Compound, light emitting material, and light emitting element

Abstract

This compound is represented by the general formula and has a long emission life. In the general formula, one to three moieties among R1 to R5 are each a donor group, the others are each H, D, a cyano group, an aryl group or an alkyl group, L is a single bond or a linking group, X1 is N or C, and Y is a carbazol-9-yl group or an aryl group.

Description

Compound, light-emitting material and light-emitting device

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

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

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

[0004] Since this principle was clarified, various researches have led to the discovery of various delayed fluorescent materials. These include many compounds in which a donor group and an acceptor group are substituted on a benzene ring. For example, a compound has been proposed that has a skeleton in which a carbazol-9-yl group, which is a donor group, and a cyano group and a substituted triazinyl group, which are acceptor groups, are substituted on a benzene ring (see Patent Document 1).

[0005] WO2019 / 191665A1

[0006] Even if a material emitting delayed fluorescence has been developed, one that has extremely good properties and no practical problems has not yet been provided. Therefore, it would be even more useful if a delayed fluorescent material with even better properties could be provided. However, the improvement of delayed fluorescent materials is still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful luminescent material.

[0007] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as delayed fluorescent materials for light-emitting devices, and have conducted extensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as delayed fluorescent materials.

[0008] As a result of intensive research to achieve the above object, the present inventors have found that a compound having a structure that satisfies certain conditions is useful as a light-emitting material. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] A compound represented by the following general formula (1): General formula (1) [In general formula (1), R １ ~R ５ One to three of R are donor groups, １ ~R ５ 0 to 1 of R are cyano groups; １ ~R ５ 0 to 3 of R are hydrogen atoms or deuterium atoms, １ ~R ５ 0 to 2 of R are substituted or unsubstituted aryl groups, and the remaining R １ ~R ５ is a substituted or unsubstituted alkyl group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ may be bonded to each other to form a cyclic structure. L represents a single bond or a linking group. X １ is N or C-R ６ represents X ２ is N or C-R ７ Represents R６ and R ７ each independently represents a hydrogen atom, a deuterium atom, or a substituent. Y represents a substituted or unsubstituted carbazol-9-yl group, or a substituted or unsubstituted aryl group. However, when Y represents a substituted or unsubstituted aryl group, R １ ~R ５ 0 to 2 of R are hydrogen atoms or deuterium atoms.] [2] R １ ~R ５ [3] The compound according to [1], wherein one of R ２ [4] The compound according to [2], wherein R is a cyano group. １ ~R ５ [5] The compound according to any one of [1] to [3], wherein one or two of R ５ [6] The compound according to [4], wherein R is a donor group. １ [7] The compound according to [5], wherein R is a hydrogen atom or a deuterium atom. １ ~R ５ [8] The compound according to any one of [1] to [6], wherein one or two of R are substituted or unsubstituted aryl groups. ４is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. [9] The compound according to any one of [1] to [8], wherein Y is a substituted or unsubstituted carbazol-9-yl group.

[10] The compound according to any one of [1] to [8], wherein Y is a substituted or unsubstituted aryl group.

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

[10] , wherein L is a single bond.

[12] The compound according to any one of [1] to

[11] , which has at least one deuterium atom.

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

[12] .

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

[12] .

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

[12] .

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

[12] .

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

[12] .

[18] The organic light-emitting element according to

[17] , wherein the element has a layer containing the compound, and the layer also contains a host material.

[19] The organic light-emitting element according to

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

[20] The organic light-emitting element according to

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

[21] The organic light-emitting element according to

[18] or

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

[22] The organic light-emitting element according to

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

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

[17] to

[22] , wherein the organic light-emitting element is an organic electroluminescence element.

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

[17] to

[23] , wherein the organic light-emitting element emits delayed fluorescence.

[0009] The compound of the present invention exhibits excellent light-emitting properties and is useful as a material for an organic light-emitting device.

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２ In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the representation of an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted location. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0011] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described.

[0012] In general formula (1), R １ ~R ５ One to three of R are donor groups, １ ~R ５ 0 to 1 of R are cyano groups; １ ~R ５ 0 to 3 of R are hydrogen atoms or deuterium atoms, １ ~R ５ 0 to 2 of R are substituted or unsubstituted aryl groups, and the remaining R １ ~R ５ is a substituted or unsubstituted alkyl group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５may be bonded to each other to form a cyclic structure. L represents a single bond or a linking group. X １ is N or C-R ６ represents X ２ is N or C-R ７ Represents R ６ and R ７ each independently represents a hydrogen atom, a deuterium atom, or a substituent. Y represents a substituted or unsubstituted carbazol-9-yl group, or a substituted or unsubstituted aryl group. However, when Y is a substituted or unsubstituted aryl group, R １ ~R ５ of which 0 to 2 are hydrogen atoms or deuterium atoms.

[0013] R in general formula (1) １ ~R ５ One to three of R are donor groups. １ ~R ５ The donor groups that can be used do not include substituted or unsubstituted aryl groups. The "donor group" can be selected from groups with a negative Hammett σp value. The "acceptor group" 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 a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is the constant (σp) specific to the substituent in the para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of the benzene derivative without a substituent, k is the rate constant of the benzene derivative substituted with a substituent, K0 is the equilibrium constant of the benzene derivative without a substituent, K is the equilibrium constant of the benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0014] R １ ~R ５The donor group 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 −1.1 or less.

[0015] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is 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. Here, the two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0016] R １ ~R ５ The donor group which can be taken as the donor group is preferably a group represented by the following general formula (a).

[0017] In the general formula (a), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N. Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １４ and R １５ , R １５ and R１６ , R １６ and R １７ may be bonded to each other to form a cyclic structure.

[0018] Z １ ~Z ４ In one embodiment of the present invention, the number of N's is preferably 0 to 3, more preferably 0 to 2. １ ~Z ４ In one aspect of the present invention, the number of N is 1. １ ~Z ４ The number of N is 0. １４ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. １４ ~R １７ When two or more of R represent substituents, the two or more substituents may be the same or different. １４ ~R １７ It is preferred that 0 to 2 of these be substituents. For example, one may be a substituent, or none may be a substituent (R １４ ~R １７ may be a hydrogen atom or a deuterium atom). １４ and R １５ , R １５ and R １６ , R １６ and R １７may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic ring or a heteroaromatic ring is preferred. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure 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. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７ In one embodiment of the present invention, a pair of R １４ and R １５ , R １５ and R １６ , R １６ and R １７ are not bonded to each other to form a ring structure.

[0019] In the general formula (a), Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is C, and Ar ５ is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. ５ An example of the aromatic ring that can be used by Ar is a benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. ５ The heteroaromatic ring that can be adopted by Z is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment 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 embodiment of the present invention, Z ５ is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. 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. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, may be substituted with a substituent selected from Substituent Group B, may be substituted with a substituent selected from Substituent Group C, may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E.

[0020] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0021] In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or 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 may be bonded to each other to form a cyclic structure. １ ~Z ４ , R １４ ~R １７ For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. ６ ~Z ９ , R １８ ~R ２１ is Z in general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order to Z in general formula (a). １ ~Z ４ , R １４ ~R １７ In one aspect of the present invention, Z １ ~Z ４ , Z ６ ~Z ９In one embodiment of the present invention, the number of N's is preferably 0 to 2, and more preferably 0 or 1. １ ~Z ４ , Z ６ ~Z ９ In a preferred embodiment of the present invention, the number of N groups is 1. １ ~Z ４ , Z ６ ~Z ９ The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0022] R １ ~R ５ The donor group that can be taken by is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, or may be substituted with a substituent selected from Substituent Group B, or may be substituted with a substituent selected from Substituent Group C, or may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E. Furthermore, one or more rings may be further fused to the two benzene rings that constitute the carbazol-9-yl group. In one preferred embodiment of the present invention, １ ~R ５ The donor group may be a carbazol-9-yl group which may be substituted with a group selected from Substituent Group E and which may have one or more fused rings. When a compound with a short emission wavelength is desired, it is preferable to employ a carbazol-9-yl group substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group or an aryl group. When a carbazol-9-yl group not fused with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.

[0023] In one aspect of the present invention, R １ ~R ５The donor group R can take is a carbazol-9-yl group in which one or more rings are fused, and hereinafter this is referred to as a "ring-fused carbazol-9-yl group." １ ~R ５ The ring-fused carbazol-9-yl group represented by the formula (I) may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from Substituent Group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-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 a deuterium atom, an alkyl group, and an aryl group.

[0024] The total number of fused rings in the ring-fused 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 a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0025] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring formed by further condensing these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In one embodiment of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from Substituent Group E (excluding cases where the substituent is only a deuterium atom), and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In one embodiment of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group to which a benzothieno structure is fused, for example, two or more carbazol-9-yl groups.

[0026] As the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group can be used. Furthermore, as the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used. Furthermore, examples of the ring-fused carbazol-9-yl group include a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, and a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group.

[0027] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0028] In the following, R in general formula (1) １ ~R ５ The specific examples given here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may have a further ring condensed thereto), but the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C ６ H ５ ) and * indicates the bond position. Methyl groups are omitted, so for example, D2 has one methyl group. However, deuterated methyl groups are ３ Also, C ６ D ５ represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0029] The compounds D1 to D459 above, in which all hydrogen atoms have been replaced with deuterium atoms, are disclosed as D722 to D1180.

[0030] R １ ~R ５ Among the donor groups that can be employed, specific examples that are not substituted or unsubstituted carbazol-9-yl groups are listed below. However, the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples.

[0031] All hydrogen atoms in D1181 to D1208 are replaced with deuterium atoms, and these are disclosed as D1233 to D1260. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1260. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1180. １ ~R ５The donor group that R can take is selected from the group consisting of D17 to D76, D83 to D118, D185 to D298, D359 to D453, D472 to D519, D526 to D653, and D704 to D710. １ ~R ５ The donor group that R can take is selected from the group consisting of D77 to D82, D119 to D184, D299 to D358, D455 to D459, D520 to D525, D654 to D703, and D712 to D721. １ ~R ５ The donor group that R can take is selected from the group consisting of D460 to D1180 and D1214 to D1260. １ ~R ５ In a preferred embodiment of the present invention, the donor group R １ ~R ５ The donor groups that can be taken are D1 to D13, D17 to D22, D37, D47 to D52, D77 to D82, D119 to D131, D134, D137, D140, D146, D149, D152, D155, D158, D161, D164, D167, D170, D173, D176, D179, D182, D198, D454, D466 to D471, D521 to D525, D54 In a more preferred embodiment of the present invention, R is selected from the group consisting of D3, D712 to D716, D722 to D734, D739 to D743, D758, D768 to D773, D798 to D803, D840 to D852, D855, D858, D861, D867, D870, D873, D876, D879, D882, D885, D888, D891, D894, D897, D900, D903, D919, and D1175. １ ~R ５ The donor group which can be taken by is selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D198, D543, D722, D729, D730, D740, D758, D771, D798, and D919.

[0032] In one aspect of the present invention, R １ ~R ５ In one aspect of the present invention, one of R１ ~R ５ In one embodiment of the present invention, two of R １ ~R ５ In a preferred embodiment of the present invention, at least three of R ５ is a donor group. In one embodiment of the present invention, R ５ In one embodiment of the present invention, only R ３ and R ５ is a donor group. In one embodiment of the present invention, at least R ３ and R ５ In one aspect of the invention, R ３ and R ４ and R ５ In one embodiment of the present invention, only R ３ is a donor group. In one embodiment of the present invention, at least R ４ is a donor group.

