Compound, luminescent material, and luminescent element

Abstract

To provide a compound having excellent luminescent properties.SOLUTION: Provided is a compound represented by general formula (1). Either R2 or R3 and Z each represent a group represented by general formula (A); one of R1 to R5 represents a donating group and one or two thereof each represent an aryl group; X1 and X2 each represent N, C-H, C-CN, etc.; Ar1 and Ar2 each represent an aryl group or a heteroaryl group; and L represents a single bond or a linking group.SELECTED DRAWING: None

Description

[Technical field]

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

[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 developing and combining newly developed electron transport materials, hole transport materials, luminescent materials, etc. that constitute organic electroluminescence elements. Among these, research into organic electroluminescence elements that use delayed fluorescent materials has also been seen.

[0003] A delayed fluorescent material is a material that emits fluorescence when it returns from an excited singlet state to a ground state after reverse intersystem crossing from an excited triplet state to an excited singlet state in an excited state. Fluorescence by such a route is observed later than fluorescence from an excited singlet state directly generated from a ground state (normal fluorescence), and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency only by fluorescence from an excited singlet state directly generated. On the other hand, in a delayed fluorescent material, not only an excited singlet state but also an excited triplet state can be used for fluorescence emission by a route via the above-mentioned reverse intersystem crossing, and therefore a higher luminous efficiency can be obtained than that of a normal fluorescent material.

[0004] Since this principle was clarified, various delayed fluorescent materials have been discovered through various studies, and their application to organic light-emitting devices such as organic electroluminescence devices has been proposed. Many of these materials include 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 diphenyltriazinyl group, which is an acceptor group, are substituted on a benzene ring (see Patent Document 1). [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] WO2022 / 031033A1 Summary of the Invention [Problem to be solved by the invention]

[0006] Even if a material emits delayed fluorescence, one that has extremely good properties and has no practical problems has not yet been provided. Therefore, if a delayed fluorescent material with even better properties could be provided, it would be even more useful. 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 such circumstances, the present inventors have conducted extensive research with the aim of providing a compound more useful as a delayed fluorescent material for a light-emitting element. They have also conducted extensive research with the aim of deriving and generalizing a general formula for a compound more useful as a delayed fluorescent material. [Means for solving the problem]

[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) [ka]

[0009] In the general formula (1), Z and R 2 , or Z and R 3 R represents the same group represented by the following general formula (A).1 ~R 5 represents a donor group, and R 1 ~R 5 one or two of represent a substituted or unsubstituted aryl group; R 1 ~R 5 One or two of represent a hydrogen atom or a deuterium atom. General formula (A) [ka]

[0010] In the general formula (A), X 1 is N or CR 6 represents X 2 is N or CR 7 Represents R 6 and R 7 Each independently represents a hydrogen atom, a deuterium atom, or a cyano group. 1 and X 2 are not both C-CN. 1 and Ar 2 Each of X independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and X 2 When is N, Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted heteroaryl group. L represents a single bond or a divalent linking group. * represents the bonding position. [2] Z and R 2 is the same group represented by general formula (A). [3] Z and R 3 is the same group represented by general formula (A). [4] R 4 is a substituted or unsubstituted aryl group. [5] R 1 is a hydrogen atom or a deuterium atom. [6] Ar 2is a substituted or unsubstituted heteroaryl group. [7] Ar 1 is a substituted or unsubstituted aryl group. [8] Ar 1 is a substituted or unsubstituted heteroaryl group. [9] X 1 and X 2 and are both N.

[10] X 1 and X 2 The compound according to any one of [1] to [8], wherein only one of the following is N.

[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 device according to

[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

[18] , wherein the layer containing the compound contains a delayed fluorescent material in addition to the compound and the host material, and the minimum 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 device according to

[18] , wherein the device 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 device according to

[18] or

[19] , wherein the amount of light emitted from the compound is the largest among the materials contained in the device.

[22] The organic light-emitting element according to

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

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

[17] to

[22] , which is an organic electroluminescence device.

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

[17] to

[23] , which emits delayed fluorescence. Effect of the Invention

[0011] The compound of the present invention exhibits excellent light-emitting properties and is useful as a material for an organic light-emitting device. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "~" means a range including the numerical values ​​before and after "~" 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 of this specification, hydrogen atoms are represented as H or are omitted. For example, when the atom bonded to the ring-structuring carbon atom of a benzene ring is omitted, H is assumed to be bonded to the ring-structuring carbon atom at the omitted position. In this specification, the term "substituent" means an atom or atomic group other than hydrogen atoms and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0013] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described. General formula (1) [ka]

[0014] In the general formula (1), Z and R 2 , or Z and R 3 R represents the same group represented by the following general formula (A). 1 ~R 5 represents a donor group, and R 1 ~R 5 one or two of represent a substituted or unsubstituted aryl group; R 1 ~R 5 One or two of represent a hydrogen atom or a deuterium atom. General formula (A) [ka]

[0015] In the general formula (A), X 1 is N or CR 6 represents X 2 is N or CR 7 Represents R 6 and R 7 Each independently represents a hydrogen atom, a deuterium atom, or a cyano group. 1 and X 2 are not both C-CN. 1 and Ar 2 Each of X independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and X 2 When is N, Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted heteroaryl group. L represents a single bond or a divalent linking group. * represents the bonding position.

[0016] R in general formula (1) 1 ~R 5 One of the R groups is a donor group. 1 ~R 5The donor groups which may 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 LP Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following formula holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp In the above formula, k0 is the rate constant of a benzene derivative having no substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative having no substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett's σp value" in the present invention and the numerical values ​​of each substituent, the description of the σp value in Hansch, C. et.al., Chem. Rev., 91, 165-195 (1991) can be referred to.

[0017] R 1 ~R 5 The donor group that can be used has a σp of preferably −0.3 or less, more preferably −0.5 or less, and even more preferably −0.7 or less. For example, it may be selected from the range of −0.9 or less, or from the range of −1.1 or less.

[0018] 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, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.The two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0019] R 1 ~R 5 The donor group which can be taken is preferably a group represented by the following general formula (a). [ka]

[0020] In the general formula (a), Z 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N. Z 5 represents C or N, and Ar 5 R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. 14 and R 15 , R 15 and R 16 , R 16 and R 17 may be bonded to each other to form a cyclic structure.

[0021] Z 1 ~Z 4 Among these, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one embodiment of the present invention, Z1 ~Z 4 In one embodiment of the present invention, the number of N is 1. 1 ~Z 4 Of these, the number of N is 0. R 14 ~R 17 each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the substituent group E. 14 ~R 17 When two or more of R represent substituents, those two or more substituents may be the same or different. 14 ~R 17 Of these, 0 to 2 are preferably 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). R 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 ring in which these are condensed. An aromatic ring or a heteroaromatic ring is preferable. An example of the aromatic ring is a substituted or unsubstituted 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. The heteroaromatic ring means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be adopted 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. Benzofuran, benzothiophene, and indole may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the 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 the 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, 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.

[0022] In the general formula (a), Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. 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. Ar 5 An example of the aromatic ring that can be used is a benzene ring. The benzene ring may be further condensed with another benzene ring or may be condensed with a heterocycle 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, the heteroaromatic ring can be 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. 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 mentioned here may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E.

[0023] Z in general formula (a) 5When is C, it is preferably a group represented by the following general formula (b). [ka]

[0024] In the general formula (b), Z 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N, Z 6 is CR 18 or N, Z 7 is CR 19 or N, Z 8 is CR 20 or N, Z 9 is CR 21 or N. R 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. Z in general formula (b) 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 17Please refer to the explanation in the following. In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 Among these, the number of N is preferably 0 to 2, and more preferably 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 In a preferred embodiment of the present invention, the number of N is 1. 1 ~Z 4 , Z 6 ~Z 9 Among these, the number of N is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0025] R 1 ~R 5 The donor group that R can adopt 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 the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. In addition, the two benzene rings constituting the carbazol-9-yl group may further be condensed with one or more rings. In a preferred embodiment of the present invention, R 1 ~R 5 The donor group may be a carbazol-9-yl group which may be substituted with a group selected from the substituent group E and may have one or more rings condensed thereto. When a compound with a short emission wavelength is desired, it is preferable to adopt a carbazol-9-yl group substituted with a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group. When a carbazol-9-yl group not condensed with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2-7 positions, more preferably at least one of the 3-position or the 6-position, and even more preferably the 3-position and the 6-position.

[0026] In one aspect of the invention, R 1 ~R 5 The donor group R can take is a carbazol-9-yl group having one or more fused rings, which will be referred to below as a "ring-fused carbazol-9-yl group." 1 ~R 5 The ring-fused carbazol-9-yl group may be unsubstituted, or may be substituted with a substituent selected from the substituent group A, or may be substituted with a substituent selected from the substituent group B, or may be substituted with a substituent selected from the substituent group C, or may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from the 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.

[0027] 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).

[0028] The ring-fused carbazole-9-yl group is a group bonded by a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, and may be a ring further fused with these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferable. An example of the aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be further fused with another benzene ring, or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle means a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be adopted 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 the substituent group E (excluding the case where only a deuterium atom is used), and more preferably bonded to an aryl group which may be substituted with an alkyl group or an aryl group. In the present invention, it is preferable to adopt a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms is fused. Among them, a carbazol-9-yl group in which a benzofuro structure is fused, a carbazol-9-yl group in which a benzothieno structure is fused, or a carbazol-9-yl group in which an indolo structure is fused can be preferably adopted. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group in which a benzofuro structure is fused, for example, two or more. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group condensed with a benzothieno structure, for example, has two or more carbazol-9-yl groups.

