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

Abstract

The compound represented by the following general formula has a long emission lifetime. 1-3 of R1-R5 are donor groups, the rest are H, D, cyano, aryl or alkyl, L is a single bond or a linking group, X1 is N or C, and Y is carbazole-9-yl or aryl.

Description

Technical Field

[0001] This invention relates to a compound useful as a luminescent material and a luminescent element using the same. Background Technology

[0002] Research is actively underway to improve the luminous efficiency of light-emitting elements such as organic electroluminescent devices (organic EL devices). Particular attention has been paid to enhancing luminous efficiency by developing and combining new electron transport materials, hole transport materials, and luminescent materials that constitute organic electroluminescent devices. Research related to organic electroluminescent devices utilizing delayed fluorescence materials is also being observed.

[0003] Delayed fluorescence materials are those that emit fluorescence upon returning to the ground state after a reverse intersystem crossing from an excited triplet state to an excited singlet state in the excited state. The fluorescence generated by this pathway is observed later than fluorescence from an excited singlet state directly generated from the ground state (normal fluorescence), hence the name delayed fluorescence. Here, for example, in the case of excitation of a luminescent compound via carrier injection, the generation probability of the excited singlet state is statistically 25% to 75%; therefore, there is a limit to the improvement in luminescence efficiency if only fluorescence from the directly generated excited singlet state is used. On the other hand, in delayed fluorescence materials, in addition to the excited singlet state, the excited triplet state can also be used for fluorescence emission via the aforementioned reverse intersystem crossing pathway, thus achieving higher luminescence efficiency compared to conventional fluorescent materials.

[0004] Once this principle was clarified, various delayed fluorescence materials were discovered through different studies. Among them are compounds in which multiple benzene rings are replaced by donor and acceptor groups. For example, a compound with a skeleton in which the benzene ring is replaced by a carbazole-9-yl group as a donor group, a cyano group as an acceptor group, and a substituted triazine group was proposed (see Patent Document 1). Previous technical documents Non-patent literature

[0005] Non-patent document 1: WO2019 / 191665A1 Summary of the Invention The technical problem to be solved by the invention

[0006] To date, no material has been provided that, even for materials emitting delayed fluorescence, possesses extremely good properties and poses no practical problems. Therefore, it would be even more useful to provide delayed fluorescence materials with superior properties. However, improvements to delayed fluorescence materials are still in the experimental stage, and it is not easy to generalize the chemical structures of useful luminescent materials.

[0007] In this context, the inventors have repeatedly conducted research with the aim of providing compounds that are more useful as delayed fluorescence materials for light-emitting elements. Furthermore, they have conducted in-depth research with the aim of deriving general formulas for compounds that are more useful as delayed fluorescence materials and generalizing them. means for solving technical problems

[0008] As a result of in-depth research conducted to achieve the aforementioned objectives, the inventors discovered that compounds having structures that satisfy specific conditions are useful as luminescent materials. The present invention is made based on this insight, and specifically, has the following structure. [1] A compound represented by the following general formula (1). General formula (1) [Chemical Formula 1] In general formula (1), R 1 ~R 5 One to three of them are donor groups, R 1 ~R 5 The 0th to 1st group is a cyano group, R 1 ~R 5 The 0 to 3 atoms in R are hydrogen or deuterium atoms. 1 ~R 5 Of these, 0 to 2 are substituted or unsubstituted aryl groups, and the remaining R... 1 ~R 5 R is a substituted or unsubstituted alkyl group. 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 They can bond together to form a cyclic structure. L represents a single bond or a linking group. X 1 Indicates N or CR 6 X 2 Indicates N or CR 7 R 6 and R 7 Each of these can be represented independently as a hydrogen atom, a deuterium atom, or a substituent. Y represents either a substituted or unsubstituted carbazole-9-yl group or a substituted or unsubstituted aryl group. Where Y is a substituted or unsubstituted aryl group, R 1 ~R 5 The 0 to 2 atoms are either hydrogen or deuterium atoms. [2] According to the compound described in [1], wherein R 1 ~R 5 One of them is a cyano group. [3] According to the compound described in [2], wherein R 2 It is a cyano group. [4] The compound according to any one of [1] to [3], wherein R 1 ~R 5 One or two of them are donor groups. [5] According to the compound described in [4], wherein R 5 It is a donor group. [6] According to the compound described in [5], wherein R 1 It consists of hydrogen or deuterium atoms. [7] The compound according to any one of [1] to [6], wherein R 1 ~R 5 One or two of them are substituted or unsubstituted aryl groups. [8] According to the compound described in [7], wherein R 4 It consists of a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. [9] The compound according to any one of [1] to [8], wherein Y is a substituted or unsubstituted carbazole-9-yl.

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

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

[10] , wherein L is a single bond.

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

[11] has at least one deuterium atom.

[13] A luminescent material comprising any one of the compounds described in [1] to

[12] .

[14] A delayed phosphor, comprising any one of the compounds described in [1] to

[12] .

[15] A membrane comprising any one of the compounds described in [1] to

[12] .

[16] An organic semiconductor device comprising any one of the compounds described in [1] to

[12] .

[17] An organic light-emitting element comprising any one of the compounds described in [1] to

[12] .

[18] The organic light-emitting element according to

[17] , wherein the element has a layer comprising the compound, the layer further comprising a host material.

[19] According to the organic light-emitting element of

[18] , the layer containing the compound contains, in addition to the compound and the host material, a delayed fluorescence material, wherein the minimum excitation singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound.

[20] The organic light-emitting element according to

[18] , wherein the element has a layer comprising the compound, the layer further comprising a light-emitting material having a structure different from that of the compound.

[21] The organic light-emitting element according to

[18] or

[19] , wherein the light emission from the compound is the greatest among the materials contained in the element.

[22] According to the organic light-emitting element of

[20] , 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 element according to any one of

[17] to

[22] is an organic electroluminescent element.

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

[17] to

[23] emits delayed fluorescence. Invention Effects

[0009] The compounds of this invention exhibit excellent luminescent properties. The compounds of this invention are useful as materials for organic light-emitting elements. Detailed Implementation

[0010] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples of the invention, but the invention is not limited to such embodiments or specific examples. Furthermore, in this specification, the numerical range indicated by “~” represents the range of values ​​described before and after “~” as lower and upper limits. Also, some or all of the hydrogen atoms present in the molecules of the compounds used in the present invention can be replaced by deuterium atoms (…). 2 (H, Deuterium D). In the chemical structural formulas of this specification, the hydrogen atom is represented by H or its representation is omitted. For example, when the atom representing the carbon atom bonded to the ring skeleton of the benzene ring is omitted, H forms a carbon atom bond with the ring skeleton at the omitted position. In this specification, the term "substituent" refers to an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" indicates that the hydrogen atom can be substituted by a deuterium atom or a substituent.

[0011] [Compounds represented by general formula (1)] The compounds represented by the following general formula (1) will be described. General formula (1) [Chemical Formula 2]

[0012] In general formula (1), R 1 ~R 5 One to three of them are donor groups, R 1~R 5 The 0th to 1st group is a cyano group, R 1 ~R 5 The 0 to 3 atoms in R are hydrogen or deuterium atoms. 1 ~R 5 Of these, 0 to 2 are substituted or unsubstituted aryl groups, and the remaining R... 1 ~R 5 R is a substituted or unsubstituted alkyl group. 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 They can bond together to form a cyclic structure. L represents a single bond or a linking group. X 1 Indicates N or CR 6 X 2 Indicates N or CR 7 R 6 and R 7 Each of these can independently represent a hydrogen atom, a deuterium atom, or a substituent. Y represents a substituted or unsubstituted carbazole-9-yl group or a substituted or unsubstituted aryl group. Specifically, when Y is a substituted or unsubstituted aryl group, R... 1 ~R 5 The 0 to 2 atoms are either hydrogen or deuterium atoms.

[0013] R in general formula (1) 1 ~R 5 One to three of them are donor groups. R 1 ~R 5 The donor groups that can be used do not contain substituted or unsubstituted aryl groups. Regarding the "donor group," selection can be made from groups with negative Hammett σp values. Regarding the "acceptor group," selection can be made from groups with positive Hammett σp values. Hammett's σp value, proposed by L.P. Hammett, quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is the following equation holding between the substituents in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp The constant (σp) is specific to the substituents in the formula. In the above formula, k0 represents the rate constant of the benzene derivative without substituents, k represents the rate constant of the benzene derivative substituted with substituents, K0 represents the equilibrium constant of the benzene derivative without substituents, K represents the equilibrium constant of the benzene derivative substituted with substituents, and ρ represents the reaction constant determined by the type and conditions of the reaction. For explanations related to the "Hamette's σp value" in this invention and the values ​​of each substituent, please refer to the records related to the σp values ​​in Hansch, C. et.al., Chem. Rev., 91, 165–195 (1991).

[0014] R 1 ~R 5 The σp of the donor group that can be used is preferably -0.3 or less, more preferably -0.5 or less, and even more preferably -0.7 or less. For example, it can be selected from the range of -0.9 or less or from the range of -1.1 or less.

[0015] The donor group in this invention is preferably a group containing a substituted amino group. It can be a substituted amino group, or an aryl group formed by the bonding of substituted amino groups, wherein the phenyl group is formed by the bonding of substituted amino groups. In a preferred embodiment of this invention, the donor group is a substituted amino group. The substituents bonded to the nitrogen atom in the substituted amino group are preferably substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, more preferably substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino or a substituted or unsubstituted diheteroarylamino. The two aryl groups constituting the diarylamino can be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino can be bonded to each other.

[0016] R 1 ~R 5 The donor group that can be used is preferably the group represented by the following general formula (a). [Chemical Formula 3]

[0017] In general formula (a), Z 1 CR 14 Or N, Z 2 CR 15 Or N, Z 3 Indicates CR 16 Or N, Z 4 CR 17 Or N. Z 5 Represents C or N, Ar 5Indicates a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. R 14 and R 15 R 15 and R 16 R 16 and R 17 They can bond together to form a ring structure.

[0018] Z 1 ~Z 4 The number of N values ​​is preferably 0 to 3, more preferably 0 to 2. In one embodiment of the invention, Z... 1 ~Z 4 The number of N is 1. In one aspect of the invention, Z 1 ~Z 4 The number of N values ​​is 0. R 14 ~R 17 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. Regarding substituents, for example, selection can be made from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In R... 14 ~R 17 When two or more substituents are represented in R, these two or more substituents can be the same or different. 14 ~R 17 The 0 to 2 of them are preferably substituents, for example, one can be a substituent or none can be a substituent (R). 14 ~R 17 (It consists of hydrogen or deuterium atoms). R 14 and R 15 R 15 and R 16 R 16 and R 17They can bond together to form a cyclic structure. The cyclic structure can be any of aromatic rings, heteroaromatic rings, aliphatic hydrocarbon rings, and aliphatic heterocycles, and can also be a fused ring of these. Aromatic rings and heteroaromatic rings are preferred. As aromatic rings, substituted or unsubstituted benzene rings can be cited as examples. Other benzene rings can be further fused to the benzene ring, and heterocycles such as pyridine rings can also be fused. A heteroaromatic ring refers to a ring containing heteroatoms as ring skeleton atoms and exhibiting aromaticity, preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring. In one aspect of the invention, furan rings, thiophene rings, and pyrrole rings can be used as heteroaromatic rings. In a preferred aspect of the invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole described herein can be unsubstituted, or substituted with substituents selected from substituent group A, B, C, D, or E. Preferably, the substituted or unsubstituted aryl group is bonded to the nitrogen atom of the pyrrole ring constituting the indole as a substituent; for example, substituents selected from any of substituent groups A to E can be cited. The cyclic structure can be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the invention, R... 14 and R 15 R 15 and R 16 R 16 and R 17 One group of elements bonds together to form a ring structure. In one embodiment of the invention, R 14 and R 15 R 15 and R 16 R 16 and R 17 They do not bond with each other to form a ring structure.

[0019] In general formula (a), Z 5 Represents C or N, Ar 5 This indicates a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the invention, Z 5 For C, Ar 5 Z is a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one aspect of the invention, Z 5 For N, Ar 5 These are heterocyclic aromatic rings, whether substituted or not. As Ar 5Aromatic rings that can be used include, for example, the benzene ring. Other benzene rings, or heterocycles such as pyridine rings, can be further fused to the benzene ring. Ar 5 The heteroaromatic ring that can be used is preferably a 5- to 7-membered ring, for example, a 5-membered or 6-membered ring. In one aspect of the 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 aspect of the invention, Z 5 C represents the heteroaromatic ring, which 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. In one embodiment of the invention, Z... 5 The N-aryl ring is a pyrrole ring of indole, either substituted or unsubstituted, or an imidazole ring of benzimidazole, either substituted or unsubstituted. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole described herein may be unsubstituted, or may be substituted by substituents selected from substituent group A, B, C, D, or E.

[0020] Z in general formula (a) 5 When the group is C, it is preferably the group represented by the following general formula (b). [Chemical Formula 4]

[0021] In general formula (b), Z 1 CR 14 Or N, Z 2 CR 15 Or N, Z 3 CR 16 Or N, Z 4 CR 17 Or N, Z 6 CR 18 Or N, Z 7 CR 19 Or N, Z 8 CR 20 Or N, Z 9 CR 21 Or N. R 14 and R 15 R 15 and R 16 R 16 and R 17 R 18 and R19 R 19 and R 20 R 20 and R 21 They can bond together to form a ring structure. Regarding Z in general formula (b) 1 ~Z 4 R 14 ~R 17 Please refer to the corresponding explanation in general formula (a). Z in general formula (b) 6 ~Z 9 R 18 ~R 21 In sequence with Z of general formula (a) 1 ~Z 4 R 14 ~R 17 Correspondingly, regarding these contents, you can refer to the Z of general formula (a). 1 ~Z 4 R 14 ~R 17 Explanation. In one aspect of the invention, Z 1 ~Z 4 Z 6 ~Z 9 The number of N values ​​is preferably 0 to 2, more preferably 0 or 1. In one embodiment of the invention, Z... 1 ~Z 4 Z 6 ~Z 9 The number of N is 1. In a preferred embodiment of the invention, Z 1 ~Z 4 Z 6 ~Z 9 The number of N is 0. When it is 0, it indicates that the carbazo-9-yl group is substituted or unsubstituted.

[0022] R 1 ~R 5 The donor group that can be used is preferably a substituted or unsubstituted carbazole-9-yl group. The carbazole-9-yl group can be unsubstituted, or it can be substituted by a substituent selected from substituent group A, substituent selected from substituent group B, substituent selected from substituent group C, substituent selected from substituent group D, or substituent selected from substituent group E. Furthermore, one or more rings can be further fused together on the two benzene rings constituting the carbazole-9-yl group. In a preferred embodiment of the invention, R... 1 ~R 5The donor group that can be used is a carbazole-9-yl group that can be substituted by a group selected from substituent group E and can be fused with one or more rings. When it is desired to obtain a compound with a short emission wavelength, a carbazole-9-yl group substituted with an aryl group that can be substituted with a deuterium atom, an alkyl group, or an aryl group is preferred. When the unfused carbazole-9-yl group is substituted, the substitution position is not particularly limited, but it is preferably at least one of positions 2 to 7, more preferably at least one of positions 3 or 6, and even more preferably at positions 3 and 6.

[0023] In one aspect of the invention, R 1 ~R 5 The donor group that can be used is a carbazole-9-yl group fused with one or more rings, which will be referred to below as "cyclic fused carbazole-9-yl". 1 ~R 5 The cyclic fused carbazole-9-yl group can be unsubstituted, or substituted with substituents selected from substituent group A, B, C, D, or E. Preferably, it is unsubstituted or substituted with substituents selected from substituent group E. In one embodiment of the invention, the cyclic fused carbazole-9-yl group is unsubstituted. In a preferred embodiment, the cyclic fused carbazole-9-yl group is substituted with an aryl group, which can be substituted by one atom or group selected from the group consisting of deuterium, alkyl, and aryl, or by a combination of two or more groups.

[0024] The total number of fused rings in the 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 invention, the number of rings constituting the fused ring is 5. Furthermore, the number of rings described herein includes the number of rings of the fused carbazole (i.e., 3).