[0033] R in general formula (1) １ ~R ５ In a preferred embodiment of the present invention, 0 to 1 of R ２ is a cyano group. １ is a cyano group. ３ is a cyano group. １ ~R ５ is not a cyano group.

[0034] R in general formula (1) １ ~R ５ In one embodiment of the present invention, 0 to 3 of R are hydrogen atoms or deuterium atoms, preferably 1 to 3 are hydrogen atoms or deuterium atoms, and more preferably 1 to 2 are hydrogen atoms or deuterium atoms. １ ~R ５ In one aspect of the present invention, only one of R １ ~R ５ In one aspect of the present invention, only two of R １ ~R ５In one aspect of the present invention, three of R １ ~R ５ In a preferred embodiment of the present invention, at least R １ is a hydrogen atom or a deuterium atom. １ and R ３ is a hydrogen atom or a deuterium atom. １ and R ３ In one aspect of the present invention, only R １ and R ２ In one aspect of the present invention, only R １ and R ２ and R ３ is a hydrogen atom or a deuterium atom.

[0035] R in general formula (1) １ ~R ５ Of these, 0 to 2 are substituted or unsubstituted aryl groups. １ ~R ５ The aryl group may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, or a substituted or unsubstituted naphthalen-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one embodiment of the present invention, the aryl group is unsubstituted.１ ~R ５ Specific examples of substituted or unsubstituted aryl groups that can be used are listed below. However, the aryl groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[0036] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar25 are substituted with deuterium atoms are exemplified here as Ar45 to Ar69 in this order. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar1 to Ar69. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar14, Ar19, Ar20, Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar26 to Ar69. １ ~R ５ The aryl group which can be taken by Ar is selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63 and Ar64.

[0037] R in general formula (1) １ ~R ５ In one embodiment of the present invention, 0 to 2 of R are substituted or unsubstituted aryl groups, and preferably 0 to 1 are substituted or unsubstituted aryl groups. １ ~R ５ In one aspect of the present invention, only one of R １ ~R ５ In one embodiment of the present invention, only two of R １~R ５ In a preferred embodiment of the present invention, at least R ４ is a substituted or unsubstituted aryl group. ３ is a substituted or unsubstituted aryl group. ２ is a substituted or unsubstituted aryl group. ３ and R ４ is a substituted or unsubstituted aryl group. ２ and R ４ is a substituted or unsubstituted aryl group.

[0038] R in general formula (1) １ ~R ５ may be a substituted or unsubstituted alkyl group. １ ~R ５ The alkyl group may be linear, branched, or cyclic. Two or more of the linear, cyclic, and branched groups may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the substituent of the alkyl group is one or more selected from the group consisting of an aryl group and a deuterium atom. In a preferred embodiment of the present invention, the alkyl group is unsubstituted and can be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.

[0039] In one embodiment of the present invention, R in general formula (1) １ ~R ５ In one embodiment of the present invention, 0 to 4 of R １ ~R ５ In one aspect of the present invention, only one of R １ ~R ５ In one embodiment of the present invention, only two of R １ ~R ５ In one embodiment of the present invention, only three of R １ ~R ５ In one embodiment of the present invention, four of R １ ~R ５ In a preferred embodiment of the present invention, at least R ４ is a substituted or unsubstituted alkyl group. ３ is a substituted or unsubstituted alkyl group. ２ is a substituted or unsubstituted alkyl group. １ is a substituted or unsubstituted alkyl group. ３ and R ４ is a substituted or unsubstituted alkyl group. ２ and R ４ is a substituted or unsubstituted alkyl group.

[0040] R in general formula (1) １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ may be bonded to each other to form a cyclic structure. For details of the cyclic structure and a preferred range, see R １４ and R １５ In one embodiment of the present invention, R１ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ In one embodiment of the present invention, a pair of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ are not bonded to each other to form a ring structure.

[0041] In general formula (1), L represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L is a single bond. In one embodiment of the present invention, L is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group can be selected from the group consisting of the above-mentioned R １ ~R ５ The explanation and preferred range of the aryl group in the description section can be referred to. Examples of heteroarylene groups include linking groups in which at least one of the ring skeletal carbon atoms constituting an arylene group is substituted with a nitrogen atom. Specific examples of L are listed below. However, L that can be employed in the present invention should not be construed as being limited by these specific examples. Note that methyl groups are omitted in the following specific examples. For this reason, for example, L3 to L5 are substituted with a methyl group. * indicates the bonding position. L1 is a single bond.

[0042]

[0043] All hydrogen atoms present in L2 to L13 are substituted with deuterium atoms and are disclosed as L14 to L25. In one aspect of the present invention, L is selected from the group consisting of L1 to L25. In one aspect of the present invention, L is selected from the group consisting of L1 to L7, and L14 to L19. In one aspect of the present invention, L is selected from the group consisting of L1, L8 to L13, and L20 to L25. In one aspect of the present invention, L is selected from the group consisting of L2 to L25. In one aspect of the present invention, L is L1.

[0044] Y in general formula (1) represents a substituted or unsubstituted carbazol-9-yl group or a substituted or unsubstituted aryl group. In one embodiment of the present invention, Y is a substituted or unsubstituted carbazol-9-yl group. In another embodiment of the present invention, Y is a substituted or unsubstituted aryl group. The substituted or unsubstituted carbazol-9-yl group that Y can take is a group represented by Z in general formula (b) above. １ ~Z ４ , Z ６ ~Z ９ is not N. That is, Z in general formula (b) １ is C-R １４ represents Z ２ is C-R １５ represents Z ３ is C-R １６ represents Z ４ is C-R １７ represents Z ６ is C-R １８ represents Z ７ is C-R １９ represents Z ８ is C-R ２０ represents Z ９ is C-R ２１ The substituted or unsubstituted carbazol-9-yl group that Y can take may be a carbazol-9-yl group in which one or more rings are fused. For details and preferred ranges of substituted or unsubstituted carbazol-9-yl groups including such ring-fused carbazol-9-yl groups, see R １ ~R ５In addition, specific examples of the substituted or unsubstituted carbazol-9-yl group that Y can take include the above-mentioned D1 to D1180, and the above-mentioned descriptions related to D1 to D1180 can also be referred to for the groups that can be selected and preferred groups for Y. In one embodiment of the present invention, the substituted or unsubstituted carbazol-9-yl group represented by Y is a substituted or unsubstituted carbazol-9-yl group represented by R １ ~R ５ In one embodiment of the present invention, the structure of the donor group represented by at least one of the following is the same as that of the substituted or unsubstituted carbazol-9-yl group represented by Y and R １ ~R ５ In one embodiment of the present invention, the substituted or unsubstituted carbazol-9-yl group represented by Y is represented by R １ ~R ５ The structure of the donor group represented by R １ ~R ５ The description and preferred range of the substituted or unsubstituted aryl group represented by R can be referred to. Specific examples of the substituted or unsubstituted aryl group that Y can take include Ar1 to Ar69 above, and the above description related to Ar1 to Ar69 can be referred to for the groups that can be selected and preferred groups for Y. In one embodiment of the present invention, the substituted or unsubstituted aryl group represented by Y is １ ~R ５ In one embodiment of the present invention, the structure of the substituted or unsubstituted aryl group represented by Y and the structure of the substituted or unsubstituted aryl group represented by R １ ~R ５ In one embodiment of the present invention, the substituted or unsubstituted aryl group represented by Y has the same structure as R １ ~R ５ When Y is a substituted or unsubstituted aryl group, R １ ~R ５ Y is a substituted or unsubstituted aryl group, and R １ ~R ５A compound in which 0 to 2 of the groups are hydrogen atoms or deuterium atoms exhibits a more preferable effect than a compound in which 3 or more of the groups are hydrogen atoms or deuterium atoms. １ ~R ５ When Y is a substituted or unsubstituted aryl group, for example, R １ ~R ５ When Y is a substituted or unsubstituted aryl group, for example, R １ ~R ５ are neither hydrogen atoms nor deuterium atoms.

[0045] X in general formula (1) １ is N or C-R ６ represents X ２ is N or C-R ７ In one aspect of the present invention, X １ is N and X ２ is C-R ７ In one aspect of the present invention, X １ is C-R ６ and X ２ is N. In a preferred embodiment of the present invention, X １ and X ２ Both are N. R ６ and R ７ each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituents herein may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one aspect of the present invention, R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R is an alkyl group optionally substituted with a deuterium atom. In one aspect of the present invention, R is a deuterium atom, an alkyl group, or an aryl group optionally substituted with an aryl group.

[0046] In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazol-9-yl group, and X １ and X ２is N, and L is a single bond. On the premise that these conditions are satisfied, an embodiment that further satisfies the following additional conditions can be exemplified. In one embodiment of the present invention, R ５ is a donor group. In one embodiment of the present invention, R ２ is a cyano group. In one embodiment of the present invention, R ４ is a substituted or unsubstituted aryl group. ３ is a substituted or unsubstituted aryl group. １ ~R ５ one of which is a donor group, one of which is a cyano group, one of which is a substituted or unsubstituted aryl group, and the remaining two of which are each independently a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ２ is a cyano group, and R ４ is a substituted or unsubstituted aryl group, and R １ and R ３ are each independently a hydrogen atom or a deuterium atom. ５ may be the same or different. In one embodiment of the present invention, R １ ~R ５ one of which is a donor group, one of which is a cyano group, two of which are independently substituted or unsubstituted aryl groups, and the remaining one of which is a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ２ is a cyano group, and R ３ and R ４ are each independently a substituted or unsubstituted aryl group, R １ is a hydrogen atom or a deuterium atom. ３ and R ４ Y and R may be the same or different. ５ may be the same or different. In one embodiment of the present invention, R １ ~R ５ one of which is a donor group, one of which is a substituted or unsubstituted aryl group, and the remaining three of which are each independently a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ４is a substituted or unsubstituted aryl group, and R １ and R ２ and R ３ are each independently a hydrogen atom or a deuterium atom. ５ may be the same or different. In one embodiment of the present invention, R １ ~R ５ one of which is a donor group, two of which are each independently a substituted or unsubstituted aryl group, and the remaining two of which are each independently a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ３ and R ４ are each independently a substituted or unsubstituted aryl group, R １ and R ２ are each independently a hydrogen atom or a deuterium atom. ３ and R ４ Y and R may be the same or different. ５ may be the same or different. In one embodiment of the present invention, R １ ~R ５ two of which are donor groups, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining one is a hydrogen atom or a deuterium atom, for example, R ３ and R ５ are each independently a donor group, and R ２ is a cyano group, and R ４ is a substituted or unsubstituted aryl group, and R １ is a hydrogen atom or a deuterium atom. ３ and R ５ may all be the same or all be different, and Y and R ３ Even if only Y and R are the same, ５ Even if only ３ and R ５ In one embodiment of the present invention, only R １ ~R ５ two of which are independently a donor group, one is a substituted or unsubstituted aryl group, and the remaining two are independently a hydrogen atom or a deuterium atom, for example, R ３ and R５ are each independently a donor group, and R ４ is a substituted or unsubstituted aryl group, and R １ and R ２ are each independently a hydrogen atom or a deuterium atom. ３ and R ５ may all be the same or all be different, and Y and R ３ Even if only Y and R are the same, ５ Even if only ３ and R ５ In one embodiment of the present invention, only R １ ~R ５ three of which are independently donor groups, one of which is a cyano group, and the remaining one of which is a hydrogen atom or a deuterium atom, e.g., R ３ and R ４ and R ５ are each independently a donor group, and R ２ is a cyano group, and R １ is a hydrogen atom or a deuterium atom. ３ and R ４ and R ５ may all be the same or all different, and R ３ and R ４ Even if only the same, R ４ and R ５ Even if only the same, R ３ and R ５ Even if only the same, R ３ and R ４ and R ５ Only the two may be the same.