[0029] 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. In addition, 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. In addition, as the ring-fused carbazol-9-yl group, 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, or a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group can also be used.

[0030] The number of substituents when the ring-fused carbazol-9-yl group is substituted is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or may be, for example, 2. In a preferred embodiment of the present invention, either the 3-position or the 6-position of the ring-fused carbazol-9-yl group is substituted. 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 as viewed from 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 as viewed from 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 a substituent at all of the substitutable para-positions of the benzene ring as viewed from the heteroatom present in the ring-fused carbazol-9-yl group.

[0031] In the following, R in general formula (1) 1 ~R 5 Specific examples of donor groups that can be used are shown below. The specific examples shown here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may be further condensed with a ring), but the donor groups that can be used in the present invention are not limited to the following specific examples. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents a bond position. Methyl groups are not shown, so for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD3. Also, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom. [ka] JPEG2025058779000008.jpg245170JPEG2025058779000009.jpg241170JPEG2025058779000010.jpg238170JPEG2025058779000011.jpg233170JPEG2025058779000012.jpg226170JPEG2025058779000013.jpg216170JPEG2025058779000014.jpg213170JPEG2025058779000015.jpg211170JPEG2025058779000016.jpg212167JPEG2025058779000017.jpg210170JPEG2025058779000018.jpg255170JPEG2025058779000019.jpg238170JPEG2025058779000020.jpg230170JPEG2025058779000021.jpg249170JPEG2025058779000022.jpg238169JPEG2025058779000023.jpg232170JPEG2025058779000024.jpg247170JPEG2025058779000025.jpg242167JPEG2025058779000026.jpg230170JPEG2025058779000027.jpg213170JPEG2025058779000028.jpg224170JPEG2025058779000029.jpg244170JPEG2025058779000030.jpg203170JPEG2025058779000031.jpg229170JPEG2025058779000032.jpg247168JPEG2025058779000033.jpg210170JPEG2025058779000034.jpg244170JPEG2025058779000035.jpg248170JPEG2025058779000036.jpg253170JPEG2025058779000037.jpg245170JPEG2025058779000038.jpg243170JPEG2025058779000039.jpg242164JPEG2025058779000040.jpg216170JPEG2025058779000041.jpg247170JPEG2025058779000042.jpg238166J PEG2025058779000043.jpg212170JPEG2025058779000044.jpg238170JPEG2025058 779000045.jpg229170JPEG2025058779000046.jpg233170JPEG2025058779000047. jpg219170JPEG2025058779000048.jpg206170JPEG2025058779000049.jpg160168.

[0032] D722 to D1180 are disclosed as compounds obtained by substituting all hydrogen atoms present in the above D1 to D459 with deuterium atoms.

[0033] R 1 ~R 5 Among the donor groups that can be used, specific examples other than a substituted or unsubstituted carbazol-9-yl group are listed below. However, the donor groups that can be used in the present invention should not be construed as being limited to the following specific examples. [ka] JPEG2025058779000051.jpg213170JPEG2025058779000052.jpg93170

[0034] All hydrogen atoms present in the above D1181 to D1208 are replaced with deuterium atoms and are disclosed as D1233 to D1260. In one aspect of the invention, R 1 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D1260. 1 ~R 5 The donor group that can be taken by R 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 can be taken by R is selected from the group consisting of D460 to D1180 and D1214 to D1260. 1 ~R 5 The donor group which can be taken is selected from the group consisting of D460 to D1180. In a preferred embodiment of the present invention, R 1 ~R 5 The donor groups that can be used 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 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 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.

[0035] In one aspect of the invention, R 5 is a donor group. In one embodiment of the present invention, R4 is a donor group. In one embodiment of the present invention, R 3 is a donor group, and R 2 is a group represented by general formula (A). In one embodiment of the present invention, R 2 is a donor group, and R 3 is a group represented by general formula (A). In one embodiment of the present invention, R 1 is a donor group.

[0036] R in general formula (1) 1 ~R 5 One or two of these are substituted or unsubstituted aryl groups. R 1 ~R 5 The aryl group may be a single 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 naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected from, for example, the substituent group A, the substituent group B, the substituent group C, the substituent group D, or the 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 aspect of the invention, the aryl group is unsubstituted. In the following, R 1 ~R 5Specific examples of substituted or unsubstituted aryl groups that can be used are given below. However, the aryl groups that can be used in the present invention should not be construed as being limited to 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. [ka] JPEG2025058779000054.jpg206167JPEG2025058779000055.jpg148164

[0037] 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 that order. In one aspect of the invention, R 1 ~R 5 The aryl group that can be taken by R is selected from the group consisting of Ar1 to Ar69. 1 ~R 5 The aryl group R may be 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 can be taken by R is selected from the group consisting of Ar26 to Ar69. 1 ~R 5 The aryl group which can be taken is selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64.

[0038] In one aspect of the invention, R 1 ~R 5 In one embodiment of the present invention, only one of R 1 ~R 5 Two of the groups are substituted or unsubstituted aryl groups. In a preferred embodiment of the present invention, at least R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least R 3 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least R 2 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least R 1 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 4 and R 5 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 3 and R 4 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 2 and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 3 and R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 and R 5 is a substituted or unsubstituted aryl group.

[0039] R in general formula (1) 1 ~R 5 In one embodiment of the present invention, one or two of R 1 ~R 5 In one embodiment of the present invention, only one of R 1 ~R 5 Two of the atoms are hydrogen or deuterium. In a preferred embodiment of the present invention, at least R 1 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 2 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 3is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 4 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 5 is a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, R 1 In a preferred embodiment of the present invention, only R 5 In a preferred embodiment of the present invention, only R 1 and R 5 is a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, R 1 and R 2 is a hydrogen atom or a deuterium atom.

[0040] R 1 ~R 5 is never a cyano group. Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 do not bond to each other to form a ring structure.

[0041] In the general formula (1), Z and R 2 , or Z and R 3 In one embodiment of the present invention, Z and R 2 are the same group represented by general formula (A). In one embodiment of the present invention, Z and R 3 is the same group represented by general formula (A).

[0042] [ka]

[0043] In the general formula (A), X 1 and X 2 Each independently represents N or CY. Each Y independently represents a hydrogen atom, a deuterium atom, or a cyano group. 1 and X2 are not both C-CN. 1 and Ar 2 Each of X independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and X 2 When is N, Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted heteroaryl group. L represents a single bond or a divalent linking group. * represents the bonding position.

[0044] X in general formula (A) 1 is N or CR 6 represents X 2 is N or CR 7 Represents R 6 and R 7 each independently represents a hydrogen atom, a deuterium atom, or a cyano group. In one aspect of the invention, X 1 and X 2 are both N. In one embodiment of the present invention, X 1 is N and X 2 CR 7 and preferably R 7 is a cyano group, for example, R 7 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, X 2 is N and X 1 CR 6 For example, R 6 is a cyano group, for example, R 6 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, X 1 CR 6 and X 2 CR 7 Then, R 6 and R 7 and X cannot both be cyano groups. 1 CR 6 and X 2 CR 7 In one aspect of the present invention, when 6 and R 7Only one of the X's is a cyano group, and the other is a hydrogen atom or a deuterium atom. 1 CR 6 and X 2 CR 7 In one aspect of the present invention, when 6 and R 7 are each independently a hydrogen atom or a deuterium atom.

[0045] Ar in general formula (A) 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar 1 and Ar 2 The substituted or unsubstituted aryl group may be a single 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 pyrene ring. Specific examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14 or 6 to 10. Ar 1 and Ar 2 Specific examples of the substituted or unsubstituted aryl group that may be taken by R 1 ~R 5 Specific examples of the substituted or unsubstituted aryl group which may be taken by the formula (I) can be referred to. Ar 1 and Ar 2The substituted or unsubstituted heteroaryl group which may be taken by is preferably a group bonded via a nitrogen atom constituting an aromatic heterocycle. Examples of the aromatic heterocycle containing a bonded nitrogen atom include a pyrrole ring, a pyridine ring, a pyrimidine ring, and a triazine ring. These aromatic heterocycles containing a bonded nitrogen atom may be substituted, or may be condensed with other rings. Examples of the other rings include an aromatic hydrocarbon ring and an aromatic heterocycle, and the ring to which these rings are further condensed may be condensed with the aromatic heterocycle containing a nitrogen atom. In one embodiment of the present invention, Ar 1 and Ar 2 Examples of the substituted or unsubstituted heteroaryl group that can be taken by R include the donor group represented by the above general formula (a), and further include the donor group represented by the above general formula (b). 1 ~R 5 The explanation and specific examples of the donor groups that can be used can be referred to. In one aspect of the present invention, Ar 1 and Ar 2 is a substituted or unsubstituted aryl group. In one aspect of the present invention, Ar 1 and Ar 2 One of the groups is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted carbazol-9-yl group). 1 and Ar 2 is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted carbazol-9-yl group). 1 and X 2 When is N, Ar 1 and Ar 2 At least one of the groups is a substituted or unsubstituted heteroaryl group. Ar 1 and Ar 2 The substituted or unsubstituted carbazol-9-yl group in the above general formula (b) can be represented by the following formula: 1 ~Z 4 , Z 6 ~Z 9In other words, Z in the general formula (b) corresponds to the case where none of 1 is CR 14 represents Z 2 is CR 15 represents Z 3 is CR 16 represents Z 4 is CR 17 represents Z 6 is CR 18 represents Z 7 is CR 19 represents Z 8 is CR 20 represents Z 9 is CR 21 This corresponds to the case where Ar 1 and Ar 2 The substituted or unsubstituted carbazol-9-yl group which may be taken by R may be a carbazol-9-yl group having one or more fused rings. For the explanation and preferred range of the substituted or unsubstituted carbazol-9-yl group including such a ring-fused carbazol-9-yl group, see R 1 ~R 5 The corresponding description of Ar 1 and Ar 2 Specific examples of the substituted or unsubstituted carbazol-9-yl group that can be taken by Ar include D1 to D1180 above. 1 and Ar 2 Regarding the groups that can be selected as well as the preferred groups, the above descriptions related to D1 to D1180 can be referred to. 1 and Ar 2 The 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 Ar 1 and Ar 2 The substituted or unsubstituted carbazol-9-yl group represented by R 1 ~R 5 The structure of the donor group represented by one of the groups is different.

