, D521-D525, and D54. 3. Selected from the group consisting of D712-D716, D722-734, D739-D743, D758, D768-D773, D798-D803, D840-D852, D855, D858, D861, D867, D870, D873, D876, D879, D882, D885, D888, D891, D894, D897, D900, D903, D919, D1175. In a more preferred embodiment of the present invention, R １ ~R ５ The donor groups that can be adopted are selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D79, D198, D466, D467, D486, D522, D543, D722, D729, D730, D740, D758, D771, D798, D800, and D919.

[0031] In one aspect of the present invention, R １ ~R ５Two of these are donor groups bonded by nitrogen atoms. In a preferred embodiment of the present invention, R １ ~R ５ Three of these are donor groups bonded by nitrogen atoms. In one aspect of the present invention, R １ ~R ５ Four of these are donor groups bonded by nitrogen atoms. In one aspect of the present invention, R １ ~R ５ Five of these are donor groups bonded by nitrogen atoms. In one aspect of the present invention, R １ ~R ５ The donor group bonded by at least two nitrogen atoms is the same. In one aspect of the present invention, R １ ~R ５ All donor groups bonded to the nitrogen atom are identical. In one aspect of the present invention, the donor groups bonded to the nitrogen atom are the same as R １ ~R ５ Only two of them. In one aspect of the present invention, the donor group bonded by the nitrogen atom is the same as R. １ ~R ５ Only three of them. In one aspect of the present invention, at least R １ This is a donor group bonded by a nitrogen atom. In one aspect of the present invention, at least R ２ This is a donor group bonded by a nitrogen atom. In one aspect of the present invention, at least R ３ This is a donor group bonded by a nitrogen atom. In one aspect of the present invention, at least R ４ This is a donor group bonded by a nitrogen atom. In one aspect of the present invention, at least R ５ R is a donor group bonded with a nitrogen atom. In one aspect of the present invention, R ２ and R ３ Only is R a donor group bonded by a nitrogen atom. ２ and R ４ Only is a donor group bonded by a nitrogen atom. In one aspect of the present invention, R １ and R ２ Only is R a donor group bonded by a nitrogen atom. １ and R ３ Only is R a donor group bonded by a nitrogen atom.１ and R ５ Only is R a donor group bonded by a nitrogen atom. １ and R ５ Only is a donor group bonded by a nitrogen atom. In a preferred embodiment of the present invention, R ２ and R ３ and R ４ Only is R a donor group bonded by a nitrogen atom. １ and R ３ and R ４ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ４ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ３ Only is R a donor group bonded by a nitrogen atom. １ and R ３ and R ５ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ５ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ３ and R ４ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ３ and R ５ Only is R a donor group bonded by a nitrogen atom. １ and R ２ and R ４ and R ５ Only is R a donor group bonded by a nitrogen atom. １ ~R ５ All of these are donor groups bonded by nitrogen atoms. R in general formula (1) １ ~R ５The donor group bonded by the nitrogen atom represented by is preferably one (for example, just two, just three, just four, or just five) of which is a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), and is, for example, a fused or unsubstituted carbazole-9-yl group. R in general formula (1) １ ~R ５ The donor group bonded by the nitrogen atom represented by is preferably entirely a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), for example a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), for example a fused substituted or unsubstituted carbazole-9-yl group, for example a fused substituted or unsubstituted carbazole-9-yl group (a substituted or unsubstituted ring-fused carbazole-9-yl group). If it is fused, the number of rings in the fused ring formed by the fusion is preferably 4 to 10, more preferably 5 to 9, for example 5, for example 7, for example 9. In a preferred embodiment of the present invention, R １ ~R ５ Two or more of these are substituted or unsubstituted ring-condensed carbazole-9-yl groups. In another preferred embodiment of the present invention, R １ ~R ５ At least one of them is a substituted or unsubstituted ring-condensed carbazole-9-yl group, R １ ~R ５ At least one of the other groups is a substituted or unsubstituted carbazole-9-yl group that is not ring-fused.

[0032] R in general formula (1) １ ~R ５ Preferably, 0 to 2 of these atoms are hydrogen atoms or deuterium atoms; for example, only 1 is a hydrogen atom or deuterium atom, or for example, 2 are hydrogen atoms or deuterium atoms. １ ~R ５ None of these may be hydrogen atoms or deuterium atoms. In a preferred embodiment of the present invention, R １ and R ５At least one of them is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R １ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R ２ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R ３ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R ４ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R ５ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R １ Only R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ２ Only R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ３ Only R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ４ Only R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ５ Only R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R １ and R ２ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R １ and R ３ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R １ and R ４ is a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, R １ and R ５ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ２ and R ３ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ２ and R ４ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ２ and R ５ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ３ and R ４ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ３ and R ５ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R ４and R ５ It is either a hydrogen atom or a deuterium atom.

[0033] R in general formula (1) １ ~R ５ Of these, those that are not donor groups bonded by hydrogen, deuterium, or nitrogen atoms are non-acceptor heteroaryl groups bonded by carbon atoms, or substituted or unsubstituted aryl groups. Here, "non-acceptor" means that the Hammett σp value of the entire group is 0.3 or less, preferably less than 0, and may be, for example, -0.2 or less, -0.4 or less, or -0.6 or less. １ ~R ５ The heteroaryl group that can be adopted has a structure in which a heteroaromatic ring is fused to a benzene ring, and it is preferable that the group is bonded to the carbon atoms constituting the ring skeleton of the benzene ring. There may be one or two heteroaromatic rings fused to the benzene ring. Furthermore, a benzene ring or another heteroaromatic ring may be fused to the heteroaromatic ring fused to the benzene ring. Preferably, a benzene ring is fused to the heteroaromatic ring fused to the benzene ring. The heteroatoms constituting the ring skeleton of the heteroaromatic ring are preferably nitrogen atoms, oxygen atoms, or sulfur atoms, for example, nitrogen atoms, for example, oxygen atoms, or sulfur atoms. The heteroaromatic ring referred to here means an aromatic ring containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring can be adopted. The most preferred is a 5-membered ring. In one preferred embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the heteroaromatic ring. Furthermore, the hydrogen atoms of the benzene ring and heteroaromatic ring may be substituted with deuterium atoms or substituents. The deuterium atoms or substituents referred to here may be selected from, for example, group A, group B, group C, group D, group E, or from any of the groups A to E described below. In one embodiment of the present invention, R １ ~R ５Examples of heteroaryl groups that can be adopted include dibenzofuran-1-yl, dibenzofuran-2-yl, dibenzofuran-3-yl, dibenzofuran-4-yl, dibenzothiophen-1-yl, dibenzothiophen-2-yl, dibenzothiophen-3-yl, and dibenzothiophen-4-yl, and the hydrogen atoms of these groups may be substituted with deuterium atoms or substituents. In one aspect of the present invention, R １ ~R ５ Examples of heteroaryl groups that can be adopted include carbazole-1-yl, carbazole-2-yl, carbazole-3-yl, and carbazole-4-yl groups, and the hydrogen atoms of these groups may be substituted with deuterium atoms or substituents. In the following, R １ ~R ５ Specific examples of heteroaryl groups that may be substituted are given below. However, the heteroaryl groups that can be used in the present invention are not limited to the following examples. In the following examples, * indicates the bond position. Also, the methyl group is omitted from the notation. Therefore, X20 and X40 represent structures substituted with a methyl group.

[0034] X113 to X173 are disclosed in which all hydrogen atoms in X1 to X60 above are replaced with deuterium atoms. In one embodiment of the present invention, a heteroaryl group is selected from X1 to X40, X61 to X92, and X113 to X152. In one embodiment of the present invention, a heteroaryl group is selected from X41 to X60, X93 to X112, and X153 to X173. In one embodiment of the present invention, a heteroaryl group is selected from X61 to X112. In one embodiment of the present invention, a heteroaryl group is selected from X113 to X173. In a preferred embodiment of the present invention, a heteroaryl group selected from the group consisting of X3, X23, X43, X95, X115, X135, and X155 is used.

[0035] R １ ~R ５The substituted or unsubstituted aryl groups that can be formed are described below in Y １ and Y ２ Explanation and specific examples of substituted or unsubstituted aryl groups that can be formed by Y １ and Y ２ Specific examples of substituted aryl groups that can be adopted can be referenced. In one aspect of the present invention, R １ ~R ５ The aryl group that can be adopted is selected from the group consisting of Ar1 to Ar69. In one aspect of the present invention, R １ ~R ５ The aryl groups that can be adopted are selected from the group consisting of Ar1, Ar12, and Ar14.

[0036] In one aspect of the present invention, R １ ~R ５ Each of these independently represents a donor group bonded by a hydrogen atom, a deuterium atom, or a nitrogen atom, or a non-acceptor heteroaryl group bonded by a carbon atom, R １ ~R ５ Two or more of these are donor groups bonded by nitrogen atoms. In a preferred embodiment of the present invention, R １ ~R ５ Three or more of these are donor groups bonded by nitrogen atoms, and the remainder are hydrogen atoms or deuterium atoms, more preferably R １ ~R ５ Three of these are donor groups bonded by nitrogen atoms, and the remaining two are hydrogen atoms or deuterium atoms, in which case for example, at least R ２ It is a donor group bonded by a nitrogen atom, for example, at least R ３ This is a donor group bonded with a nitrogen atom. More preferably R ２ ~R ４ It is a donor group bonded by a nitrogen atom, R １ and R ５ is a hydrogen atom or a deuterium atom. In another preferred embodiment of the present invention, R １ ~R ５Three or more of these are donor groups bonded by nitrogen atoms, and at least one of them is a fused substituted or unsubstituted carbazole-9-yl group. In this case, it is preferable that the three or more donor groups bonded by nitrogen atoms are not all the same group. More preferably, R １ ~R ５ The three are donor groups bonded by nitrogen atoms, and at least one of them is a fused substituted or unsubstituted carbazole-9-yl group, R １ ~R ５ The remaining two atoms are hydrogen atoms or deuterium atoms. More preferably, R ２ ~R ４ R is a donor group bonded by a nitrogen atom, and at least one of them is a fused substituted or unsubstituted carbazole-9-yl group, １ and R ５ It is either a hydrogen atom or a deuterium atom.