[0047] In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazol-9-yl group, and X １ is CH and X ２ is N, and L is a single bond. Assuming that these conditions are met, an embodiment that also meets the additional condition in the previous paragraph can be exemplified. In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazol-9-yl group, and X １ is N and X ２is CH, and L is a single bond. Provided that these conditions are met, there can be exemplified embodiments that also satisfy the additional conditions in the previous paragraph.

[0048] In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X １ and X ２ is N, and L is a single bond. On the premise that these conditions are satisfied, an embodiment that further satisfies the following additional conditions can be exemplified. In one embodiment of the present invention, R ５ is a donor group. In one embodiment of the present invention, R ２ is a cyano group. In one embodiment of the present invention, R ４ is a substituted or unsubstituted aryl group. ３ is a substituted or unsubstituted aryl group. １ ~R ５ one of which is a donor group, one of which is a cyano group, one of which is a substituted or unsubstituted aryl group, and the remaining two of which are each independently a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ２ is a cyano group, and R ４ is a substituted or unsubstituted aryl group, and R １ and R ３ are each independently a hydrogen atom or a deuterium atom. ４ may be the same or different. In one embodiment of the present invention, R １ ~R ５ one of which is a donor group, one of which is a cyano group, two of which are independently substituted or unsubstituted aryl groups, and the remaining one of which is a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ２ is a cyano group, and R ３ and R ４ are each independently a substituted or unsubstituted aryl group, R １ is a hydrogen atom or a deuterium atom. ３ and R ４ may all be the same or all be different, and Y and R３ Even if only Y and R are the same, ４ Even if only ３ and R ４ In one embodiment of the present invention, only R １ ~R ５ one of which is a donor group, two of which are each independently a substituted or unsubstituted aryl group, and the remaining two of which are each independently a hydrogen atom or a deuterium atom, for example, R ５ is a donor group, and R ３ and R ４ are each independently a substituted or unsubstituted aryl group, R １ and R ２ are each independently a hydrogen atom or a deuterium atom. ３ and R ４ may all be the same or all be different, and Y and R ３ Even if only Y and R are the same, ４ Even if only ３ and R ４ Alternatively, for example, only R ５ is a donor group, and R ２ and R ４ are each independently a substituted or unsubstituted aryl group, R １ and R ３ are each independently a hydrogen atom or a deuterium atom. ２ and R ４ may all be the same or all be different, and Y and R ２ Even if only Y and R are the same, ４ Even if only ２ and R ４ In one embodiment of the present invention, only R １ ~R ５ two of which are independently donor groups, one of which is a cyano group, one of which is a substituted or unsubstituted aryl group, and the remaining one of which is a hydrogen atom or a deuterium atom, e.g., R ３ and R ５ are each independently a donor group, and R ２ is a cyano group, and R ４is a substituted or unsubstituted aryl group, and R １ is a hydrogen atom or a deuterium atom. ３ and R ５ Y and R may be the same or different. ４ may be the same or different. In one embodiment of the present invention, R １ ~R ５ two of which are donor groups, one is a substituted or unsubstituted aryl group, and the remaining two are each independently a hydrogen atom or a deuterium atom, for example, R ３ and R ５ are each independently a donor group, and R ４ is a substituted or unsubstituted aryl group, and R １ and R ２ are each independently a hydrogen atom or a deuterium atom. ３ and R ５ Y and R may be the same or different. ４ may be the same or different. In one embodiment of the present invention, R １ ~R ５ three of which are independently donor groups, one of which is a cyano group, and the remaining one of which is a hydrogen atom or a deuterium atom, e.g., R ３ and R ４ and R ５ are each independently a donor group, and R ２ is a cyano group, and R １ is a hydrogen atom or a deuterium atom. ３ and R ４ and R ５ may all be the same or all different, and R ３ and R ４ Even if only the same, R ４ and R ５ Even if only the same, R ３ and R ５ Only the two may be the same.

[0049] In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X １ is CH and X ２is N, and L is a single bond. Assuming that these conditions are met, an embodiment that also meets the additional condition in the previous paragraph can be exemplified. In one embodiment of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X １ is N and X ２ is CH, and L is a single bond. Provided that these conditions are met, there can be exemplified embodiments that also satisfy the additional conditions in the previous paragraph.

[0050] When it is desired to provide a compound emitting light with a short wavelength, it is preferable to employ a compound having a deuterium atom, a carbazol-9-yl group substituted with an aryl group which may be substituted with an alkyl group or an aryl group, and a cyano group in the molecule.

[0051] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing no hydrogen atoms but containing deuterium atoms.

[0052] In the present specification, the term "substituent group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio 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 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more groups, selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 atoms constituting the ring skeleton), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. As used herein, "substituent group B" refers to one atom or group, or a combination of two or more selected from 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 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring atoms), a heteroaryloxy group (e.g., having 5 to 30 ring atoms), and a diarylamino group (e.g., having 0 to 20 carbon atoms). As used herein, "substituent group C" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). As used herein, the term "substituent group D" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one atom or group, or a combination of two or more, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms). In the present specification, when "substituted or unsubstituted" or "optionally substituted" is described, the substituent may be selected, for example, from substituent group A, from substituent group B, from substituent group C, from substituent group D, or from substituent group E.

[0053] Specific examples of the compound represented by general formula (1) are shown in Tables 1 to 4 below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, among the compounds represented by general formula (1), Y is a perdeuterated carbazol-9-yl group (D722) and X １ and X ２ are both N, L is a single bond, and R １ and R ３ is a hydrogen atom, and R ２ is a cyano group, and R ４ is a phenyl group (Ar1), and R ５ Specifically, R of the compound having the following structure is ５ The structures of compounds 1 to 1260 are individually identified by listing them in order in Table 1.

[0054] Table 2 shows the structures of compounds 1 to 86940 as variations of the structures shown in Table 1. In Table 2, among the compounds represented by general formula (1), Y is a perdeuterated carbazol-9-yl group (D722), and X １ and X ２ are both N, L is a single bond, and R １ and R ３ is a hydrogen atom, and R ２ is a cyano group, and R ４is Ar1 to Ar69, and R ５ Specifically, R of the compound having the following structure is ４ and R ５ The structures of compounds 1 to 86940 are individually identified by showing them in order in Table 2. In the column of compounds 1 to 1260 in Table 2, Y is fixed to D722 and X １ and X ２ is fixed to N, L is fixed to a single bond, and R １ and R ３ is fixed to a hydrogen atom, and R ２ is fixed to the cyano group, and R ４ is fixed to Ar1, and R ５ In other words, the column of Compounds 1 to 1260 in Table 2 shows the structures of Compounds 1 to 1260 in Table 1 all together in one column. The column of Compounds 1261 to 2520 in Table 2 shows the structures of Compounds 1 to 2520 in Table 2 where Y is fixed to D722 and X １ and X ２ is fixed to N, L is fixed to a single bond, and R １ and R ３ is fixed to a hydrogen atom, and R ２ is fixed to the cyano group, and R ４ is fixed to Ar2, and R ５ In Table 2, the compounds 2521 to 3780 are identified as compounds 1261 to 2520, in which Y is fixed to D722 and X １ and X ２ is fixed to N, L is fixed to a single bond, and R １ and R ３ is fixed to a hydrogen atom, and R ２ is fixed to the cyano group, and R ４ is fixed to Ar3, and R ５ The structures of the compounds are specified in the same manner in the subsequent rows. In the last row of compounds 85681 to 86940, Y is fixed to D722 and X １ and X ２ is fixed to N, L is fixed to a single bond, and R １ and R ３is fixed to a hydrogen atom, and R ２ is fixed to the cyano group, and R ４ is fixed to Ar69, and R ５ The compounds D1 to D1260 are identified as compounds 85681 to 86940, respectively.

[0055] In Table 3, the structures of compounds 1 to 5708388 are shown as variations of the structures shown in Table 2. In Table 3, the structures of compounds 1 to 5708388 are shown as variations of the structures shown in Table 2. １ , X ２ , L, R １ ~R ５ The "-" in the L column of Table 3 represents a single bond. In the columns of Compounds 1 to 86940 in Table 3, Y is fixed to D722 and X １ and X ２ is fixed to N, L is fixed to a single bond, and R １ and R ３ is fixed to a hydrogen atom, and R ２ is fixed to the cyano group, and R ４ is any one of Ar1 to Ar69, and R ５ In this section, compounds in which R is any of D1 to D1260 are specified as compounds 1 to 86940. ４ varies from Ar1 to 69, and R ５ varies from D1 to D1260, but when there are two types of variables, the first one (the one written to the left of Table 3) is fixed first, and the second one (the one written to the right of Table 3) is varied, and the compound numbers are assigned in order. ４ First, fix it to Ar1, and then use R ５ These are designated D1 to D1260 in order and are identified as compounds 1 to 1260 in order. ４ is fixed to Ar2, and R ５ These are designated D1 to D1260 in order and are identified as compounds 1261 to 2520 in order. ４ is fixed to Ar3, and R ３These are sequentially designated as D1 to D1260 and then identified as compounds 2521 to 3780. ４ is fixed to Ar69, and R ５ These are designated D1 to D1260 in order and are identified as compounds 85681 to 86940 in order. That is, the column of compounds 1 to 86940 in Table 3 shows the structures of compounds 1 to 86940 in Table 2 all together in one column. From the column of compounds 86941 to 173880 in Table 3, the structures of compounds 5707129 to 5708388 in the bottom column are identified in the same manner. Note that, as shown in the rightmost column of Table 3, for example, for compounds 5707129 to 5708388 in the bottom column, R ３ and R ４ and R ５ is the same.

[0056] In Table 3, structures in which Y in general formula (1) is a perdeuterated carbazol-9-yl group (D722) are identified as the structures of compounds 1 to 3370794, and structures in which Y is a perdeuterated phenyl group (Ar45) are identified as the structures of compounds 3370795 to 5708388. Table 4 lists, in tabular form, compounds in which Y is changed from D722 to a value shown in Table 4 for each of compounds 1 to 3370794. In Table 4, to make the correspondence easier to understand, compounds 1 to 3370794 in which Y is D722 are listed in the first row. In the second row of Table 4, for example, compound 1(1) represents a compound having a structure in which Y in compound 1 is replaced with D1. Furthermore, compound 2(1) represents a compound having a structure in which Y in compound 2 is replaced with D1. In the same manner, compound 3370794(1) represents a compound having a structure in which Y in compound 3370794 is replaced with D1. The structures of compounds 1(2) to 3370794(2) onward in the third row are also specified in the same manner as in the second row.