[0046] In general formula (A), 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 represented by the above R. 1 ~R 5 Refer to the description and preferred range of the aryl group in the description section of "1. Heteroarylene group" can be exemplified by a linking group in which at least one of the ring skeleton carbon atoms constituting an arylene group is substituted with a nitrogen atom. Specific examples of L are given below. However, L that can be adopted in the present invention is not limited to these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates a bond position. L1 is a single bond.

[0047] [ka]

[0048] All hydrogen atoms present in the above L2 to L13 are replaced 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, L14 to L19. In one aspect of the present invention, L is selected from the group consisting of L1, L8 to L13, 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.

[0049] Examples of compounds represented by general formula (1) are given below. As the compound group 1 of the present invention, X represented by the general formula (A) 1 and X 2Compound group 1 is a compound group in which R 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 1a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 1b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 1c in which each of R is independently a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group. For each of these compound groups 1a to 1d, there can be mentioned an embodiment that further satisfies the following additional condition. 1 is a donor group. In one embodiment of the present invention, R 2 or R 3 is a donor group. In one embodiment of the present invention, R 4 is a donor group. In one embodiment of the present invention, R 5 is a donor group. In one embodiment of the present invention, R 1 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 or R 3 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 2 or R 3is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 4 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 5 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, R 4 and R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 and R 4 , or R 3 and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 and R 5 , or R 3 and R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 ~R 5 are hydrogen or deuterium atoms. 1 and R 5 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 1 and R 2 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 2 and R 5 , or R 3 and R 5 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R 1 and R 5 is a hydrogen atom or a deuterium atom, and R 2 or R 3 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 2 or R 3 is a donor group, and R 4 and R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R5 is a hydrogen atom or a deuterium atom, and R 2 or R 3 is a donor group, and R 1 and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 2 and R 5 , or R 3 and R 5 is a hydrogen atom or a deuterium atom, and R 1 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 and R 2 , or R 1 and R 3 is a hydrogen atom or a deuterium atom, and R 5 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 5 is a donor group, and R 2 and R 4 , or R 3 and R 4 is a substituted or unsubstituted aryl group.

[0050] As the compound group 2 of the present invention, X represented by the general formula (A) 1 is N and X 2 CR 7 and R 7 Compound group 2 is a compound group in which R in general formula (1) is a hydrogen atom or a deuterium atom, and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 2a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 2b in which R is a substituted or unsubstituted heteroaryl group;2 is a group represented by general formula (A), and Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group; and R 3 is a group represented by general formula (A), and Ar 1 and Ar 2 R in the general formula (1) is a compound group 2d in which each independently represents a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 2e, in which each of R is independently a substituted or unsubstituted aryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group. For each of these compound groups 2a to 2f, there can be mentioned an embodiment which further satisfies the additional conditions described for compound groups 1a to 1d.

[0051] As the compound group 3 of the present invention, X represented by the general formula (A) 1 is N and X 2 CR 7 and R 7 Compound group 3 is a compound group in which R in general formula (1) is a cyano group and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 3a in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 3b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2are each independently a substituted or unsubstituted heteroaryl group; and 3 is a group represented by general formula (A), and Ar 1 and Ar 2 R in the general formula (1) is a compound group 3d in which each independently represents a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 and compound group 3e, each of which is independently a substituted or unsubstituted aryl group; and compound group 3b, each of which is independently a substituted or unsubstituted aryl group, 3 is a group represented by general formula (A), and Ar 1 and Ar 2 and each independently represent a substituted or unsubstituted aryl group. For each of these compound groups 3a to 3f, examples can be given of an embodiment that further satisfies the additional conditions described for compound groups 1a to 1d.

[0052] As the compound group 4 of the present invention, X represented by the general formula (A) 1 CR 6 and X 2 is N and R 6 Compound group 4 is a compound group in which R in general formula (1) is a hydrogen atom or a deuterium atom, and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 4a in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 4b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 4c in which each of R is independently a substituted or unsubstituted heteroaryl group; 3is a group represented by general formula (A), and Ar 1 and Ar 2 R in the general formula (1) is a compound group 4d in which each independently represents a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 4e in which each of R is independently a substituted or unsubstituted aryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group. For each of these compound groups 4a to 4f, there can be mentioned an embodiment which further satisfies the additional conditions described for compound groups 1a to 1d.

[0053] As the compound group 5 of the present invention, X 1 CR 6 and X 2 is N and R 6 Compound group 5 is a compound group in which R in general formula (1) is a cyano group and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 5a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 5b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 and compound group 5c, in which each of R 3 is a group represented by general formula (A), and Ar 1 and Ar 2R in the general formula (1) is a compound group 5d in which each independently represents a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 and compound group 5e, each of which is independently a substituted or unsubstituted aryl group; and compound group 5e, each of which is independently a substituted or unsubstituted aryl group, 3 is a group represented by general formula (A), and Ar 1 and Ar 2 and each independently represent a substituted or unsubstituted aryl group. For each of these compound groups 5a to 5f, examples can be given of an embodiment that further satisfies the additional conditions described for compound groups 1a to 1d.

[0054] As the compound group 6 of the present invention, X represented by the general formula (A) 1 CR 6 and X 2 CR 7 and R 6 and R 7 Compound group 6 includes a compound group in which R 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 6a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 6b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 6c in which each of R is independently a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2R in the general formula (1) is a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 and compound group 6e, each of which is independently a substituted or unsubstituted aryl group; and compound group 6b, each of which is independently a substituted or unsubstituted aryl group, 3 is a group represented by general formula (A), and Ar 1 and Ar 2 and each independently represent a substituted or unsubstituted aryl group. For each of these compound groups 6a to 6f, examples can be given of an embodiment that further satisfies the additional conditions described for compound groups 1a to 1d.

[0055] As the compound group 7 of the present invention, X 1 CR 6 and X 2 CR 7 and R 6 is a cyano group, and R 7 Compound group 7 is a compound group in which R in the general formula (1) is a hydrogen atom or a deuterium atom, and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 7a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 7b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 7c, in which each of R 3 is a group represented by general formula (A), and Ar 1 and Ar 2R in the general formula (1) is a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 7e, in which each of R is independently a substituted or unsubstituted aryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2 and each independently represent a substituted or unsubstituted aryl group. For each of these compound groups 7a to 7f, there can be mentioned an embodiment which further satisfies the additional conditions described for compound groups 1a to 1d.

[0056] As the compound group 8 of the present invention, X 1 CR 6 and X 2 CR 7 and R 6 is a hydrogen atom or a deuterium atom, and R 7 Compound group 8 is a compound group in which R in general formula (1) is a cyano group and L is a single bond. 2 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 8a, in which R is a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 is a substituted or unsubstituted aryl group, Ar 2 Compound group 8b in which R is a substituted or unsubstituted heteroaryl group; 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 8c in which each of R is independently a substituted or unsubstituted heteroaryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2R in the general formula (1) is a substituted or unsubstituted heteroaryl group. 2 is a group represented by general formula (A), and Ar 1 and Ar 2 Compound group 8e, in which each of R is independently a substituted or unsubstituted aryl group; 3 is a group represented by general formula (A), and Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group. For each of these compound groups 8a to 8f, there can be mentioned an embodiment which further satisfies the additional conditions described for compound groups 1a to 1d.

[0057] In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 1 to 5. In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 2 to 5. In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 6 to 8. In one embodiment of the present invention, the compound is selected from compound groups 3, 5, 7, and 8 (e.g., from compound groups 3 and 5). In one embodiment of the present invention, the compound is selected from compound groups 1, 2, 4, and 6 (e.g., from compound groups 1, 2, and 4, or from compound groups 2 and 4). In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 1a, 1c, 2a, 2c, 2e, 3a, 3c, 3e, 4a, 4c, 4e, 5a, 5c, 5e, 6a, 6c, 6e, 7a, 7c, 7e, 8a, 8c, and 8e, for example, from compound groups 1a, 1c, 2a, 2c, 2e, 3a, 3c, 3e, 4a, 4c, 4e, 5a, 5c, and 5e, for example, from compound groups 1a and 1c, for example, from compound groups 2a, 2c, 2e, 3a, 3 Select from, for example, c, 3e, 4a, 4c, 4e, 5a, 5c, 5e; select from, for example, 1a, 2a, 3a, 4a, 5a, 6a, 7a, 8a; select from, for example, 1c, 2c, 3c, 4c, 5c, 6c, 7c, 8c; select from, for example, 2f, 3f, 4f, 5f, 6f, 7f, 8f; select from, for example, 1a, 2a, 3a, 4a, 5a; select from, for example, 1c, 2c, 3c, 4c, 5c; select from, for example, 2f, 3f, 4f, 5f.In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 1b, 1d, 2b, 2d, 2f, 3b, 3d, 3f, 4b, 4d, 4f, 5b, 5d, 5f, 6b, 6d, 6f, 7b, 7d, 7f, 8b, 8d, and 8f, for example, from compound groups 1b, 1d, 2b, 2d, 2f, 3b, 3d, 3f, 4b, 4d, 4f, 5b, 5d, and 5f, for example, from compound groups 1b and 1d, for example, from compound groups 2b, 2d, 2f, 3b, 3 d, 3f, 4b, 4d, 4f, 5b, 5d, 5f, for example, selecting from 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, for example, selecting from 1d, 2d, 3d, 4d, 5d, 6d, 7d, 8d, for example, selecting from 2f, 3f, 4f, 5f, 6f, 7f, 8f, for example, selecting from 1b, 2b, 3b, 4b, 5b, for example, selecting from 1d, 2d, 3d, 4d, 5d, for example, selecting from 2f, 3f, 4f, 5f.