[0025] The fused carbazole-9-yl group is a group bonded to the nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring can be any one of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, and can also be a ring formed by further fusion of these. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of aromatic hydrocarbon rings include substituted or unsubstituted benzene rings. Other benzene rings can be further fused to the benzene ring, and heterocycles such as pyridine rings can also be fused. An aromatic heterocycle refers to a ring containing heteroatoms as ring skeleton constituent atoms and exhibiting aromaticity, preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring. In one aspect of the invention, a furan ring, a thiophene ring, or a pyrrole ring can be used as the aromatic heterocycle. In one aspect of the 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. Furthermore, a substituent selected from the substituent group E is preferably bonded to the nitrogen atom of the pyrrole ring (except in the case of only a deuterium atom), and more preferably an aryl group that can be substituted by an alkyl or aryl group is bonded. In the invention, a carbazole-9-yl ring fused with one or more atoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms is preferably used. Carbazole-9-yl rings fused with benzofuran structures, carbazole-9-yl rings fused with benzothiophene structures, and carbazole-9-yl rings fused with indole structures are preferably used. In one aspect of the invention, at least one carbazole-9-yl ring fused with a benzofuran structure is used, for example, two or more. In one aspect of the invention, a carbazole-9-yl group having at least one benzothiophene fused together is used, for example, having two or more.

[0026] As a cyclic fused carbazole-9-yl, it can be substituted or unsubstituted benzofuran[2,3-a]carbazole-12-yl, substituted or unsubstituted benzofuran[3,2-a]carbazole-12-yl, substituted or unsubstituted benzofuran[2,3-b]carbazole-7-yl, substituted or unsubstituted benzofuran[3,2-b]carbazole-11-yl, substituted or unsubstituted benzofuran[2,3-c]carbazole-8-yl, or substituted or unsubstituted benzofuran[3,2-c]carbazole-5-yl. Furthermore, as a cyclic fused carbazole-9-yl group, substituted or unsubstituted benzothieno[2,3-a]carbazole-12-yl, substituted or unsubstituted benzothieno[3,2-a]carbazole-12-yl, substituted or unsubstituted benzothieno[2,3-b]carbazole-7-yl, substituted or unsubstituted benzothieno[3,2-b]carbazole-11-yl, substituted or unsubstituted benzothieno[2,3-c]carbazole-8-yl, or substituted or unsubstituted benzothieno[3,2-c]carbazole-5-yl can also be used. Furthermore, as a cyclic fused carbazole-9-yl group, substituted or unsubstituted 11-phenylindolo[2,3-a]carbazole-12-yl, substituted or unsubstituted 5-phenylindolo[3,2-a]carbazole-12-yl, substituted or unsubstituted 5-phenylindolo[2,3-b]carbazole-7-yl, substituted or unsubstituted 5-phenylindolo[3,2-b]carbazole-11-yl, substituted or unsubstituted 5-phenylindolo[2,3-c]carbazole-8-yl, or substituted or unsubstituted 12-phenylindolo[3,2-a]carbazole-5-yl can also be used.

[0027] When the cyclic fused carbazole-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, for example, 1 or 2. In a preferred embodiment of the invention, any one of the 3 or 6 positions of the cyclic fused carbazole-9-yl group is substituted. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there is at least one substituent at the para position of the benzene ring. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there is at least one substituent only at the para position of the benzene ring. In a preferred embodiment of the invention, from the perspective of the heteroatom present in the cyclic fused carbazole-9-yl group, there are substituents at all substituted para positions of the benzene ring.

[0028] The following shows R of general formula (1). 1 ~R 5Specific examples of donor groups that can be used. Specific examples shown here are substituted or unsubstituted carbazole-9-yl groups (with further fused rings on the carbazole ring), but the donor groups that can be used in this invention are not limited to the following specific examples. Furthermore, in the following specific examples, Ph represents phenyl (C6H5), * indicates the bonding position. The methyl group is omitted, therefore, for example, D2 has one methyl group. The deuterated methyl group is represented as CD3. And, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom. [Chemical Formula 5-1] [Chemical Formula 5-2] [Chemical Formula 5-3] [Chemical Formula 5-4] [Chemical Formula 5-5] [Chemical Formulas 5-6] [Chemical Formulas 5-7] [Chemical Formula 5-8] [Chemical Formulas 5-9] [Chemical Formula 5-10] [Chemical Formula 5-11] [Chemical Formula 5-12] [Chemical Formula 5-13] [Chemical Formula 5-14] [Chemical Formula 5-15] [Chemical Formula 5-16] [Chemical Formula 5-17] [Chemical Formula 5-18] [Chemical Formula 5-19] [Chemical Formula 5-20] [Chemical Formula 5-21] [Chemical Formula 5-22] [Chemical Formula 5-23] [Chemical Formula 5-24] [Chemical Formula 5-25] [Chemical Formula 5-26] [Chemical Formula 5-27] [Chemical Formula 5-28] [Chemical Formula 5-29] [Chemical Formula 5-30] [Chemical Formula 5-31] [Chemical Formula 5-32] [Chemical Formula 5-33] [Chemical Formula 5-34] [Chemical Formula 5-35] [Chemical Formula 5-36] [Chemical Formula 5-37] [Chemical Formula 5-38] [Chemical Formula 5-39] [Chemical Formula 5-40] [Chemical Formula 5-41] [Chemical Formula 5-42] [Chemical Formula 5-43]

[0029] Compounds in which all hydrogen atoms in D1 to D459 are replaced with deuterium atoms are disclosed as D722 to D1180.

[0030] The following are examples of R 1 ~R 5 Specific examples of donor groups that can be used are not substituted or unsubstituted carbazole-9-yl donor groups. However, the donor groups that can be used in this invention are not to be limited by the following specific examples. [Chemical Formula 6-1] [Chemical Formula 6-2] [Chemical Formula 6-3]

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

[0032] In one aspect of the invention, R 1 ~R 5 One of them is a donor group. In one embodiment of the invention, R 1 ~R 5 Two of them are donor groups. In one embodiment of the invention, R 1 ~R 5 Three of them are donor groups. In a preferred embodiment of the invention, at least R 5 As a donor group. In one embodiment of the invention, only R... 5As a donor group. In one embodiment of the invention, at least R... 3 and R 5 As a donor group. In one aspect of the invention, at least only R... 3 and R 5 As a donor group. In one embodiment of the invention, only R... 3 and R 4 and R 5 As a donor group. In one embodiment of the invention, at least R... 3 As a donor group. In one embodiment of the invention, at least R... 4 It is a donor group.

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

[0034] R in general formula (1) 1 ~R 5 Of these, 0 to 3 are hydrogen or deuterium atoms, preferably 1 to 3 are hydrogen or deuterium atoms, and more preferably 1 to 2 are hydrogen or deuterium atoms. In one embodiment of the invention, R 1 ~R 5 Only one of them is a hydrogen atom or a deuterium atom. In one aspect of the invention, R 1 ~R 5 Only two of them are hydrogen or deuterium atoms. In one aspect of the invention, R 1 ~R 5 Three of them are hydrogen atoms or deuterium atoms. In one aspect of the invention, R 1 ~R 5 None of them are hydrogen atoms or deuterium atoms. In a preferred embodiment of the invention, at least R 1 It is a hydrogen atom or a deuterium atom. In one aspect of the invention, at least R 1 and R 3 It is a hydrogen atom or a deuterium atom. In one aspect of the invention, only R... 1 and R 3 It is a hydrogen atom or a deuterium atom. In one aspect of the invention, only R... 1 and R 2 It is a hydrogen atom or a deuterium atom. In one aspect of the invention, R 1 and R 2 and R 3It consists of hydrogen or deuterium atoms.

[0035] R in general formula (1) 1 ~R 5 The 0 to 2 aryl groups are either substituted or unsubstituted. R 1 ~R 5 The aryl group can be a monocyclic ring or a fused ring composed of two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example, selected from 2 to 4. Specific examples of the ring include benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, and triphenylene rings. In one aspect of the invention, the aryl group is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphth-1-yl, or a substituted or unsubstituted naphth-2-yl, preferably a substituted or unsubstituted phenyl. Regarding the substituents of the aryl group, for example, they can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In one aspect of the invention, the substituents of the aryl group are selected from one or more of the group consisting of alkyl, aryl, and deuterium atoms. In a preferred aspect of the invention, the aryl group is substituted by at least one deuterium atom. In one aspect of the invention, the aryl group is unsubstituted. The following are examples of R. 1 ~R 5 Specific examples of substituted or unsubstituted aryl groups that can be used. The aryl groups that can be used in this invention are not limited by the following specific examples. In the following specific examples, * indicates a bonding position. Furthermore, the methyl group is omitted. Therefore, Ar2 to Ar7 represent structures substituted with a methyl group. [Chemical Formula 7-1] [Chemical Formula 7-2] [Chemical Formula 7-3]

[0036] Apart from the specific examples mentioned above, groups in Ar1 to Ar25 that replace all hydrogen atoms with deuterium atoms are exemplified here as Ar45 to Ar69. In one aspect of the invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar1 to Ar69. In a preferred embodiment of the invention, R 1 ~R 5The aryl group that can be used is selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar14, Ar19, Ar20, Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64. In a preferred embodiment of the invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar26 to Ar69. In a preferred embodiment of the invention, R 1 ~R 5 The aryl groups that can be used are selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63, and Ar64.

[0037] R in general formula (1) 1 ~R 5 Of the aryl groups, 0 to 2 are substituted or unsubstituted, preferably 0 to 1 are substituted or unsubstituted. In one embodiment of the invention, R 1 ~R 5 Only one of the aryl groups is either substituted or unsubstituted. In one aspect of the invention, R 1 ~R 5 Only two of them are substituted or unsubstituted aryl groups. In one aspect of the invention, R 1 ~R 5 Neither of them are substituted or unsubstituted aryl groups. In a preferred embodiment of the invention, at least R 4 The aryl group may be substituted or unsubstituted. In one aspect of the invention, at least R 3 The aryl group may be substituted or unsubstituted. In one aspect of the invention, at least R 2 The aryl group may be substituted or unsubstituted. In one aspect of the invention, R 3 and R 4 The aryl group may be substituted or unsubstituted. In one aspect of the invention, R 2 and R 4 The aryl group can be substituted or not.

[0038] R in general formula (1) 1 ~R 5 It can be a substituted or unsubstituted alkyl group. R 1 ~R 5The alkyl group can be any of the following: straight-chain, branched, or cyclic. Furthermore, two or more of the straight-chain, cyclic, and branched groups can be mixed together. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isohexyl, n-octyl, isooctyl, n-nonyl, isonyl, n-decyl, isodecyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group can be further substituted with, for example, a deuterium atom, aryl, alkoxy, aryloxy, or a halogen atom. In one embodiment of the invention, the alkyl substituent is one or more selected from the group consisting of aryl and deuterium atoms. In a preferred embodiment of the invention, the alkyl group is unsubstituted, for example, selected from the group consisting of methyl, ethyl, isopropyl, and tert-butyl.

[0039] In one aspect of the invention, R of general formula (1) 1 ~R 5 The 0 to 4 alkyl groups are substituted or unsubstituted alkyl groups. In one embodiment of the invention, R 1 ~R 5 Only one of them is a substituted or unsubstituted alkyl group. In one aspect of the invention, R 1 ~R 5 Only two of them are substituted or unsubstituted alkyl groups. In one aspect of the invention, R 1 ~R 5 Only three of them are substituted or unsubstituted alkyl groups. In one aspect of the invention, R 1 ~R 5 Four of them are substituted or unsubstituted alkyl groups. In one embodiment of the invention, R 1 ~R 5 None of them are substituted or unsubstituted alkyl groups. In a preferred embodiment of the invention, at least R 4 The alkyl group may be substituted or unsubstituted. In one aspect of the invention, at least R 3 The alkyl group may be substituted or unsubstituted. In one aspect of the invention, at least R 2 The alkyl group may be substituted or unsubstituted. In one aspect of the invention, at least R 1 R is a substituted or unsubstituted alkyl group. In one embodiment of the invention, R 3 and R 4 R is a substituted or unsubstituted alkyl group. In one embodiment of the invention, R 2 and R 4 It can be a substituted or unsubstituted alkyl group.

[0040] R in general formula (1) 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 They can bond together to form a ring structure. For details on the ring structure and preferred configurations, please refer to R. 14 and R 15 The above description relates to the formed ring-shaped structure. In one aspect of the invention, R... 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 One group of elements bonds together to form a ring structure. In one embodiment of the invention, R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 They do not bond with each other to form a ring structure.

[0041] In general formula (1), L represents a single bond or a divalent linking group. Examples of divalent linking groups include substituted or unsubstituted arylene groups and substituted or unsubstituted heteroarylene groups. In a preferred embodiment of the invention, L is a single bond. In another embodiment of the invention, L is a substituted or unsubstituted arylene group. In another embodiment of the invention, L is a substituted or unsubstituted heteroarylene group. Regarding the aryl portion constituting the arylene group, reference can be made to the R group described above. 1 ~R 5 The description and preferred range of aryl groups are listed in the description section. Examples of heteroarylene groups include linking groups that replace at least one carbon atom in the ring skeleton constituting the arylene with a nitrogen atom. Specific examples of L are given below. However, the L used in this invention is not to be interpreted as limiting in these specific examples. Furthermore, in the following specific examples, the methyl group is omitted. Therefore, for example, L3 to L5 are substituted with a methyl group. * indicates the bonding position. L1 is a single bond.

[0042] [Chemical Formula 8]

[0043] Compounds in which all hydrogen atoms present in L2 to L13 are replaced by deuterium atoms are disclosed as L14 to L25. In one embodiment of the present invention, L is selected from the group consisting of L1 to L25. In one embodiment of the present invention, L is selected from the group consisting of L1 to L7 and L14 to L19. In one embodiment of the present invention, L is selected from the group consisting of L1, L8 to L13, and L20 to L25. In one embodiment of the present invention, L is selected from the group consisting of L2 to L25. In one embodiment of the present invention, L is L1.

[0044] In general formula (1), Y represents a substituted or unsubstituted carbazole-9-yl group or a substituted or unsubstituted aryl group. In one aspect of the invention, Y is a substituted or unsubstituted carbazole-9-yl group. In one aspect of the invention, Y is a substituted or unsubstituted aryl group. Y can be a substituted or unsubstituted carbazole-9-yl group equivalent to Z in the above general formula (b). 1 ~Z 4 Z 6 ~Z 9 None of them are cases of N. That is, Z is equivalent to general formula (b). 1 CR 14 Z 2 CR 15 Z 3 CR 16 Z 4 CR 17 Z 6 CR 18 Z 7 CR 19 Z 8 CR 20 Z 9 CR 21 In this case, the substituted or unsubstituted carbazole-9-yl group that can be used in Y can be a carbazole-9-yl group fused with one or more rings. For descriptions and preferred ranges of substituted or unsubstituted carbazole-9-yl groups containing such ring-fused carbazole-9-yl groups, please refer to R. 1 ~R 5 The corresponding descriptions. Furthermore, as specific examples of substituted or unsubstituted carbazole-9-yl groups that can be used in Y, examples D1 to D1180 can be cited above. Regarding the groups or preferred groups that Y can choose from, the descriptions related to D1 to D1180 can also be referred to above. In one aspect of the present invention, the substituted or unsubstituted carbazole-9-yl group represented by Y and R... 1 ~R 5At least one of the donor groups represented in the invention has the same structure. In one embodiment of the invention, the substituted or unsubstituted carbazole-9- group represented by Y is identical to R. 1 ~R 5 All the donor groups represented have the same structure. In one aspect of the invention, the substituted or unsubstituted carbazole-9-group represented by Y is related to R. 1 ~R 5 The donor groups represented have different structures. Regarding the substituted or unsubstituted aryl groups that Y can use, please refer to R. 1 ~R 5 The description and preferred range of substituted or unsubstituted aryl groups are as follows. Specific examples of substituted or unsubstituted aryl groups that can be used in Y include Ar1 to Ar69 described above. Regarding the groups or preferred groups that can be selected from Y, reference can also be made to the above description related to Ar1 to Ar69. In one aspect of the invention, the substituted or unsubstituted aryl group represented by Y and R... 1 ~R 5 At least one of the substituted or unsubstituted aryl groups represented by Y has the same structure. In one aspect of the invention, the substituted or unsubstituted aryl group represented by Y is identical to R. 1 ~R 5 All substituted or unsubstituted aryl groups represented have the same structure. In one aspect of the invention, the substituted or unsubstituted aryl group represented by Y is the same as R. 1 ~R 5 The structures of the substituted or unsubstituted aryl groups are different. When Y is a substituted or unsubstituted aryl group, R 1 ~R 5 The first two atoms are hydrogen or deuterium atoms. When Y is a substituted or unsubstituted aryl group, it interacts with R. 1 ~R 5 Compounds with 0 to 2 hydrogen or deuterium atoms show a better effect compared to compounds with 3 or more hydrogen or deuterium atoms. When Y is a substituted or unsubstituted aryl group, for example, R... 1 ~R 5 Two of them are hydrogen or deuterium atoms. When Y is a substituted or unsubstituted aryl group, for example, R... 1 ~R 5 One of them is a hydrogen atom or a deuterium atom. When Y is a substituted or unsubstituted aryl group, for example, R... 1 ~R 5 Neither of them are hydrogen atoms nor deuterium atoms.