[0057] All compounds identified by the above numbers are considered to be individually disclosed. It should be noted that, among the specific examples of compounds listed above, when rotamers exist, the mixture of rotamers and each separated rotamer are also considered to be disclosed herein. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 5708388 and compounds 1(n) to 3370794(n) [where n is 1 to 209]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 3370794 and compounds 1(n) to 3370794(n) [where n is 1 to 141]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 3370795 to 5708388 and compounds 1(n) to 3370794(n) [where n is 142 to 209].

[0058] Examples of preferred compounds represented by formula (1) are listed below.

[0059] Other preferred examples of the compounds represented by formula (1) are given below.

[0060] Other preferred examples of the compounds represented by formula (1) are given below.

[0061] Other preferred examples of the compounds represented by formula (1) are given below.

[0062] Other preferred examples of the compounds represented by formula (1) are given below.

[0063] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0064] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0065] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0066] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４ each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0067] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0068] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group.

[0069] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0070] In some embodiments, the compound represented by general formula (1) is a light-emitting material. Compounds represented by general formula (1) include compounds with long luminescence lifetimes. Compounds represented by general formula (1) can improve luminescence characteristics when used in organic light-emitting devices. For example, compounds represented by general formula (1) include compounds that can extend device lifetimes when used in organic light-emitting devices. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. Compounds represented by general formula (1) include compounds with a high proportion of delayed fluorescent components. For example, compounds in which 80% or more of the total emission is the delayed fluorescent component, for example, compounds in which 90% or more of the total emission is the delayed fluorescent component, are included. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means.In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. In some embodiments of the present disclosure, an organic semiconductor device can be fabricated using a compound represented by general formula (1). The organic semiconductor device referred to here may be an organic optical device mediated by light or an organic device not mediated by light. The organic optical device may be an organic light-emitting device that emits light, an organic light-receiving device that receives light, or a device that causes light-mediated energy transfer within the device. In some embodiments of the present disclosure, the compound represented by general formula (1) can be used to fabricate organic optical devices such as organic electroluminescence devices and solid-state imaging devices (e.g., CMOS image sensors). In some embodiments of the present disclosure, the compound represented by general formula (1) can be used to fabricate CMOS (complementary metal-oxide semiconductor) devices.

[0071] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴ The quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0072] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. The compound represented by general formula (1) can be synthesized by combining R １ ~R ５ One to three of these groups are donor groups, and for example, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is a donor group can be synthesized by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole. For details of the reaction conditions, please refer to the synthesis examples described below.

[0073] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0074] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture of the individual compounds may be used by heating, melting, and cooling. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

[0075] [Examples of Use of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferably used in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of compounds represented by general formula (1) of the present invention as light-emitting materials for organic light-emitting devices. In some embodiments, compounds represented by general formula (1) of the present invention can be effectively used as light-emitting materials in the light-emitting layer of organic light-emitting devices. In some embodiments, compounds represented by general formula (1) include delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of compounds represented by general formula (1) as delayed fluorescent materials. In some embodiments, the present invention can be used as a host material and can be used together with one or more light-emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF. In some embodiments, the compounds represented by general formula (1) can also be used as hole-transporting materials. In some embodiments, the compounds represented by general formula (1) can be used as electron-transporting materials. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves the light extraction efficiency from the emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound represented by general formula (1) as an emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device).In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic light-emitting device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole-transporting layer, a hole-injecting layer, an electron-blocking layer, a hole-blocking layer, an electron-injecting layer, an electron-transporting layer, and an exciton-blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0076] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0077] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[0078]

[0079] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0080] Further preferred light-emitting materials include compounds represented by the following general formula (2).

[0081] In general formula (2), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of the C-R groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0082] In one aspect of the present invention, X ２ When is O or NR, R ７ is an acceptor group, or R ６ and R ７ are bonded to each other to form an acceptor group, or R ７ and R ８In one embodiment of the present invention, X ３ When is O or NR, R １０ is an acceptor group, or R ９ and R １０ are bonded to each other to form an acceptor group, or R １０ and R １１ In one embodiment of the present invention, X ４ When is O or NR, R １５ is an acceptor group, or R １４ and R １５ are bonded to each other to form an acceptor group, or R １５ and R １６ In one embodiment of the present invention, X ２ is NR, R is a substituted or unsubstituted phenyl group, and R ８ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ３ is NR, R is a substituted or unsubstituted phenyl group, and R ９ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ４ is NR, R is a substituted or unsubstituted phenyl group, and R １６ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. １ is NR, R is a substituted or unsubstituted phenyl group, and R １In one embodiment of the present invention, the compound is represented by the following general formula (2a):

[0083] In general formula (2a), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of Ar is O or NR, and the remaining may be O or NR or may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ Each of C-R in general formula (2a) independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ , C-R ３ , C-R ６ , C-R ７ , C-R ８ , C-R９ , C-R １０ , C-R １１ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0084] Further preferred light-emitting materials include compounds represented by the following general formula (3).

[0085] In general formula (3), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0086] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. ３ and R １０ are each independently a substituted amino group. １ and R ３ , and R ２ and R １０ In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0087] Further preferred light-emitting materials include compounds represented by the following general formula (4).

[0088] In general formula (4), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0089] In one aspect of the present invention, Z １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. １ ~R ９ are each independently a substituted or unsubstituted aryl group or an acceptor group, or R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５are bonded to each other to form a ring, and R ５ and R ６ and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. ８ is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, a benzothiophene ring, and an indole ring.

[0090] Further preferred light-emitting materials include compounds having a fused ring structure A (in which a hydrogen atom may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring.

[0091] In the structure α, X １ and X ２ each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent; Z and X ２ In the fused ring structure A, the structure fused to b and X may be bonded to each other to form a cyclic structure. １ , b and Z, Z and X ２ may be bonded to each other to form a cyclic structure.

[0092] Further preferred light-emitting materials include compounds represented by the following general formula (5).

[0093] In the general formula (5), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0094] Further preferred light-emitting materials include compounds represented by the following general formula (6).

[0095] In the general formula (6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ ~R ７ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0096] Further preferred light-emitting materials include compounds represented by the following general formula (7).

[0097] In the general formula (7), X ４ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ａ ~R ７ａ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ａ and R ５ａ , R ５ａ and R ６ａ , R ６ａ and R ７ａ , R ７ａ and R １ may be bonded to each other to form a cyclic structure. ２ and Z２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0098] Further preferred light-emitting materials include compounds represented by the following general formula (8).

[0099] In the general formula (8), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ８ ~R １４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0100] Further preferred light-emitting materials include compounds represented by the following general formula (9).

[0101] In the general formula (9), Z １ and Z ４each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R １５ ~R １７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , Z ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0102] Further preferred light-emitting materials include compounds represented by the following general formula (10).

[0103] In the general formula (10), Z １ and Z ５ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z ３ and R３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0104] Further preferred light-emitting materials include compounds represented by the following general formula (11).

[0105] In the general formula (11), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２１ ~R ２７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ , R ２６ and R ２７ may be bonded to each other to form a cyclic structure.

[0106] Further preferred light-emitting materials include compounds represented by the following general formula (12).

[0107] In the general formula (12), Z １ and Z６ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２８ ~R ３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ may be bonded to each other to form a cyclic structure.

[0108] Further preferred light-emitting materials include compounds represented by the following general formula (13).

[0109] In the general formula (13), Z １ and Z ７ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and Z ７ , Z７ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.)

[0110] Further preferred light-emitting materials include compounds represented by the following general formula (14).

[0111] In the general formula (14), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ３１ ~R ４４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R ３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ , R ３７ and R ３８ , R ３８ and R ３９ , R ３９ and R ４０ , R ４０ and R ４１ , R ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ may be bonded to each other to form a cyclic structure.

[0112] Further preferred light-emitting materials include compounds represented by the following general formula (15).

[0113] In the general formula (15), Z １ and Z ８ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ５１ ~R ６０ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , R ５１ and R ５２ , R ５２ and R ５３ , R ５３ and R ５４ , R ５４ and R ５５ , R ５５ and R ５６ , R ５６ and R ５７ , R ５７ and R ５８ , R ５８ and R ５９ , R ５９ and R ６０ , R ６０ and Z ８ may be bonded to each other to form a cyclic structure.

[0114] Further preferred light-emitting materials include compounds represented by the following general formula (16).

[0115] In the general formula (16), Z １ , Z ８ and Z ９ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８ may be bonded to each other to form a cyclic structure.

[0116] Further preferred light-emitting materials include compounds represented by the following general formula (17).

[0117] In the general formula (17), Z １ , Z ９ and Z １０ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６７ ~R ６９ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７０ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , Z ９ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ , R ６９ and Z １０ , Z １０ and R ７０ may be bonded to each other to form a cyclic structure.

[0118] Further preferred light-emitting materials include compounds represented by the following general formula (18).

[0119] (In the general formula (18), Z １ , Z １１and Z １２ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0120] Further preferred light-emitting materials include compounds represented by the following general formula (19).

[0121] In the general formula (19), Z １ and Z １１ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７６ ~R ８２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R ７５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R ７８ , R７８ and R ７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0122] Further preferred light-emitting materials include compounds represented by the following general formula (20).

[0123] In the general formula (20), X ５ represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R １０１ ~R １３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １０１ and R １０２ , R １０２ and R １０３ , R １０３ and R １０４ , R １０４ and R １０５ , R １０５ and R １０６ , R １０６ and R １０７ , R １０７ and R １０８ , R １０８ and R １０９ , R １０９ and R １１０ , R １１０ and R １１１ , R １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , R １１４ and R １１５ , R １１５ and R １１６ , R １１６ and R １１７ , R １１７ and R １１８ , R １１８ and R １１９ , R １１９ and R １２０ , R １２０ and R １２１ , R１２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R １２５ , R １２５ and R １２６ , R １２６ and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R １３０ and R １０１ may be bonded to each other to form a cyclic structure.

[0124] Further preferred light-emitting materials include compounds represented by the following general formula (21).

[0125] In general formula (21), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R ２ and R６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １ may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0126] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. １ and Z １ are bonded to each other to form a ring structure. １ and Z １ are bonded to each other to form a pyrrole ring.

[0127] Further preferred light-emitting materials include compounds represented by the following general formula (22).

[0128] In the general formula (22), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring. For a detailed description of the compound represented by general formula (22), a preferred range, and specific examples thereof, reference can be made to

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of the present specification.

[0129] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0130] In some embodiments, the host material is selected from the group consisting of: In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of the present invention may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0131] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0132] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0133] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0134] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0135] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0136]

[0137] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0138] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0139] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0140]

[0141] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0142]

[0143] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0144] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0145]

[0146] Electron Transport Layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0147]

[0148] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0149]

[0150] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0151] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0152] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0153] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0154] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0155] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0156] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0157] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0158] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0159] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0160] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0161] The features of the present invention will be explained in more detail below with reference to synthesis examples and examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the synthesis examples below, compounds represented by general formula (1) were synthesized.