[0037] In general formula (1), Y １ and Y ２ represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Y １ and Y ２ It is impossible for both to be either hydrogen atoms or deuterium atoms. That is, Y １ and Y ２ At least one of them is a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, preferably both being these groups. In one aspect of the present invention, Y １ and Y ２ Each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. In one aspect of the present invention, Y １ and Y ２ At least one of them is a substituted or unsubstituted aryl group. In one aspect of the present invention, Y １ and Y ２ Each of these is independently a substituted or unsubstituted aryl group, for example Y １ and Y ２ They are identical, for example Y １and Y ２ They are different. In one aspect of the present invention, Y １ and Y ２ One of them is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group. In one aspect of the present invention, Y １ and Y ２ Each of these is independently a substituted or unsubstituted heteroaryl group, for example Y １ and Y ２ They are identical, for example Y １ and Y ２ They are different. Y １ and Y ２ The substituted or unsubstituted aryl group that can be formed may be a monoring or a fused ring formed by the fusion of two or more rings. 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 rings include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and pyrene rings. Specific examples of aryl groups include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group. The number of constituent atoms of the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and can be selected within the range of 6 to 14 or within the range of 6 to 10. In the following, Y １ and Y ２ Specific examples of aryl groups that may be substituted are given below. However, the aryl groups that can be used in this invention are not limited to the following examples. In the following examples, * indicates the bond position. Also, methyl groups are omitted from the notation. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[0038] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar25 are replaced with deuterium atoms are exemplified here as Ar45 to Ar69, in order. １ and Y ２The aryl group that can be adopted is selected from the group consisting of Ar1 to Ar69. In one preferred embodiment of the present invention, Y １ and Y ２ The aryl groups that can be adopted are selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar13, Ar14, Ar19, Ar20, Ar36, Ar37, Ar38, Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar57, Ar58, Ar63, and Ar64. In a more preferred embodiment of the present invention, Y １ and Y ２ The aryl groups that can be adopted are selected from the group consisting of Ar1, Ar12, Ar13, Ar14, Ar36, Ar37, Ar38, Ar45, Ar56, Ar57, and Ar58. In one aspect of the present invention, Y １ and Y ２ The aryl group that can be adopted is selected from the group consisting of Ar26 to Ar69. In one aspect of the present invention, Y １ and Y ２ The aryl groups that can be adopted are selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64.

[0039] Y １ and Y ２ The substituted or unsubstituted heteroaryl group that can be adopted is preferably a group bonded to a nitrogen atom constituting an aromatic heterocycle. Examples of aromatic heterocycles containing the bonded nitrogen atom include pyrrole rings, pyridine rings, pyrimidine rings, and triazine rings. These aromatic heterocycles containing the bonded nitrogen atom may be substituted, or other rings may be fused to them. Examples of other rings include aromatic hydrocarbon rings and aromatic heterocycles, and rings formed by further fusion of these rings may be fused to the aforementioned aromatic heterocycle containing the nitrogen atom. In one aspect of the present invention, Y １ and Y ２ Examples of substituted or unsubstituted heteroaryl groups that can be adopted include the donor group represented by the aforementioned general formula (a), and further, the donor group represented by the aforementioned general formula (b), and further, R related to these general formulas. １ ~R ５You can refer to the explanation and specific examples of the donor groups that can be adopted. In one aspect of the present invention, Y １ and Y ２ The heteroaryl group that can be adopted is selected from the aforementioned D1 to D1260. In one preferred embodiment of the present invention, Y １ and Y ２ The heteroaryl group that can be adopted is selected from the aforementioned D1 to D1180. In one preferred embodiment of the present invention, Y １ and Y ２ The donor groups that can be adopted are selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D79, D198, D466, D467, D486, D522, D543, D722, D729, D730, D740, D758, D771, D798, D800, and D919. More preferably, they are selected from the group consisting of D1, D8, D9, D19, D37, D50, D466, D467, D486, D722, D729, D730, D740, D758, and D771.

[0040] In general formula (1), R １ ~R ５ Two of them will not combine to form a ring structure. That is, R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ These do not bond to each other to form a cyclic structure. The compound represented by general formula (1) has a structure in which the benzene ring can freely rotate around the single bond between the upper pyrimidine ring and the lower benzene ring. For this reason, R in this specification １ , R ２ The descriptions are as follows: ５ , R ４ It is possible to interpret this as the description of R. ４ Even if a compound has a specific group, rotating the benzene ring will result in R ２ If a compound can be considered to have a specific group, and that compound also satisfies all the other conditions of general formula (1), then it can be said to be a compound included in general formula (1).

[0041] As compound group 1 used in the present invention, R of general formula (1) ２ and R ３ and R ４ A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 1 is R ２ and R ３ and R ４ Compound group 1a, R ２ and R ４ If they are the same, R ３ Different compound group 1b, R ２ and R ３ If they are the same, R ４ Different compound groups 1c, R ２ and R ３ and R ４ All are different compound groups 1d, R ２ and R ３ and R ４ Compound group 1e, R, where at least one of them has at least one deuterium atom ２ and R ３ and R ４ This includes compound group 1f, which has a hydrogen atom but no deuterium atom, and compound group 1g, which does not have a deuterium atom in the compound. Compound groups 1a to 1g each further include cases that satisfy at least one of the following additional conditions. In one aspect of the present invention, the donor groups bonded by a nitrogen atom are not all the same group. In one aspect of the present invention, at least one (preferably two or more) of the donor groups bonded by a nitrogen atom is a substituted or unsubstituted ring-condensed carbazole-9-yl group. In one aspect of the present invention, at least one (preferably two or more) of the donor groups bonded by a nitrogen atom is a substituted or unsubstituted ring-condensed carbazole-9-yl group, and at least one other is a substituted or unsubstituted carbazole-9-yl group in which the ring is not condensed. In one aspect of the present invention, R other than the donor group bonded by a nitrogen atom １ ~R ５ is a hydrogen atom or a deuterium atom. In one aspect of the present invention, Y １ and Y ２ Each is independently a substituted or unsubstituted aryl group. In one aspect of the present invention, Y １ and Y ２Each of these is independently a substituted or unsubstituted heteroaryl group. In one aspect of the present invention, Y １ and Y ２ One of the groups is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group. In one aspect of the present invention, Y １ and Y ２ They are identical. In one aspect of the present invention, R １ and R ５ Each is independently a hydrogen atom or a deuterium atom, Y １ and Y ２ Each is independently a substituted or unsubstituted aryl group. In one aspect of the present invention, R １ and R ５ is a hydrogen atom, Y １ and Y ２ Each is independently a substituted or unsubstituted aryl group. In one aspect of the present invention, R １ and R ５ is a hydrogen atom, Y １ and Y ２ Each of these is an independently substituted or unsubstituted aryl group that does not contain a deuterium atom.

[0042] As compound group 2 used in the present invention, R of general formula (1) １ and R ３ and R ５ A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 2 is R １ and R ３ and R ５ Compound group 2a, R is identical. ３ and R ５ If they are the same, R １ Different compound group 2b, R １ and R ５ If they are the same, R ３ Different compound groups 2c, R １ and R ３ and R ５ This includes all different compound groups 2d. Compound groups 2a to 2d each also include cases where at least one of the additional conditions described in compound group 1 is satisfied.

[0043] As compound group 3 used in the present invention, R of general formula (1) １ and R２ and R ５ A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 3 is R １ and R ２ and R ５ Compound group 3a, R is identical. ２ and R ５ If they are the same, R １ Different compound group 3b, R １ and R ５ If they are the same, R ２ Different compound groups 3c, R １ and R ２ If they are the same, R ５ Different compound group 3d, R １ and R ２ and R ５ This includes all different compound groups 3e. Compound groups 3a to 3e each also include cases where at least one of the additional conditions described in compound group 1 is satisfied.

[0044] As compound group 4 used in the present invention, R of general formula (1) １ and R ２ and R ４ A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 4 is R １ and R ２ and R ４ Compound group 4a, R ２ and R ４ If they are the same, R １ Different compound group 4b, R １ and R ４ If they are the same, R ２ 4c, R, a group of different compounds １ and R ２ If they are the same, R ４ 4d, R, different compound groups １ and R ２ and R ４ This includes all different compound groups 4e. Compound groups 4a to 4e each also include cases where at least one of the additional conditions described in compound group 1 is satisfied.

[0045] As the compound group 5 used in the present invention, R of general formula (1) １ and R ３ and R ４A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 5 is R １ and R ３ and R ４ Compound group 5a, R ３ and R ４ If they are the same, R １ Different compound group 5b, R １ and R ４ If they are the same, R ３ Different compound groups 5c, R １ and R ３ If they are the same, R ４ Different compound group 5d, R １ and R ３ and R ４ This includes all different compound groups 5e. Compound groups 5a to 5e each also include cases where at least one of the additional conditions described in compound group 1 is satisfied.