[0058] In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound groups 1a, 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5a, 5b, 6a, 6b, 7a, 7b, 8a, 8b, e.g., from compound groups 1a, 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5a, 5b, e.g., from compound groups 1a and 1b, e.g., from compound groups 2a, 2b, 3a, 3b, 4a, 4b, 5a, 5b, e.g., from 1a, 2a, 3a, 4a, 5a, 6a, 7a, 8a, e.g., from 1b, 2b, 3b, 4b, 5b, 6b, 7b, 8b, e.g., from 1a, 2a, 3a, 4a, 5 .... In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound group 1c, 1d, 2c, 2d, 3c, 3d, 4c, 4d, 5c, 5d, 6c, 6d, 7c, 7d, 8c, 8d, for example, selected from compound group 1c, 1d, 2c, 2d, 3c, 3d, 4c, 4d, 5c, 5d, for example, selected from compound group 1c, 1d, for example, selected from compound group 2c, 2d, 3c, 3d, 4c, 4d, 5c, 5d, for example, selected from 1c, 2c, 3c, 4c, 5c, 6c, 7c, 8c, for example, selected from 1d, 2d, 3d, 4d, 5d, 6d, 7d, 8d, for example, selected from 1c, 2c, 3c, 4c, 5c, for example, selected from 1d, 2d, 3d, 4d, 5d. In one embodiment of the present invention, the compound represented by general formula (1) is selected from compound group 2e, 2f, 3e, 3f, 4e, 4f, 5e, 5f, 6e, 6f, 7e, 7f, 8e, 8f, for example, selected from compound group 2e, 2f, 3e, 3f, 4e, 4f, 5e, 5f, for example, selected from compound group 2e, 3e, 4e, 5e, 6e, 7e, 8e, for example, selected from 2f, 3f, 4f, 5f, 6f, 7f, 8f, for example, selected from 2e, 3e, 4e, 5e, for example, selected from 2f, 3f, 4f, 5f.

[0059] When it is desired to provide a compound that emits light at a short wavelength, it is preferable to employ a compound that has 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 in the molecule, and also has a cyano group.

[0060] The compound represented by the general formula (1) preferably does not contain metal atoms, and may be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by the general formula (1) may also be a compound composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen ... and nitrogen atoms. Furthermore, the compound represented by the general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.

[0061] 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 selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 ring skeleton atoms), 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. In this specification, "substituent group B" means 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 skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). In this specification, the term "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 skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" 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), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms). As used herein, the term "substituent group E" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted", the substituent may be selected, for example, from Substituent Group A, or may be selected from Substituent Group B, or may be selected from Substituent Group C, or may be selected from Substituent Group D, or may be selected from Substituent Group E.

[0062] Specific examples of the compound represented by general formula (1) are shown in the following Tables 1 to 4. 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 the general formula (1), R 1 and R 3is a hydrogen atom, and R 2 is a group represented by general formula (A), and R 4 is a phenyl group (Ar1), and X in the general formula (A) 1 and X 2 are both N, and Ar 1 is a perdeuterated phenyl group (Ar45), and Ar 2 is a perdeuterated carbazol-9-yl group (D722), L is a single bond, 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 showing them in order in Table 1. [ka] [Table 1] JPEG2025058779000060.jpg246170JPEG2025058779000061.jpg245169JPEG2025058779000062.jpg251160

[0063] In Table 2, the structures of compounds 1 to 86940 are shown as variations of the structures shown in Table 1. In Table 2, among the compounds represented by general formula (1), R 1 and R 3 is a hydrogen atom, and R 2 is a group represented by general formula (A), and X in general formula (A) 1 and X 2 are both N, and Ar 1 is a perdeuterated phenyl group (Ar45), and Ar 2 is a perdeuterated carbazol-9-yl group (D722), L is a single bond, and R 4 is 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. The columns of compounds 1 to 1260 in Table 2 are1 and R 3 is fixed to a hydrogen atom, and R 2 is fixed to a group represented by general formula (A), and X 1 and X 2 are both fixed to N, and Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2 is fixed to a perdeuterated carbazol-9-yl group (D722), L is fixed to a single bond, and R 4 is fixed at Ar1, and R 5 In other words, the columns of compounds 1 to 1260 in Table 2 show the structures of compounds 1 to 1260 in Table 1 all together in one column. The columns of compounds 1261 to 2520 in Table 2 show the structures of compounds 1 to 1260 in Table 1 all together in one column. 1 and R 3 is fixed to a hydrogen atom, and R 2 is fixed to a group represented by general formula (A), and X 1 and X 2 are both fixed to N, and Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2 is fixed to a perdeuterated carbazol-9-yl group (D722), L is fixed to a single bond, and R 4 is fixed at Ar2, and R 5 The compounds 2521 to 3780 in Table 2 are identified as compounds 1261 to 2520 in the order of D1 to D1260. 1 and R 3 is fixed to a hydrogen atom, and R 2 is fixed to a group represented by general formula (A), and X 1 and X 2 are both fixed to N, and Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2 is fixed to a perdeuterated carbazol-9-yl group (D722), L is fixed to a single bond, and R 4 is fixed at Ar3, and R 5The compounds D1 to D1260 are identified as compounds 2521 to 3780 in the order of D1 to D1260. The structures of the compounds are identified in the same way in the subsequent rows, and the final row of compounds 85681 to 86940 is identified as compounds 2521 to 3780 in the order of D1 to D1260. 1 and R 3 is fixed to a hydrogen atom, and R 2 is fixed to a group represented by general formula (A), and X 1 and X 2 are both fixed to N, and Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2 is fixed to a perdeuterated carbazol-9-yl group (D722), L is fixed to a single bond, and R 4 is fixed to Ar69, and R 5 The compounds D1 to D1260 are identified as compounds 85681 to 86940, respectively. [ka] [Table 2]

[0064] In Table 3, the structures of compounds 1 to 1897560 are shown as variations of the structures shown in Table 2. In Table 3, X in general formula (1) 1 , X 2 , Ar 1 , Ar 2 , L, R 1 ~R 5 The structure is specified by indicating "-" in the L column of Table 3. The column for compounds 1 to 86940 in Table 3 indicates X 1 and X 2 is fixed at N, and Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2 is fixed to a perdeuterated carbazol-9-yl group (D722), 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 69, and R 5Compounds 1 to 86940 are identified as those in which R is any one of D1 to D1260. 4 varies from Ar1 to 69, and R 5 The number of R that appears first (the number on the left side of Table 3) is fixed first, and the number of R that appears later (the number on the right side of Table 3) is varied, and the compound numbers are assigned in order. 4 First, fix it to Ar1, and then use R 5 The compounds D1 to D1260 are identified as compounds 1 to 1260 in order. 4 Fix Ar2 and R 5 The compounds D1 to D1260 are identified as compounds 1261 to 2520, respectively. Next, R 4 Fix Ar3 and R 3 The compounds D1 to D1260 are identified in order as compounds 2521 to 3780. By continuing the identification in the same manner, 4 Fixed to Ar69, R 5 The compounds D1 to D1260 are identified as compounds 85681 to 86940 in order. That is, the columns of compounds 1 to 86940 in Table 3 show the structures of compounds 1 to 86940 in Table 2 all together in one column. The columns of compounds 86941 to 173880 in Table 3 and the bottom columns of compounds 1810621 to 1897560 are identified in the same manner. Note that, as described in the rightmost column of Table 3, for example, for the columns of compounds 86941 to 173880, R 4 and R 5 is the same. [Table 3]

[0065] In Table 3, Ar 1 is fixed to a perdeuterated phenyl group (Ar45), and Ar 2The structure in which is a perdeuterated carbazol-9-yl group (D722) was identified as the structure of compounds 1 to 1897560. Table 4 shows the structure of each of compounds 1 to 1897560. 1 and Ar 2 The compounds in which the Ar group is changed as shown in Table 4 are displayed in the form of a table. 1 is a perdeuterated phenyl group (Ar45), and Ar 2 Compounds 1 to 1897560, in which the Ar group is a perdeuterated carbazol-9-yl group (D722), are shown in the first row. In the second row of Table 4, for example, compound 1(1) is 2 Compound 2(1) is a compound having a structure in which Ar of Compound 2 is substituted with D1. 2 In the same manner, compound 1897560(1) is the compound 1897560 with Ar replaced by D1. 2 The structures of compounds 1(2) to 1897560(2) onward in the third row are specified in the same manner as in the second row. [Table 4] JPEG2025058779000067.jpg255147JPEG2025058779000068.jpg255146JPEG2025058779000069.jpg255152JPEG20250587790 00070.jpg255148JPEG2025058779000071.jpg255154JPEG2025058779000072.jpg255163JPEG2025058779000073.jpg162160

[0066] All compounds identified by the above numbers are considered to be individually disclosed. In addition, when rotamers exist among the above specific compound examples, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification. In one embodiment of the present invention, a compound is selected from the group of compounds specified in Table 4. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 1897560 and compounds 1(n) to 1897560(n) [wherein n is 1 to 772]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 1897560 and compounds 1(n) to 1897560(n) [wherein n is 1 to 704]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 1897560 and compounds 1(n) to 1549800(n) [wherein n is 1 to 704]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1549801 to 1897560 and compounds 1549801(n) to 1897560(n) [wherein n is 1 to 772].