[0045] X in general formula (1) 1 Indicates N or CR 6 X 2Indicates N or CR 7 In one aspect of the invention, X 1 Let N, X 2 For CR 7 In one aspect of the invention, X 1 For CR 6 X 2 Let N be the number of elements. In a preferred embodiment of the invention, X is... 1 and X 2 All are N. R 6 and R 7 Each of these can independently represent a hydrogen atom, a deuterium atom, or a substituent. The substituents described herein can be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In one embodiment of the invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the invention, R is an alkyl group that can be substituted with a deuterium atom. In one embodiment of the invention, R is an aryl group that can be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0046] In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazole-9-yl group, X 1 and X 2 N is a single bond and L is a single bond. Assuming these conditions are met, examples can be given of ways that also satisfy the following additional conditions. In one embodiment of the invention, R... 5 Further, it is a donor group. In one embodiment of the invention, R... 2 Further, it is cyano. In one aspect of the invention, R 4 Further, it may be a substituted or unsubstituted aryl group. In one aspect of the invention, R 3 Further, the aryl group may be substituted or unsubstituted. In one aspect of the invention, the following can also be cited: R 1 ~R 5 One of the atoms is a donor group, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining two are independently hydrogen or deuterium atoms, for example, R. 5 As a donor group, R 2 It is cyano, R 4 For substituted or unsubstituted aryl groups, R 1 and R 3 Each can be independently a hydrogen atom or a deuterium atom. Y and R 5 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 One of them is a donor group, one is a cyano group, two are independently substituted or unsubstituted aryl groups, and the remaining one is a hydrogen atom or a deuterium atom, for example, R.5 As a donor group, R 2 It is cyano, R 3 and R 4 R is independently either a substituted or unsubstituted aryl group. 1 It can be a hydrogen atom or a deuterium atom. R 3 and R 4 They can be the same or different. Y and R 5 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 One of them is a donor group, one is a substituted or unsubstituted aryl group, and the remaining three are each independently a hydrogen atom or a deuterium atom, for example, R 5 As a donor group, R 4 For substituted or unsubstituted aryl groups, R 1 and R 2 and R 3 Each can be independently a hydrogen atom or a deuterium atom. Y and R 5 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 One of them is a donor group, two are independently substituted or unsubstituted aryl groups, and the remaining two are independently hydrogen or deuterium atoms, for example, R 5 As a donor group, R 3 and R 4 R is independently either a substituted or unsubstituted aryl group. 1 and R 2 Each can be independently a hydrogen atom or a deuterium atom. R 3 and R 4 They can be the same or different. Y and R 5 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 Two of them are donor groups, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining one is a hydrogen atom or a deuterium atom, such as R. 3 and R 5 Each is an independent donor group, R 2 It is cyano, R 4 For substituted or unsubstituted aryl groups, R 1 It consists of hydrogen or deuterium atoms. Y and R 3 and R 5 They can all be the same, they can all be different, or only Y and R can be different. 3 The same, or only Y and R. 5 The same, or only R 3 and R5 The same. In one aspect of the invention, the following situation can also be cited: R 1 ~R 5 Two of the atoms are independently donor groups, one is a substituted or unsubstituted aryl group, and the remaining two are independently hydrogen or deuterium atoms, for example, R. 3 and R 5 Each is an independent donor group, R 4 For substituted or unsubstituted aryl groups, R 1 and R 2 Each can be independently a hydrogen atom or a deuterium atom. Y and R 3 and R 5 They can all be the same, they can all be different, or only Y and R can be different. 3 The same, or only Y and R. 5 The same, or only R 3 and R 5 The same. In one aspect of the invention, the following situation can also be cited: R 1 ~R 5 The three groups in the group are each an independent donor group, one is a cyano group, and the remaining one is a hydrogen atom or a deuterium atom, for example, R. 3 and R 4 and R 5 Each is an independent donor group, R 2 It is cyano, R 1 It consists of hydrogen or deuterium atoms. Y and R 3 and R 4 and R 5 They can all be the same, they can all be different, or only R. 3 and R 4 The same, or only R 4 and R 5 The same, or only R 3 and R 5 The same, or only R 3 and R 4 and R 5 same.

[0047] In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazole-9-yl group, X 1 For CH, X 2 N represents a single bond and L represents a single bond. Given these conditions, we can illustrate ways to satisfy the additional conditions mentioned earlier. In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted carbazole-9-yl group, X 1 Let N, X 2CH represents a single bond, and L represents a single bond. Given these conditions, we can illustrate ways to satisfy additional conditions from the previous paragraph.

[0048] In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X... 1 and X 2 N is a single bond and L is a single bond. Assuming these conditions are met, examples can be given of ways that also satisfy the following additional conditions. In one embodiment of the invention, R... 5 Further, it is a donor group. In one embodiment of the invention, R... 2 Further, it is cyano. In one aspect of the invention, R 4 Further, it may be a substituted or unsubstituted aryl group. In one aspect of the invention, R 3 Further, the aryl group may be substituted or unsubstituted. In one aspect of the invention, the following can also be cited: R 1 ~R 5 One of the atoms is a donor group, one is a cyano group, one is a substituted or unsubstituted aryl group, and the remaining two are independently hydrogen or deuterium atoms, for example, R. 5 As a donor group, R 2 It is cyano, R 4 For substituted or unsubstituted aryl groups, R 1 and R 3 Each can be independently a hydrogen atom or a deuterium atom. Y and R 4 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 One of them is a donor group, one is a cyano group, two are independently substituted or unsubstituted aryl groups, and the remaining one is a hydrogen atom or a deuterium atom, for example, R. 5 As a donor group, R 2 It is cyano, R 3 and R 4 R is independently either a substituted or unsubstituted aryl group. 1 It consists of hydrogen or deuterium atoms. Y and R 3 and R 4 They can all be the same, they can all be different, or only Y and R can be different. 3 The same, or only Y and R. 4 The same, or only R 3 and R 4 The same. In one aspect of the invention, the following situation can also be cited: R 1 ~R 5 One of them is a donor group, two are independently substituted or unsubstituted aryl groups, and the remaining two are independently hydrogen or deuterium atoms, for example, R 5 As a donor group, R3 and R 4 R is independently either a substituted or unsubstituted aryl group. 1 and R 2 Each can be independently a hydrogen atom or a deuterium atom. Y and R 3 and R 4 They can all be the same, they can all be different, or only Y and R can be different. 3 The same, or only Y and R. 4 The same, or only R 3 and R 4 The same. And, for example, the following cases can be cited: R 5 As a donor group, R 2 and R 4 R is independently either a substituted or unsubstituted aryl group. 1 and R 3 Each can be independently a hydrogen atom or a deuterium atom. Y and R 2 and R 4 They can all be the same, they can all be different, or only Y and R can be different. 2 The same, or only Y and R. 4 The same, or only R 2 and R 4 The same. In one aspect of the invention, the following situation can also be cited: R 1 ~R 5 Two of them are independent donor groups: one is a cyano group, and the other is a substituted or unsubstituted aryl group. The remaining one is a hydrogen atom or a deuterium atom, for example, R. 3 and R 5 Each is an independent donor group, R 2 It is cyano, R 4 For substituted or unsubstituted aryl groups, R 1 It can be a hydrogen atom or a deuterium atom. R 3 and R 5 They can be the same or different. Y and R 4 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 Two of them are donor groups, one is a substituted or unsubstituted aryl group, and the remaining two are hydrogen or deuterium atoms, respectively, for example, R. 3 and R 5 Each is an independent donor group, R 4 For substituted or unsubstituted aryl groups, R 1 and R 2 Each can be independently a hydrogen atom or a deuterium atom. R 3 and R 5 They can be the same or different. Y and R4 They can be the same or different. In one aspect of the invention, the following situations can also be cited: R 1 ~R 5 The three groups in the group are each an independent donor group, one is a cyano group, and the remaining one is a hydrogen atom or a deuterium atom, for example, R. 3 and R 4 and R 5 Each is an independent donor group, R 2 It is cyano, R 1 It can be a hydrogen atom or a deuterium atom. R 3 and R 4 and R 5 They can all be the same, they can all be different, or only R. 3 and R 4 The same, or only R 4 and R 5 The same, or only R 3 and R 5 same.

[0049] In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X... 1 For CH, X 2 N represents a single bond and L represents a single bond. Given these conditions, we can illustrate ways to satisfy the additional conditions mentioned earlier. In one aspect of the present invention, Y in general formula (1) is a substituted or unsubstituted aryl group, and X... 1 Let N, X 2 CH represents a single bond, and L represents a single bond. Given these conditions, we can illustrate ways to satisfy additional conditions from the previous paragraph.

[0050] When it is desired to provide a compound with a short emission wavelength, it is preferable to use a compound having a carbazole-9-yl group that is substituted with an aryl group that can be replaced by a deuterium atom or an alkyl or aryl group and has a cyano group.

[0051] The compound represented by general formula (1) is preferably free of metal atoms and can be a compound composed only of 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 general formula (1) is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Furthermore, the compound represented by general formula (1) can be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) can be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. The compound represented by general formula (1) can be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, and nitrogen atoms. In addition, the compound represented by general formula (1) can be a compound containing deuterium atoms but not hydrogen atoms.

[0052] In this specification, "substituent group A" represents a group selected from deuterium, hydroxyl, halogen (e.g., fluorine, chlorine, bromine, iodine), alkyl (e.g., 1-40 carbon atoms), alkoxy (e.g., 1-40 carbon atoms), alkylthio (e.g., 1-40 carbon atoms), aryl (e.g., 6-30 carbon atoms), aryloxy (e.g., 6-30 carbon atoms), arylthio (e.g., 6-30 carbon atoms), heteroaryl (e.g., 5-30 ring skeleton atoms), heteroaryloxy (e.g., 5-30 ring skeleton atoms). A group obtained by combining one or more atoms or groups from the group consisting of 5 to 30, heteroarylthio (e.g., 5 to 30 atoms constituting the ring skeleton), acyl (e.g., 1 to 40 carbon atoms), alkenyl (e.g., 1 to 40 carbon atoms), alkynyl (e.g., 1 to 40 carbon atoms), alkoxycarbonyl (e.g., 1 to 40 carbon atoms), aryloxycarbonyl (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl (e.g., 1 to 40 carbon atoms), silyl (e.g., trialkylsilyl with 1 to 40 carbon atoms), and nitro. In this specification, "substituent group B" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., 1 to 40 carbon atoms), alkoxy (e.g., 1 to 40 carbon atoms), aryl (e.g., 6 to 30 carbon atoms), aryloxy (e.g., 6 to 30 carbon atoms), heteroaryl (e.g., 5 to 30 ring skeleton atoms), heteroaryloxy (e.g., 5 to 30 ring skeleton atoms), and diarylamino (e.g., 0 to 20 carbon atoms). In this specification, "substituent group C" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms), heteroaryl (e.g., 5 to 20 cyclic skeleton atoms), and diarylamino (e.g., 12 to 20 carbon atoms). In this specification, "substituent group D" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium atom, alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms) and heteroaryl (e.g., 5 to 20 cyclic skeleton atoms). In this specification, "substituent group E" means a group obtained by selecting one atom or group or a combination of two or more from the group consisting of deuterium, alkyl (e.g., carbon 1 to 20) and aryl (e.g., carbon 6 to 22). In this specification, the substituents described as "substituted or unsubstituted" or "substitutable" can be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0053] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 4 below. The compounds represented by general formula (1) that can be used in this invention should not be interpreted limitingly by these specific examples. Table 1 shows compounds represented by general formula (1) where Y is a fully deuterated carbazole-9-yl (D722), X... 1 and X 2 All are N, L are single bonds, R 1 and R 3 For hydrogen atoms, R 2 It is cyano, R 4 For phenyl (Ar1), R 5 Specific examples of compounds D1 to D1260 are shown in Table 1. Specifically, the R values ​​of compounds having the following structures are listed sequentially. 5 The structures of compounds 1 through 1260 were determined. [Chemical Formula 9] [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4]

[0054] Table 2 shows the structures of compounds 1 to 86940 as variants of the structures shown in Table 1. Table 2 also shows compounds of general formula (1) where Y is per-deuterated carbazole-9-yl (D722), X... 1 and X 2 All are N, L are single bonds, R 1 and R 3 For hydrogen atoms, R 2 It is cyano, R 4 Ar1 to Ar69, R 5 Specific examples of compounds D1 to D1260 are shown in Table 2. Specifically, the R values ​​of compounds having the following structures are listed sequentially. 4 and R 5 The structures of compounds 1 through 86940 were determined. In the compound segment 1 through 1260 of Table 2, Y was fixed as D722, and X... 1 and X 2 N and L are fixed as single bonds, and R is fixed as a single bond. 1 and R 3 Fixed as hydrogen atoms, R 2 Fixed as cyano, R 4 Fixed as Ar1, R 5 Compounds D1 to D1260 are sequentially designated as compounds 1 to 1260. That is, the structures of compounds 1 to 1260 from Table 1 are summarized in section 1 of Table 2. In section 1261 to 2520 of Table 2, Y is fixed as D722, and X... 1 and X 2 N and L are fixed as single bonds, and R is fixed as a single bond. 1 and R 3 Fixed as hydrogen atoms, R 2 Fixed as cyano, R 4 Fixed as Ar2, R 5 The compounds D1 to D1260 were sequentially designated as compounds 1261 to 2520. In the compound segment 2521 to 3780 in Table 2, Y was fixed as D722 and X. 1 and X 2 N and L are fixed as single bonds, and R is fixed as a single bond. 1 and R 3 Fixed as hydrogen atoms, R 2 Fixed as cyano, R 4 Fixed as Ar3, R 5Compounds D1 to D1260 were subsequently identified as compounds 2521 to 3780. The following sections were also identified in the same manner, with Y fixed as D722 and X in the final section of compounds 85681 to 86940. 1 and X 2 N and L are fixed as single bonds, and R is fixed as a single bond. 1 and R 3 Fixed as hydrogen atoms, R 2 Fixed as cyano, R 4 Fixed as Ar69, R 5 The compounds D1 to D1260 were identified as compounds 85681 to 86940, respectively. [Chemical Formula 10] [Table 2]

[0055] In Table 3, the structures of compounds 1 to 5708388 are shown as variants of the structures shown in Table 2. In Table 3, the structures of Y and X of general formula (1) are shown. 1 X 2 L, R 1 ~R 5 To determine the structure. In the L column of Table 3, the "-" indicates a single bond. In the compound 1–86940 segment of Table 3, Y is fixed as D722, and X… 1 and X 2 N and L are fixed as single bonds, and R is fixed as a single bond. 1 and R 3 Fixed as hydrogen atoms, R 2 Fixed as cyano, R 4 For any one of Ar1 to Ar69, R 5 Compounds listed as any one of D1 to D1260 are designated as compounds 1 to 86940. In this section, R... 4 It varies between Ar1 and Ar69, R 5 The numbers vary between D1 and D1260. However, when there are two groups that vary in this way, the group that appears first (the group listed on the left side of Table 3) is fixed first, and then the group that appears later (the group listed on the right side of Table 3) is varied, thus assigning the compound numbers sequentially. That is, the group that appears first, R... 4 First it was fixed as Ar1, then R appeared. 5 The compounds, sequentially designated as D1 to D1260, were designated as compounds 1 to 1260. Next, R... 4 Fixed as Ar2, R 5The compounds, sequentially designated as D1 to D1260, were designated as compounds 1261 to 2520. Next, R... 4 Fixed as Ar3, R 3 Compounds sequentially designated as D1 to D1260 were subsequently identified as compounds 2521 to 3780. Following the same procedure, R was finally determined. 4 Fixed as Ar69, R 5 The compounds, designated D1 to D1260, are sequentially identified as compounds 85681 to 86940. That is, the structures of compounds 1 to 86940 in Table 3 are summarized in section 1. The structures of compounds from 86941 to 173880 in Table 3 to compounds 5707129 to 5708388 at the bottom are also identified in the same manner. Furthermore, as shown in the rightmost column of Table 3, for example, regarding compounds 5707129 to 5708388 at the bottom, R... 3 and R 4 and R 5 same. [Table 3-1] [Table 3-2]