[0162] (Synthesis Example 1) Synthesis of intermediate a of compound A

[0163] A mixture of 3-bromo-4-fluorobenzonitrile (10.0 g, 50 mmol), phenyl-d5-boronic acid (7.0 g, 55.3 mmol), potassium carbonate (13.8 g, 100.0 mmol), tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.50 mmol), tetrahydrofuran (THF, 375 mL), and ion-exchanged water (125 mL) was stirred at 75°C for 20 hours. After cooling to room temperature, saturated brine was added, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The solid was filtered and washed with ethyl acetate. The crude product was purified by flash column chromatography (hexane / ethyl acetate = 5:1) to obtain 9.70 g (48.0 mmol, 96% yield) of intermediate a as a white solid. 1 H-NMR (400 MHz, DMSO-d6): δ 8.09 (dd, J = 6.5, 2.4 Hz, 1H), 7.93-7.97 (m, 1H), 7.58 (dd, J= 10.4, 8.8 Hz, 1H). ASAP MS spectral analysis: C 13 H3D5FN: Calculated 202.10, Observed 203.10 [M+H + ]

[0164] Synthesis of intermediate b Under a nitrogen atmosphere, a 1.0 M diisopropylamide THF / hexane solution (40 mL, 40 mmol) was slowly added dropwise to a THF solution (200 mL) of intermediate a (8.09 g, 40 mmol) at −78°C. After stirring for 1 hour, a 1 M zinc chloride THF solution (60 mL, 60 mmol) was added, and the mixture was warmed to room temperature. After stirring for 1 hour, 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.46 g, 20 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.16 g, 1.0 mmol) were added. The mixture was warmed to 80°C and stirred for 20 hours. After cooling to room temperature, the resulting solid was filtered and washed with ethyl acetate. The solid was recovered and stirred with toluene under reflux. After cooling to room temperature, the solid was filtered and washed with toluene and hexane to obtain 5.90 g (9.0 mmol, 45% yield) of intermediate b as a pale yellow solid. ASAP MS spectrum analysis: 41 H4D 18 F2N6: Calculated 654.30, Observed 655.40 [M+H + ]

[0165] Synthesis of Compound A

[0166] Carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol) were added to a mixture of intermediate b (3.27 g, 5.00 mmol) and N,N-dimethylformamide (DMF, 100 mL), and the mixture was stirred at 150°C for 1 hour. The reaction solution was cooled to room temperature, and the solid was filtered and washed with toluene. The resulting filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. After removing the solvent, the resulting solid was reprecipitated with toluene / hexane, and the resulting solid was collected. The solid was dissolved in toluene and filtered through Celite / silica. The filtrate was concentrated, and the resulting solid was reprecipitated with toluene / hexane, yielding 2.82 g (2.92 mmol, 58% yield) of yellow compound A. 1H-NMR (400 MHz, DMSO-d6): δ 8.38 (d, J = 2 Hz, 2H), 7.66 (d, J = 1.6 Hz, 2H). ASAP MS spectrum analysis: C 65 H4D 34 N8: Calculated value 964.54, observed value 965.71 [M+H + ]

[0167] (Synthesis Example 2) Synthesis of intermediate c of compound B

[0168] Under a nitrogen atmosphere, a 1.3 M lithium bis(trimethylsilyl)amide THF solution (25 mL, 32.5 mmol) was slowly added dropwise to a mixture of carbazole-1,2,3,4,5,6,7,8-d8 (5.26 g, 11.0 mmol) and THF (60 mL) at -78°C, and the mixture was stirred for 30 minutes. To the resulting white suspension, a THF (50 mL) solution of 4,6-dichloro-2-(methylsulfonyl)pyrimidine (6.81 g, 30.0 mmol) was slowly added dropwise. After stirring for 1 hour, a saturated aqueous ammonium chloride solution was added, and the reaction vessel was warmed to room temperature. The resulting solid was filtered, washed with ion-exchanged water, methanol, and hexane, and dried under reduced pressure to obtain 7.66 g (23.8 mmol, 79% yield) of white intermediate c. 1 H-NMR (400 MHz, DMSO-d): δ 7.84 (s, 1H). ASAP MS spectrum analysis: C 16 H2D8Cl2N3: Calculated 321.07, Observed 322.11 [M+H + ]

[0169] Synthesis of intermediate d

[0170] Under a nitrogen atmosphere, a 1.0 M diisopropylamide THF / hexane solution (40 mL, 40 mmol) was slowly added dropwise to a THF solution (200 mL) of intermediate c (8.09 g, 40 mmol) at -78°C. After stirring for 1 hour, a 1 M zinc chloride THF solution (60 mL, 60 mmol) was added, and the mixture was warmed to room temperature. After stirring for 1 hour, 9-(4,6-dichloropyrimidin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.45 g, 20 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.16 g, 1.0 mmol) were added. The mixture was warmed to 80°C and stirred for 18 hours. After cooling to room temperature, the resulting solid was filtered and washed with ethyl acetate and hexane, yielding 5.70 g (8.7 mmol, 44% yield) of intermediate d as a yellow solid. ASAP MS Spectral Analysis: C 41 H4D 18 F2N5: Calculated 653.31, Observed 654.43 [M+H + ]

[0171] Synthesis of Compound B

[0172] Carbazole-1,2,3,4,5,6,7,8-d8 (1.55 g, 8.80 mmol) and potassium carbonate (1.66 g, 12.0 mmol) were added to a mixture of intermediate d (2.62 g, 4.00 mmol) and DMF (80 mL), and the mixture was stirred at 150°C for 1 hour. The reaction solution was cooled to room temperature, and the solid was filtered and washed with toluene. The resulting filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. After removing the solvent, the resulting solid was reprecipitated with toluene / hexane, and the resulting solid was collected. The crude product was purified by flash column chromatography (toluene / hexane 10:1), and the resulting solid was reprecipitated with ethyl acetate / hexane, yielding 2.23 g (2.31 mmol, 58% yield) of yellow compound B. 1 H-NMR (400 MHz, DMSO-d6): δ 8.32 (d, J = 2 Hz, 2H), 7.44 (d, J = 2.0 Hz, 2H), 6.09 (s, 1H). ASAP MS spectrum analysis: C 66 H5D 34N7: Calculated value 963.54, observed value 964.09 [M+H + ]

[0173] Synthesis of intermediate e

[0174] A mixture of 1,3-dibromo-2-fluorobenzene (10.04 g, 39.354 mmol), phenyl-d5-boronic acid (5.02 g, 39.54 mmol), potassium carbonate (16.39 g, 118.6 mmol), tetrakis(triphenylphosphine)palladium(0) (1.37 g, 1.18 mmol), THF (131 mL), and ion-exchanged water (43 mL) was stirred at 90°C for 22 hours. After cooling to room temperature, saturated brine was added, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (hexane), yielding 7.1 g (27.7 mmol, 70% yield) of intermediate e as a white solid. 1 H-NMR (400 MHz, DMSO-d): δ 7.49-7.54 (m, 1H), 7.33-7.38 (m, 1H), 7.06-7.10 (m, 1H). ASAP MS spectral analysis: C 12 H3D5BrF: Calculated 255.01, Observed 255.03 [M+H + ]

[0175] Synthesis of intermediate f

[0176] Carbazole-1,2,3,4,5,6,7,8-d8 (15.82 g, 90.3 mmol) and tripotassium phosphate (31.9 g, 150.5 mmol) were added to a mixture of intermediate e (9.62 g, 37.6 mmol) and DMF (380 mL), and the mixture was stirred at 120°C for 20 hours. The reaction vessel was cooled to room temperature, ion-exchanged water was added, and the mixture was extracted with acetic acid, washed with saturated brine, dried over magnesium sulfate, and filtered. The resulting crude product was purified by flash column chromatography (dichloromethane / hexane 1:3), and the resulting solid was reprecipitated with chloroform / hexane to give 9.973 g (24.24 mmol, 65% yield) of white intermediate f.1 H-NMR (400 MHz, CDCl 3) : δ7.81 (dd, J = 7.6, 1.6 Hz, 1H), 7.56 (dd, J = 7.6, 2.0 Hz, 1H), 7.47 (t, J=7.6, 1H). ASAP MS spectrum analysis: C 24 H3D 13 BrN: Calculated 410.13, Observed 410.30 [M+H + ]

[0177] Synthesis of intermediate g

[0178] Under a nitrogen atmosphere, intermediate f (9.90 g, 24.1 mmol) was weighed into a three-neck flask, degassed, and purged with nitrogen gas. THF (96 mL) was added, and the mixture was cooled to -78°C. A 2.3 M n-butyllithium hexane solution (11.5 mL) was then slowly added. After stirring at -78°C for 30 minutes, trimethylboronic acid was added and the mixture was stirred for an additional 30 minutes, followed by stirring at room temperature for 1 hour. The reaction solution was ice-cooled, and 7 mL of 10% hydrochloric acid was added. The mixture was stirred at room temperature for 1 hour. Ion-exchanged water was then added, the mixture was extracted with ethyl acetate, washed with saturated saline, dried over magnesium sulfate, and filtered. The resulting solid was washed with hexane to obtain 7.39 g (19.6 mmol, 81% yield) of white intermediate g. 1 H-NMR (400 MHz, CDCl3): δ8.09 (dd, J = 7.2, 2.0 Hz, 1H), 7.70-7.63 (m, 2H), 4.06 (s, 2H).

[0179] Synthesis of Compound C

[0180] Toluene (1.86 mL) and ion-exchanged water (0.37 mL) were added to a mixture of 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.15 g, 0.46 mmol), intermediate g (0.42 g, 1.11 mmol), potassium carbonate (0.26 g, 2.47 mmol), and 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.01 g, 0.014 mmol) under a nitrogen atmosphere, and the mixture was stirred at 70° C. for 6 hours. Intermediate g (0.31 g, 0.9 g, 0.8 mmol) was added and the mixture was stirred for an additional 12 hours. Then, 1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.02 g, 0.028 mmol) was added and the mixture was stirred for an additional 90 minutes. After cooling to room temperature, ion-exchanged water was added and the mixture was extracted with ethyl acetate. The combined organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The resulting crude product was purified by flash column chromatography (toluene / hexane 1:2), and the resulting solid was reprecipitated with toluene / acetonitrile to obtain 0.12 g (0.13 mmol, yield 29%) of pale yellow compound C. 1 H-NMR (400 MHz, CDCl3): δ7.71 (dd, J = 7.6, 1.6 Hz, 2H), 7.52 (t, J = 7.6 Hz, 2H), 7.19 (dd, J = 4.0, 2.0 Hz, 2H). ASAP MS spectral analysis: C 63 H6D 34 N6: Calculated value 914.54, observed value 914.99 [M+H + ]

[0181] (Synthesis Example 4) Synthesis of intermediate h for compound D

[0182] A 2.0 M THF solution of isopropylmagnesium chloride (17.8 mL, 35.6 mmol) was added dropwise to a THF solution (320 mL) of 5-bromo-2,3,4-trifluorobenzonitrile (8.0 g, 33.9 mmol) at -78°C under a nitrogen stream, and the mixture was stirred for 30 minutes. Tributyltin chloride (13.2 g, 40.6 mmol) was then added, and the mixture was stirred for 30 minutes. The mixture was warmed to room temperature and stirred for an additional 3 hours, after which saturated ammonium chloride was added to quench the reaction. The organic layer was separated, and the aqueous layer was extracted with toluene. The organic layers were combined, washed with saturated brine, dried over magnesium sulfate, and filtered. After concentrating the solvent under reduced pressure, 2,4-dichloro-6-(phenyl-d5)-1,3,5-triazine (3.9 g, 16.9 mmol), bistriphenylphosphine palladium dichloride (1.9 g, 2.7 mmol), and toluene (400 mL) were added to the crude product, and the mixture was heated under reflux for 14 hours. After completion of the reaction, the reaction solution was passed through a silica pad, and the silica gel was washed with toluene. The filtrate was concentrated and then recrystallized from toluene to obtain 4.1 g (8.7 mmol, yield 52%) of intermediate h. 1 H-NMR (400 MHz, CDCl3): 8.68-8.63 (m, 2H) ASAP MS spectrum analysis: C 23 H2D5F6N5: Calculated 472.09, Observed 473.21 [M+H + ]