[0067] Preferred examples of the compounds represented by formula (1) are given below. [ka] JPEG2025058779000075.jpg145165

[0068] Other preferred examples of the compounds represented by formula (1) are given below. [ka] JPEG2025058779000077.jpg82170

[0069] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0070] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0071] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0072] Preferred examples of the compounds represented by formula (1) are given below. [ka]

[0073] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0074] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0075] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0076] Other preferred examples of the compounds represented by formula (1) are given below. [ka]

[0077] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by deposition, for example, 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. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by the general formula (1) may be formed into a film by a coating method regardless of the molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by the general formula (1) has the advantage that it is easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method to, and is easy to purify to increase the purity.

[0078] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and the polymer may be polymerized to obtain a polymer, which may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, which may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled together to obtain a dimer or trimer, which may be used as a light-emitting material.

[0079] 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. [ka]

[0080] 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 further preferably 2 to 10. The linking group is -X 11 -L 11 In this case, it is preferable that X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.11 represents a linking group, which is preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenylene group. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represents a substituent, preferably 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 further 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 can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0081] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0082] A polymer having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any site of general formula (1), reacting the hydroxyl group as a linker with the compound below to introduce a polymerizable group, and polymerizing the polymerizable group. [ka]

[0083] The polymer containing the structure represented by general formula (1) in the molecule may be a polymer consisting of only repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type or of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, examples of repeating units include those derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene.

[0084] In an embodiment, the compound represented by the general formula (1) is a light-emitting material. The compounds represented by the general formula (1) include compounds with a short luminescence life of delayed fluorescence. For example, the compounds represented by the general formula (1) include compounds with high alignment. The compounds represented by the general formula (1) can improve the luminescence characteristics when used in an organic light-emitting device. For example, the compounds represented by the general formula (1) include compounds that can extend the element life when used in an organic light-emitting device. For example, the compounds represented by the general formula (1) include compounds that can improve the luminous efficiency when used in an organic light-emitting device. In an embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence. The compounds represented by the general formula (1) include compounds having a large proportion of delayed fluorescent components. For example, the compounds include compounds having delayed fluorescent components that account for 80% or more of the total emission, and for example, compounds having delayed fluorescent components that account for 90% or more of the total emission. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, 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, the compounds represented by general formula (1) can emit light in the red or orange region of the visible spectrum (e.g., from about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) 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) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) are capable of emitting light in the blue region of the visible spectrum (e.g., from about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet region of the spectrum (eg, 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means. In an embodiment of the present disclosure, an organic semiconductor element can be produced using a compound represented by general formula (1). The organic semiconductor element may be an organic optical element in which light is mediated, or an organic element in which light is not mediated. The organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element in which energy transfer occurs by light within the element. In an embodiment of the present disclosure, an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be produced using a compound represented by general formula (1). In an embodiment of the present disclosure, a CMOS (complementary metal oxide semiconductor) or the like can be produced using a compound represented by general formula (1).

[0085] The electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations. For example, the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) can be solved using time-dependent density functional theory with a family of functions known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals as a basis to screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, the donor moiety ("D") can be selected, for example, for its HOMO energy (e.g., ionization potential) of -6.5 eV or greater, and the acceptor moiety ("A") can be selected, for example, for its LUMO energy (e.g., electron affinity) of -0.5 eV or less. The bridging moiety ("B") prevents overlap between the pi-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly restrict the acceptor and donor moieties to specific conformations. In one embodiment, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. ΔE below a certain value STvalue 4. Quantum yield above a certain value 5.HOMO level 6.LUMO Level In one embodiment, 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 value 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 compounds represented by general formula (1) exhibit 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.

[0086] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by the general formula (1) include novel compounds. The compound represented by the general formula (1) can be synthesized by combining known reactions. 1 ~R 5 One of the groups is a donor group, and for example, a substituted or unsubstituted carbazole can be reacted with a precursor in which the donor group is a fluorine atom to synthesize a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is a donor group. For details of the reaction conditions, refer to the synthesis examples described later. The compound represented by the general formula (1) has the advantage that it requires fewer steps for synthesis and has a better yield than the compound described in, for example, WO2022 / 031033A1. Compound 3-3 described in WO2022 / 031033A1 is synthesized in four steps, but the compound represented by the general formula (1) can be synthesized in three steps or less. In addition, in WO2022 / 031033A1, since the substrate and triazine have chlorine atoms in the reaction of boronic acid and triazine chloride, a decrease in yield due to reaction selectivity is unavoidable, but the compound represented by the general formula (1) can be synthesized without going through such steps.

[0087] [Constructs using the compound represented by general formula (1)] In some embodiments, the compound of formula (1) is 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 compound to form a solid film or layer. For example, the compound of formula (1) can be combined with an electroactive material to form a film. In some cases, the compound of formula (1) can be combined with a hole transport polymer. In some cases, the compound of formula (1) can be combined with an electron transport polymer. In some cases, the compound of formula (1) can be combined with a hole transport polymer and an electron transport polymer. In some cases, the compound of formula (1) can be combined with a copolymer having both hole transport and electron transport moieties. In these embodiments, electrons and / or holes formed in the solid film or layer can interact with the compound of formula (1).

[0088] [Film formation] In an embodiment, 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, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In an embodiment, 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 an embodiment, the film containing the compound of the present invention can be formed by a dry process. In an embodiment, the dry process can be a vacuum deposition method, but is not limited thereto. When the vacuum deposition method is adopted, the compounds constituting the film may be co-deposited from individual deposition sources, or may be co-deposited from a single deposition source in which the compounds are mixed. When a single deposition source is used, a mixed powder in which powders of the compounds are mixed may be used, or a compression molded body in which the mixed powder is compressed may be used, or a mixture in which each compound is heated, melted, and cooled may be used. In an embodiment, a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source can be formed by performing co-deposition under conditions in which the deposition rates (weight reduction rates) of the multiple compounds contained in a single deposition source are the same or almost the same. If the multiple compounds are mixed in the same composition ratio as the composition ratio of the film to be formed and used as the deposition source, a film having a desired composition ratio can be easily formed. In an embodiment, a temperature at which each compound to be co-deposited has the same weight reduction rate can be specified, and the temperature can be used as the temperature during co-deposition.

[0089] [Examples of use of the compound represented by formula (1)] The compound represented by the general formula (1) is useful as a material for an organic light-emitting device, and is particularly preferably used for an organic light-emitting diode. Organic Light Emitting Diode: One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention as a light-emitting material of an organic light-emitting device. In an embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In an embodiment, the compound represented by the general formula (1) includes a delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In an embodiment, the present invention provides a delayed fluorescent material having a structure represented by the general formula (1). In an embodiment, the present invention relates to the use of a compound represented by the general formula (1) as a delayed fluorescent material. In an embodiment, the compound represented by the general formula (1) can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF. In an embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In an embodiment, the compound represented by the general formula (1) can be used as an electron transport material. In an embodiment, the present invention relates to a method for generating delayed fluorescence from a compound represented by the general formula (1). In an embodiment, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer comprises a compound represented by formula (1), and the compound represented by 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 formula (1) relative to the film-forming surface affects or dictates 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 formula (1) improves the efficiency of light extraction from the light-emitting layer. One aspect of the present invention relates to an organic light-emitting device. In an embodiment, the organic light-emitting device includes an emitting layer. In an embodiment, the emitting layer includes a compound represented by general formula (1) as an emitting material. In an embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In an embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In an embodiment, the compound represented by general formula (1) assists the light emission of other emitting materials included in the emitting layer (as a so-called assist dopant or host material). The light-emitting layer containing an assist dopant contains at least a host material, an assist dopant, and a light-emitting material. The host material has the highest excited singlet energy level, and the light-emitting material has the lowest. In addition, the amount of light emitted from the light-emitting layer is the largest from the light-emitting material. The host material may be a delayed fluorescent material or a material that does not emit delayed fluorescence. The light-emitting layer may contain two or more host materials, in which case some or all of them may be delayed fluorescent materials, or all of them may be materials that do not emit delayed fluorescence. The light-emitting material may be a delayed fluorescent material or a material that does not emit delayed fluorescence, and may be a fluorescent material or a phosphorescent material. In the light-emitting layer containing an assist dopant, the compound represented by general formula (1) may be used as a host material, an assist dopant, or a light-emitting material. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least a light-emitting layer. In some embodiments, the organic layer includes only a light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with a hole injection function, and the electron transport layer may be an electron injection transport layer with an electron injection function.

[0090] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. In some embodiments, the light-emitting layer includes a light-emitting material and a host material. In some embodiments, the light-emitting material is one or more compounds represented by general formula (1). In some embodiments, in order to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet excitons and triplet excitons generated in the light-emitting material are trapped in the light-emitting material. In some embodiments, a host material is used in the light-emitting layer in addition to the light-emitting material. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has an excited singlet energy and an excited triplet energy, at least one of which is higher than those of the light-emitting material of the present invention. In some embodiments, the singlet excitons and triplet excitons generated in the light-emitting material of the present invention are trapped in the molecules of the light-emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently trapped to improve the light emission efficiency. In some embodiments, the host material in which the singlet and triplet excitons are not sufficiently trapped, i.e., high light emission efficiency can be achieved, although high light emission efficiency is still obtained, can be used in the present invention without any particular limitation. 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 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.