[0056] In Table 3, the structure of Y in general formula (1) being per-deuterated carbazole-9-yl (D722) is identified as the structure of compounds 1 to 3370794, and the structure of Y being per-deuterated phenyl (Ar45) is identified as the structure of compounds 3370795 to 5708388. In Table 4, for each of compounds 1 to 3370794, the compounds with Y changed from D722 as shown in Table 4 are listed in tabular form. In Table 4, to make the correspondence easy to understand, compounds 1 to 3370794 with Y being D722 are shown in the first paragraph. In the second paragraph of Table 4, for example, compound 1 (1) represents a compound having a structure in which Y of compound 1 is replaced with D1. And compound 2 (1) represents a compound having a structure in which Y of compound 2 is replaced with D1. Following the same approach, compound 3370794(1) represents a compound having a structure in which Y of compound 3370794 is replaced by D1. The structures of compounds 1(2) to 3370794(2) in paragraph 3 are also determined in the same way as in paragraph 2. [Table 4-1] [Table 4-2]

[0057] The compounds identified in the above numbering are disclosed individually. Furthermore, in specific examples of the above compounds where rotational isomers are present, mixtures of rotational isomers and isolated rotational isomers are also disclosed in this specification. In one embodiment of the invention, compounds are selected from the group of compounds consisting of compounds 1 to 5708388 and compounds 1(n) to 3370794(n) [wherein n is 1 to 209]. In another embodiment of the invention, compounds are selected from the group of compounds consisting of compounds 1 to 3370794 and compounds 1(n) to 3370794(n) [wherein n is 1 to 141]. In yet another embodiment of the invention, compounds are selected from the group of compounds consisting of compounds 3370795 to 5708388 and compounds 1(n) to 3370794(n) [wherein n is 142 to 209].

[0058] Examples of preferred groups of compounds represented by general formula (1) are given below. [Chemical Formula 11]

[0059] Here are examples of another preferred group of compounds represented by general formula (1). [Chemical Formula 12]

[0060] Here are examples of another preferred group of compounds represented by general formula (1). [Chemical Formula 13-1] [Chemical Formula 13-2]

[0061] Here are examples of another preferred group of compounds represented by general formula (1). [Chemical Formula 14]

[0062] Here are examples of another preferred group of compounds represented by general formula (1). [Chemical Formula 15]

[0063] Regarding the molecular weight of the compound represented by general formula (1), for example, when attempting to form an organic layer containing the compound represented by general formula (1) by vapor deposition, it 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). Compounds represented by general formula (1) can be coated to form films regardless of their molecular weight. Even compounds with relatively large molecular weights can be coated to form films. Compounds represented by general formula (1) have advantages such as easy solubility in organic solvents. Therefore, compounds represented by general formula (1) are easily applicable to coating and are easy to purify to improve purity.

[0064] Alternatively, the present invention can be used to use compounds containing multiple structures represented by general formula (1) within the molecule as luminescent materials. For example, a polymer obtained by pre-existing a polymeric group in the structure represented by general formula (1) and then polymerizing that polymeric group can be considered as a luminescent material. For example, a monomer containing a polymeric functional group at any site in general formula (1) can be prepared, and a polymer with repeating units can be obtained by polymerizing it alone or copolymerizing it with other monomers, and this polymer can be used as a luminescent material. Alternatively, dimers or trimers can be obtained by coupling compounds having the structure represented by general formula (1) to each other, and these can be used as luminescent materials.

[0065] As an example of a polymer having repeating units containing the structure represented by general formula (1), a polymer containing the structure represented by either of the following two general formulas can be cited. [Chemical Formula 16]

[0066] In the above general formula, Q represents a group containing the structure represented by general formula (1), and L 1 and L 2 This indicates a linking group. The linking group preferably has 0 to 20 carbon atoms, more preferably 1 to 15, and even more preferably 2 to 10. The linking group preferably has a -X symbol. 11 -L 11 - The linking group representing the structure. Here, X 11 Represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11 The linking group is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms. In the above general formula, R 101 R 102 R 103 and R 104Each substituent is represented independently. Preferably, it is a substituted or unsubstituted alkyl group with 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group with 1 to 6 carbon atoms, or a halogen atom; more preferably, it is an unsubstituted alkyl group with 1 to 3 carbon atoms, an unsubstituted alkoxy group with 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, it is an unsubstituted alkyl group with 1 to 3 carbon atoms or an unsubstituted alkoxy group with 1 to 3 carbon atoms. L 1 and L 2 The linking groups can be bonded to any site in the general formula (1) that constitutes Q. Two or more linking groups can be connected to one Q to form a cross-linked structure or a network structure.

[0067] As a specific example of a repeating unit, the structure represented by the following formula can be cited. [Chemical Formula 17]

[0068] Polymers having repeating units containing these formulas can be synthesized by introducing a hydroxyl group into any part of the general formula (1) beforehand, using it as a linking group to react the following compound to introduce a polymerizable group, and then polymerizing the polymerizable group. [Chemical Formula 18]

[0069] Polymers containing the structure represented by general formula (1) within their molecules can be polymers composed solely of repeating units having the structure represented by general formula (1), or polymers containing repeating units having structures other than those represented by general formula (1). Furthermore, the repeating units containing the structure represented by general formula (1) in the polymer can be a single type or two or more types. As repeating units that do not have the structure represented by general formula (1), examples include repeating units derived from monomers commonly used for copolymerization. For example, repeating units derived from monomers such as ethylene and styrene that have olefinic unsaturated bonds can be cited.

[0070] In one embodiment, the compound represented by general formula (1) is a luminescent material. The compound represented by general formula (1) includes compounds with long luminescence lifetimes. When used in organic light-emitting elements, the compound represented by general formula (1) can improve luminescence characteristics. For example, the compound represented by general formula (1) includes compounds that can extend the lifetime of the element when used in organic light-emitting elements. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. The compound represented by general formula (1) contains a high proportion of delayed fluorescence components. For example, a compound containing more than 80% of the total luminescence as delayed fluorescence components, and for example, more than 90% of the total luminescence as delayed fluorescence components. In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the UV region, the blue, green, yellow, orange, and red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or the near-infrared region when excited by thermal or electronic means. In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm) when excited by thermal or electronic means. In one embodiment of the present invention, the compound represented by general formula (1) is able to 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 one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the ultraviolet spectral region (e.g., 280–400 nm) when excited by thermal or electronic means. In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. In one embodiment of the present invention, an organic semiconductor element using a compound represented by general formula (1) can be fabricated. The organic semiconductor element described herein can be a light-involved organic optical element or a light-non-involved organic element. The organic optical element can 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 due to light within the element. In one embodiment of the present invention, an organic optical element such as an organic electroluminescent element or a solid-state imaging element (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In one embodiment of the present invention, a CMOS (complementary metal oxide semiconductor) or the like using a compound represented by general formula (1) can be fabricated.

[0071] The electronic properties of a small molecule chemical library can be calculated using quantum chemical calculations based on well-known ab initio. For example, as a basis set, analysis of the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) using time-dependent density functional theory, which utilizes the three-parameter Lee-Yang-Parr mixture functionals known as 6-31G* and Becke, can screen for molecular fragments (partially) with HOMOs above a specific threshold and LUMOs below a specific threshold. Thus, for example, when a HOMO energy (e.g., ionization potential) above -6.5 eV is present, the donor portion (“D”) can be selected. And, for example, when a LUMO energy (e.g., electron affinity) below -0.5 eV is present, the acceptor portion (“A”) can be selected. The bridge portion (“B”) is, for example, a strongly conjugated system that strictly restricts the acceptor and donor portions to unique three-dimensional structures, thereby preventing repetition between the π-conjugated systems of the donor and acceptor portions. In one embodiment, the compound library is screened using more than one of the following properties. 1. Emission near a specific wavelength 2. Calculated triplet states above a specific energy level 3. ΔE below a specific value ST value 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In one embodiment, the difference between the lowest excited singlet state and the lowest excited triplet state at 77K (ΔE) ST The voltage is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, ΔE STValues ​​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 one embodiment, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0072] [Synthetic methods for compounds represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. The compounds represented by general formula (1) can be synthesized by combining known reactions. Regarding the compounds represented by general formula (1), R... 1 ~R 5 One to three of the groups are donor groups. For example, compounds of general formula (1) with substituted or unsubstituted carbazole-9-yl as donor groups can be synthesized by reacting a substituted or unsubstituted carbazole with a precursor in which the donor group is a fluorine atom. For details on the reaction conditions, please refer to the synthesis examples described later.

[0073] [Structures of compounds represented by general formula (1)] In one embodiment, a solid film or layer is formed by combining the compound represented by general formula (1), dispersing the compound, covalently bonding the compound, coating the compound, carrying the compound, or using the compound together with one or more materials associated with the compound (e.g., small molecules, polymers, metals, metal complexes, etc.). For example, the compound represented by general formula (1) can be combined with an electroactive material to form a film. In some cases, the compound represented by general formula (1) can be combined with a hole transport polymer. In some cases, the compound represented by general formula (1) can be combined with an electron transport polymer. In some cases, the compound represented by general formula (1) can be combined with both a hole transport polymer and an electron transport polymer. In some cases, the compound represented by general formula (1) can be combined with a copolymer having both a hole transport portion and an electron transport portion. Through the embodiments described above, electrons and / or holes formed in the solid film or layer can interact with the compound represented by general formula (1).

[0074] [Membrane formation] In one embodiment, a film comprising a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution obtained by dissolving a composition comprising the compound of the present invention is applied to a surface, and after removing the solvent, a film is formed. Examples of wet processes include spin coating, slot coating, inkjet printing, gravure printing, offset printing, and flexographic printing, but are not limited to these. In the wet process, a suitable organic solvent capable of dissolving the composition comprising the compound of the present invention is selected. In one embodiment, a substituent (e.g., an alkyl group) that improves solubility with respect to the organic solvent can be introduced into the compound contained in the composition. In one embodiment, a film containing the compound of the present invention can be formed by a dry process. In one embodiment, vacuum evaporation can be used as the dry process, but it is not limited to this. When using vacuum evaporation, the compound constituting the film can be co-deposited from a single evaporation source, or from a single evaporation source containing a mixture of compounds. When using a single evaporation source, a mixed powder obtained by mixing compound powders can be used, a compression molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating, melting, and cooling the individual compounds can be used. In one embodiment, by performing co-evaporation under conditions where the evaporation rates (weight reduction rates) of the multiple compounds contained in a single evaporation source are consistent or substantially consistent, a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the evaporation source can be formed. If multiple compounds are mixed with the same composition ratio as the composition ratio of the formed film and used as the evaporation source, a film with the desired composition ratio can be easily formed. In one embodiment, the temperature at which the co-deposited compounds achieve the same weight reduction rate can be determined, and this temperature is used as the temperature during co-evaporation.

[0075] [Examples of the use of compounds represented by general formula (1)] The compound represented by general formula (1) is useful as a material for organic light-emitting elements. In particular, it is preferred for use in organic light-emitting diodes and the like. Organic light-emitting diodes (OLEDs): One aspect of the present invention relates to the use of a compound of general formula (1) of the present invention as a luminescent material for an organic light-emitting element. In one embodiment, the compound of general formula (1) of the present invention can be effectively used as a luminescent material in the luminescent layer of an organic light-emitting element. In one embodiment, the compound of general formula (1) comprises a delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having the structure represented by general formula (1). In one embodiment, the present invention relates to the use of a compound of general formula (1) as a delayed phosphor. In one embodiment, the compound of general formula (1) of the present invention can be used as a host material and can be used together with one or more luminescent materials, which may be fluorescent materials, phosphorescent materials, or TADF. In one embodiment, the compound of general formula (1) can also be used as a hole transport material. In one embodiment, the compound of general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from a compound of general formula (1). In one embodiment, an organic light-emitting element comprising the compound as a luminescent material emits delayed fluorescence and exhibits high luminous efficiency. In one embodiment, the light-emitting layer comprises a compound represented by general formula (1), which is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) on the film-forming surface affects or determines the propagation direction of light emitted by the arranged compounds. In one embodiment, by aligning the compounds in the propagation direction of light emitted by the light-emitting layer, the light extraction efficiency from the light-emitting layer is improved. One aspect of the present invention relates to an organic light-emitting element. In one embodiment, the organic light-emitting element comprises a light-emitting layer. In one embodiment, the light-emitting layer comprises a compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by general formula (1) assists in the luminescence of other light-emitting materials contained in the light-emitting layer (as a so-called auxiliary dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet state energy level, which is contained between the lowest excited singlet state energy level of the host material contained in the light-emitting layer and the lowest excited singlet state energy level of another light-emitting material contained in the light-emitting layer. In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least one light-emitting layer. In one embodiment, the organic layer includes only one light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers, and exciton blocking layers. In one embodiment, the hole transport layer can be a hole injection and transport layer with hole injection function, and the electron transport layer can be an electron injection and transport layer with electron injection function.

[0076] Emissive layer: In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, rebond to form excitons. In one embodiment, the layer emits light. In one embodiment, only a luminescent material is used as the luminescent layer. In one embodiment, the luminescent layer comprises a luminescent material and a host material. In one embodiment, the luminescent material is one or more compounds represented by general formula (1). In one embodiment, in order to improve the luminous efficiency of organic electroluminescent elements and organic photoluminescent elements, singlet and triplet excitons generated in the luminescent material are confined within the luminescent material. In one embodiment, a host material is used in addition to the luminescent material in the luminescent layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excitation singlet energy and an excitation triplet energy, at least one of which is higher than those energies of the luminescent material of the present invention. In one embodiment, singlet and triplet excitons generated in the luminescent material of the present invention are confined within the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently confined to promote luminous efficiency. In one embodiment, the singlet and triplet excitons are not sufficiently confined, but a high luminous efficiency is still obtained; that is, a host material capable of achieving a high luminous efficiency can be used in the present invention without particular limitation. In one embodiment, luminescence occurs in the luminescent material within the luminescent layer of the element of the present invention. In one embodiment, the emitted light comprises both fluorescence and delayed fluorescence. In one embodiment, the emitted light comprises light emitted from the host material. In one embodiment, the emitted light consists of light emitted from the host material. In one embodiment, the emitted light comprises light emitted from the compound represented by general formula (1) and light emitted from the host material. In one embodiment, TADF molecules and the host material are used. In one embodiment, TADF is an auxiliary dopant that excites a singlet state energy lower than that of the host material in the luminescent layer and an excitation singlet state energy higher than that of the luminescent material in the luminescent layer.

[0077] When using the compound represented by general formula (1) as an auxiliary dopant, various compounds can be used as luminescent materials (preferably fluorescent materials). As such luminescent materials, anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, benzo[a]ene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthracene derivatives, pyrrolemethylene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, juulolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn), etc., can be used. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons can be combined with each other. The following examples illustrate luminescent materials that can be used in combination with auxiliary dopants having the structure represented by general formula (1).

[0078] [Chemical Formula 19-1] [Chemical Formula 19-2] [Chemical Formula 19-3]

[0079] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 may be used, in particular, as luminescent materials used together with auxiliary dopants having the structure represented by general formula (1).