[0183] Synthesis of Compound D

[0184] Under a nitrogen atmosphere, a DMF solution (100 mL) of intermediate h (4 g, 8.4 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (10.4 g, 59.2 mmol), and potassium carbonate (9.3 g, 67.2 mmol) was stirred at 110°C for 8 hours. The reaction vessel was returned to room temperature, and water and methanol were added. The resulting solid was filtered out and washed with water and methanol. The crude product was purified by column chromatography (toluene / hexane = 7:3) and reprecipitation (CHCl ３ The residue was purified with hexane / MeOH to obtain 8.6 g of Compound D (6.1 mmol, yield 73%). 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 2H). ASAP MS spectrum analysis: C 95 H2D 53 N 11 : Theoretical value 1402.80, Observed value 1403.55 [M+H + ]

[0185] (Synthesis Example 5) Synthesis of intermediate i for compound E

[0186] A mixture of 5-bromo-2-fluorobenzonitrile (10.0 g, 50.0 mmol), phenyl-d5-boronic acid (7.0 g, 55.1 mmol), tetrakis(triphenylphosphine)palladium(0) (2.9 g, 2.51 mmol), potassium carbonate (13.8 g, 100 mmol), tetrahydrofuran (THF, 120 mL), and ion-exchanged water (40 mL) was stirred at 75°C for 15 hours. After cooling to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (ethyl acetate:hexane = 1:40) and recrystallized from hexane to give 9.0 g (44.5 mmol, 89% yield) of intermediate i as a white solid. 1 H NMR (400 MHz, CDCl3):δ 7.83-7.78 (m, 2H), 7.29 (td,J = 8.6, 0.6 Hz, 1H).

[0187] Synthesis of intermediate j

[0188] A mixture of 2,2,6,6-tetramethylpiperidine (6.94 g, 49.1 mmol) and THF (80 mL) was cooled to −75°C, and a 1.6 M solution of n-butyllithium in hexane (30 mL, 48.0 mmol) was added, followed by stirring at 0°C for 30 minutes. This mixture was cooled to −75°C, and a 1 M solution of diethylzinc in hexane (52 mL, 52.0 mmol) was added, followed by stirring at −75°C for 30 minutes, followed by stirring at 0°C for 30 minutes. Intermediate i (4.03 g, 19.9 mmol) was dissolved in THF (10 mL) and added dropwise to the mixture cooled to −75°C. This mixture was stirred at −75°C for 3 hours. Iodine (35.4 g, 139 mmol) was dissolved in THF (70 mL) and added dropwise to the mixture cooled to −75°C. This mixture was stirred at -75°C for 30 minutes and then at room temperature for 15 hours. A 10 wt% aqueous solution of sodium thiosulfate (200 mL) was added to this reaction solution and stirred at room temperature for 1 hour. The mixture was then filtered through Celite, and the resulting solid was washed with ethyl acetate. The filtrate was separated into an organic phase and an aqueous phase, and the organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane), yielding 6.44 g (19.6 mmol, 98% yield) of intermediate j as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.18 (dd, J = 5.7, 2.3 Hz, 1H), 7.78 (dd, J = 5.5, 2.1 Hz, 1H).

[0189] Synthesis of intermediate l

[0190] A mixture of intermediate j (12.6 g, 38.4 mmol) and THF (380 mL) was cooled to -75°C, and a 1.0 M solution of isopropyl magnesium chloride in THF (42 mL, 42.0 mmol) was added, followed by stirring at -75°C for 1 hour. A 1 M solution of zinc chloride in THF (115 mL, 115 mmol) was added to the mixture, and the mixture was stirred at -75°C for 10 minutes and then at room temperature for 1 hour. THF was distilled off, and compound k (5.18 g, 16.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.928 g, 0.803 mmol) were added, followed by stirring at 125°C for 11 hours. After the reaction solution was cooled to room temperature, the precipitated solid was filtered off and washed with THF. The resulting filtrate was concentrated, and methanol was added to cause reprecipitation. The obtained solid was washed with methanol and then hexane, and the solid was dried to obtain 4.65 g (7.10 mmol, yield 44%) of intermediate 1 as a white solid. 1 H NMR (400 MHz, DMSO-d6) δ 8.88 (dd, J = 7.1, 2.5 Hz, 2H), 8.41 (dd, J = 5.3, 2.5 Hz, 2H). APCI-MS spectral analysis: C 41 H5D 18 F2N6: Calculated 655.31, Observed 655.61 [(M+H) + ].

[0191] Synthesis of Compound E

[0192] A mixture of intermediate 1 (4.59 g, 7.01 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (2.70 g, 15.4 mmol), potassium carbonate (2.91 g, 21.1 mmol), and DMF (140 mL) was stirred at 150°C for 1 hour. After the reaction solution was cooled to room temperature, methanol and ion-exchanged water were added to carry out reprecipitation. The resulting solid was separated by filtration and washed with ion-exchanged water, methanol, and hexane, in that order. The crude product was purified by flash column chromatography (toluene), yielding 3.02 g (3.13 mmol, 45% yield) of compound E as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.73 (d, J = 2.3 Hz, 2H), 8.17 (d, J = 2.3 Hz, 2H). APCI-MS spectral analysis: C 65 H5D 34 N8: Calculated value 965.54, observed value 966.09 [(M+H) + ].

[0193] (Synthesis Example 6) Synthesis of intermediate n of compound F

[0194] A mixture of 2,2,6,6-tetramethylpiperidine (6.96 g, 48 mmol) and THF (80 mL) was cooled to -75°C, and then a 1.6 M n-butyllithium hexane solution (30 mL, 48 mmol) was added and stirred at 0°C for 30 minutes. This mixture was cooled to -75°C, and a 1 M diethylzinc hexane solution (52 mL, 52 mmol) was added and stirred for 30 minutes, followed by stirring at 0°C for 30 minutes. This mixture was cooled to -75°C, and then compound m (4.04 g, 20 mmol) dissolved in THF (10 mL) was added dropwise, and the mixture was stirred for 5 hours. Iodine (41.8 g, 160 mmol) dissolved in THF (80 mL) was added to the mixture and stirred for 30 minutes, followed by warming to room temperature and stirring for 14 hours. A 10 wt% aqueous solution of sodium thiosulfate (200 mL) was added to the reaction solution, which was stirred for 1 hour. The mixture was then filtered through Celite to separate the organic and aqueous phases. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane / DCM), and the resulting solid was washed with hexane to yield 6.08 g (18.5 mmol, 93% yield) of intermediate n as a white solid. 1 H-NMR (400 MHz, CDCl3): δ8.03 (dd, J = 5.2, 2.0 Hz, 1H), 7.71 (dd, J = 6.4, 2.4 Hz, 1H). APCI-MS spectral analysis: C 13 H2D5FIN: Theoretical value 327.99, Observed value 328.13 [M + ].

[0195] Synthesis of intermediate o

[0196] A mixture of intermediate n (5.72 g, 17.5 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (3.64 g, 21 mmol), potassium carbonate (3.63 g, 26.3 mmol), and DMF (175 mL) was stirred at 100°C for 3 hours. After cooling the reaction solution to room temperature, ion-exchanged water was added, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and washed with diethyl ether. The resulting solid was purified by flash column chromatography (DCM:hexane = 1:2 to 1:1). The resulting solid was washed with hexane to give 6.78 g (14.0 mmol, 81% yield) of intermediate o as a white solid. 1 H-NMR (400 MHz, CDCl3): δ8.34 (d, J = 2.0 Hz, 1H), 7.88 (d, J = 2.0 Hz, 1H). APCI-MS spectral analysis: C 25 H3D 13 IN2: Calculated value 484.12, observed value 484.22 [(M+H) + ].

[0197] Synthesis of intermediate p

[0198] A mixture of 3,6-di-tert-butylcarbazole (8.40 g, 30 mmol), sodium hydride (60%, dispersed in liquid paraffin, 1.37 g, 33 mmol), and THF (150 mL) was stirred at room temperature for 90 minutes. This mixture was added dropwise over 30 minutes to a mixture of cyanuric chloride (8.29 g, 45 mmol) and THF (150 mL) cooled to -75°C, and the mixture was warmed to room temperature and stirred for 1 hour. After cooling the reaction solution to 0°C, ion-exchanged water (150 mL) was added, the mixture was warmed to room temperature, and filtered. The resulting solid was washed with ion-exchanged water, methanol, and hexane, in that order, and recrystallized from toluene to obtain 4.81 g (11.2 mmol, 37% yield) of intermediate p as a white solid. 1H-NMR (400 MHz, CDCl3): δ8.75 (d, J = 8.8 Hz, 2H), 7.98 (d, J = 1.6 Hz, 2H), 7.58 (dd, J = 8.8, 2.0 Hz, 2H), 1.46 (s, 18H). APCI-MS spectral analysis: C 23 H 25 Cl2N4: Calculated 427.15, Observed 427.39 [(M+H) + ].

[0199] Synthesis of Compound F

[0200] A mixture of intermediate o (6.78 g, 14.0 mmol) and THF (140 mL) was cooled to -75°C, and then a 1 M solution of isopropyl magnesium chloride in THF (15 mL, 15 mmol) was added and stirred for 1 hour. A 1 M solution of zinc chloride in THF (42 mL, 42 mmol) was added to the mixture and stirred for 30 minutes, then the temperature was raised to room temperature and stirred for 1 hour. Intermediate p (2.49 g, 5.83 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.337 g, 0.29 mmol) were added to the mixture and stirred at 80°C for 14 hours. The reaction solution was cooled to room temperature, ion-exchanged water was added, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane=4:1), and the resulting solid was washed with hexane to obtain 4.83 g (4.52 mmol, yield 77%) of compound F as a white solid. 1 H-NMR (400 MHz, DMSO-d6): δ8.38 (d, J = 1.6 Hz, 2H), 8.01 (d, J = 2.0 Hz, 2H), 7.74 (d, J = 2.0 Hz, 2H), 7.60 (d, J = 8.8 Hz, 2H), 6.78 (dd, J = 8.8, 21.6 Hz, 2H), 1.31 (s, 18H). APCI-MS spectral analysis: C 73 H 29 D 26N8: Calculated value 1069.62, Observed value 1069.96 [(M+H) + ].