[0046] The compound group 6 used in the present invention is R of general formula (1). １ and R ２ and R ３ A group of compounds can be listed in which each is a donor group bonded independently by a nitrogen atom. Compound group 6 is R １ and R ２ and R ３ Compound group 6a, R ２ and R ３ If they are the same, R １ Different compound groups 6b, R １ and R ３ If they are the same, R ２ 6c, R, a group of different compounds １ and R ２ If they are the same, R ３ 6d, R, which are different groups of compounds. １ and R ２ and R ３ This includes all different compound groups 6e. Compound groups 6a to 6e each also include cases where at least one of the additional conditions described in compound group 1 is satisfied.

[0047] When a compound with a short emission wavelength is provided, it is preferable to use a compound having a carbazole-9-yl group that is substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group or an aryl group within the molecule.

[0048] The compound represented by general formula (1) preferably does not contain metal atoms and may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In one 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 atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the compound represented by general formula (1) may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. The compound represented by general formula (1) may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Furthermore, the compound represented by general formula (1) may be a compound that does not contain hydrogen atoms but contains deuterium atoms. The compound represented by general formula (1) may be a compound that does not contain deuterium atoms but contains hydrogen atoms. The compound represented by general formula (1) may also be a compound containing both a deuterium atom and a hydrogen atom.

[0049] In this specification, "Group A" means deuterium atoms, hydroxyl groups, halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), alkyl groups (e.g., C1-C40), alkoxy groups (e.g., C1-C40), alkylthio groups (e.g., C1-C40), aryl groups (e.g., C6-C30), aryloxy groups (e.g., C6-C30), arylthio groups (e.g., C6-C30), heteroaryl groups (e.g., ring skeleton constituent atoms numbering 5-30), heteroaryloxy groups (e.g., This group consists of alkyl groups (e.g., ring skeleton with 5 to 30 constituent atoms), heteroarylthio groups (e.g., ring skeleton with 5 to 30 constituent atoms), acyl groups (e.g., 1 to 40 carbon atoms), alkenyl groups (e.g., 1 to 40 carbon atoms), alkynyl groups (e.g., 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups with 1 to 40 carbon atoms), and nitro groups. The alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups, alkenyl groups, alkynyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups referred to here may be substituted with substituents having a structure in which one or more of the deuterium atoms constituting group A and any of the substituents listed above are bonded. In this specification, "Group B" refers to the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 5 to 30 atoms in the ring skeleton), an heteroaryl group (e.g., having 5 to 30 atoms in the ring skeleton), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). The alkyl group, alkoxy group, aryl group, aryloxy group, heteroaryl group, heteroaryloxy group, and diarylaminoamino group referred to herein may be substituted with substituents having a structure in which one or more of the deuterium atoms constituting Group B and any of the substituents listed above are bonded.In this specification, "Group C" refers to the group consisting of a deuterium atom, alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and diarylamino groups (e.g., 12 to 20 carbon atoms). The alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups referred to here may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to the deuterium atom constituting Group C. In this specification, "Group D" refers to the group consisting of a deuterium atom, alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), and heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton). The alkyl groups, aryl groups, and heteroaryl groups referred to here may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to the deuterium atom constituting Group D. In this specification, "Group E" refers to the group consisting of a deuterium atom, alkyl groups (e.g., 1 to 20 carbon atoms), and aryl groups (e.g., 6 to 22 carbon atoms). The alkyl and aryl groups referred to herein may be substituted with substituents having a structure in which one or more of the deuterium atoms constituting group E and any of the substituents described above are bonded. When "substituted or unsubstituted" or "may be substituted" is described herein, the deuterium atoms or substituents to be substituted may be selected from, for example, group A, group B, group C, group D, or group E.

[0050] Tables 1-1 to 1-5 below illustrate specific examples of compounds represented by general formula (1). However, the compounds represented by general formula (1) that can be used in the present invention should not be interpreted as being limited by these specific examples. Tables 1-1 to 1-4 show, among the compounds represented by general formula (1), Y １ and Y ２ is a phenyl group (Ar1), and R １ and R ５ is a hydrogen atom, R ２ , R ３ , R ４The following are specific examples of compounds that are identical and are one of D1 to D1260. That is, the R of a compound having the following structure ２ , R ３ , R ４ The structures of compounds 1 to 1260 are individually identified by showing them sequentially in Tables 1-1 to 1-4.

[0051] Tables 2-1 to 2-12 show the structures of compounds 1 to 392784 as variations of the structure represented by general formula (1). Tables 2-1 to 2-12 show the structures of compounds Y, among those represented by general formula (1). １ and Y ２ is a phenyl group (Ar1), and R １ ~R ５ Specific examples of compounds in which the group is identified in Tables 2-1 to 2-12 are shown. That is, the R of a compound having the following structure １ ~R ５ The structures of compounds 1 to 392784 are individually identified by showing them sequentially in Tables 2-1 to 2-12. The rows for compounds 1 to 1260 in Table 2-1 are Y １ and Y ２ R is fixed to a phenyl group (Ar1), １ and R ５ R is fixed to a hydrogen atom (H), ２ , R ３ , R ４ Compounds that are identical and have D1 to D1260 are identified in order as compounds 1 to 1260. That is, the row for compounds 1 to 1260 in Table 2-1 shows the structures of compounds 1 to 1260 from Tables 1-1 to 1-4 together in one row. The row for compounds 1261 to 2519 in Table 2-1 is Y １ and Y ２ R is fixed to a phenyl group (Ar1), １ and R ５ R is fixed to a hydrogen atom (H), ３ It is fixed to D1, R ２ and R ４ Compounds that are identical and have D2 to D1260 are identified in order as compounds 1261 to 2519. The row for compounds 2520 to 3778 in Table 2-1 is Y１ and Y ２ R is fixed to a phenyl group (Ar1), １ and R ５ R is fixed to a hydrogen atom (H), ３ It is fixed to D8, R ２ and R ４ Compounds that are identical and have the same D1-D7 and D9-D1260 are identified as compounds 2520-3778 in order. The structures of the compounds in the following rows are identified in the same manner. Note that, as shown in the far right column of Tables 2-1 to 2-12, for example, compounds 1-1260 in the top row, R ２ and R ３ and R ４ This indicates that they are the same.

[0052] Tables 2-1 to 2-12 show the Y in general formula (1). １ and Y ２ The structures of compounds 1 to 392784, in which Y is fixed to a phenyl group (Ar1), were identified. Tables 3-1 to 3-5 show the structures of each of compounds 1 to 392784. １ and Y ２ Compounds in which the phenyl group (Ar1) was changed as shown in Tables 3-1 to 3-5 are displayed in order in a table format. In Tables 3-1 to 3-5, Y is used to make the correspondence easier to understand. １ and Y ２ The first row shows compounds 1 to 392784 in which the phenyl group (Ar1) is displayed. In the second row of Table 3-1, for example, compound 1 (1) is the Y of compound 1. １ and Y ２ This shows a compound having a structure in which is substituted with Ar2. Also, compound 2(1) is Y of compound 2. １ and Y ２ This shows a compound having a structure in which is substituted with Ar2. In the same manner, compound 392784(1) is Y of compound 392784.１ and Y ２ This shows compounds having a structure in which Ar2 is substituted. The structures of compounds 1(2) to 392784(2) and subsequent compounds in the third row are identified in the same way as in the second row.

[0053] All compounds identified by the above numbers are disclosed individually. Furthermore, if rotational isomers exist for any of the above specific compound examples, a mixture of rotational isomers and each separated rotational isomer are also disclosed herein. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 392784 and compounds 1(n) to 392784(n) [where n is 1 to 437]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 392784 and compounds 1(n) to 392784(n) [where n is 1 to 68]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 392784(n) [where n is 69 to 233]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 392784(n) [where n is 234 to 310]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compound 1(n) to 392784(n) [where n is 311 to 325]. In another aspect of the present invention, a compound is selected from the group of compounds consisting of compound 1(n) to 392784(n) [where n is 326 to 437].

[0054] Examples of preferred compounds represented by general formula (1) are listed below.

[0055] Examples of compounds represented by general formula (1) are listed below.

[0056] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and can also be 1000 or less, for example, when the organic layer containing the compound represented by general formula (1) is intended to be used as a film by vapor deposition. 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) is useful as a light-emitting material and can be used as a delayed fluorescence material. For example, some compounds represented by general formula (1) have a short delayed fluorescence lifetime. For example, some compounds represented by general formula (1) have a large delayed fluorescence component during emission. Organic light-emitting devices using the compound represented by general formula (1) have good light-emitting properties. For example, some compounds represented by general formula (1) can extend the device lifetime when used in organic light-emitting devices. For example, some compounds represented by general formula (1) can lower the driving voltage when used in organic light-emitting devices. For example, some compounds represented by general formula (1) have high orientation when a film is formed. The compound represented by general formula (1) may be formed as a film by coating regardless of its molecular weight. Using the coating method, it is possible to form films even with compounds that have relatively large molecular weights. Compounds represented by general formula (1) have the advantage of being readily soluble in organic solvents. For this reason, compounds represented by general formula (1) are easy to apply the coating method to and are also easy to purify to increase their purity.

[0057] Applying the present invention, it is conceivable to use compounds containing multiple structures represented by general formula (1) within the molecule as luminescent materials. For example, polymerizable groups may be pre-existing in the structure represented by general formula (1), and polymerized to obtain polymers obtained by polymerizing these polymerizable groups may be used as luminescent materials. For example, a monomer containing a polymerizable functional group at any part of general formula (1) may be prepared, and this may be polymerized alone or copolymerized with other monomers to obtain polymers having repeating units, which may then be used as luminescent materials. Alternatively, dimers or trimers may be obtained by coupling compounds having the structure represented by general formula (1), and these may be used as luminescent materials.

[0058] Examples of polymers having repeating units that include a structure represented by general formula (1) include polymers that include a structure represented by either of the following two general formulas.