[0080] As a further preferred luminescent material, compounds represented by the following general formula (2) can also be cited. [Chemical Formula 20]

[0081] In general formula (2), R 1 R 3 ~R 16 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 2 Indicates acceptor group, or R 1 and R 2 They bond together to form acceptor groups, or R 2 and R 3 They bond together to form acceptor groups. R 3 and R4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 7 and R 8 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 R 15 and R 16 They can bond together to form a ring structure. X 1 O or NR, R represents a substituent. X 2 ~X 4 In the middle, X 3 and X 4 At least one of them is O or NR, and the remaining part can be O or NR, or it can be unconnected. When unconnected, the two ends independently represent hydrogen atoms, deuterium atoms, or substituents, respectively. CR in general formula (2) 1 CR 3 CR 4 CR 5 CR 6 CR 7 CR 8 CR 9 CR 10 CR 11 CR 12 CR 13 CR 14 CR 15 CR 16 It can be replaced by N.

[0082] In one aspect of the invention, in X 2 When R is O or NR 7 For acceptor groups, or R 6 and R 7 They bond together to form acceptor groups, or R 7 and R 8 They bond together to form acceptor groups. In one aspect of the invention, in X... 3 When R is O or NR 10 For acceptor groups, or R 9and R 10 They bond together to form acceptor groups, or R 10 and R 11 They bond together to form acceptor groups. In one aspect of the invention, in X... 4 When R is O or NR 15 For acceptor groups, or R 14 and R 15 They bond together to form acceptor groups, or R 15 and R 16 They bond together to form acceptor groups. In one aspect of the invention, in X... 2 NR and R are substituted or unsubstituted phenyl groups and are obtained by reacting with R. 8 When the bonded carbon atoms directly bond to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is replaced by an acceptor group. In one aspect of the invention, in X... 3 NR and R are substituted or unsubstituted phenyl groups and are obtained by reacting with R. 9 When the bonded carbon atoms directly bond to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is replaced by an acceptor group. In one aspect of the invention, in X... 4 NR and R are substituted or unsubstituted phenyl groups and are obtained by reacting with R. 16 When the bonded carbon atoms directly bond to form a carbazole ring, at least one of the 3-position and 6-position of the carbazole ring is replaced by an acceptor group. In one aspect of the invention, in X... 1 NR and R are substituted or unsubstituted phenyl groups and are obtained by reacting with R. 1 When the bonded carbon atoms are directly bonded to form a carbazole ring, the 3-position of the carbazole ring is replaced by an acceptor group (wherein the 3-position is located on the phenyl group). In one aspect of the invention, the compound is represented by the following general formula (2a). [Chemical Formula 21]

[0083] In general formula (2a), R 1 R 3 R 6 ~R 11 R 14 ~R 16 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 2 Indicates acceptor group, or R 1 and R 2 They bond together to form acceptor groups, or R 2 and R 3 They bond with each other to form acceptor groups. R 6 and R 7 R7 and R 8 R 9 and R 10 R 10 and R 11 R 14 and R 15 R 15 and R 16 They can bond together to form a ring structure. X 1 O or NR, R represents a substituent. X 2 ~X 4 In the middle, X 3 and X 4 At least one of the atoms in Ar is O or NR, and the remaining part can be O or NR, or it can be left unconnected. When unconnected, the two ends independently represent a hydrogen atom, a deuterium atom, or a substituent. 1 and Ar 2 Each aryl group, whether substituted or unsubstituted, or a heteroaryl group, can be represented independently. CR in general formula (2a) 1 CR 3 CR 6 CR 7 CR 8 CR 9 CR 10 CR 11 CR 14 CR 15 CR 16 It can be replaced by N.

[0084] As a further preferred luminescent material, compounds represented by the following general formula (3) can also be cited. [Chemical Formula 22]

[0085] In general formula (3), R 1 and R 2 Each of the following independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R. 3 ~R 16 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 1 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 R 6 and R 7 R 7 and R8 R 8 and R 9 R 9 and R 2 R 2 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 R 15 and R 16 R 16 and R 1 They can bond together to form a ring structure. CR in general formula (3) 3 CR 4 CR 5 CR 6 CR 7 CR 8 CR 9 CR 10 CR 11 CR 12 CR 13 CR 14 CR 15 CR 16 It can be replaced by N.

[0086] In one aspect of the invention, R 1 and R 2 Each is independently a substituted or unsubstituted phenyl group that can be fused with other rings. In one aspect of the invention, R 3 and R 10 Each is independently substituted with an amino group. In one embodiment of the invention, R 1 and R 3 and R 2 and R 10 At least one of the components is bonded to each other to form a cyclic structure. In one aspect of the invention, the cyclic structure comprises a benzozaborane ring.

[0087] As a further preferred luminescent material, compounds represented by the following general formula (4) can also be cited. [Chemical Formula 23]

[0088] In general formula (4), Z 1 and Z 2R represents, independently, a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 ~R 9 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. 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 R 7 and R 8 R 8 and R 9 They can bond together to form a ring structure. Among them, Z... 1 Z 2 R 1 and R 2 The rings formed by bonding together, R 2 and R 3 The rings formed by bonding together, R 4 and R 5 The rings formed by mutual bonding and R 5 and R 6 At least one of the rings formed by mutual bonding is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and is R 1 ~R 9 At least one of them is a substituted or unsubstituted aryl group or acceptor group, or Z 1 and Z 2 At least one of them is a ring having an aryl or acceptor group as a substituent. In the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, the carbon atoms that can be substituted can be replaced by nitrogen atoms. CR in general formula (4) 1 CR 2 CR 3 CR 4 CR 5 CR 6 CR 7 CR 8 CR 9 It can be replaced by N.

[0089] In one aspect of the invention, Z 1 and Z 2Each of the following is independently a fused non-fused benzene ring (with or without substituted benzene rings), a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or a pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. In one embodiment of the invention, R 1 ~R 9 Each is independently a substituted or unsubstituted aryl or acceptor group, or selected from R. 1 and R 2 The rings formed by bonding together, R 2 and R 3 The rings formed by bonding together, R 4 and R 5 The rings formed by mutual bonding and R 5 and R 6 One or more rings in the group consisting of rings bonded together are furan rings formed by the fusion of substituted or unsubstituted benzene rings, thiophene rings formed by the fusion of substituted or unsubstituted benzene rings, or pyrrole rings formed by the fusion of substituted or unsubstituted benzene rings. In one aspect of the invention, R 8 The aryl group or acceptor group may be substituted or unsubstituted. In one embodiment of the invention, it comprises two or more rings selected from the group consisting of the benzofuran ring, the benzothiophene ring, and the indole ring.

[0090] As a further preferred luminescent material, examples include compounds having the following structure α: a carbon-carbon bond a 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 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; where the hydrogen atoms in the structure can be replaced by deuterium atoms or substituents. [Chemical Formula 24]

[0091] In structure α, X 1 and X 2 Each of these groups independently represents a nitrogen atom or an oxygen atom formed by the bonding of substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups; Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaryl ring; R 1 Z and X represent hydrogen atoms, deuterium atoms, or substituents. 2 They can bond together to form a ring structure. In the fused ring structure A, the structure fused with b and X 1The structure fused with b and Z, Z and X 2 They can bond together to form a ring structure.

[0092] As a further preferred luminescent material, compounds represented by the following general formula (5) can also be cited. [Chemical Formula 25]

[0093] In general formula (5), Z 1 Z represents a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 2 and Z 3 R represents, independently, a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3 Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 R 2 and Z 2 Z 2 and Z 3 Z 3 and R 3 They can bond together to form a ring structure. Among them, R... 2 and Z 2 Z 2 and Z 3 Z 3 and R 3 At least one group of them bonds to each other to form a ring structure.

[0094] As a further preferred luminescent material, compounds represented by the following general formula (6) can also be cited. [Chemical Formula 26]

[0095] In general formula (6), X 3 Z represents an oxygen atom or a sulfur atom. 2 and Z 3 R represents, independently, a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 4 ~R 7 R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 2 and Z 2 Z 2 and Z 3 Z 3 and R 3 R 4 and R 5 R 5 and R 6 R 6 and R 7 They can bond together to form a ring structure. Among them, R... 2 and Z 2 Z 2 and Z 3 Z 3 and R 3 At least one group of them bonds to each other to form a ring structure.

[0096] As a further preferred luminescent material, compounds represented by the following general formula (7) can also be cited. [Chemical Formula 27]

[0097] In general formula (7), X 4 Z represents an oxygen atom or a sulfur atom. 2 and Z 3 R represents, independently, a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 4a ~R 7a R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3 Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 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 They can bond together to form a ring structure. Among them, R... 2 and Z 2 Z 2 and Z 3 Z 3 and R 3At least one group of them bonds to each other to form a ring structure.

[0098] As a further preferred luminescent material, compounds represented by the following general formula (8) can also be cited. [Chemical Formula 28]

[0099] In general formula (8), Z 1 Z represents a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 3 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 8 ~R 14 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 3 This indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and Z 3 Z 3 and R 3 They can bond together to form a ring structure.

[0100] As a further preferred luminescent material, compounds represented by the following general formula (9) can also be cited. [Chemical Formula 29]

[0101] In general formula (9), Z 1 and Z 4 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 3 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 15 ~R 17Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 3 This indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Z 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 They can bond together to form a ring structure.

[0102] As a further preferred luminescent material, compounds represented by the following general formula (10) can also be cited. [Chemical Formula 30]

[0103] In general formula (10), Z 1 and Z 5 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 3 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3 Each can be independently represented as either 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 They can bond together to form a ring structure. Among them, R... 2 and Z 2 Z 2 and Z 3 Z 3 and R 3 At least one group of them bonds to each other to form a ring structure.

[0104] As a further preferred luminescent material, compounds represented by the following general formula (11) can also be cited. [Chemical Formula 31]

[0105] In general formula (11), Z 1 Z represents a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 2 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 21 ~R 27 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 2 Indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 R 2 and Z 2 Z 2 and R 21 R 21 and R 22 R 22 and R 23 R 23 and R 24 R 24 and R 25 R 25 and R 26 R 26 and R 27 They can bond together to form a ring structure.

[0106] As a further preferred luminescent material, compounds represented by the following general formula (12) can also be cited. [Chemical Formula 32]

[0107] In general formula (12), Z 1 and Z 6 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 2 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 and R 28 ~R 30 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 2 Indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 R 2 and Z 2 Z 2 and R28 R 28 and R 29 R 29 and R 30 R 30 and Z 6 They can bond together to form a ring structure.

[0108] As a further preferred luminescent material, compounds represented by the following general formula (13) can also be cited. [Chemical Formula 33]

[0109] In general formula (13), Z 1 and Z 7 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings. 2 R indicates a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 1 R represents a hydrogen atom, a deuterium atom, or a substituent. 2 and R 3 Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 R 2 and Z 2 Z 2 and Z 7 Z 7 and R 3 They can bond together to form a ring structure. Among them, R... 2 and Z 2 Z 2 and Z 7 Z 7 and R 3 At least one group of them bonds to each other to form a ring structure.

[0110] As a further preferred luminescent material, compounds represented by the following general formula (14) can also be cited. [Chemical Formula 34]

[0111] In general formula (14), Z 1 This indicates a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R 1 and R 31 ~R 44Each can be independently represented as either a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 R 31 and R 32 R 32 and R 33 R 33 and R 34 R 34 and R 35 R 35 and R 36 R 36 and R 37 R 37 and R 38 R 38 and R 39 R 39 and R 40 R 40 and R 41 R 41 and R 42 R 42 and R 43 R 43 and R 44 They can bond together to form a ring structure.

[0112] As a further preferred luminescent material, compounds represented by the following general formula (15) can also be cited. [Chemical Formula 35]

[0113] In general formula (15), Z 1 and Z 8 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R. 1 and R 51 ~R 60 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 1 and Z 1 R 51 and R 52 R 52 and R 53 R 53 and R 54 R 54 and R 55 R 55 and R 56 R 56 and R 57 R 57 and R58 R 58 and R 59 R 59 and R 60 R 60 and Z 8 They can bond together to form a ring structure.

[0114] As a further preferred luminescent material, compounds represented by the following general formula (16) can also be cited. [Chemical Formula 36]

[0115] In general formula (16), Z 1 Z 8 and Z 9 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R. 1 and R 61 ~R 66 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 1 and Z 1 Z 9 and R 61 R 61 and R 62 R 62 and R 63 R 63 and R 64 R 64 and R 65 R 65 and R 66 R 66 and Z 8 They can bond together to form a ring structure.

[0116] As a further preferred luminescent material, compounds represented by the following general formula (17) can also be cited. [Chemical Formula 37]

[0117] In general formula (17), Z 1 Z 9 and Z 10 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R. 1 and R 67 ~R 69Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 70 Indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 Z 9 and R 67 R 67 and R 68 R 68 and R 69 R 69 and Z 10 Z 10 and R 70 They can bond together to form a ring structure.

[0118] As a further preferred luminescent material, compounds represented by the following general formula (18) can also be cited. [Chemical Formula 38]

[0119] In general formula (18), Z 1 Z 11 and Z 12 Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R. 1 and R 72 ~R 74 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent, R 71 Indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 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 They can bond together to form a ring structure.

[0120] As a further preferred luminescent material, compounds represented by the following general formula (19) can also be cited. [Chemical Formula 39]

[0121] In general formula (19), Z 1 and Z 11Each of these can be independently represented as a furan ring formed by the fusion of substituted or unsubstituted benzene rings, a thiophene ring formed by the fusion of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the fusion of substituted or unsubstituted benzene rings, R. 1 and R 76 ~R 82 R represents, independently, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 75 Indicates a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 R 75 and Z 11 Z 11 and R 76 R 76 and R 77 R 77 and R 78 R 78 and R 79 R 79 and R 80 R 80 and R 81 R 81 and R 82 They can bond together to form a ring structure.

[0122] As a further preferred luminescent material, compounds represented by the following general formula (20) can also be cited. [Chemical Formula 40]

[0123] In general formula (20), X 5 R represents a nitrogen atom formed by the bonding of an oxygen atom, a sulfur atom, or a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 101 ~R 130 Each can independently represent 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 R110 and R 111 R 111 and R 112 R 112 and R 113 R 113 and R 114 R 114 and R 115 R 115 and R 116 R 116 and R 117 R 117 and R 118 R 118 and R 119 R 119 and R 120 R 120 and R 121 R 121 and R 122 R 122 and R 123 R 123 and R 124 R 124 and R 125 R 125 and R 126 R 126 and R 127 R 127 and R 128 R 128 and R 129 R 129 and R 130 R 130 and R 101 They can bond together to form a ring structure.

[0124] As a further preferred luminescent material, compounds represented by the following general formula (21) can also be cited. [Chemical Formula 41]

[0125] In general formula (21), R 1 and R 2 Each of the following 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 R represents, independently, a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. 3 ~R 9 Each can independently represent a hydrogen atom, a deuterium atom, or a substituent. Wherein, R... 1 R 2 Z1 and Z 2 At least one of them contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. R 1 and Z 1 Z 1 and R 3 R 3 and R 4 R 4 and R 5 R 5 and Z 2 Z 2 and R 2 R 2 and R 6 R 6 and R 7 R 7 and R 8 R 8 and R 9 R 9 and R 1 They can bond together to form a ring structure. In the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, the carbon atoms that can be substituted can be replaced by nitrogen atoms. CR in general formula (21) 3 CR 4 CR 5 CR 6 CR 7 CR 8 CR 9 It can be replaced by N.

[0126] In one aspect of the invention, R 1 and R 2 Each group is independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group comprising one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. In one embodiment of the invention, Z 1 and Z 2 Each of the following is independently a fused benzene ring: a fused non-fused benzene ring (with or without substituted benzene rings), a fused furan ring (with or without substituted benzene rings), a fused thiophene ring (with or without substituted benzene rings), a fused pyrrole ring (with or without substituted benzene rings), a fused benzofuran ring (with or without substituted benzene rings), a fused benzothiophene ring (with or without substituted benzene rings), or a fused indole ring (with or without substituted indole rings). In one embodiment of the invention, R 1 and Z 1They bond together to form a ring structure. In one aspect of the invention, R 1 and Z 1 They bond together to form a pyrrole ring.