[0091] When the compound represented by the general formula (1) is used as an assist dopant, various compounds can be used as a light-emitting material (preferably a fluorescent material). As such light-emitting materials, anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), and the like can be used. These exemplary skeletons may or may not have a substituent. These exemplary skeletons may be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.

[0092] [ka] JPEG2025058779000090.jpg228162JPEG2025058779000091.jpg223170JPEG2025058779000092.jpg57167

[0093] 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 the assist dopant having the structure represented by general formula (1).

[0094] Further preferred light-emitting materials include compounds represented by the following general formula (2). [ka]

[0095] In the 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 together to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 may be bonded to each other to form a cyclic structure. 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of the groups is O or NR, and the remaining group may be O or NR or may not be linked. When not linked, each of the two ends 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.

[0096] In one aspect of the invention, X 2 When is O or NR, R 7 is an acceptor group or R 6 and R 7 are bonded together to form an acceptor group, or R 7 and R 8 are bonded to each other to form an acceptor group. 3 When is O or NR, R 10 is an acceptor group or R 9 and R 10 are bonded together to form an acceptor group, or R 10 and R 11 are bonded to each other to form an acceptor group. 4 When is O or NR, R 15 is an acceptor group or R 14 and R 15 are bonded together to form an acceptor group, or R 15 and R 16 are bonded to each other to form an acceptor group. 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 it 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 it 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 16In one embodiment of the present invention, when X is directly bonded to the carbon atom to which it 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 1 is bonded to the carbon atom to form a carbazole ring, the 3-position of the carbazole ring is substituted with an acceptor group (wherein the 3-position is on the phenyl group). In one embodiment of the present invention, the compound is represented by the following general formula (2a). [ka]

[0097] 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 together to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. R 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. X 2 ~X 4 Of these, X 3 and X 4At least one of the groups is O or NR, and the remaining group may be O or NR or may not be linked. When not linked, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2 Each of the groups independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 , C.R. 3 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0098] Further preferred light-emitting materials include compounds represented by the following general formula (3). [ka]

[0099] In the 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 , R10 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.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.

[0100] In one aspect of the invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. In one embodiment of the present invention, R 3 and R 10 are each independently a substituted amino group. 1 and R 3 , and R 2 and R 10 At least one combination of the above is bonded to each other to form a cyclic structure. In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0101] Further preferred light-emitting materials include compounds represented by the following general formula (4). [ka]

[0102] In the 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 ring structure. 1 , Z 2 , R 1 and R 2 are bonded together to form a ring, R 2 and R 3 are bonded together to form a ring, R 4 and R 5 A ring formed by bonding together with R 5 and R 6 At least one of the rings formed by bonding to each other is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole, and R 1 ~R 9 At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or 1 and Z 2 At least one of the 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.

[0103] 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 together to form a ring, R 2 and R 3 are bonded together to form a ring, R 4 and R 5 A ring formed by bonding together with 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, the benzothiophene ring, and the indole ring.

[0104] Further preferred light-emitting materials include compounds having a fused ring structure A (wherein a hydrogen atom in the structure 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. [ka]

[0105] 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, and Z and X 2 may be bonded to each other to form a cyclic structure. In the fused ring structure A, the structure fused to b and X 1 , b and Z, Z and X 2 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 (5). [ka]

[0107] In the general formula (5), Z 1represents 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 of Z 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 ring structure, provided that R 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.

[0108] Further preferred light-emitting materials include compounds represented by the following general formula (6). [ka]

[0109] In the general formula (6), X 3 represents an oxygen atom or a sulfur atom, and 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 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2and 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 ring structure, provided that R 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.

[0110] Further preferred light-emitting materials include compounds represented by the following general formula (7). [ka]

[0111] In the general formula (7), X 4 represents an oxygen atom or a sulfur atom, and 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 ring structure, provided that R2 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.

[0112] Further preferred light-emitting materials include compounds represented by the following general formula (8). [ka]

[0113] 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.

[0114] Further preferred light-emitting materials include compounds represented by the following general formula (9). [ka]

[0115] In the general formula (9), Z 1 and Z 4 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 15 ~R 17 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure.

[0116] Further preferred light-emitting materials include compounds represented by the following general formula (10). [ka]

[0117] 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 1represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 Each of Z 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 R 3 may be bonded to each other to form a ring structure, provided that R 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.

[0118] Further preferred light-emitting materials include compounds represented by the following general formula (11). [ka]

[0119] 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 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 21 , R 21 and R 22 , R 22 and R 23 , R23 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.

[0120] Further preferred light-emitting materials include compounds represented by the following general formula (12). [ka]

[0121] In the general formula (12), Z 1 and Z 6 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 and R 28 ~R 30 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and Z 6 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 (13). [ka]

[0123] 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 , Z 7 and R 3 may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 At least one pair of is bonded to each other to form a ring structure.

[0124] Further preferred light-emitting materials include compounds represented by the following general formula (14). [ka]

[0125] 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.

[0126] Further preferred light-emitting materials include compounds represented by the following general formula (15). [ka]

[0127] 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 55and 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.

[0128] Further preferred light-emitting materials include compounds represented by the following general formula (16). [ka]

[0129] In the general formula (16), Z 1 , Z 8 and Z 9 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 61 ~R 66 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , R 66 and Z 8 may be bonded to each other to form a cyclic structure.

[0130] Further preferred light-emitting materials include compounds represented by the following general formula (17). [ka]

[0131] 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 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , Z 9 and R 67 , R 67 and R 68 , R 68 and R 69 , R 69 and Z 10 , Z 10 and R 70 may be bonded to each other to form a cyclic structure.

[0132] Further preferred light-emitting materials include compounds represented by the following general formula (18). [ka]

[0133] (In the general formula (18), Z 1 , Z 11 and Z 12 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 72 ~R 74 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 71R 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.

[0134] Further preferred light-emitting materials include compounds represented by the following general formula (19). [ka]

[0135] 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 R represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , R 81 and R 82may be bonded to each other to form a cyclic structure.

[0136] Further preferred light-emitting materials include compounds represented by the following general formula (20). [ka]

[0137] 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 , R 121 and R 122 , R122 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.

[0138] Further preferred light-emitting materials include compounds represented by the following general formula (21). [ka]

[0139] In the 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 , Z2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 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.

[0140] In one aspect of the 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 together to form a ring structure. In one embodiment of the present invention, R 1 and Z 1 are bonded to each other to form a pyrrole ring.

[0141] Further preferred light-emitting materials include compounds represented by the following general formula (22). [ka]

[0142] 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 24and 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 18 are bonded to each other to form a single bond to form a pyrrole ring, and X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 When they are bonded together to form a single bond, R 1 ~R 6 At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 are bonded to each other to form an aromatic ring or a heteroaromatic ring. For a detailed description of the compound represented by the general formula (22), a preferred range and specific examples thereof, reference can be made to

[0010] to

[0119] of WO2022 / 270354A1, which is hereby incorporated by reference as part of this specification. For example, the following compounds can be exemplified. [ka]

[0143] Further preferred light-emitting materials include compounds represented by the following general formula (23). [ka]

[0144] In the general formula (23), Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 3 represents a substituted or unsubstituted aryl group having at least one deuterium atom. R represents a hydrogen atom or a deuterium atom. D 1 and D. 2 each independently represents a donor group bonded via a nitrogen atom. Ar 1 and Ar 2 The description, preferred range and specific examples of Ar 1 and Ar 2 The description, preferred ranges and specific examples of Ar 3 In the aryl group, at least one or all of the hydrogen atoms directly bonded to the ring skeleton atoms of the aryl group are preferably replaced with deuterium atoms (it is preferable that at least one deuterium atom is bonded to the ring skeleton atoms). For example, a substituted or unsubstituted perdeuterated phenyl group (e.g., an unsubstituted perdeuterated phenyl group) can be mentioned. 1 and D. 2 The definition of the donor group that can be taken is the same as that of the donor group of general formula (1). In addition, the above general formulas (a) and (b) and the preferred range and specific examples of the donor group represented by these general formulas are 1 and D. 2 can also be applied to. Specific examples of the compound represented by general formula (23) are shown below, but the compounds represented by general formula (23) that can be used in the present invention should not be construed as being limited to these specific examples. [ka]

[0145] The compound represented by the general formula (23) can be synthesized by reacting a precursor in which the donor group is a fluorine atom with a substituted or unsubstituted carbazole to obtain a compound represented by the general formula (23) in which a substituted or unsubstituted carbazole-9-yl group is a donor group. For details of the reaction conditions, the following synthesis example of the compound represented by the general formula (23) can be referred to. [ka]