[0059] In the general formula above, Q represents a group containing the structure represented by general formula (1), and L １ and L ２ The symbol 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 It is preferable that the structure is represented by -. Here, X １１ L represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ R represents a linking group, which is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms. In the above general formula, R １０１ , R １０２ , R １０３ and R １０４Each of these 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, it is 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, it is an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms. １ and L ２ The linking group represented by can bond to any part of the general formula (1) that constitutes Q. Two or more linking groups may be linked to a single Q to form a cross-linked structure or a network structure.

[0060] As a concrete example of a repeating unit structure, we can cite the structure represented by the following formula.

[0061] Polymers having repeating units including these formulas can be synthesized by introducing a hydroxyl group to any of the sites in general formula (1), reacting it with the following compounds as a linker to introduce polymerizable groups, and then polymerizing those polymerizable groups.

[0062] A polymer containing a structure represented by general formula (1) within its molecule may consist only of repeating units having the structure represented by general formula (1), or it may contain 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 two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers commonly used in copolymerization. For example, repeating units derived from monomers having ethylenically unsaturated bonds, such as ethylene and styrene, can be cited.

[0063] Compounds represented by general formula (1) are compounds that can be used in various semiconductor devices. For example, they can be used in organic light-emitting devices that emit light, organic photodetectors that receive light, and devices that generate energy transfer by light within the device. For example, organic electroluminescent devices can be fabricated using compounds represented by general formula (1). For example, CMOS (complementary metal-oxide-semiconductor) devices can be fabricated using compounds represented by general formula (1). For example, solid-state image sensors (e.g., CMOS image sensors) can be fabricated using compounds represented by general formula (1). Among the compounds represented by general formula (1), there are compounds that can emit delayed fluorescence. Among the compounds represented by general formula (1), there are compounds with a large proportion of delayed fluorescence components. For example, there are compounds in which 70% or more of the total emission is the delayed fluorescence component, compounds in which 80% or more is the delayed fluorescence component, and compounds in which 90% or more of the total emission is the delayed fluorescence component. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the UV region, the blue, green, yellow, orange, or red regions 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 when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the red or orange regions of the visible spectrum (e.g., about 620 nm to about 780 nm, or about 650 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the orange or yellow regions of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, or about 570 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a 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 this disclosure, a compound represented by general formula (1) may 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 this disclosure, a compound represented by general formula (1) may emit light in the ultraviolet spectral region (e.g., 280 to 400 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means.

[0064] The electronic properties of a small molecule chemical library can be calculated using known ab initio quantum chemical calculations. For example, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be analyzed using time-dependent density functional theory with 6-31G*, Becke's three parameters, and a set of functions known as the Lee-Yang-Parr hybrid functional as a basis, to screen molecular fragments (parts) having HOMO above a certain threshold and LUMO below a certain threshold. This allows for the selection of donor parts ("D") when the HOMO energy (e.g., ionization potential) is above -6.5 eV, for example. Alternatively, when the LUMO energy (e.g., electron affinity) is below -0.5 eV, for example, acceptor parts ("A") can be selected. The bridge portion ("B") is a strongly conjugated system that can strictly restrict the receptor and donor portions to specific stereochemistrys, for example, thereby preventing duplication between the π-conjugated systems of the donor and receptor portions. In one embodiment, the compound library is selected using one or more of the following characteristics: 1. Emission near a specific wavelength; 2. A calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ Value 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In one embodiment, the difference (ΔE) between the lowest singlet excited state and the lowest triplet excited state at 77K 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 one embodiment, ΔE ＳＴ The values ​​are 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 some embodiments, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example, 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 higher.

[0065] [Synthesis method of compounds represented by general formula (1)] Compounds represented by general formula (1) include novel compounds. Compounds represented by general formula (1) can be synthesized by combining known reactions. Compounds represented by general formula (1) are R １ ~R ５ Of these, 2 to 5 are donor groups. For example, by reacting a precursor in which the donor group is a fluorine atom with a substituted or unsubstituted carbazole, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is the donor group can be synthesized. For details of the reaction conditions, please refer to the synthesis examples described later.

[0066] [Constructions using compounds represented by general formula (1)] In some embodiments, a solid film or layer is formed by combining the compound represented by general formula (1) with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse the compound, covalently bond with the compound, coat the compound, support the compound, or associate with the compound. For example, a film can be formed by combining the compound represented by general formula (1) with an electroactive material. In some cases, the compound represented by general formula (1) may be combined with a hole transport polymer. In some cases, the compound represented by general formula (1) may be combined with an electron transport polymer. In some cases, the compound represented by general formula (1) may be combined with both a hole transport polymer and an electron transport polymer. In some cases, the compound represented by general formula (1) may be combined with a copolymer having both a hole transport portion and an electron transport portion. Through these embodiments, electrons and / or holes formed in a solid film or layer can be made to interact with the compound represented by general formula (1).

[0067] [Film Formation] In one embodiment, a film containing the compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing the composition with the compound represented by general formula (1) is applied to a surface, and the film is formed after the solvent is removed. 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 with the compound represented by general formula (1) is selected and used. In one embodiment, substituents (e.g., alkyl groups) that increase the solubility in organic solvents can be introduced into the compound contained in the composition. In one embodiment, a film containing the compound represented by general formula (1) can be formed by a dry process. In one embodiment, but is not limited to, vacuum deposition can be used as the dry process. When vacuum deposition is used, the compounds constituting the film may be co-deposited from individual deposition sources, or they may be co-deposited from a single deposition source containing a mixture of compounds. When using a single deposition source, a mixed powder of compound powders may be used, a compressed molded body made by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In one embodiment, by performing co-deposition 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, a film with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. By mixing multiple compounds in the same composition ratio as the composition ratio of the formed film to create a deposition source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound has the same weight loss rate can be identified, and that temperature can be adopted as the temperature during co-deposition.

[0068] [Organic Light-Emitting Devices] Organic light-emitting devices containing compounds represented by general formula (1) will be described. Organic light-emitting devices using compounds represented by general formula (1) have excellent performance. For example, some organic light-emitting devices containing compounds represented by general formula (1) have improved orientation of the light-emitting layer by using the compound represented by general formula (1). For example, some organic light-emitting devices containing compounds represented by general formula (1) have a longer device life by using the compound represented by general formula (1). For example, some organic light-emitting devices containing compounds represented by general formula (1) have improved luminescence efficiency by using the compound represented by general formula (1). For example, some organic light-emitting devices containing compounds represented by general formula (1) have a lower driving voltage by using the compound represented by general formula (1). For example, some organic light-emitting devices containing compounds represented by general formula (1) have a higher proportion of delayed fluorescence component during emission by using the compound represented by general formula (1). For example, some organic light-emitting devices containing compounds represented by general formula (1) have a shorter delayed fluorescence lifetime by using the compound represented by general formula (1). In one aspect of the present invention, a compound represented by general formula (1) is used as the light-emitting material for an organic light-emitting device. For example, a compound represented by general formula (1) is used as the light-emitting material in the light-emitting layer. Among the compounds represented by general formula (1), there are compounds with a large amount of delayed fluorescence component. For this reason, in one aspect of the present invention, a compound represented by general formula (1) is used as a delayed fluorescence material to generate delayed fluorescence from the compound represented by general formula (1), for example, and achieve high photoluminescence efficiency. In one aspect of the present invention, a compound represented by general formula (1) is used as a host material. In one aspect of the present invention, a compound represented by general formula (1) is used together with one or more light-emitting materials. The light-emitting material here may be a fluorescent material, a phosphorescent material, or a delayed fluorescence material. For example, a fluorescent material with a lower minimum excitation singlet energy than the compound represented by general formula (1) is used together with the compound represented by general formula (1). In one aspect of the present invention, a compound represented by general formula (1) is used as a hole transport material. In one aspect of the present invention, a compound represented by general formula (1) is used as an electron transport material.In one embodiment, the light-emitting layer of the organic light-emitting element contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) with respect to the film-forming surface affects or determines the direction of light propagation emitted by the aligned compound. In one embodiment, the light extraction efficiency from the light-emitting layer is improved by aligning the direction of light propagation emitted by the compound represented by general formula (1). The organic light-emitting element of the present invention is particularly preferably used as an organic light-emitting diode, etc. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). 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 lowest excited singlet energy level of the compound represented by general formula (1) contained in the light-emitting layer lies 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 other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element 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 a light-emitting layer. In one embodiment, the organic layer includes only a 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 hole transport layers, hole injection layers, electron barrier layers, hole barrier layers, electron injection layers, electron transport layers, and exciton barrier layers. In one embodiment, 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.