[0127] As a further preferred luminescent material, compounds represented by the following general formula (22) can also be cited. [Chemical Formula 42]

[0128] In general formula (22), X 1 and X 2 One of them is a nitrogen atom, and the other is a boron atom. R 1 ~R 26 A 1 A 2 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. 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 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 They can bond together to form a ring structure. Among them, in X... 1 When R is a nitrogen atom, 17 and R 18 They bond together to form single bonds to form a pyrrole ring, in X 2 When R is a nitrogen atom, 21 and R 22 They bond together to form single bonds, thus forming a pyrrole ring. Specifically, in X... 1 For nitrogen atoms, R 7 and R 8 and R 21 and R 22 A six-membered ring is formed through nitrogen atom bonding, R 17 and R 18 When they bond together to form a single bond, R 1 ~R 6 At least one of them is a substituted or unsubstituted aryl group, or R 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 R 5 and R 6 Any one of them can bond with each other to form an aromatic ring or a heteroaromatic ring. For a detailed description, preferred range and specific examples of the compounds represented by general formula (22), please refer to WO2022 / 270354A1,

[0010] to

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

[0129] In one embodiment, when using the main material, the amount of the compound of the present invention, which is a luminescent material contained in the luminescent layer, is 0.1% by weight or more. In one embodiment, when using the main material, the amount of the compound of the present invention, which is a luminescent material contained in the luminescent layer, is 1% by weight or more. In one embodiment, when using the main material, the amount of the compound of the present invention, which is a luminescent material contained in the luminescent layer, is 50% by weight or less. In one embodiment, when using the main material, the amount of the compound of the present invention, which is a luminescent material contained in the luminescent layer, is 20% by weight or less. In one embodiment, when using the main material, the amount of the compound of the present invention, which is a luminescent material contained in the luminescent layer, is 10% by weight or less. In one embodiment, the host material in the light-emitting layer is an organic compound that incorporates both hole transport and electron transport functions. In another embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of the emitted light. In yet another embodiment, the host material in the light-emitting layer is an organic compound with a high glass transition temperature.

[0130] In some implementations, the body material is selected from the group consisting of: [Chemical Formula 43-1] [Chemical Formula 43-2] In one embodiment, the luminescent layer comprises two or more TADF molecules with different structures. For example, it can be configured as a luminescent layer comprising three materials whose excited singlet state energy levels increase in the order of the host material, the first TADF molecule, and the second TADF molecule. In this case, the difference ΔE between the lowest excited singlet state energy level of the first TADF molecule and the second TADF molecule and the lowest excited triplet state energy level at 77K is... STThe concentrations are 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. Furthermore, 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 can be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the light-emitting layer can be set as follows: the host material is set to 10-70% by weight, the first TADF molecule is set to 10-80% by weight, and the second TADF molecule is set to 0.1-30% by weight. In one embodiment, the composition within the light-emitting layer can be set as follows: the host material is set to 20-45% by weight, the first TADF molecule is set to 50-75% by weight, and the second TADF molecule is set to 5-20% by weight. In one embodiment, the light-emitting quantum yield φPL1(A) induced by photoexcitation of the co-evaporated film of the first TADF molecule and the host material (the concentration of the first TADF molecule in the co-evaporated film = A% by weight) and the light-emitting quantum yield φPL2(A) induced by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-evaporated film = A% by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photoluminescence quantum yield φPL2(B) induced by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-evaporated film = B wt%) satisfies the relationship φPL2(B) > φPL2(100) induced by photoexcitation of a single film of the second TADF molecule. In one embodiment, the light-emitting layer can contain three TADF molecules with different structures. The compound of the present invention can be any one of a plurality of TADF compounds contained in the light-emitting layer. In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an auxiliary dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain any metallic elements. In one embodiment, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the luminescent layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescence material. Preferred delayed fluorescence materials include segments 0008-0048 and 0095-0133 of WO2013 / 154064, segments 0007-0047 and 0073-0085 of WO2013 / 011954, segments 0007-0033 and 0059-0066 of WO2013 / 011955, and segments 0008-007 of WO2013 / 081088. Paragraphs 1 and 0118–0133, paragraphs 0009–0046 and 0093–0134 of Japanese Patent Application Publication No. 2013-256490, paragraphs 0008–0020 and 0038–0040 of Japanese Patent Application Publication No. 2013-116975, paragraphs 0007–0032 and 0079–0084 of Japanese Patent Application Publication No. WO2013 / 133359, and paragraph 0008 of Japanese Patent Application Publication No. WO2013 / 161437. Paragraphs 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of Japanese Patent Application Publication No. 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of Japanese Patent Application Publication No. 2014-9224, paragraphs 0013 to 0025 of Japanese Patent Application Publication No. 2017-119663, and paragraphs 0013 to 0026 of Japanese Patent Application Publication No. 2017-119664. Compounds contained in the general formula described in Japanese Patent Application Publication No. 2017-222623 (paragraphs 0012-0025), Japanese Patent Application Publication No. 2017-226838 (paragraphs 0010-0050), Japanese Patent Application Publication No. 2018-100411 (paragraphs 0012-0043), and Japanese Patent Application Publication No. WO2018 / 047853 (paragraphs 0016-0044), especially exemplary compounds, and compounds capable of emitting delayed fluorescence.Furthermore, Japanese Patent Application Publication Nos. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, and WO2014 / 13312 are preferred among these publications. Communiqué No. 1, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO201 Japanese Publication Nos. 5 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Publication Nos. 2015-129240, WO2015 / 129714, and WO2015 / 12971 The luminescent materials and compounds capable of emitting delayed fluorescence described in Publications No. 5, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541 are hereby incorporated herein by reference as part of this specification.

[0131] The following describes the components of an organic electroluminescent element and its layers other than the light-emitting layer.

[0132] Substrate: In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and can be any of those substrates commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz and silicon.

[0133] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (above 4 eV). 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 fabricated by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, where high precision (e.g., above about 100 μm) may not be required for the pattern, the pattern can be formed using a mask of a preferred shape used when vapor deposition or sputtering on the electrode material. In some embodiments, wet film formation methods, such as printing and coating, are used when a coating material (such as an organic conductive compound) can be applied. In some embodiments, the anode has a transmittance greater than 10% when the emitted light passes through it, and the sheet resistance of the anode is less than several hundred ohms per square meter. In some embodiments, the thickness of the anode is 10–1,000 nm. In some embodiments, the thickness of the anode is 10–200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0134] cathode: In some embodiments, the cathode is made of a metal (below 4 eV) (referred to as an electron-injecting metal), alloy, conductive compound, or combination thereof, with an electrode material having a low work function. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, indium, lithium-aluminum mixtures, and rare earth metals. In some embodiments, a mixture of the electron-injecting metal and a second metal is used, the second metal being a stable metal with a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al₂O₃) mixtures, lithium-aluminum mixtures, and aluminum. In some embodiments, the mixture enhances electron-injection characteristics and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film using vapor deposition or sputtering. In some embodiments, the film resistivity of the cathode is below several hundred ohms per square meter. In some embodiments, the thickness of the cathode is in the range of 10 nm to 5 μm. In some embodiments, the thickness of the cathode is in the range of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent element is transparent or translucent in order to transmit the emitted light. In some embodiments, transparent or translucent electroluminescent elements enhance the luminous brightness. In some embodiments, the cathode is formed using a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, the element comprises both a transparent or translucent anode and cathode.

[0135] Injection layer: The injection layer is a layer located between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminous intensity. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the luminescent layer or hole transport layer, and between the cathode and the luminescent layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Here are some examples of preferred compounds that can be used as hole injection materials.

[0136] [Chemical Formula 44]

[0137] Next, preferred examples of compounds that can be used as electron injection materials will be given. [Chemical Formula 45]

[0138] Barrier layer: A blocking layer is a layer capable of suppressing the diffusion of charges (electrons or holes) and / or excitons located in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, an electron blocking layer is located between the light-emitting layer and the hole transport layer, and suppresses electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, a hole blocking layer is located between the light-emitting layer and the electron transport layer, and suppresses holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer suppresses exciton diffusion to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. The terms "electron blocking layer" or "exciton blocking layer" as used herein include layers that function as both electron blocking layers and exciton blocking layers.

[0139] Cavity blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer suppresses holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material described for the electron transport layer. Here are some examples of preferred compounds that can be used in hole-blocking layers.

[0140] [Chemical Formula 46]

[0141] Electron blocking layer: Holes are transported by an electron blocking layer. In some embodiments, the electron blocking layer suppresses electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material described for the hole transport layer. Here are specific examples of preferred compounds that can be used as electron blocking materials.

[0142] [Chemical Formula 47-1] [Chemical Formula 47-2]

[0143] Exciton blocking layer: An exciton blocking layer suppresses the diffusion of excitons generated via the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons within the light-emitting layer. In some embodiments, it enhances the luminous efficiency of the device. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side, or on both sides. In some embodiments, when the exciton blocking layer is on the anode side, it may be located between and adjacent to the hole transport layer and the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, it may be located between and adjacent to the light-emitting layer and the cathode. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is located between the anode and the exciton blocking layer, with 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 located between the cathode and the exciton blocking layer, with the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the luminescent material, respectively.

[0144] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the characteristics of hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in this invention are not limited, and examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkyl derivatives, pyrazolene derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene 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 amines, and styrene amine 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.

[0145] [Chemical Formula 48]

[0146] Electron transport layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode into 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 this invention are not limited, and can include nitro-substituted fluorene derivatives, dibenzoquinone derivatives, thiopiperanoxide derivatives, carbodiimide, fluorenemethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, aziridine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are given below.

[0147] [Chemical Formula 49]

[0148] Furthermore, examples of compounds that are preferred as materials that can be added to each organic layer are given. For example, they can be considered as stabilizing materials.

[0149] [Chemical Formula 50]

[0150] Preferred materials that can be used in organic electroluminescent devices are specifically illustrated, but the materials that can be used in this invention are not limited to the following exemplary compounds. Furthermore, even compounds illustrated as materials with specific functions can be used as materials with other functions.

[0151] Device: In some implementations, the light-emitting layer is incorporated into the device. For example, the device includes, but is not limited to, OLED bulbs, OLED lights, television screens, computer monitors, mobile phones, and tablet computers. In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be used to facilitate charge transfer or energy transfer within the device and / or be suitable as hole transport materials. Examples of such devices include, for instance, 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 photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0152] Light bulb or lamp: In some embodiments, the electronic device includes an OLED, which includes an anode, a cathode, and at least one organic layer containing a light-emitting layer located between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations 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 is an OLED lamp, the OLED lamp comprising: The circuit board has a first surface with a mounting surface and a second surface opposite to it, and defines at least one opening. At least one OLED is disposed on the mounting surface and has a structure in which the at least one OLED includes an anode, a cathode and at least one organic layer containing a light-emitting layer located between the anode and the cathode and emits light; Housing, used for circuit board; and At least one connector is disposed at an end of the housing, and the housing and the connector define an encapsulation suitable for mounting to a lighting device. In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board to emit light in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0153] Monitor or screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, methods including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD) are used to deposit the compounds involved in the present invention onto a substrate. In some embodiments, the substrate is a photoplate structure suitable for double-sided etching, providing pixels with a unique aspect ratio. The screen (which may also be referred to as a mask) is used in methods for manufacturing OLED displays. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and promotes large swept-bevel openings in the horizontal direction. This allows for tight patterning of pixels required for high-definition displays while optimizing chemical vapor deposition onto the TFT substrate. Internal patterning of pixels allows for the construction of 3D pixel openings with varying aspect ratios in both the horizontal and vertical directions. Furthermore, imaging "strips" or halftone circles within the pixel region suppress etching in specific areas until these specific patterns are undercut and leave the substrate. At this point, all pixel regions are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone patterns allows etching to be suppressed at different rates within the pixel, enabling locally deeper etching to form steep vertical bevels. The preferred material for vapor deposition masks is invar steel. Invar steel is a metal alloy that is cold-rolled into thin sheets in a steel mill. Invar steel cannot be used as a nickel mask for electrodeposition onto a spin mandrel. A suitable and low-cost method for forming opening regions within a vapor deposition mask is a wet chemical etching method. 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 other embodiments, the screen or display pattern is fabricated using plasma etching.

[0154] Method for manufacturing the device: OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit panels. Generally, each unit panel on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate; applying a planarization film onto the TFT; and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0155] In another aspect of the invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising: The process of forming a barrier layer on the substrate of the motherboard; The process of forming multiple display units from unit board units on the barrier layer; The process of forming an encapsulation layer on each of the display units of the unit board; and The process of coating an organic film on the interface portion between the unit plates. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edge portions of the barrier layer are covered with an organic film formed of polyimide or acrylamide. In some embodiments, the organic film facilitates the gentle cutting of the motherboard into unit panels. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and a source / drain electrode. Each of the plurality of display units may include a thin-film transistor (TFT), a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film coated on the interface portion is formed of the same material as the planarization film and is formed simultaneously with the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer, with a passivation layer, a planarization film, and an encapsulation layer therebetween, and the encapsulation layer covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film neither contacts the display unit nor the encapsulation layer.

[0156] Each of the organic film and the planarization film may comprise either polyimide or acryloyl groups. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the substrate may be formed of polyimide. The method may further include mounting a carrier substrate formed of glass material onto another surface of the substrate before forming the barrier layer on one surface of the substrate formed of polyimide, and separating the carrier substrate from the substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylamide, as in the case of an organic film formed on the edge portion of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge portion of the barrier layer such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0157] In some embodiments, the light-emitting layer has a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the opposing electrode, thereby causing the organic light-emitting layer to emit light and thus forming an image. Hereinafter, the image forming unit having a TFT layer and light-emitting units will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display units and preventing external moisture penetration can be formed as a thin-film encapsulation structure having alternating layers of organic and inorganic films. In some embodiments, the encapsulation layer has a thin-film encapsulation structure having multiple layers of films. In some embodiments, the organic film coated on the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0158] In one embodiment, the OLED display is flexible and uses a soft substrate formed of polyimide. In some embodiments, the substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit plate. For example, while forming the substrate over the entire surface of the motherboard, the barrier layer is formed according to the size of each unit plate, thereby forming a groove at the interface portion between the unit plate barrier layers. Each unit plate can be cut along the groove.

[0159] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, wherein a groove is formed in the barrier layer, wherein at least a portion of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, a TFT layer is formed for each unit panel, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are disposed on the TFT layer to cover the TFT layer. The groove at the interface portion is covered with an organic film, such as a polyimide or acrylamide, while a planarization film formed of, for example, polyimide or acrylamide is formed. This is to prevent cracking by allowing the organic film to absorb shocks generated when each unit panel is cut along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the shock generated when each unit panel is cut along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, because the grooves at the interface portions between the barrier layers are covered with an organic film, and this organic film absorbs impacts that would otherwise be transferred to the barrier layers, each unit panel can be cut gently, and cracking in the barrier layers can be prevented. In one embodiment, the organic film covering the grooves at the interface portions is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected as a single layer, then because external moisture may penetrate into the display unit through the planarization film and a portion of the residual organic film, the organic film and the planarization film are spaced apart from each other so that the organic film is separated from the display unit.

[0160] In some embodiments, a display unit is formed by forming light-emitting units, and an encapsulation layer is disposed on the display unit to cover it. Thus, after the motherboard is fully manufactured, a carrier substrate supporting the substrate is separated from the substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate separates from the substrate due to the difference in thermal expansion coefficients between the carrier substrate and the substrate. In some embodiments, the motherboard is cut into unit panels. In some embodiments, the motherboard is cut along the interface portion between the unit panels using a cutting machine. In some embodiments, because the grooves at the interface portion along which the motherboard is cut are covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting. In some implementations, the method reduces the defect rate of the product and stabilizes its quality. Another approach is an OLED display having: a barrier layer formed on a substrate; a display unit formed on the barrier layer; an encapsulation layer formed on the display unit; and an organic film coated on the edge portion of the barrier layer. Example

[0161] The following examples and embodiments further illustrate the features of the present invention. The materials, processing methods, and processing steps shown below can be appropriately modified without departing from the spirit of the invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below. Furthermore, the evaluation of luminescence characteristics was performed using a source meter (Keithley 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd. E5273A), an optical power meter (Newport Corporation 1930C), a spectrometer (Ocean Optics USB2000), a spectroradiometer (TOPCON CORPORATION SR-3), and a streak camera (Hamamatsu Photonics KK C4334). Moreover, the energies of HOMO and LUMO were measured using an atmospheric photoelectron spectrometer (RIKEN KEIKI CO., LTD. AC-3, etc.). The compounds contained in general formula (1) were synthesized in the following synthetic examples.