[0146] Under a nitrogen atmosphere, a mixture of 2,4-difluoro-3-iodopyridine (18.00 g, 74.69 mmol), phenyl-d5-boronic acid (10.43 g, 82.16 mmol), tetrakis(triphenylphosphine)palladium(0) (4.32 g, 3.73 mmol), and potassium carbonate (30.97 g, 224.08 mmol) was added to a mixture of 1,4-dioxane (150 mL) / water (75 mL) that had been degassed in advance, heated to 100 ° C., and stirred overnight. After the reaction was completed, the mixture was cooled to room temperature, and water and ethyl acetate were added. The organic layer was extracted and concentrated, and the resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain intermediate 1 (12.08 g, 61.57 mmol, yield 82.4%). ASAP mass spectrum analysis: Calculated 196.21, Observed 196.86. Under a nitrogen atmosphere, degassed tetrahydrofuran (50 mL) was added to intermediate 1 (3.00 g, 15.29 mmol) and stirred at -75°C for 30 minutes. Lithium diisopropylamide (22.93 mL, 22.93 mmol) was added dropwise to the mixture and stirred for 60 minutes. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (4.27 g, 22.93 mmol) was added and stirred for 1 hour. The mixture was returned to room temperature, and 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (5.35 g, 18.35 mmol), tetrakis(triphenylphosphine)palladium(0) (0.53 g, 0.46 mmol), potassium carbonate (6.34 g, 45.87 mmol), and water (25 mL) were added, and the mixture was heated to 80°C and stirred for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the precipitate was filtered. The precipitate was washed with hot toluene and ethyl acetate to obtain intermediate 2 (4.56 g, 10.10 mmol, yield 66.1%). 1 H NMR (400 MHz, CDCl3): δ 9.20 (s, 1H), 8.18-8.15 (m, 4H), 7.64-7.58 (m, 6H). ASAP mass spectrum analysis: Calculated 451.49, Observed 451.77. Under a nitrogen atmosphere, dimethylformamide (200 mL) was added to a mixture of intermediate 2 (4.10 g, 9.09 mmol), 5H-benzofuro[3,2-c]carbazole (7.41 g, 28.80 mmol), and potassium carbonate (4.90 g, 35.45 mmol), and the mixture was heated to 150° C. and stirred overnight. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The precipitate was purified by silica gel column chromatography and then recrystallized to obtain the compound represented by general formula (23) (5.05 g, 5.45 mmol, yield 54.1%). 1H NMR (400 MHz, CDCl3): δ 9.63 (s, 1H), 8.45-8.41 (m, 1H), 8.25-8.23 (m, 1H), 7.95-7.67 (m, 6H), 7.44-7.28 (m, 15H), 7.25-7.09 (m, 7H). ASAP mass spectrum analysis: Calculated 926.06, Observed 926.82.

[0147] In the present invention, delayed fluorescent materials having structures other than those of the general formulas (2) to (23) can also be used. For example, delayed fluorescent materials having the following structures can also be used. [ka]

[0148] In some embodiments, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained 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 a light-emitting material contained 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 a light-emitting material contained 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 a light-emitting material contained 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 a light-emitting material contained in the light-emitting layer is 10% by weight or less. In some embodiments, the host material of the light-emitting layer is an organic compound that has hole transport and electron transport functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0149] In some embodiments, the host material is selected from the group consisting of: [ka] JPEG2025058779000122.jpg192159

[0150] In one embodiment, 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 the lowest excited singlet energy level and the lowest excited triplet energy level of 77K. 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 molecule in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In an embodiment, 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 molecule, and 0.1 to 30 wt % of the second TADF molecule. In one embodiment, the composition in the light-emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule. In one embodiment, the light emission quantum yield φPL1(A) by light excitation of the co-deposited film of the first TADF molecule and the host material (the concentration of the first TADF molecule in this co-deposited film is A% by weight) and the light emission quantum yield φPL2(A) by light excitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-deposited film is A% by weight) satisfy the relational expression φPL1(A)>φPL2(A). In one embodiment, the light emission quantum yield φPL2(B) by light excitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-deposited film is B% by weight) and the light emission quantum yield φPL2(100) by light excitation of the single film of the second TADF molecule satisfy the relational expression φPL2(B)>φPL2(100). In some embodiments, the light-emitting layer can contain three structurally different TADF molecules. The compound of the present invention can be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be made of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-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 may be a known delayed fluorescent material.Preferred delayed fluorescent materials include those described in paragraphs 0008-0048 and 0095-0133 of WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. JP 2013-256490 A, paragraphs 0009 to 0046 and 0093 to 0134; JP 2013-116975 A, paragraphs 0008 to 0020 and 0038 to 0040; WO 2013 / 133359 A, paragraphs 0007 to 0032 and 0079 to 0084; WO 2013 / 161437 A, paragraph 0 JP 2014-9352 A, paragraphs 0007-0041 and 0060-0069, JP 2014-9224 A, paragraphs 0008-0048 and 0067-0076, JP 2017-119663 A, paragraphs 0013-0025, JP 2017-119664 A, paragraphs 0013-0026, JP 2017-119664 A, The compounds included in the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly the example compounds, which are capable of emitting delayed fluorescence, are included.In addition, the following publications are included herein: JP2013-253121A, WO2013 / 133359A, WO2014 / 034535A, WO2014 / 115743A, WO2014 / 122895A, WO2014 / 126200A, WO2014 / 136758A, WO2014 / 133121A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714A, WO2015 / 129715A, WO2015 / 13350 The luminescent materials described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, which are capable of emitting delayed fluorescence, can be preferably used. Note that the above publications described in this paragraph are hereby incorporated by reference as part of this specification.

[0151] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0152] Base material: 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.

[0153] 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 more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering. In some embodiments, the film is patterned by a photolithographic method. In some embodiments, if the pattern does not need to be highly accurate (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering on 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, the anode has a transmittance of more than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0154] 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 selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. 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, one of the anode and cathode of the organic electroluminescent device is transparent or semi-transparent to transmit emitted light. In some embodiments, a transparent or semi-transparent 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 semi-transparent cathode, hi some embodiments, an element includes an anode and a cathode, both of which are transparent or semi-transparent.

[0155] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances 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 light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are given below.

[0156] [ka]

[0157] Next, preferred examples of compounds that can be used as the electron injection material will be given. [ka]

[0158] 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 barrier 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 barrier 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 barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the term "electron barrier layer" or "exciton barrier layer" includes layers that have both the functions of an electron barrier layer and of an exciton barrier layer.

[0159] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transport 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 can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.

[0160] [ka]

[0161] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer blocks 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 can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron blocking material are given below.

[0162] [ka] JPEG2025058779000127.jpg46170

[0163] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the light-emitting layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the light-emitting 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, the layer may be present between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is present on the cathode side, the layer may be present between the light-emitting layer and the cathode and adjacent to the light-emitting 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 light-emitting 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 light-emitting 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.

[0164] 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 hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, 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 porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are given below.

[0165] [ka]

[0166] 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, fluorenylidene methane 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 polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0167] [ka]

[0168] In addition, examples of compounds that can be added to each organic layer are given below, which may be used as stabilizing materials, for example.

[0169] [ka]

[0170] Although the preferred materials that can be used in the organic electroluminescence element are specifically exemplified, the materials that can be used in the present invention are not limited to the following exemplified compounds. In addition, even if a compound is exemplified as a material having a specific function, it can be diverted to a material having other functions.

[0171] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. 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 may be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions may be useful for facilitating charge or energy transfer within the device and / or as hole transport materials, such as organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0172] Bulb or Lamp: In some embodiments, the 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 includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device comprises: a circuit board having a first side having a mounting surface and an opposing 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 a light-emitting 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 comprises a plurality of OLEDs mounted on a circuit board such that light is emitted in a plurality of directions. In some embodiments, some 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.

[0173] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. 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 in two-sided etching to provide pixels of unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of an OLED display. The corresponding artwork pattern design allows for the placement of very steep narrow tie bars between pixels in the vertical direction, as well as large wide angled openings in the horizontal direction. This allows for the fine patterning of pixels required for high resolution displays while optimizing chemical vapor deposition onto the TFT backplane. The internal patterning of the pixel allows for the construction of three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Additionally, the use of imaged "stripes" or halftone circles in the pixel area protects etching in certain areas until those particular patterns are undercut and removed from the substrate. At that point, all pixel areas are treated with similar etch rates, but the depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with different protection rates within the pixel, allowing for the localized deep etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold rolled into long thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable and low-cost method for forming open areas in the deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0174] How the device is manufactured: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, 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, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Usually, 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, a light-emitting layer, a counter electrode and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0175] In another aspect of the invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in the form of a cell panel; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example made of SiNx, and the ends of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be cut softly into cell panels. 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 formed of the same material as the planarization film and is formed at the same time as the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to the display unit or the encapsulation layer.

[0176] Each of the organic film and the planarization film may include 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 prior to forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate prior to 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 for covering the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an 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 directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0177] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source / drain electrode of a TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is disposed at an interval with each of the plurality of display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the end of the barrier layer.

[0178] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, a barrier layer is formed on a surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0179] In some embodiments, the method further includes a step of cutting along the interface, where a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, the 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 the TFT layer to cover the TFT layer. At the same time as the planarization film, which is made of, for example, polyimide or acrylic, is formed, the groove of the interface is covered with an organic film, which is made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the groove at the interface by having the organic film absorb the impact that occurs. That is, if all the barrier layers are completely exposed without the organic film, when each cell panel is cut along the groove at the interface, the impact that occurs will be transmitted to the barrier layer, thereby increasing the risk of cracks. However, in one embodiment, the groove of the interface between the barrier layers is covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel can be cut softly and prevent cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface are spaced apart from each other. For example, when 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 part of the organic film, so the organic film and the planarization film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0180] In some embodiments, the display unit is formed by forming a light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, the carrier substrate is separated 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 interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, the barrier layer is prevented from cracking during cutting. In some embodiments, the methods reduce product defect rates and stabilize product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. EXAMPLES

[0181] The characteristics of the present invention will be described in more detail below with reference to synthesis examples and examples. The materials, processing contents, processing procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the specific examples shown below. The evaluation of the emission characteristics was performed 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 C4334). The energy of the HOMO and LUMO was measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the following synthesis examples, compounds within the general formula (1) were synthesized.