[0069] Emitting layer: In some embodiments, the emissive 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 emissive material is used as the emissive layer. In some embodiments, the emissive layer includes an emissive material and a host material. In some embodiments, the emissive material is one or more compounds represented by general formula (1). In some embodiments, singlet and triplet excitons generated in the emissive material are confined within the emissive material to improve the light emission efficiency of organic electroluminescent elements and organic photoluminescent elements. In some embodiments, a host material is used in addition to the emissive material in the emissive layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excitation singlet energy and excitation triplet energy, at least one of which is higher than those of the emissive material of the present invention. In some embodiments, singlet and triplet excitons generated in the emissive material of the present invention are confined within the molecules of the emissive 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, even though high photoluminescence efficiency can still be obtained; that is, any host material capable of achieving high photoluminescence efficiency can be used in the present invention without particular limitation. In some embodiments, photoluminescence occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the synchrotron radiation includes both fluorescence and delayed fluorescence. In some embodiments, the synchrotron radiation includes synchrotron radiation from the host material. In some embodiments, the synchrotron radiation consists of synchrotron radiation from the host material. In some embodiments, the synchrotron radiation includes synchrotron radiation from a compound represented by general formula (1) and synchrotron radiation from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant with a lower excitation singlet energy than the host material in the light-emitting layer and a higher excitation singlet energy than the light-emitting material in the light-emitting layer. In some embodiments, the organic electroluminescent device has a layer containing a compound represented by general formula (1). In some embodiments, the layer also includes the host material.In one embodiment, the layer containing the compound represented by general formula (1) and a host material also includes a delayed fluorescence material having a structure outside the range of general formula (1), wherein the lowest excitation singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound represented by general formula (1). In this embodiment, when the organic electroluminescent element is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent element has a layer containing the compound represented by general formula (1) and a light-emitting material having a structure outside the range of general formula (1) (this layer may further contain a host material). In this embodiment, when the organic electroluminescent element is energized, the amount of light emitted from the light-emitting material having a structure outside the range of general formula (1) is maximized.

[0070] 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). 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, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluorantene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, duroridine derivatives, thiazole derivatives, and derivatives having metals (Al, Zn). These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons may be combined with each other. Below, examples of luminescent materials that can be used in combination with an assist dopant having the structure represented by general formula (1) are given.

[0071]

[0072] Furthermore, the compounds described in paragraphs 0220 to 0239 of Publication WO2015 / 022974 can also be particularly preferred as luminescent materials used together with an assist dopant having a structure represented by general formula (1).

[0073] Further preferred luminescent materials include compounds represented by the following general formula (2).

[0074] In general formula (2), R １ , R ３ ~R １６ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ Either they are bonded to each other to form an acceptor group, or R ２ and R ３ These groups are 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 They may be joined to each other to form a ring structure. １ represents O or NR, and R represents a substituent. X ２ ~X ４ Of these, X ３ and X ４At least one of the atoms is O or NR, and the other may be O or NR, but may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. C-R in general formula (2) 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 It may be replaced with N.

[0075] In one aspect of the present invention, X ２ When R is O or NR, ７ Is R an acceptor group? ６ and R ７ Either they are bonded to each other to form an acceptor group, or R ７ and R ８ These are bonded to each other to form an acceptor group. In one aspect of the present invention, X ３ When R is O or NR, １０ Is R an acceptor group? ９ and R １０ Either they are bonded to each other to form an acceptor group, or R １０ and R １１ These are bonded to each other to form an acceptor group. In one aspect of the present invention, X ４ When R is O or NR, １５ Is R an acceptor group? １４ and R １５ Either they are bonded to each other to form an acceptor group, or R １５ and R １６ These are bonded to each other to form an acceptor group. In one aspect of the present invention, X ２ NR is NR, and R is a substituted or unsubstituted phenyl group. ８When a carbazole ring is formed by direct bonding with a carbon atom to which is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In one aspect of the present invention, X ３ NR is NR, and R is a substituted or unsubstituted phenyl group. ９ When a carbazole ring is formed by direct bonding with a carbon atom to which is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In one aspect of the present invention, X ４ NR is NR, and R is a substituted or unsubstituted phenyl group. １６ When a carbazole ring is formed by direct bonding with a carbon atom to which is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In one aspect of the present invention, X １ NR is NR, and R is a substituted or unsubstituted phenyl group. １ When a carbazole ring is formed by direct bonding with a carbon atom to which is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is located on the phenyl group). In one aspect of the present invention, the compound is represented by the following general formula (2a).

[0076] In general formula (2a), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ Either they are bonded to each other to form an acceptor group, or R ２ and R ３ These groups 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 , R１４ and R １５ , R １５ and R １６ They may be joined to each other to form a ring structure. １ represents O or NR, and R represents a substituent. X ２ ~X ４ Of these, X ３ and X ４ At least one of the atoms is O or NR, and the other may be O or NR but not linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. C-R in general formula (2a) 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 It may be replaced with N.

[0077] Further preferred luminescent materials include compounds represented by the following general formula (3).

[0078] 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 Each of these 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 R８ , 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 They may be bonded to each other to form a ring structure. C-R in general formula (3) 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 This may be replaced with N.

[0079] In one aspect of the present invention, R １ and R ２ R is a substituted or unsubstituted phenyl group, each independently of which other rings may be fused to it. In one aspect of the present invention, R ３ and R １０ Each of these is independently a substituted amino group. In one aspect of the present invention, R １ and R ３ , and, R ２ and R １０ At least one combination of these elements is bonded to each other to form a cyclic structure. In one aspect of the present invention, the cyclic structure includes a benzoazavorin ring.

[0080] Further preferred luminescent materials include compounds represented by the following general formula (4).

[0081] In general formula (4), Z １ and Z ２ Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R １ ~R ９ Each of these 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 They may be bonded to each other to form a ring structure. However, Z １ Z ２ , R １ and R ２ A ring formed by the bonding of these elements, R ２ and R ３ A ring formed by the bonding of these elements, R ４ and R ５ A ring formed by the bonding of these elements, and R ５ and R ６ At least one of the rings formed by the bonding of these elements is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole, and R １ ~R ９ At least one of them is a substituted or unsubstituted aryl group, or an acceptor group, or Z １ and Z ２ At least one of the rings has an aryl group or an acceptor group as a substituent. The substituted carbon atoms among the benzene ring skeleton constituent carbon atoms of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with nitrogen atoms. C-R in general formula (4) １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R６ , C-R ７ , C-R ８ , C-R ９ It may be replaced with N.

[0082] In one aspect of the present invention, Z １ and Z ２ However, each is independently a substituted or unsubstituted uncondensed benzene ring, a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. In one embodiment of the present invention, R １ ~R ９ However, each is independently a substituted or unsubstituted aryl group, or an acceptor group, or R １ and R ２ A ring formed by the bonding of these elements, R ２ and R ３ A ring formed by the bonding of these elements, R ４ and R ５ A ring formed by the bonding of these elements, and R ５ and R ６ One or more rings selected from the group consisting of rings formed by the bonding of to each other are a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or a pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings. In one aspect of the present invention, R ８ The group is a substituted or unsubstituted aryl group, or an acceptor group. In one aspect of the present invention, the group includes two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0083] Further preferred luminescent materials include compounds having a fused ring structure A (where hydrogen atoms in the structure may be substituted with deuterium atoms or substituents) in which 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 is fused to the carbon-carbon bond a of the structure α below, or 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 is fused to the carbon-carbon bond b.

[0084] In structure α, X １ and X ２ Each of the following independently represents a substituted or unsubstituted aryl group, or a nitrogen atom or oxygen atom to which a substituted or unsubstituted aryl group is bonded; 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, and Z and X ２ They may be bonded to each other to form a ring structure. In the fused ring structure A, the structure condensed with b and X １ , a condensed structure with b and Z, Z and X ２ They may be joined together to form a ring structure.

[0085] Further preferred luminescent materials include compounds represented by the following general formula (5).

[0086] In general formula (5), Z １ This represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z ２ and Z ３ Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring, R １ R represents a hydrogen atom, a deuterium atom, or a substituent.２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ３ Z ３ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0087] Further preferred luminescent materials include compounds represented by the following general formula (6).

[0088] In general formula (6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring, R １ and R ４ ~R ７ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ３ Z ３ and R３ At least one pair of them are bonded to each other to form a cyclic structure.

[0089] Further preferred luminescent materials include compounds represented by the following general formula (7).

[0090] In general formula (7), X ４ represents an oxygen atom or a sulfur atom, and Z ２ and Z ３ each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R １ and R ４ａ to R ７ａ represent a hydrogen atom, a deuterium atom or a substituent, and R ２ and R ３ each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R ２ and Z ２ and Z ２ and Z ３ and Z ３ and R ３ and R ４ａ and R ５ａ and R ５ａ and R ６ａ and R ６ａ and R ７ａ and R ７ａ and R １ may be bonded to each other to form a cyclic structure. However, at least one pair of R ２ and Z ２ and Z ２ and Z ３ and Z ３ and R ３ are bonded to each other to form a cyclic structure.

[0091] Further preferred luminescent materials include compounds represented by the following general formula (8).

[0092] In general formula (8), Z １ represents a furan ring condensed with a substituted or unsubstituted benzene ring, a thiophene ring condensed with a substituted or unsubstituted benzene ring, or an N - substituted pyrrole ring condensed with a substituted or unsubstituted benzene ring, Z３ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １ and R ８ ~R １４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ３ Z 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 They may be joined together to form a ring structure.

[0093] Further preferred luminescent materials include compounds represented by the following general formula (9).

[0094] In general formula (9), Z １ and Z ４ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ３ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １ and R １５ ~R １７ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ３ Z 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 １６and R １７ R １７ and Z ３ Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0095] Further preferred luminescent materials include compounds represented by the following general formula (10).

[0096] In the general formula (10), Z １ and Z ５ each independently represents a furan ring condensed with a substituted or unsubstituted benzene ring, a thiophene ring condensed with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring condensed 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. Z １ and R １ R ２ and Z ５ Z ５ and Z ３ Z ３ and R ３ may be bonded to each other to form a cyclic structure. However, at least one pair of R ２ and Z ２ Z ２ and Z ３ Z ３ and R ３ is bonded to each other to form a cyclic structure.

[0097] Further preferred luminescent materials include compounds represented by the following general formula (11).

[0098] In the general formula (11), Z １represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z ２ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １ and R ２１ ~R ２７ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ２ R 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 They may be joined together to form a ring structure.

[0099] Further preferred luminescent materials include compounds represented by the following general formula (12).