[0162] (Synthetic Example 1) Synthesis of Compound A Synthesis of intermediate a [Chemical Formula 51]

[0163] A mixture of 3-bromo-4-fluorobenzyl nitrile (10.0 g, 50 mmol), phenyl-d5-boronic acid (7.0 g, 55.3 mmol), potassium carbonate (13.8 g, 100.0 mmol), tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.50 mmol), tetrahydrofuran (THF, 375 mL), and deionized water (125 mL) was stirred at 75 °C for 20 hours. After cooling to room temperature, the organic and aqueous phases were separated by adding saturated brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The solid was filtered off and washed with ethyl acetate. The crude product was purified by rapid column chromatography (hexane / ethyl acetate = 5:1) to give intermediate a (48.0 mmol, 96% yield) as a white solid, yielding 9.70 g. 1H-NMR (400MHz, DMSO-d6): δ8.09 (dd, J=6.5, 2.4Hz, 1H), 7.93-7.97 (m, 1H), 7.58 (dd, J=10.4, 8.8Hz, 1H). ASAP MS spectral analysis: C 13 H3D5FN: Theoretical value 202.10, observed value 203.10 [M+H] + ]

[0164] Synthesis of intermediate b [Chemical Formula 52] Under nitrogen atmosphere, a 1.0 M diisopropylamino THF / hexane solution (40 mL, 40 mmol) was slowly added dropwise to a 200 mL THF solution of intermediate a (8.09 g, 40 mmol) at -78 °C. After stirring for 1 hour, a 1 M THF solution of zinc chloride (60 mL, 60 mmol) was added, and the mixture was heated to room temperature. After stirring for 1 hour, 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (6.46 g, 20 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.16 g, 1.0 mmol) were added. The mixture was heated to 80 °C and stirred for 20 hours. After cooling to room temperature, the obtained solid was filtered and washed with ethyl acetate. The solid was recovered and stirred under reflux in toluene. After cooling to room temperature, the solid was filtered and washed with toluene and hexane to obtain intermediate b (9.0 mmol, 45% yield) as a pale yellow solid of 5.90 g. ASAP MS spectral analysis: C 41 H4D 18 F2N6: Theoretical value 654.30, observed value 655.40 [M+H] + ]

[0165] Synthesis of Compound A [Chemical Formula 53]

[0166] A mixture of intermediate b (3.27 g, 5.00 mmol) and N,N-dimethylformamide (DMF, 100 mL) was added to carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol), and stirred at 150 °C for 1 hour. The reaction solution was cooled to room temperature, the solid was filtered off, and washed with toluene. The filtrate was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. After solvent removal, the solid was redetermined with toluene / hexane, and the resulting solid was recovered. The solid was dissolved in toluene and filtered through diatomaceous earth / silica. The solid obtained by concentrating the filtrate with toluene / hexane was redetermined to give 2.82 g of yellow compound A (2.92 mmol, 58% yield). 1 H-NMR (400MHz, DMSO-d6): δ8.38 (d,J=2Hz,2H), 7.66 (d,J=1.6Hz,2H). ASAP MS spectral analysis: C 65 H4D 34 N8: Theoretical value 964.54, observed value 965.71 [M+H] + ]

[0167] (Synthetic Example 2) Synthesis of Compound B Synthesis of intermediate C [Chemical Formula 54]

[0168] Under nitrogen atmosphere, a 1.3 M lithium bis(trimethylsilyl)amide THF solution (25 mL, 32.5 mmol) was slowly added dropwise to a mixture of carbazole-1,2,3,4,5,6,7,8-d8 (5.26 g, 11.0 mmol) and THF (60 mL) at -78 °C, and the mixture was stirred for 30 minutes. A 50 mL THF solution of 4,6-dichloro-2-(methanesulfonyl)pyrimidine (6.81 g, 30.0 mmol) was slowly added dropwise to the resulting white suspension. After stirring for 1 hour, a saturated aqueous ammonium chloride solution was added, and the reaction solution was heated to room temperature. The obtained solid was filtered off, washed successively with deionized water, methanol, and hexane, and dried under reduced pressure to obtain 7.66 g of a white intermediate c (23.8 mmol, 79% yield). 1 H-NMR (400MHz, DMSO-d6): δ7.84 (s, 1H). ASAP MS spectral analysis: C 16H2D8Cl2N3: Theoretical value 321.07, observed value 322.11 [M+H + ]

[0169] Synthesis of intermediate d [Chemical Formula 55]

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

[0171] Synthesis of compound B [Chemical Formula 56]

[0172] A mixture of intermediate d (2.62 g, 4.00 mmol) and DMF (80 mL) was added to carbazole-1,2,3,4,5,6,7,8-d8 (1.55 g, 8.80 mmol) and potassium carbonate (1.66 g, 12.0 mmol), and stirred at 150 °C for 1 hour. The reaction solution was cooled to room temperature, the solid was filtered off, and washed with toluene. The filtrate was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. After solvent removal, the solid was redetermined with toluene / hexane, and the resulting solid was recovered. The crude product was purified by rapid column chromatography (toluene / hexane 10:1), and the solid was redetermined with ethyl acetate / hexane to give 2.23 g of yellow compound B (2.31 mmol, 58% yield). 1H-NMR (400MHz, DMSO-d6): δ8.32 (d,J=2Hz,2H), 7.44 (d,J=2.0Hz,2H), 6.09 (s,1H). ASAP MS spectral analysis: C 66 H5D 34 N7: Theoretical value 963.54, observed value 964.09 [M+H] + ]

[0173] Synthesis of intermediate e [Chemical Formula 57]

[0174] A mixture of 1,3-dibromo-2-fluorobenzene (10.04 g, 39.354 mmol), phenyl-d5-boronic acid (5.02 g, 39.54 mmol), potassium carbonate (16.39 g, 118.6 mmol), tetrakis(triphenylphosphine)palladium(0) (1.37 g, 1.18 mmol), THF (131 mL), and deionized water (43 mL) was stirred at 90 °C for 22 hours. After cooling to room temperature, the organic and aqueous phases were separated by adding saturated brine. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (hexane) to give intermediate e (27.7 mmol, 70% yield) as a white solid, weighing 7.1 g. 1 H-NMR (400MHz, DMSO-d6): δ7.49-7.54 (m,1H), 7.33-7.38 (m,1H), 7.06-7.10 (m,1H). ASAP MS spectral analysis: C 12 H3D5BrF: Theoretical value 255.01, observed value 255.03 [M+H + ]

[0175] Synthesis of intermediate f [Chemical Formula 58]

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

[0177] Synthesis of intermediate g [Chemical Formula 59]

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

[0179] Synthesis of compound C [Chemical Formula 60]

[0180] Under nitrogen atmosphere, toluene (1.86 mL) and deionized water (0.37 mL) were added to a mixture of 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.15 g, 0.46 mmol), intermediate g (0.42 g, 1.11 mmol), potassium carbonate (0.26 g, 2.47 mmol), and 1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.01 g, 0.014 mmol), and the mixture was stirred at 70 °C for 6 hours. After adding intermediate g (0.319 g, 0.8 mmol) and stirring for another 12 hours, 1,1-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.02 g, 0.028 mmol) was added and the mixture was stirred for another 90 minutes. After cooling to room temperature, deionized water was added, and extraction was performed with ethyl acetate. The combined organic phases were washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The crude product was purified by rapid column chromatography (toluene / hexane 1:2), and the solid was reprecipitated with toluene / acetonitrile to give 0.12 g of pale yellow compound C (0.13 mmol, yield 29%). 1 H-NMR (400MHz, CDCl3): δ7.71 (dd,J=7.6,1.6Hz,2H), 7.52 (t,J=7.6Hz,2H), 7.19 (dd,J=4.0,2.0Hz,2H). ASAP MS spectral analysis: C 63 H6D 34 N6: Theoretical value 914.54, observed value 914.99 [M+H] + ]

[0181] (Synthetic Example 4) Synthesis of Compound D Synthesis of intermediate h [Chemical Formula 61]

[0182] Under a nitrogen atmosphere, at -78°C, 17.8 mL of 2.0 M magnesium isopropyl chloride THF solution (320 mL) was added dropwise to a THF solution of 5-bromo-2,3,4-trifluorobenzyl nitrile (8.0 g, 33.9 mmol) and stirred for 30 minutes. Then, 13.2 g of tributyltin chloride (40.6 mmol) was added and stirred for another 30 minutes. After warming to room temperature and stirring for 3 hours, saturated ammonium chloride was added to stop the reaction. The organic phase was separated, the aqueous phase was extracted with toluene, the organic phases were combined, washed with saturated brine, dried with magnesium sulfate, and filtered. After concentrating the solvent under reduced pressure, 2,4-dichloro-6-(phenyl-d5)-1,3,5-triazine (3.9 g, 16.9 mmol), bis(triphenylphosphine)palladium dichloride (1.9 g, 2.7 mmol), and toluene (400 mL) were added to the crude product, and the mixture was heated under reflux for 14 hours. After the reaction was complete, the reaction solution was passed through a silica gel pad, and the silica gel was washed with toluene. The filtrate was concentrated and recrystallized with toluene to obtain 4.1 g of intermediate h (8.7 mmol, yield 52%). 1 H-NMR (400MHz, CDCl3):8.68-8.63 (m, 2H) ASAP MS spectral analysis: C 23 H2D5F6N5: Theoretical value 472.09, observed value 473.21 [M+H + ]

[0183] Synthesis of compound D [Chemical Formula 62]

[0184] Under nitrogen atmosphere, a DMF solution (100 mL) of intermediate h (4 g, 8.4 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (10.4 g, 59.2 mmol), and potassium carbonate (9.3 g, 67.2 mmol) was stirred at 110 °C for 8 hours. The reaction solution was brought to room temperature, water and methanol were added, and the resulting solid was filtered off and washed with water and methanol. The crude product was purified by column chromatography (toluene / hexane = 7:3) and reprecipitation (CHCl3 / MeOH) to obtain 8.6 g of compound D (6.1 mmol, 73% yield). 1 H NMR (400MHz, CDCl3) δ8.13 (s, 2H). ASAP MS spectral analysis: C 95 H2D 53 N 11Theoretical value 1402.80, observed value 1403.55 [M+H] + ]

[0185] (Synthetic Example 5) Synthesis of Compound E Synthesis of intermediate i [Chemical Formula 63]

[0186] A mixture of 5-bromo-2-fluorobenzyl nitrile (10.0 g, 50.0 mmol), phenyl-d5-boronic acid (7.0 g, 55.1 mmol), tetrakis(triphenylphosphine)palladium(0) (2.9 g, 2.51 mmol), potassium carbonate (13.8 g, 100 mmol), tetrahydrofuran (THF, 120 mL), and deionized water (40 mL) was stirred at 75 °C for 15 hours. After cooling the mixture to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (ethyl acetate:hexane = 1:40) and recrystallized from hexane to give intermediate i (44.5 mmol, 89% yield) as a white solid, yielding 9.0 g. 1 H NMR (400MHz, CDCl3): δ7.83-7.78 (m, 2H), 7.29 (td, J=8.6, 0.6Hz, 1H).

[0187] Synthesis of intermediate j [Chemical Formula 64]

[0188] A mixture of 2,2,6,6-tetramethylpiperidine (6.94 g, 49.1 mmol) and THF (80 mL) was cooled to -75 °C, and a 1.6 M hexane solution of n-butyllithium (30 mL, 48.0 mmol) was added, followed by stirring at 0 °C for 30 min. The mixture was then cooled to -75 °C, and a 1 M hexane solution of diethylzinc (52 mL, 52.0 mmol) was added, followed by stirring at -75 °C for 30 min, and then at 0 °C for 30 min. Intermediate i (4.03 g, 19.9 mmol) was dissolved in THF (10 mL) and added dropwise to the mixture cooled to -75 °C. The mixture was stirred at -75 °C for 3 h. Iodine (35.4 g, 139 mmol) was dissolved in THF (70 mL) and added dropwise to the mixture cooled to -75 °C. The mixture was stirred at -75°C for 30 minutes and then at room temperature for 15 hours. A 10% (w / w) sodium thiosulfate aqueous solution (200 mL) was added to the reaction solution, and after stirring at room temperature for 1 hour, the mixture was filtered through diatomaceous earth and the obtained solid was washed with ethyl acetate. The filtrate was separated into an organic and an aqueous phase, and the organic phase was washed with saturated brine. The solution was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (dichloromethane) to give intermediate j (19.6 mmol, 98% yield) as a pale yellow solid, weighing 6.44 g. 1 H NMR (400MHz, CDCl3): δ8.18 (dd,J=5.7,2.3Hz,1H), 7.78 (dd,J=5.5,2.1Hz,1H).

[0189] Synthesis of intermediate l [Chemical Formula 65]

[0190] A mixture of intermediate j (12.6 g, 38.4 mmol) and THF (380 mL) was cooled to -75 °C, and a 1.0 M THF solution of isopropyl magnesium chloride (42 mL, 42.0 mmol) was added, followed by stirring at -75 °C for 1 hour. A 1 M THF solution of zinc chloride (115 mL, 115 mmol) was added to the mixture, and the mixture was stirred at -75 °C for 10 minutes, followed by stirring at room temperature for 1 hour. THF was removed by distillation, and compound k (5.18 g, 16.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.928 g, 0.803 mmol) were added, followed by stirring at 125 °C for 11 hours. After cooling the reaction solution to room temperature, the precipitated solid was filtered off and washed with THF. The resulting filtrate was concentrated, methanol was added, and reprecipitation was performed. The obtained solid was washed successively with methanol and hexane, and then dried to obtain 4.65 g of white solid intermediate l (7.10 mmol, yield 44%). 1 H NMR (400MHz, DMSO-d6) δ8.88 (dd,J=7.1,2.5Hz,2H), 8.41 (dd,J=5.3,2.5Hz,2H). APCI-MS spectral analysis: C 41 H5D 18 F2N6: Theoretical value 655.31, observed value 655.61 [(M+H)] + ].

[0191] Synthesis of compound E [Chemical Formula 66]

[0192] A mixture of intermediate L (4.59 g, 7.01 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (2.70 g, 15.4 mmol), potassium carbonate (2.91 g, 21.1 mmol), and DMF (140 mL) was stirred at 150 °C for 1 hour. After cooling the reaction solution to room temperature, methanol and deionized water were added, followed by reprecipitation. The obtained solid was filtered off and washed successively with deionized water, methanol, and hexane. The crude product was purified by rapid column chromatography (toluene) to obtain 3.02 g of a yellow solid containing compound E (3.13 mmol, 45% yield). 1 H NMR (400MHz, DMSO-d6) δ8.73 (d, J=2.3Hz, 2H), 8.17 (d, J=2.3Hz, 2H). APCI-MS spectral analysis: C 65 H5D 34 N8: Theoretical value 965.54, observed value 966.09 [(M+H)] + ].

[0193] (Synthetic Example 6) Synthesis of Compound F Synthesis of intermediate n [Chemical Formula 67]

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

[0195] Synthesis of intermediate O [Chemical Formula 68]

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

[0197] Synthesis of intermediate p [Chemical Formula 69]

[0198] A mixture of 3,6-di-tert-butylcarbazole (8.40 g, 30 mmol), sodium hydride (60%, dispersed in liquid paraffin, 1.37 g, 33 mmol), and THF (150 mL) was stirred at room temperature for 90 minutes. After 30 minutes, this mixture was added dropwise to a mixture of cyanuric chloride (8.29 g, 45 mmol) and THF (150 mL) cooled to -75 °C. The mixture was then heated to room temperature and stirred for 1 hour. The reaction solution was cooled to 0 °C, 150 mL of deionized water was added, the mixture was heated to room temperature, and filtered. The obtained solid was washed successively with deionized water, methanol, and hexane, and recrystallized from toluene to give 4.81 g of a white solid intermediate p (11.2 mmol, 37% yield). 1 H-NMR (400MHz, CDCl3): δ8.75 (d,J=8.8Hz,2H), 7.98 (d,J=1.6Hz,2H), 7.58 (dd,J=8.8,2.0Hz,2H), 1.46 (s,18H). APCI-MS spectral analysis: C23 H 25 Cl2N4: Theoretical value 427.15, observed value 427.39 [(M+H)] + ].