[0182] (Synthesis Example 1) Synthesis of Compound A Synthesis of intermediate a [ka]

[0183] Under a nitrogen atmosphere, 1.0M diisopropylamide THF / hexane solution (20mL, 20.0mmol) was slowly dropped into a tetrahydrofuran (THF) solution (50mL) of 2,4-dibromo-1-fluorobenzene (5.0g, 20.0mmol) at -78℃. After stirring for 2 hours, pinacol isopropoxyboronate (4.5g, 24.1mmol) was added. After stirring for 30 minutes, ion-exchanged water (12mL) was added and the temperature was raised to room temperature. Tetrakis(triphenylphosphine)palladium(0) (0.70g, 0.60mmol), iodobenzene-d5 (5.0g, 23.9mmol), and potassium carbonate (5.5g, 39.8mmol) were added to the resulting reaction solution and stirred at 50℃ for 3 hours. After cooling to room temperature, the resulting reaction mixture was filtered. The solid was washed with ethyl acetate and then separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The crude product was purified by column chromatography (hexane) to obtain 2.84 g (8.48 mmol, 42% yield) of intermediate a as a colorless, transparent liquid. 1 H NMR (400 MHz, CDCl3): δ 7.67 (dd, J = 5.8, 2.8 Hz, 1H) 7.55 (dd, J = 5.6, 2.4 Hz, 1H). ASAP MS Spectral Analysis: C 12 H2D5Br2F: Calculated 332.92, Observed 332.85 [M]

[0184] Synthesis of intermediate b [ka]

[0185] A reaction mixture of intermediate a (3.69 g, 11.0 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.40 g, 0.55 mmol), potassium acetate (7.6 g, 77.0 mmol), bis(pinacolato)diboron (10.1 g, 55.1 mmol), and 1,4-dioxane (110 mL) was stirred at 110° C. for 15 hours. The reaction mixture was cooled to room temperature and then filtered through silica. The filtrate was concentrated, and the reaction mixture was dissolved in methylene chloride and filtered through silica. The filtrate was concentrated, and the resulting pale yellow solid was washed with hexane to obtain 2.91 g (6.78 mmol, 61% yield) of intermediate b as a white solid. 1 H NMR (400 MHz, CDCl3): δ 8.16 (dd, J = 5.6, 1.6 Hz, 1H) 7.97 (dd, J = 8.4, 1.6 Hz, 1H), 1.36 (s, 12H), 1.33 (s, 12H). ASAP MS Spectral Analysis: C 12 H2D5Br2F: Calculated 429.27, Observed 430.44 [M+H + ]

[0186] Synthesis of intermediate c [ka]

[0187] Intermediate b (2.87 g, 6.7 mmol) was dissolved in THF (100 mL) and ion-exchanged water (30 mL), and 2-chloro-4,6-di(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (5.52 g, 14.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.29 g, 0.34 mmol), and sodium carbonate (3.59 g, 33.9 mmol) were added and stirred at 75 ° C for 16 hours. The resulting gray solid was filtered off. The solid was washed with ion-exchanged water and THF. The collected solid was washed in hot toluene and filtered to obtain 5.63 g (6.67 mmol, 98% yield) of white solid intermediate c. ASAP MS Spectral Analysis: C 54 H2D 31 FN8: Calculated 843.48, Observed 844.81. [M+H + ]

[0188] Synthesis of Compound A [ka]

[0189] A reaction mixture of intermediate c (12.66 g, 15.0 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (3.15 g, 18.0 mmol), potassium carbonate (3.11 g, 22.5 mmol), and 1-methyl-2-pyrrolidone (NMP, 300 mL) was stirred at 180° C. for 2 hours. The reaction solution was filtered through Celite, and the Celite was washed with ethyl acetate. Hexane was added to the filtrate, and the resulting solid was filtered off and washed with methanol. The obtained crude product was dissolved in toluene and then passed through a Celite / silica pad. The filtrate was concentrated, and the obtained solid was washed with acetonitrile to obtain 10.55 g (10.56 mmol, 70% yield) of pale green compound A. ASAP MS Spectral Analysis: C 66 H2D 39 N9: Calculated value 998.59, observed value 999.13 [M+H + ]

[0190] (Example 1) Preparation and evaluation of thin films Compounds A and H1 were evaporated onto a quartz substrate from different evaporation sources at a vacuum level of 1×10 -3 The deposition was carried out at less than 1 Pa to form a thin film having a thickness of 100 nm and a concentration of compound A of 20 wt %. Using Comparative Compound 1 instead of Compound A, a thin film was formed in the same manner. The photoluminescence of each thin film formed when irradiated with 300 nm excitation light was analyzed, and the photoluminescence quantum yield (PLQY) and the lifetime (τ2) of the delayed fluorescence component were measured. In addition, the orientation value (S) of compound A and comparative compound 1 in each thin film formed was measured according to the method described in Scientific Reports 2017,7,8405. The results are shown in the table below. It was confirmed that the compound represented by general formula (1) has a high PLQY, a short delayed fluorescence lifetime, and high orientation. [Table 5]

[0191] (Example 2) Preparation and evaluation of organic electroluminescence device Each thin film was deposited on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm by vacuum deposition at a vacuum degree of 5.0 × 10 -5 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed on it to a thickness of 30 nm, TrisPCz was further formed on it to a thickness of 10 nm, and H1 was formed on it to a thickness of 5 nm. Next, H1 and compound A were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm to be used as an emitting layer. The concentration of compound A in the emitting layer was 30% by weight. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30% by weight and 70% by weight, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, and an organic electroluminescence element was used. Using Comparative Compound 1 instead of Compound A, an organic electroluminescence device was prepared in the same manner. Each organic electroluminescence element was driven at 2.0 mA / cm 2The external quantum efficiency (EQE) was measured by emitting light at 100 Hz. The time (LT95) until the luminous intensity decreased to 95% of the time at the start of driving was also measured. The results are shown in the following table as relative values ​​when the value of the organic electroluminescence element using comparative compound 1 is taken as 1. The organic electroluminescence element using compound A had an EQE of 1.11 times and an LT95 of 5.6 times, compared to the organic electroluminescence element using comparative compound 1. From this, it was confirmed that the compound represented by general formula (1) improves the luminous efficiency and the element life. [Table 6]

[0192] Example 3: Preparation and evaluation of organic electroluminescence device using assist dopant An organic electroluminescence element was produced by the same method as in Example 2, except that the light-emitting layer was formed by co-evaporating H1, compound A, and ET1 from different evaporation sources to form a layer having a thickness of 40 nm containing 69.7% by weight of H1 as a host material, 30% by weight of compound A as an assist dopant, and 0.3% by weight of ET1 as a dopant (light-emitting material). Using Comparative Compound 2 and Comparative Compound 3 instead of Compound A, organic electroluminescence devices were prepared in the same manner. Each organic electroluminescence element was driven at 2.0 mA / cm 2 The external quantum efficiency (EQE) was measured by emitting light at 1000 nm. The results are shown in the table below. Only the organic electroluminescence element using compound A achieved a high EQE of more than 24%. This confirmed that the luminous efficiency was improved even in the organic electroluminescence element using the compound represented by formula (1) as an assist dopant. [Table 7]

[0193] [ka]

[0194] [ka] [Industrial Applicability]

[0195] By using the compound represented by the general formula (1), an organic light-emitting device having good light-emitting properties can be provided, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) 【Chemistry 1】 [In the general formula (1), Z and R ２ , or Z and R ３ R represents the same group as that represented by the following general formula (A). １ ~R ５ represents a donor group, and R １ ~R ５ One or two of R represent a substituted or unsubstituted aryl group; １ ~R ５ One or two of represent a hydrogen atom or a deuterium atom. General formula (A) 【Chemistry 2】 In the general formula (A), X １ is N or C-R ６ represents X ２ is N or C-R ７ Represents ６ and R ７ each independently represents a hydrogen atom, a deuterium atom, or a cyano group; １ and X ２ Ar and Ar are not both C-CN. １ and Ar ２ Each of X independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ and X ２ When is N, Ar １ and Ar ２ At least one of the groups is a substituted or unsubstituted heteroaryl group. L represents a single bond or a divalent linking group. * represents the bonding position.]

2. Z and R ２ The compound according to claim 1 , wherein

3. Z and R ３ The compound according to claim 1 , wherein

4. R ４ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group.

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

6. Ar ２ The compound according to claim 1 , wherein is a substituted or unsubstituted heteroaryl group.

7. Ar １ The compound according to claim 6 , wherein is a substituted or unsubstituted aryl group.

8. Ar １ The compound according to claim 6 , wherein is a substituted or unsubstituted heteroaryl group.

9. X １ and X ２ The compound of claim 1 , wherein both are N.

10. X １ and X ２ The compound of claim 1 , wherein only one of is N.

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 material 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 the compound according to any one of claims 1 to 12.

18. 20. 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 layer containing the compound 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. The organic light-emitting element according to claim 18.

20. 20. The organic light-emitting device of claim 18, wherein the device has a layer that includes the compound, the layer also including a light-emitting material that has a different structure than the compound.

21. The organic light-emitting device according to claim 18 , wherein the compound emits the greatest amount of light of any of the materials contained in the device.

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

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

24. The organic light-emitting device according to claim 17, which emits delayed fluorescence.

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