[0100] In general formula (12), Z １ and Z ６ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ２ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １ and R ２８ ~R ３０ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ２ R 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 They may be joined together to form a ring structure.

[0101] Further preferred luminescent materials include compounds represented by the following general formula (13).

[0102] In general formula (13), Z １ and Z ７ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ２ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 ２ and Z ７ Z ７ and R ３ They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ７ Z ７ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0103] Further preferred luminescent materials include compounds represented by the following general formula (14).

[0104] In general formula (14), Z １ R represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. １ and R ３１ ~R ４４ Each of these 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 They may be joined to each other to form a ring structure.

[0105] Further preferred luminescent materials include compounds represented by the following general formula (15).

[0106] In general formula (15), Z １ and Z ８ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ５１ ~R ６０ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z１ , 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 They may be joined to each other to form a ring structure.

[0107] Further preferred luminescent materials include compounds represented by the following general formula (16).

[0108] In general formula (16), Z １ Z ８ and Z ９ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ６１ ~R ６６ Each of these 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 They may be joined together to form a ring structure.

[0109] Further preferred luminescent materials include compounds represented by the following general formula (17).

[0110] In general formula (17), Z １ Z ９ and Z １０ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ６７ ~R ６９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ７０ R 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 They may be joined together to form a ring structure.

[0111] Further preferred luminescent materials include compounds represented by the following general formula (18).

[0112] In general formula (18), Z １ Z １１ and Z １２ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ７２ ~R ７４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ７１ R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R７１ and Z １１ Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ They may be joined together to form a ring structure.

[0113] Further preferred luminescent materials include compounds represented by the following general formula (19).

[0114] In general formula (19), Z １ and Z １１ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ７６ ~R ８２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R ７５ R 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 R ７８ , R ７８ and R ７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ They may be joined together to form a ring structure.

[0115] Further preferred luminescent materials include compounds represented by the following general formula (20).

[0116] In general formula (20), X ５R 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. １０１ ~R １３０ Each of these 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 １２０ and 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 , R１３０ and R １０１ They may be joined together to form a ring structure.

[0117] Further preferred luminescent materials include compounds represented by the following general formula (21).

[0118] 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 of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R ３ ~R ９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. However, R １ , R ２ Z １ and Z ２ At least one of these includes 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 R ２ , 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 These may be bonded to each other to form a cyclic structure. Among the benzene ring skeleton constituent carbon atoms that make up the benzofuran ring, the benzothiophene ring, and the indole ring, the replaceable carbon atoms may be substituted with nitrogen atoms. C-R in general formula (21) ３ , C-R４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ It may be replaced with N.

[0119] In one aspect of the present invention, R １ and R ２ However, each independently comprises a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or 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. In one aspect of the present invention, Z １ and Z ２ However, each is independently a substituted or unsubstituted uncondensed benzene ring, a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, a benzene ring formed by the condensation of a substituted or unsubstituted benzofuran ring, a benzene ring formed by the condensation of a substituted or unsubstituted benzothiophene ring, or a benzene ring formed by the condensation of a substituted or unsubstituted indole ring. In one embodiment of the present invention, R １ and Z １ These are bonded together to form a ring structure. In one aspect of the present invention, R １ and Z １ These elements are bonded to each other, forming a pyrrole ring.

[0120] Further preferred luminescent materials include compounds represented by the following general formula (22).

[0121] In general formula (22), X １ and X ２ In this case, one atom is a nitrogen atom, and the other is a boron atom. １ ~R ２６ A １ A ２ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３and 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 They may be joined to each other to form a ring structure. However, X １ When R is a nitrogen atom, １７ and R １８ They bond to each other to form a single bond and create a pyrrole ring, X ２ When R is a nitrogen atom, ２１ and R ２２ They bond to each other to form a single bond and create a pyrrole ring. However, X １ is a nitrogen atom, R ７ and R ８ and R ２１ and R ２２ The nitrogen atoms bond to form a six-membered ring, R １７ and R １８ When R is bonded to each other to form a single bond,１ ~R ６ At least one of them is a substituted or unsubstituted aryl group, or R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ One of these is bonded to another to form an aromatic ring or a heteroaromatic ring. For a detailed description, preferred range and specific examples of the compounds represented by general formula (22), refer to

[0010] to

[0119] of WO2022 / 270354A1, which are incorporated herein by reference as part of this specification.

[0122] In one embodiment, when a host material is used, the amount of the compound used in the present invention as a light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 10% by weight or less. In one embodiment, the host material of the light-emitting layer is an organic compound having hole transport function and electron transport function. In one embodiment, the host material of the light-emitting layer is an organic compound that prevents an increase in the wavelength of synchrotron radiation. In one embodiment, the host material of the light-emitting layer is an organic compound having a high glass transition temperature.

[0123] In some embodiments, the host material is selected from the group consisting of: In one embodiment, the light-emitting layer contains two or more structurally different TADF molecules. For example, the light-emitting layer can contain three materials in which the excited singlet energy levels are highest in the host material, followed by the first TADF molecule and then the second TADF molecule. In this case, both the first TADF molecule and the second TADF molecule have a difference ΔE between their lowest excited singlet energy level and their lowest excited triplet energy level of 77K. ＳＴThe luminescence voltage is 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 luminescent layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the luminescent layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the luminescent layer may be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the luminescent layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecules, and 0.1 to 30% by weight of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20-45% by weight of the host material, 50-75% by weight of the first TADF molecule, and 5-20% by weight of the second TADF molecule. In one embodiment, the photo-excited emission quantum yield φPL1(A) of a co-evaporated film of the first TADF molecule and the host material (concentration of the first TADF molecule in this co-evaporated film = A by weight) and the photo-excited emission quantum yield φPL2(A) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = A by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photo-excited emission quantum yield φPL2(B) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = B by weight) and the photo-excited emission quantum yield φPL2(100) of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In one embodiment, the light-emitting layer can contain three different structural TADF molecules. The compound of general formula (1) may be any of the multiple TADF compounds contained in the light-emitting layer. In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain any metal elements.In one embodiment, the light-emitting layer may be made of a material composed only of 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 may be made of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer may be made of a material composed only of 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 general formula (1), the TADF material may be a known delayed fluorescence material. Preferred delayed fluorescence materials include paragraphs 0008-0048 and 0095-0133 of WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of Japanese Patent Publication No. 2013-256490, paragraphs 0008~0020 and 0038~0040 of Japanese Patent Publication No. 2013-116975, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359, paragraph 0 of WO2013 / 161437 Paragraphs 008-0054 and 0101-0121 of Japanese Patent Publication No. 2014-9352, paragraphs 0007-0041 and 0060-0069 of Japanese Patent Publication No. 2014-9224, paragraphs 0008-0048 and 0067-0076 of Japanese Patent Publication No. 2017-119663, paragraphs 0013-0025 of Japanese Patent Publication No. 2017-119664, Japanese Patent Publication No. 2 This includes compounds included in the general formulas described in paragraphs 0012 to 0025 of Japanese Patent Publication No. 017-222623, paragraphs 0010 to 0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016 to 0044 of Japanese Patent Application Publication No. WO2018 / 047853, particularly exemplary compounds that can emit delayed fluorescence.Furthermore, here we have Japanese Patent Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO20 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, JP 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 A light-emitting material that can emit delayed fluorescence, as described in Publication No. 1, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, can preferably be used. The above publications described in this paragraph are incorporated herein by reference as part of this specification.

[0124] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0125] Substrate: In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent elements, such as glass, transparent plastic, quartz, and silicon.

[0126] Anode: In some embodiments, the anode of an organic electroluminescent apparatus is made from a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and selected from 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 produced by vapor deposition 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., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto 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 synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms or less per unit area. 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.

[0127] 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-injection 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 ) mixtures, indium, lithium-aluminum mixtures and rare earth elements are selected. In some embodiments, a mixture of an electron-injection metal and a second metal which is a stable metal having a higher work function than the electron-injection metal is used. In some embodiments, the mixture is a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) are selected from a mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or cathode of the organic electroluminescent element is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, a transparent or translucent electroluminescent element improves light radiance. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with respect to the anode from the conductive transparent material described above. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[0128] 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 includes a hole injection layer and an electron injection layer. The injection layer can be located between the anode and the light-emitting layer or hole transport layer, and between the cathode and the light-emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0129]

[0130] Next, we will list some examples of preferred compounds that can be used as electron injection materials.

[0131] 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 to the outside of the light-emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole transport layer, preventing electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron transport layer, preventing holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing to the outside of the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the terms “electron barrier layer” or “exciton barrier layer” include layers that have both the functions of an electron barrier layer and an exciton barrier layer.

[0132] Hole barrier layer: The hole barrier layer functions as an electron transport layer. In some embodiments, the hole barrier layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material used for the hole barrier layer may be the same material described above for the electron transport layer. The following are examples of preferred compounds that can be used for the hole barrier layer.

[0133]

[0134] Electron barrier layer: The electron barrier layer transports holes. In some embodiments, during hole transport, the electron barrier layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material used for the electron barrier layer may be the same material described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron barrier materials are listed below.

[0135]

[0136] Exciton barrier layer: The exciton barrier layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the optical emission efficiency of the device is improved. In some embodiments, the exciton barrier layer is located on either the anode side or the cathode side and adjacent to the light-emitting layers on both sides. In some embodiments, when the exciton barrier layer is located on the anode side, it may be located between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton barrier layer is located on the cathode side, it may be located between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, electron barrier layer, or similar layer is located between the anode and the exciton barrier layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron barrier layer, hole barrier layer, or similar layer is located between the cathode and the exciton barrier layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton barrier layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the light-emitting material, respectively.