[0201] (Synthesis Example 7) Synthesis of synthetic intermediate r of compound G

[0202] Under a nitrogen atmosphere, at −78°C, a 0.5 M THF solution of lithium chloride (0.6 mL, 0.30 mmol) was added to a THF solution (300 mL) of compound q (6.67 g, 30 mmol), followed by the slow dropwise addition of a 1.0 M THF / hexane solution of diisopropylamide lithium (33 mL, 33 mmol). After stirring this mixture for 1 hour, a 1.0 M THF solution of zinc chloride (45 mL, 45 mmol) was added, and the mixture was warmed to room temperature. After stirring for 1 hour, 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (3.47 g, 15 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.87 g, 0.75 mmol) were added. The mixture was warmed to 75°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and the resulting solid was filtered off and washed with ethyl acetate. The recovered solid was stirred under toluene reflux conditions, cooled to room temperature, and then filtered. The solid was washed with toluene and hexane to obtain 6.70 g (11.9 mmol, 79% yield) of intermediate r as a white solid. APCI-MS spectrum analysis: 35 H4D 15 F2N5: Calculated value 562.25, Observed value 562.44 [M + ]

[0203] Synthesis of Compound G

[0204] Carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol) were added to a mixture of intermediate r (2.82 g, 5.00 mmol) and DMF (100 mL), and the mixture was stirred at 150°C for 1 hour. The reaction solution was cooled to room temperature, and the solid was removed by filtration through Celite. The Celite was washed with ethyl acetate. The resulting filtrate was concentrated, and methanol was added to precipitate a solid. This solid was filtered and washed with methanol and hexane. The resulting solid was dissolved in toluene and filtered through Celite / silica. The filtrate was concentrated, and the resulting solid was washed with hexane, yielding 3.59 g (4.11 mmol, 82% yield) of compound G as a yellow-green solid. 1 H NMR (400 MHz, DMSO-d6): δ 8.38 (d, J = 2 Hz, 2H), 8.07 (d, J = 2.0 Hz, 2H). APCI-MS spectral analysis: C 59 H4D 31 N7: Calculated value 872.49, observed value 872.77. [M+H + ].

[0205] (Synthesis Example 8) Synthesis of intermediate u of compound H

[0206] Under a nitrogen atmosphere, a 0.5 M THF solution (2.5 mL) of lithium chloride was added to a THF solution (80 mL) of compound s (5.0 g, 25 mmol) at room temperature. The mixed solution was cooled to -78°C, and a 1 M THF / hexane solution (27 mL) of lithium diisopropylamide (LDA) was slowly added dropwise. After stirring for 2 hours, a 1 M THF solution (31 mL) of zinc chloride was added, and the mixture was stirred for an additional 30 minutes before being returned to room temperature. To this mixture, compound t (4.0 g, 12 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.68 g, 0.59 mmol) were added, and the mixture was heated at 75°C for 18 hours. The reaction solution was cooled to room temperature, aqueous ammonium chloride solution was added, and the organic and aqueous phases were separated. The aqueous phase was extracted three times with toluene, and the combined organic phase was washed with saturated brine, dried over magnesium sulfate, filtered, and the solvent was removed. The resulting crude product was purified by silica gel column chromatography (dichloromethane / hexane=1 / 1) to obtain 4.7 g (7.0 mmol, yield 60%) of intermediate u. 1 H-NMR (400 MHz, CDCl3): δ8.67 (dd, J = 6.0, 2.0 Hz, 2H) 8.55 (d, J = 2.0 Hz, 2H) 7.95 (dd, J = 6.0, 2.0 Hz, 2H), 7.74 (t, J = 2.0 Hz, 1H), 1.43 (s, 18H). APCI-MS: Calculated value (C 43 H 25 D 10 F2N5) 669.35, Observed value (MH + ) 670.59.

[0207] Synthesis of Compound H

[0208] DMF (150 mL) was added to a mixture of intermediate u (4.4 g, 6.3 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (3.3 g, 19 mmol), and potassium carbonate (3.5 g, 25 mmol), and the mixture was heated at 150°C for 1 hour. The reaction solution was cooled to room temperature, and an aqueous ammonium chloride solution and methanol were added. The precipitate was collected, washed with water and methanol, and dried to obtain a crude product (5.7 g). This crude product was purified by silica gel column chromatography (toluene / hexane = 1 / 1 to 1 / 0) and recrystallized from a mixed solvent of toluene / hexane to obtain 5.5 g (5.6 mmol, yield 84%) of compound H. 1 H-NMR (400 MHz, CDCl3): δ7.97 (d, J = 2.0 Hz, 2H), 7.48 (d, J = 2.4 Hz, 2H), 7.44 (d, J = 2.4 Hz, 2H),7.39 (t, J = 2.0 Hz, 1H),1.09 (s, 18H). APCI-MS: Calculated value (C 67 H 25 D 26 N7) 979.58, Observed value (M + ) 979.93.

[0209] (Synthesis Example 9) Synthesis of intermediate w of compound I

[0210] To a mixture of compound v (3.3 g, 7.1 mmol), phenyl-d5-boronic acid (1.8 g, 16 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol), and potassium carbonate (3.6 g, 28 mmol), toluene (43 mL), ethanol (0.7 mL), and water (14 mL) were added and the mixture was heated to reflux under a nitrogen atmosphere for 12 hours. The reaction solution was cooled to room temperature, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine, dried over magnesium sulfate, filtered, and the solvent was removed. The resulting crude product was purified by silica gel column chromatography (hexane) to obtain 1.5 g (3.6 mmol, 52% yield) of intermediate w. 1H-NMR (400 MHz, CDCl3): δ7.85 (d, J = 1.6 Hz, 1H). APCI-MS: Calculated value (C 18 HD 10 Br2F) 413.98, observed value (M + ) 414.17.

[0211] Synthesis of intermediate x

[0212] Under a nitrogen atmosphere, a 1.3 M THF solution (15 mL, 20 mmol) of isopropylmagnesium chloride-lithium chloride complex was cooled to -15°C, and a THF solution (38 mL) of intermediate w (7.9 g, 19 mmol) was slowly added. This mixture was warmed to 0°C and stirred for 2 hours, after which dimethylformamide (2.2 mL, 28 mmol) was added and the mixture was stirred at 0°C for an additional 2 hours. 28% aqueous ammonia (13 mL) and a THF solution (12 mL) of iodine (9.6 g, 38 mmol) were added thereto and stirred overnight at room temperature. A saturated aqueous sodium bisulfite solution was added to the reaction solution to quench the reaction, and the organic and aqueous phases were separated. The aqueous phase was extracted with chloroform, and the combined organic phase was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The obtained crude product was purified using a short silica gel column (toluene / hexane=1 / 1), and the solid obtained by removing the solvent was washed with hexane to obtain 4.2 g (12 mmol, yield 61%) of intermediate x. 1 H-NMR (400 MHz, CDCl3): δ7.90 (d, J = 1.6 Hz, 1H). APCI-MS: Calculated value (C 19 HD 10 BrFN) 361.07, Observed value (M + ) 361.16.

[0213] Synthesis of intermediate y

[0214] DMF (40 mL) was added to a mixture of intermediate x (4.20 g, 11.6 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (2.25 g, 12.8 mmol), and potassium carbonate (3.22 g, 23.3 mmol), and the mixture was heated at 150°C for 2.5 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, and water was added. The resulting precipitate was collected, washed with water, methanol, and hexane, and dried to obtain a crude product. This crude product was washed with toluene and hexane to obtain 3.87 g (7.48 mmol, yield 65%) of intermediate y. 1 H-NMR (400 MHz, CDCl3): δ 8.30 (s, 1H). APCI-MS: calculated (C 31 HD 18 BrN2) 516.19, observed value (M + ) 516.30.

[0215] Synthesis of Compound I

[0216] Under a nitrogen atmosphere, a 1.3 M THF solution of isopropylmagnesium chloride-lithium chloride complex (9.4 mL, 12.2 mmol) was added to a THF solution (110 mL) of intermediate y (5.52 g, 10.6 mmol) at -15°C, and the mixture was stirred for 1 hour. After that, the mixture was warmed to 0°C and stirred for an additional 2 hours. To this mixture, a 1 M THF solution of zinc chloride (12.7 mL, 12.7 mmol) was added, and the mixture was warmed to room temperature and stirred for 30 minutes. Compound z (1.72 g, 5.32 mmol), tetrakis(triphenylphosphine)palladium(0) (0.62 g, 0.54 mmol), and N-methylpyrrolidone (66 mL) were then added, and the mixture was heated at 110°C for 18 hours. The reaction solution was cooled to room temperature, and the reaction was quenched with saturated aqueous ammonium chloride (200 mL), and methanol (400 mL) was added. The resulting precipitate was collected, washed with methanol and hexane, and dried under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (hexane / toluene = 80 / 1) to obtain 4.06 g (3.60 mmol, yield 68%) of Compound I. 1 H-NMR (400 MHz, CDCl3): δ8.41 (s, 2H). APCI-MS: Calculated value (C77 H2D 44 N8) 1126.66, observed value (MH + ) 1127.95.

[0217] (Synthesis Example 10) Synthesis of intermediate a' of compound J

[0218] A mixture of 1-bromo-4-fluoro-2-iodobenzene (39.46 g, 131 mmol), phenyl-d5-boronic acid (18.29 g, 144 mmol), tetrakis(triphenylphosphine)palladium(0) (7.56 g, 6.55 mmol), potassium carbonate (54.31 g, 393 mmol), toluene (300 mL), and ion-exchanged water (100 mL) was stirred at 100°C for 3 hours. After cooling the mixture to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (hexane) to obtain 25.73 g (100 mmol, 77% yield) of intermediate a' as a colorless, transparent liquid. 1 H NMR (400 MHz, CDCl3): δ 7.61 (dd, J = 8.8, 5.4 Hz, 1H), 7.07 (dd, J = 9.2, 3.0 Hz, 1H), 6.94 (ddd, J = 10.0, 6.8, 1.9 Hz, 1H). APCI-MS spectral analysis: C 12 H3D5BrF: Calculated 255.01, Observed 255.02 [M + ].

[0219] Synthesis of intermediate b'

[0220] A mixture of 2,2,6,6-tetramethylpiperidine (6.73 g, 47.6 mmol) and THF (80 mL) was cooled to −75°C, and a 1.6 M n-butyllithium hexane solution (30 mL, 48.0 mmol) was added, followed by stirring at 0°C for 30 minutes. This mixture was cooled to −75°C, and a 1 M diethylzinc hexane solution (52 mL, 52.0 mmol) was added, followed by stirring at −75°C for 30 minutes, followed by stirring at 0°C for 30 minutes. This mixture was cooled to −75°C, and a solution of intermediate a' (5.24 g, 20.5 mmol) in THF (8 mL) was added dropwise. Subsequently, this mixture was stirred at −30°C for 2 hours, cooled to −75°C, and a solution of iodine (41.19 g, 162 mmol) in THF (80 mL) was added dropwise. This mixture was stirred at -75°C for 30 minutes and then at room temperature for 2 hours. A 10 wt% aqueous solution of sodium thiosulfate (200 mL) was added to the reaction solution and stirred at room temperature for 12 hours. The mixture was then filtered through Celite, and the resulting solid was washed with ethyl acetate. The filtrate was separated into an organic phase and an aqueous phase, and the organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (hexane), yielding 7.04 g (18.4 mmol, 90% yield) of intermediate b' as a pale yellow, transparent liquid. 1 H NMR (400 MHz, CDCl3): δ 8.04 (d, J = 6.0 Hz, 1H), 7.05 (d, J = 8.2 Hz, 1H).