[0137] 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 properties of hole injection or transport properties and electron barrier properties. 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, indrocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, aminosubstituted 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 porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. 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.

[0138]

[0139] 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 have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier 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, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole inducer or 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.

[0140]

[0141] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0142]

[0143] While specific examples of preferred materials that can be used in organic electroluminescent elements have been provided, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials with specific functions can be repurposed as materials with other functions.

[0144] 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 includes an OLED having at least one organic layer comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode. In some embodiments, the components described herein may be incorporated into a variety of photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the components may be useful for facilitating charge transfer or energy transfer within the device and / or as hole transport materials. Examples of such devices include 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-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0145] Bulb or Lamp: In some embodiments, the electronic device includes an OLED comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is an OLED light comprising: a circuit board having a first surface with a mounting surface and a second surface opposite thereto, defining at least one opening; at least one OLED on the mounting surface having a light-emitting configuration comprising an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture. In some embodiments, the OLED light has a plurality of OLEDs mounted on the circuit board such that light is emitted in a plurality of directions. In some embodiments, some of the light emitted in the 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.

[0146] Displays or Screens: In some embodiments, the light-emitting layer of the present invention can be used in screens or displays. In some embodiments, the compounds according to the present invention are deposited onto a substrate using processes such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD), but are not limited. In some embodiments, the substrate is a photoplate structure useful in two-sided etching, providing pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern allows for the arrangement of very steep, narrow tie bars between pixels in the vertical direction, and large, wide oblique apertures in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays while optimizing chemical vapor deposition onto the TFT backplane. Internal patterning of the pixels allows for the configuration of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within a pixel area protects etching in a particular area until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at a similar etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone pattern, etching with varying degrees of protection within the pixels becomes possible, enabling localized, deep etching necessary to form steep vertical bevels. A preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming aperture regions within the 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 processed using wet chemical etching. In further embodiments, the screen or display pattern is processed using plasma etching.

[0147] Device manufacturing method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. 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, coating the TFT with a planarization film, sequentially forming pixel electrodes, a light-emitting layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel.

[0148] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units in cell panel units on the barrier layer; forming an encapsulation layer on each of the display units of the cell panel; and coating an organic film on the interface portions between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edges of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in the soft cutting of the mother panel in cell panel units. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have a thin-film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film coated on the interface portions is formed 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 unit is connected to the TFT layer by a passivation layer, a planarization film between them, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to the display unit or the encapsulation layer.

[0149] Each of the organic film and the planarization film may comprise either polyimide or 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 the steps of attaching a carrier substrate made of glass material to another surface of the base substrate before forming a barrier layer on one surface of the polyimide 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 placed on the TFT layer for coating 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 at the edges 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 at the edge of the barrier layer, so that a portion of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film surrounds the edge of the barrier layer while being in contact with the barrier layer.

[0150] 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 the source / drain electrodes 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 having a TFT layer and a light-emitting unit will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display unit and preventing the penetration of external moisture may be formed as a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the edge of the barrier layer while in contact with the barrier layer.

[0151] 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 glass material, which is then 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, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby creating grooves in the interface portions between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0152] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, where a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, a TFT layer is formed for each cell panel, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on the TFT layer and cover the TFT layer. For example, while a planarization film made of polyimide or acrylic is formed, the groove in the interface portion is covered with an organic film made of polyimide or acrylic, for example. This prevents cracking by allowing the organic film to absorb the impact generated when each cell panel is cut along the groove at the interface portion. That is, if all barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the impact generated is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between barrier layers may be covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel is cut softly and cracking in the barrier layer is prevented. In one embodiment, the organic film and the planarizing film covering the grooves of the interface portion are arranged with a gap between them. For example, if the organic film and the planarizing film are connected to each other as a single layer, there is a risk that external moisture may penetrate the display unit through the remaining parts of the planarizing film and organic film. Therefore, the organic film and the planarizing film are arranged with a gap between them so that the organic film is spaced away from the display unit.

[0153] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is placed on the display unit to cover it. This separates the carrier substrate supporting the base substrate from the base substrate after the mother panel is completely manufactured. In some embodiments, when a laser beam is radiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficients between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut in cell panel units. In some embodiments, the mother panel is cut along the interface portions between the cell panels using a cutter. In some embodiments, the grooves of the interface portions along which the mother panel is cut are covered with an organic film so that the organic film absorbs shock during cutting. In some embodiments, cracking of the barrier layer can be prevented during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film coated on the edges of the barrier layer.

[0154] The features of the present invention will be described in more detail below with reference to examples. The materials, processing content, 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 interpreted as being limited by the specific examples shown below. The luminescence characteristics were evaluated using a source meter (Keithley Corporation: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Optics Corporation: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In addition, the energy of HOMO and LUMO was measured by atmospheric photoelectron spectroscopy (RIKEN Instruments Co., Ltd.: AC-3, etc.).

[0155] (Synthesis Example 1) Synthesis of Compound A

[0156] Under a nitrogen atmosphere, a mixture of 1,2,3-trifluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzene (0.85 g, 3.29 mmol), 2-chloro-4,6-diphenyl-5-pyrimidine carbonitride (1.01 g, 3.46 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.23 g, 0.33 mmol), and sodium carbonate (0.70 g, 6.59 mmol) was added to a pre-degassed tetrahydrofuran (30 mL) / water (15 mL) mixture, and the mixture was heated to 75°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature and the water was separated. The resulting organic layer was concentrated and washed with hot toluene and ethyl acetate to obtain intermediate a (0.48 g, 1.24 mmol, yield 37.7%). ASAP mass spectral analysis: Theoretical value 387.37, observed value 388.32.

[0157] Under a nitrogen atmosphere, a mixture of intermediate a (0.70 g, 1.81 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.33 g, 1.90 mmol), and potassium carbonate (0.50 g, 3.61 mmol) was mixed with dimethylformamide (20 mL), and the mixture was heated to 50°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated material was filtered and washed with methanol. The resulting precipitate was recrystallized to obtain intermediate b (0.86 g, 1.58 mmol, yield 87.3%). ASAP mass spectrometry analysis: theoretical value 542.62, observed value 543.33.

[0158] Under a nitrogen atmosphere, a mixture of intermediate b (0.72 g, 1.33 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.70 g, 3.98 mmol), and potassium carbonate (0.73 g, 5.31 mmol) was mixed with dimethylformamide (15 mL), and the mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated compound was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound A (0.12 g, 0.14 mmol, yield 10.6%). 1 ¹H NMR (400 MHz, CDCl3): δ 9.20 (s, 2H), 8.17-8.14 (m, 4H), 7.60-7.53 (m, 6H). ASAP mass spectral analysis: Theoretical value 853.13, Observed value 852.94

[0159] (Synthesis Example 2) Synthesis of Compound B

[0160] Under a nitrogen atmosphere, a mixture of 3,4,5-trifluorobenzonitrile (10.00 g, 63.65 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (11.16 g, 63.65 mmol) was mixed with 650 mL of degassed tetrahydrofuran and stirred at -40°C for 1 hour. Sodium hydride (1.48 g, 61.74 mmol) was added to the mixture, and the temperature was raised to 0°C and stirred overnight. After the reaction was complete, the mixture was returned to room temperature, water was added, and the organic layer was separated and concentrated. The resulting solid was purified by silica gel column chromatography to obtain intermediate c (16.15 g, 51.70 mmol, yield 81.2%). 1 ¹H NMR (400 MHz, CDCl₃): δ 7.54–7.52 (d, J = 6.8 Hz, 2H). ASAP mass spectrometry: Theoretical value 312.35, observed value 312.29.

[0161] Under a nitrogen atmosphere, a mixture of intermediate c (6.00 g, 19.21 mmol), 5H-benzofl[3,2-c]carbazole (17.30 g, 67.23 mmol), and potassium carbonate (10.62 g, 76.84 mmol) was mixed with dimethylformamide (200 mL), and the mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated material was filtered and washed with methanol. The resulting precipitate was washed with toluene to obtain intermediate d. ASAP mass spectrometry: Theoretical value 786.92, observed value 787.54.

[0162] Under a nitrogen atmosphere, intermediate d (15.00 g, 19.06 mmol) was mixed with pre-degassed tetrahydrofuran (60 mL) and stirred at 0°C for 1 hour. Lithium bis(trimethylsilyl)amide (29.00 mL, 38.12 mmol) was added to the mixture, and the mixture was stirred overnight while returning to room temperature. After the reaction was complete, the mixture was cooled to 0°C and 6 M hydrochloric acid (75 mL, 450 mmol) was added. The precipitate was returned to room temperature, filtered, and washed with methanol to obtain intermediate e.

[0163] Under a nitrogen atmosphere, dimethylformamide (200 mL) was added to a mixture of intermediate e (15.52 g, 19.30 mmol), benzoylacetonitrile (5.60 g, 38.61 mmol), benzaldehyde (4.10 g, 38.61 mmol), and sodium carbonate (6.14 g, 57.91 mmol). The mixture was heated to 80°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated material was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound B (1.26 g, 1.23 mmol, yield 6.4%). 1H NMR (400 MHz, CDCl3): δ 9.30 (s, 2H), 8.26-8.25 (d, J = 7.6 Hz, 2H), 8.16-8.14 (d, J = 6.8 Hz,4H), 7.87-7.85 (d, J = 7.2 Hz,2H), 7.65-7.53 (m, 10H), 7.40-7.30 (m, 8H), 7.28-7.11 (m, 4H). ASAP mass spectrum analysis: theoretical value 1017.19, observed value 1017.92.

[0164] (Synthesis Example 3) Synthesis of Compound C

[0165] Under a nitrogen atmosphere, a mixture of intermediate c (2.00 g, 6.40 mmol), 2-phenyl-5H-benzofl[3,2-c]carbazole (7.47 g, 22.41 mmol), and potassium carbonate (3.54 g, 25.61 mmol) was mixed with dimethylformamide (60 mL), and the mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated material was filtered and washed with methanol. The resulting precipitate was washed with toluene to obtain intermediate f (2.37 g, 2.52 mmol, yield 39.4%). ASAP mass spectrometry: Theoretical value 939.12, observed value 939.98.

[0166] Under a nitrogen atmosphere, intermediate f (2.37 g, 2.52 mmol) was mixed with pre-degassed tetrahydrofuran (60 mL) and stirred at 0°C for 1 hour. Lithium bis(trimethylsilyl)amide (3.85 mL, 5.00 mmol) was added to the mixture, and the mixture was stirred overnight at room temperature. After the reaction was complete, the mixture was cooled to 0°C and 6 M hydrochloric acid (10 mL, 60.0 mmol) was added. The precipitate was filtered after being returned to room temperature and washed with methanol to obtain intermediate g.

[0167] Under a nitrogen atmosphere, a mixture of intermediate g (2.41 g, 2.52 mmol), benzoylacetonitrile (0.55 g, 3.78 mmol), benzaldehyde (0.40 g, 3.78 mmol), and sodium carbonate (0.80 g, 7.56 mmol) was mixed with dimethylformamide (30 mL), and the mixture was heated to 80°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated compound was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound C (0.88 g, 0.75 mmol, yield 29.9%). 1 ¹H NMR (400 MHz, CDCl₃): δ 9.32 (s, 2H), 8.45 (s, 2H), 8.17-8.14 (m, 4H), 7.89-7.86 (m, 2H), 7.67-7.26 (m, 30H). ASAP mass spectral analysis: Theoretical value 1169.39, observed value 1170.07.

[0168] (Synthesis Example 4) Synthesis of Compound D

[0169] Under a nitrogen atmosphere, a mixture of intermediate a (0.86 g, 2.22 mmol), 2-phenyl-5H-benzofl[3,2-c]carbazole (0.78 g, 2.33 mmol), and potassium carbonate (0.61 g, 4.44 mmol) was mixed with dimethylformamide (25 mL), and the mixture was heated to 50°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated precipitate was filtered and washed with methanol. Intermediate h was obtained by recrystallizing the resulting precipitate. ASAP mass spectrometry: Theoretical value 700.75, observed value 701.43.

[0170] Under a nitrogen atmosphere, a mixture of intermediate h (1.60 g, 2.28 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.00 g, 5.71 mmol), and potassium carbonate (0.95 g, 6.85 mmol) was mixed with dimethylformamide (25 mL), and the mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitated material was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound D (0.31 g, 0.31 mmol, yield 13.4%). 1 H NMR (400 MHz, CDCl3): δ 9.24 (s, 2H), 8.17-8.14 (m, 4H), 8.01 (s, 1H), 7.76-7.74 (d, J = 7.6 Hz 1H), 7.58-7.51 (m, 10H), 7.40-7.28 (m, 4H), 7.22-7.20 (d, J = 8.4 Hz 1H), 7.06-6.92 (m, 3H). ASAP mass spectrum analysis: theoretical value 1011.26, observed value 1012.05.

[0171] (Synthesis Example 5) Synthesis of Compound E Compound E is synthesized following the same procedure as in Synthesis Example 1.

[0172] (Example 1) Fabrication and evaluation of a thin film Compound A was laid on a quartz substrate under a vacuum of 1 × 10⁻⁶ －３ Compound A was deposited at a pressure below Pa to form a neat thin film with a thickness of 100 nm. Separately, compound A and compound H1 (described later) were deposited on a quartz substrate from different deposition sources at a vacuum of 1 × 10⁻⁶. －３A doped thin film with a concentration of compound A at 35 wt% was deposited at a pressure below Pa, forming a film with a thickness of 100 nm. Neat and doped thin films were similarly formed using compounds B, C, and comparative compound 1 instead of compound A. However, the concentration of comparative compound 1 was set to 20 wt%, and compound H2 (described later) was used instead of compound H1. The HOMO and LUMO energies were measured for each formed neat thin film. In addition, the photoluminescence of each formed doped thin film was analyzed when irradiated with 300 nm excitation light, and the emission peak wavelength (λmax), photoluminescence quantum yield (PLQY), delayed fluorescence component lifetime (τ2), and the proportion of delayed fluorescence component during emission were measured. Furthermore, the degree of orientation (S value) of compounds A-C and comparative compound 1 in each doped thin film was measured. The degree of orientation was determined according to Scientific Reports 2017. The determination was made using the method described in 7,8405. The results are shown in Table 4 below. All thin films showed a high PLQY of over 70%. On the other hand, thin films of compounds A, B, and C, represented by general formula (1), were found to have particularly short delayed fluorescence lifetimes and high orientation. Among them, compounds B and C were found to have a high proportion of delayed fluorescence component during emission and extremely high orientation. Compound E was similarly found to have a high PLQY, a high proportion of delayed fluorescence component, high orientation, and a significantly shorter delayed fluorescence lifetime than comparative compound 1.

[0173] (Example 2) Fabrication and evaluation of organic electroluminescent elements. Each thin film was deposited on a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, using a vacuum deposition method at a vacuum of 5.0 × 10⁻⁶. －５Lamination is performed using Pa. First, the compound HAT-CN described later is formed on ITO to a thickness of 10 nm, then the compound NPD described later is formed on top of it to a thickness of 30 nm, then the compound TrisPCz described later is formed on top of that to a thickness of 10 nm, and then the compound EBL1 described later is formed on top of that to a thickness of 5 nm. Next, the compound H3 described later and compound A described later are co-deposited from different deposition sources to form a 40 nm thick layer which serves as the light-emitting layer. The concentration of compound A in the light-emitting layer is 35 mass%. Next, the compound SF3-TRZ described later is formed to a thickness of 10 nm, and then the compound Liq described later and SF3-TRZ are co-deposited from different deposition sources to form a 30 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer are 30 mass% and 70 mass%, respectively. Furthermore, a layer of Liq is formed to a thickness of 2 nm, and then aluminum (Al) is deposited to a thickness of 100 nm to form a cathode, creating an organic electroluminescent element. Organic electroluminescent elements are then fabricated using the same procedure with compound B and compound C instead of compound A.

[0174] (Example 3) Fabrication and evaluation of organic electroluminescent elements using assist dopant. The only change is that the light-emitting layer is co-deposited from different deposition sources using compound H3, compound A, and compound ET1 described below, forming a layer with a thickness of 40 nm containing 64.2% by weight of compound H3, 35.0% by weight of compound A, and 0.8% by weight of compound ET1. Otherwise, an organic electroluminescent element is fabricated using the same method as in Example 2. Compound B and compound C are used instead of compound A, respectively, and each organic electroluminescent element is fabricated using the same procedure.

[0175]

[0176]

[0177] Compounds represented by general formula (1) exhibit high orientation and good luminescence properties. By using compounds represented by general formula (1), it is possible to provide organic light-emitting devices with excellent properties. For this reason, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1). General formula (1) [In general formula (1), R １ ~R ５ Each of these independently represents a donor group bonded by a hydrogen atom, a deuterium atom, or a nitrogen atom, a non-acceptor heteroaryl group bonded by a carbon atom, or a substituted or unsubstituted aryl group. However, R １ ~R ５ Two or more of these are donor groups bonded by nitrogen atoms. １ and Y ２ represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. However, Y １ and Y ２ Both of them cannot be hydrogen atoms or deuterium atoms.

2. R １ to R ５ The compound according to claim 1, wherein three or more of them are donor groups bonded by nitrogen atoms.

3. R １ ~R ５ The compound according to claim 1, wherein two of the groups are donor groups bonded by a nitrogen atom and have different structures from each other.

4. R １ ~R ５ The compound according to claim 1, wherein one or more of the groups are substituted or unsubstituted carbazole-9-yl groups.

5. R １ ~R ５ The compound according to claim 1, wherein one or more of these groups are substituted or unsubstituted ring-condensed carbazole-9-yl groups.

6. R １ ~R ５ The compound according to claim 1, wherein two or more of these are substituted or unsubstituted ring-condensed carbazole-9-yl groups.

7. R １ ~R ５ At least one of them is a substituted or unsubstituted ring-condensed carbazole-9-yl group, R １ ~R ５ The compound according to claim 1, wherein at least one of the other groups is a substituted or unsubstituted carbazole-9-yl group that is not ring-fused.

8. R １ ~R ５ The compound according to claim 1, wherein one or two of these atoms are hydrogen atoms or deuterium atoms.

9. Y １ and Y ２ The compound according to claim 1, wherein the compound is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

10. Y １ and Y ２ The compound according to claim 2, wherein at least one of the members is a substituted or unsubstituted aryl group.

11. The compound according to claim 1, comprising at least one deuterium atom in the molecule.

12. A light-emitting material comprising the compound described in any one of claims 1 to 11.

13. A film comprising the compound described in any one of claims 1 to 11.

14. An organic light-emitting element comprising the compound described in any one of claims 1 to 11.

15. The organic light-emitting element according to claim 14, which is an organic electroluminescent element.

16. The organic light-emitting element according to claim 15, wherein the organic electroluminescent element has a layer containing the compound, and the layer also contains a host material.

17. The organic light-emitting element according to claim 15, wherein the organic electroluminescent element has a layer containing the compound, and the layer also includes a light-emitting material having a structure outside the range of general formula (1).

18. The organic light-emitting element according to claim 17, wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

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