[0221] Synthesis of intermediate c'

[0222] A mixture of intermediate b' (7.04 g, 18.4 mmol), phenyl-d5-boronic acid (2.57 g, 20.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.06 g, 0.917 mmol), potassium carbonate (7.66 g, 55.4 mmol), toluene (45 mL), and ion-exchanged water (15 mL) was stirred at 100°C for 15 hours. After the reaction solution was cooled to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (hexane) to obtain 4.50 g (13.3 mmol, 72% yield) of intermediate c' as a white solid. 1 H-NMR (400 MHz, CDCl3): δ 7.75 (d, J = 7.3 Hz, 1H), 7.17 (d, J = 11.0 Hz, 1H). APCI-MS spectral analysis: C 18 H2D 10 BrF: theoretical value 336.07, observed value 336.13 [M + ].

[0223] Synthesis of intermediate d'

[0224] A mixture of intermediate c' (6.33 g, 18.7 mmol) and THF (37 mL) was cooled to -50°C, and a 1.0 M THF / hexane solution of LDA (21 mL, 21.0 mmol) was added, followed by stirring at -50°C for 2 hours. A solution of iodine (5.74 g, 22.6 mmol) dissolved in THF (11 mL) was added dropwise to this mixture, and the mixture was stirred at -50°C for 30 minutes and then at room temperature for 2 hours. A 10 wt% aqueous sodium thiosulfate solution (24 mL) was added to the reaction solution, followed by stirring at room temperature for 12 hours, and the organic and aqueous phases were separated. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane = 1:20), yielding 6.69 g (14.4 mmol, 77% yield) of intermediate d' as a white solid. 1H-NMR (400 MHz, CDCl3): δ 7.74 (d, J = 7.1 Hz, 1H). APCI-MS spectral analysis: C 18 H2D 10 BrFI: Calculated value 461.97, Observed value 462.07 [(M+H) + ].

[0225] Synthesis of intermediate e'

[0226] A mixture of intermediate d' (6.54 g, 14.1 mmol) and THF (140 mL) was cooled to -50°C, and a 1.0 M solution of isopropyl magnesium chloride in THF (15 mL, 15.0 mmol) was added, followed by stirring at -50°C for 1 hour. DMF (2.2 mL) was added to this mixture, and the mixture was stirred at 0°C for 2 hours. Ammonia (25% aqueous solution, 16 mL) and iodine (7.22 g, 28.4 mmol) were then added, followed by stirring at room temperature for 2 hours. A 10 wt% aqueous sodium thiosulfate solution (100 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours. The organic and aqueous phases were separated. The organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane = 1:1). The resulting solid was washed with diethyl ether, yielding 4.25 g (11.7 mmol, 83% yield) of intermediate e' as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 7.98 (d, J = 7.3 Hz, 1H). APCI MS spectrum analysis: C 19 HD 10 BrFN: theoretical value 361.07, observed value 361.24 [M + ].

[0227] Synthesis of intermediate g'

[0228] A mixture of intermediate e' (3.36 g, 9.27 mmol) and THF (140 mL) was cooled to -15 °C, and a 1.3 M THF solution of turbo Grignard reagent (7.5 mL, 9.69 mmol) was added and stirred at 0 °C for 1 hour. A 1 M THF solution of zinc chloride (11 mL, 11.0 mmol) was added to this mixture and stirred at room temperature for 1 hour. Compound f' (1.25 g, 3.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.223 g, 0.193 mmol) were then added and stirred at 75 °C for 19 hours. After cooling the reaction solution to room temperature, ion-exchanged water and methanol were added to cause reprecipitation, and the solid was filtered off. The resulting solid was washed with ion-exchanged water, methanol, and diethyl ether, in that order, and dried, yielding 3.08 g (3.77 mmol, 97% yield) of intermediate g' as a white solid. 1 H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 7.6 Hz, 2H). APCI-MS spectral analysis: C 53 H3D 28 F2N6: Calculated 817.43, Observed 817.70 [(M+H) + ].

[0229] Synthesis of Compound J

[0230] A mixture of intermediate g' (3.06 g, 3.74 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (1.44 g, 8.25 mmol), potassium carbonate (1.56 g, 11.3 mmol), and DMF (75 mL) was stirred at 150°C for 1 hour. After the reaction solution was cooled to room temperature, ion-exchanged water was added to cause reprecipitation. The resulting solid was separated by filtration and washed with ion-exchanged water, methanol, and hexane, in that order. The crude product was dissolved in hot toluene and subjected to silica gel filtration. The resulting filtrate was concentrated and purified by recrystallization (toluene), yielding 3.06 g (2.71 mmol, 73% yield) of compound J as a pale yellow-green solid. 1 H NMR (400 MHz, CDCl): δ 7.95 (s, 2H). APCI-MS spectral analysis: C 77 H3D 44N8: Calculated value 1127.67, observed value 1127.98 [(M+H) + ].

[0231] (Example 1) Preparation and Evaluation of Thin Film Using Compound A A thin film was prepared on a quartz substrate by vacuum deposition at a vacuum degree of 5.0 × 10 －５ Compound A and compound H1 were co-deposited to form a thin film under the condition of Pa. At this time, the concentration of compound A was 30 wt %.

[0232] Examples 2 to 10, Comparative Examples 1 and 2 Instead of compound A, any one of compounds B to J and comparative compounds A and B was used, and a thin film was formed by co-evaporation in the same manner.

[0233] The thin films prepared in each Example and Comparative Example were irradiated with 299 nm excitation light to measure the maximum emission wavelength and the lifetime (τ2) of the delayed fluorescence component. The measurement results and the HOMO and LUMO energy values ​​(absolute values) of the compounds used in each thin film are shown in Table 5. In Table 5, "-" indicates that no measurement was performed.

[0234]

[0235] As shown in Table 5, Compounds A to J have a shorter lifetime τ2 of the delayed fluorescent component than Comparative Compounds A and B, and therefore can contribute to the stability of the device. Furthermore, when the proportion of the delayed fluorescent component in the total emission was determined, the thin films using Compounds A to H had a higher proportion of the delayed fluorescent component than the thin film using Comparative Compound B.

[0236] (Example 11) Fabrication and Evaluation of Organic Electroluminescence Device Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed by vacuum deposition at a vacuum degree of 5.0 × 10 －５The layers were laminated at 100 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 30 nm, TrisPCz was further formed thereon to a thickness of 10 nm, and H1 was formed thereon to a thickness of 5 nm. Next, H1 and Compound A were co-deposited from different evaporation sources to form a 40 nm thick layer, which served as an emissive layer. The concentration of the compound in the emissive layer was 30 wt %. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different evaporation sources to form a 30 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 wt % and 70 wt %, respectively. Liq was then formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, resulting in an organic electroluminescent device. Organic electroluminescence devices were fabricated using Compound B, Compound C, Compound E, Compound F, Compound G, Compound H, Comparative Compound A, Comparative Compound B, and Comparative Compound C, respectively, in place of Compound A, following the same procedure. The external quantum efficiency (EQE) of each organic electroluminescence device was measured, and all, except for the organic electroluminescence device using Comparative Compound C, showed high values ​​exceeding 10%, confirming the usefulness of the compound represented by general formula (1). Furthermore, the time (LT95) at 1000 nits until the luminous intensity decreased to 95% of the initial value at the start of operation was measured for the organic electroluminescence devices using Compound A, Compounds E to H, and Comparative Compounds A to C. The results are shown in Table 6. The "LT95" in Table 6 is a relative value, where the LT95 of the device using Comparative Compound A is set to 1.

[0237]

[0238] As shown in Table 6, the organic electroluminescence devices of Compounds A and E to H all exhibited longer device life than the organic electroluminescence devices of Comparative Compounds A to C. In particular, it was confirmed that the organic electroluminescence device of Compound A had a device life 32.6 times longer than that of the organic electroluminescence device of Comparative Compound A. Furthermore, compared with other comparative compounds, it was confirmed that the organic electroluminescence device of Compound A had a device life 29.6 times longer than that of Comparative Compound B and 673 times longer than that of the organic electroluminescence device of Comparative Compound C. This confirmed that the organic light-emitting device using the compound represented by general formula (1) had high durability.

[0239] (Example 12) Preparation and evaluation of organic electroluminescence device An organic electroluminescence device of Compound D was prepared by the same procedure as in Example 11, except that the light-emitting layer of Example 11 was changed to a 40 nm-thick light-emitting layer in which H1, Compound D, and n-DABNA were co-deposited from different deposition sources to give a concentration of 34.2 wt % of H1, 65.0 wt % of Compound D, and 0.8 wt % of n-DABNA. ２ When driven at 12.6 mA / cm, the EQE was higher than 10%. ２ The LT95 was measured at 1000 kJ / s, and it was confirmed that the lifetime was long. The organic electroluminescence devices prepared in Examples 11 and 12 using the compounds A to H and the organic electroluminescence devices prepared in Comparative Examples A to C all had EQE and driving voltages at practical levels.

[0240]

[0241]

[0242] By using the compound represented by general formula (1), an organic light-emitting device having good light-emitting properties can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) [In the general formula (1), R １ ~R ５ One to three of R are donor groups. １ ~R ５ 0 to 1 of R are cyano groups; １ ~R ５ 0 to 3 of R are hydrogen atoms or deuterium atoms; １ ~R ５ Of these, 0 to 2 are substituted or unsubstituted aryl groups, and the remaining R １ ~R ５ R is a substituted or unsubstituted alkyl group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ may be bonded to each other to form a ring structure. L represents a single bond or a linking group. X １ is N or C-R ６ represents X ２ is N or C-R ７ Represents R ６ and R ７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; Y represents a substituted or unsubstituted carbazol-9-yl group, or a substituted or unsubstituted aryl group; provided that when Y is a substituted or unsubstituted aryl group, R １ ~R ５ of which 0 to 2 are hydrogen atoms or deuterium atoms.

2. R １ ~R ５ The compound of claim 1 , wherein one of is a cyano group.

3. R ２ The compound according to claim 2 , wherein is a cyano group.

4. R １ ~R ５ The compound according to claim 1, wherein one or two of the are donor groups.

5. R ５ The compound according to claim 4 , wherein is a donor group.

6. R １ The compound according to claim 5 , wherein is a hydrogen atom or a deuterium atom.

7. R １ ~R ５ The compound according to claim 1, wherein one or two of the are a substituted or unsubstituted aryl group.

8. R ４ The compound according to claim 7 , wherein is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group.

9. The compound according to claim 1, wherein Y is a substituted or unsubstituted carbazol-9-yl group.

10. The compound of claim 1, wherein Y is a substituted or unsubstituted aryl group.

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

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

13. A light-emitting material comprising the compound according to any one of claims 1 to 12.

14. A delayed fluorescent substance comprising the compound according to any one of claims 1 to 12.

15. A membrane comprising a compound according to any one of claims 1 to 12.

16. An organic semiconductor device comprising the compound according to any one of claims 1 to 12.

17. An organic light-emitting device comprising a compound according to any one of claims 1 to 12.

18. The organic light-emitting device of claim 17, wherein the device has a layer comprising the compound, the layer also comprising a host material.

19. The organic light-emitting element according to claim 18, wherein the layer containing the compound also contains a light-emitting material in addition to the compound and the host material, and the lowest excited singlet energy of the compound is lower than that of the host material and higher than that of the light-emitting material.

20. The organic light-emitting device according to claim 19, wherein the layer further comprises a delayed fluorescent material.

21. The organic light-emitting device according to claim 17, which is an organic electroluminescence device.

22. The organic light-emitting element according to claim 17, which emits fluorescence or delayed fluorescence.

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