[0199] Synthesis of compound F [Chemical Formula 70]

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

[0201] (Synthetic Example 7) Synthesis of Compound G Synthesis of intermediate r [Chemical Formula 71]

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

[0203] Synthesis of compound G [Chemical Formula 72]

[0204] Carbazole-1,2,3,4,5,6,7,8-d8 (1.93 g, 11.0 mmol) and potassium carbonate (2.07 g, 15.0 mmol) were added to a mixture of intermediate r (2.82 g, 5.00 mmol) and DMF (100 mL), and the mixture was stirred at 150 °C for 1 hour. The reaction solution was cooled to room temperature, and the solid was removed by filtration through diatomaceous earth, which was then washed with ethyl acetate. The filtrate was concentrated, and methanol was added to precipitate the solid. The solid was filtered off and washed with methanol and hexane. The obtained solid was dissolved in toluene and filtered through diatomaceous earth / silica. The filtrate was concentrated, and the obtained solid was washed with hexane to give 3.59 g of compound G (4.11 mmol, 82% yield) as a yellow-green solid. 1 H NMR (400MHz, DMSO-d6): δ8.38 (d,J=2Hz,2H), 8.07 (d,J=2.0Hz,2H). APCI-MS spectral analysis: C 59H4D 31 N7: Theoretical value 872.49, observed value 872.77. [M+H] + ].

[0205] (Synthetic Example 8) Synthesis of Compound H Synthesis of intermediate u [Chemical Formula 73]

[0206] Under nitrogen atmosphere, 2.5 mL of 0.5 M lithium chloride THF solution was added to 80 mL of a THF solution of compound s (5.0 g, 25 mmol) at room temperature. The mixture was cooled to -78 °C, and 27 mL of 1 M lithium diisopropylamino (LDA) THF / hexane solution was slowly added dropwise. After stirring for 2 hours, 31 mL of 1 M THF solution of zinc chloride was added, and the mixture was stirred for another 30 minutes before being brought back to room temperature. Compound t (4.0 g, 12 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.68 g, 0.59 mmol) were added to the mixture, and the mixture was heated at 75 °C for 18 hours. The reaction solution was cooled to room temperature, and an aqueous solution of ammonium chloride was added to separate the organic and aqueous phases. The aqueous phase was extracted three times with toluene, the combined organic phase was washed with saturated brine, dried with magnesium sulfate, and filtered to remove the solvent. The crude product was purified by silica gel column chromatography (dichloromethane / hexane = 1 / 1) to obtain 4.7 g of intermediate u (7.0 mmol, yield 60%). 1 H-NMR (400MHz, CDCl3): δ 8.67 (dd, J=6.0, 2.0Hz, 2H) 8.55 (d, J=2.0Hz, 2H) 7.95 (dd, J=6.0, 2.0Hz, 2H), 7.74 (t, J=2.0Hz, 1H), 1.43 (s, 18H). APCI-MS: Calculated values ​​(C 43 H 25 D 10 F2N5) 669.35, observed value (MH) + 670.59.

[0207] Synthesis of compound H [Chemical Formula 74]

[0208] A mixture of intermediate u (4.4 g, 6.3 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (3.3 g, 19 mmol), and potassium carbonate (3.5 g, 25 mmol) was added to DMF (150 mL), and the mixture was heated at 150 °C for 1 hour. The reaction solution was cooled to room temperature, and an aqueous solution of ammonium chloride and methanol were added. The precipitate was recovered, washed with water and methanol, and dried to obtain a crude product (5.7 g). The crude product was purified by silica gel column chromatography (toluene / hexane = 1 / 1 to 1 / 0), and recrystallized with a toluene / hexane mixture to obtain 5.5 g of compound H (5.6 mmol, yield 84%). 1 H-NMR (400MHz, CDCl3): δ 7.97 (d, J = 2.0Hz, 2H), 7.48 (d, J = 2.4Hz, 2H), 7.44 (d, J = 2.4Hz, 2H), 7.39 (t, J = 2.0Hz, 1H), 1.09 (s, 18H). APCI-MS: Calculated values ​​(C 67 H 25 D 26 N7) 979.58, observed value (M) + 979.93.

[0209] (Synthetic Example 9) Synthesis of Compound I Synthesis of intermediate w [Chemical Formula 75]

[0210] A mixture of compound v (3.3 g, 7.1 mmol), phenyl-d5-boronic acid (1.8 g, 16 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol), and potassium carbonate (3.6 g, 28 mmol) was added to toluene (43 mL), ethanol (0.7 mL), and water (14 mL), and the mixture was heated under reflux in nitrogen for 12 hours. The reaction solution was cooled to room temperature, and the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine, dried over magnesium sulfate, and filtered to remove the solvent. The crude product was purified by silica gel column chromatography (hexane) to give 1.5 g of intermediate w (3.6 mmol, 52% yield). 1 H-NMR (400MHz, CDCl3): δ 7.85 (d, J = 1.6Hz, 1H). APCI-MS: Calculated value (C 18 HD 10 Br2F) 413.98, observed value (M)+ 414.17.

[0211] Synthesis of intermediate x [Chemical Formula 76]

[0212] Under nitrogen atmosphere, a 1.3 M THF solution (15 mL, 20 mmol) of the isopropyl magnesium chloride-lithium chloride complex was cooled to -15 °C, and a THF solution (38 mL) of intermediate w (7.9 g, 19 mmol) was slowly added. The mixture was heated to 0 °C and stirred for 2 hours, followed by the addition of dimethylformamide (2.2 mL, 28 mmol), and further stirring at 0 °C for 2 hours. A 28% ammonia solution (13 mL) and a THF solution of iodine (9.6 g, 38 mmol) (12 mL) were added, and the mixture was stirred overnight at room temperature. The reaction was stopped by adding a saturated sodium bisulfite aqueous solution, and the organic and aqueous phases were separated. The aqueous phase was extracted with chloroform, and the combined organic phases were washed with saturated brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was purified by using a short silica gel column (toluene / hexane = 1 / 1) and the solvent was removed by washing with hexane to obtain a solid, thus yielding 4.2 g of intermediate x (12 mmol, yield 61%). 1 H-NMR (400MHz, CDCl3): δ 7.90 (d, J = 1.6Hz, 1H). APCI-MS: Calculated value (C 19 HD 10 BrFN) 361.07, observed value (M + 361.16.

[0213] Synthesis of intermediate y [Chemical Formula 77]

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

[0215] Synthesis of Compound I [Chemical Formula 78]

[0216] Under nitrogen atmosphere, at -15°C, a 1.3M THF solution of the isopropyl magnesium chloride-lithium chloride complex (9.4 mL, 12.2 mmol) was added to a THF solution (110 mL) of intermediate y (5.52 g, 10.6 mmol). After stirring for 1 hour, the mixture was heated to 0°C and stirred for another 2 hours. A 1M THF solution of zinc chloride (12.7 mL, 12.7 mmol) was then added to the mixture. After heating to room temperature and stirring for 30 minutes, compound z (1.72 g, 5.32 mmol), tetrakis(triphenylphosphine)palladium(0) (0.62 g, 0.54 mmol), and N-methylpyrrolidone (66 mL) were added, and the mixture was heated at 110°C for 18 hours. After cooling the reaction solution to room temperature, the reaction was stopped with a saturated ammonium chloride aqueous solution (200 mL), and methanol (400 mL) was added. The resulting precipitate was recovered, washed with methanol and hexane, and dried under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (hexane / toluene = 80 / 1) to obtain 4.06 g of compound I (3.60 mmol, yield 68%). 1 H-NMR (400MHz, CDCl3): δ 8.41 (s, 2H). APCI-MS: Calculated (C 77 H2D 44 N8) 1126.66, observed value (MH) + 1127.95.

[0217] (Synthetic Example 10) Synthesis of Compound J Synthesis of intermediate a' [Chemical Formula 79]

[0218] A mixture of 1-bromo-4-fluoro-2-iodobenzene (39.46 g, 131 mmol), phenyl-d5-boronic acid (18.29 g, 144 mmol), tetrakis(triphenylphosphine)palladium(0) (7.56 g, 6.55 mmol), potassium carbonate (54.31 g, 393 mmol), toluene (300 mL), and deionized water (100 mL) was stirred at 100 °C for 3 hours. After cooling the mixture to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (hexane) to give 25.73 g of a colorless, transparent liquid intermediate a' (100 mmol, 77% yield). 1 H NMR (400MHz, CDCl3): δ7.61 (dd,J=8.8,5.4Hz,1H), 7.07 (dd,J=9.2,3.0Hz,1H), 6.94 (ddd,J=10.0,6.8,1.9Hz,1H). APCI-MS spectral analysis: C 12 H3D5BrF: Theoretical value 255.01, observed value 255.02 [M] + ].

[0219] Synthesis of intermediate b' [Chemical Formula 80]

[0220] A mixture of 2,2,6,6-tetramethylpiperidine (6.73 g, 47.6 mmol) and THF (80 mL) was cooled to -75 °C, and a 1.6 M hexane solution of n-butyllithium (30 mL, 48.0 mmol) was added, followed by stirring at 0 °C for 30 min. The mixture was then cooled to -75 °C, and a 1 M hexane solution of diethylzinc (52 mL, 52.0 mmol) was added, followed by stirring at -75 °C for 30 min, and then at 0 °C for 30 min. The mixture was then cooled to -75 °C, and a solution obtained by dissolving intermediate a' (5.24 g, 20.5 mmol) in THF (8 mL) was added dropwise. Next, the mixture was stirred at -30 °C for 2 h, cooled to -75 °C, and a solution obtained by dissolving iodine (41.19 g, 162 mmol) in THF (80 mL) was added dropwise. The mixture was stirred at -75°C for 30 minutes and then at room temperature for 2 hours. A 10% (w / w) sodium thiosulfate aqueous solution (200 mL) was added to the reaction solution, and after stirring at room temperature for 12 hours, the mixture was filtered through diatomaceous earth and the obtained solid was washed with ethyl acetate. The filtrate was separated into an organic and aqueous phases, and the organic phase was washed with saturated brine. The solution was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (hexane) to give 7.04 g of a pale yellow, transparent liquid intermediate b' (18.4 mmol, 90% yield). 1 H NMR (400MHz, CDCl3): δ8.04 (d, J=6.0Hz, 1H), 7.05 (d, J=8.2Hz, 1H).

[0221] Synthesis of intermediate c' [Chemical Formula 81]

[0222] A mixture of intermediate b' (7.04 g, 18.4 mmol), phenyl-d5-boronic acid (2.57 g, 20.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.06 g, 0.917 mmol), potassium carbonate (7.66 g, 55.4 mmol), toluene (45 mL), and deionized water (15 mL) was stirred at 100 °C for 15 hours. After cooling the reaction solution to room temperature, the organic and aqueous phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (hexane) to give 4.50 g of intermediate c' (13.3 mmol, 72% yield) as a white solid. 1 H-NMR (400MHz, CDCl3): δ7.75 (d,J=7.3Hz,1H), 7.17 (d,J=11.0Hz,1H). APCI-MS spectral analysis: C 18 H2D 10 BrF: Theoretical value 336.07, observed value 336.13 [M] + ].

[0223] Synthesis of intermediate d' [Chemical Formula 82]

[0224] A mixture of intermediate c' (6.33 g, 18.7 mmol) and THF (37 mL) was cooled to -50 °C, and a 1.0 M LDA solution in THF / hexane (21 mL, 21.0 mmol) was added, followed by stirring at -50 °C for 2 hours. A solution of iodine (5.74 g, 22.6 mmol) dissolved in THF (11 mL) was added dropwise to this mixture, and the mixture was stirred at -50 °C for 30 minutes, followed by stirring at room temperature for 2 hours. A 10% (w / w) sodium thiosulfate aqueous solution (24 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours to separate the organic and aqueous phases. The organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (toluene:hexane = 1:20) to obtain 6.69 g of a white solid intermediate d' (14.4 mmol, 77% yield). 1 H-NMR (400MHz, CDCl3): δ7.74 (d, J=7.1Hz, 1H). APCI-MS spectral analysis: C 18 H2D 10 BrFI: Theoretical value 461.97, observed value 462.07 [(M+H)] + ].

[0225] Synthesis of intermediate e' [Chemical Formula 83]

[0226] A mixture of intermediate d' (6.54 g, 14.1 mmol) and THF (140 mL) was cooled to -50 °C, and a 1.0 M THF solution of isopropyl magnesium chloride (15 mL, 15.0 mmol) was added, followed by stirring at -50 °C for 1 hour. DMF (2.2 mL) was added to the mixture, and the mixture was stirred at 0 °C for 2 hours. Ammonia (25% aqueous solution, 16 mL) and iodine (7.22 g, 28.4 mmol) were then added, and the mixture was stirred at room temperature for 2 hours. A 10% (w / w) sodium thiosulfate aqueous solution (100 mL) was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours to separate the organic and aqueous phases. The organic phase was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The resulting filtrate was concentrated. The crude product was purified by rapid column chromatography (toluene:hexane = 1:1). The solid obtained was washed with diethyl ether to give 4.25 g of the pale yellow solid intermediate e' (11.7 mmol, yield 83%). 1 H-NMR (400MHz, CDCl3): δ7.98 (d, J=7.3Hz, 1H). APCIMS spectral analysis: C 19 HD 10 BrFN: Theoretical value 361.07, observed value 361.24 [M] + ].

[0227] Synthesis of intermediate g' [Chemical Formula 84]

[0228] A mixture of intermediate e' (3.36 g, 9.27 mmol) and THF (140 mL) was cooled to -15 °C, and 1.3 M Turbo Grignard reagent THF solution (7.5 mL, 9.69 mmol) was added, followed by stirring at 0 °C for 1 hour. 1 M zinc chloride THF solution (11 mL, 11.0 mmol) was added to the mixture, and stirring was continued at room temperature for 1 hour. Compound f' (1.25 g, 3.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.223 g, 0.193 mmol) were then added, and stirring was continued at 75 °C for 19 hours. After cooling the reaction solution to room temperature, deionized water and methanol were added, followed by reprecipitation, and the solid was filtered off. The obtained solid was washed successively with deionized water, methanol, and diethyl ether, and dried to obtain 3.08 g of white solid intermediate g' (3.77 mmol, 97% yield). 1H NMR (400MHz, CDCl3): δ7.80 (d, J=7.6Hz, 2H). APCI-MS spectral analysis: C 53 H3D 28 F2N6: Theoretical value 817.43, observed value 817.70 [(M+H)] + ].

[0229] Synthesis of compound J [Chemical Formula 85]

[0230] A mixture of intermediate g' (3.06 g, 3.74 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (1.44 g, 8.25 mmol), potassium carbonate (1.56 g, 11.3 mmol), and DMF (75 mL) was stirred at 150 °C for 1 hour. After cooling the reaction solution to room temperature, deionized water was added, and reprecipitation was performed. The obtained solid was filtered off and washed successively with deionized water, methanol, and hexane. The crude product was dissolved in hot toluene and filtered through silica gel. The filtrate was concentrated and purified by recrystallization (toluene) to obtain 3.06 g of a pale yellow-green solid of compound J (2.71 mmol, 73% yield). 1 H NMR (400MHz, CDCl3): δ7.95 (s, 2H). APCI-MS spectral analysis: C 77 H3D 44 N8: Theoretical value 1127.67, observed value 1127.98 [(M+H)] + ].

[0231] (Example 1) Preparation and evaluation of thin films using compound A Vacuum deposition was performed at a vacuum degree of 5.0 × 10⁻⁶. -5 Compound A and compound H1 were co-deposited on a quartz substrate under Pa conditions to form a thin film. The concentration of compound A was set to 30% by weight.

[0232] (Examples 2 to 10, Comparative Example 1, Comparative Example 2) Compound A was replaced by any one of compounds B to J, comparative compound A, or comparative compound B, and a thin film was formed by co-evaporation using the same steps.

[0233] The films prepared in each embodiment and comparative example were irradiated with 299 nm excitation light, and the emission maximum wavelength and the lifetime (τ2) of the delayed fluorescence component were measured. The results of these measurements, along with the HOMO and LUMO energy values ​​(absolute values) of the compounds used in each film, are shown in Table 5. In Table 5, "-" indicates that no measurements were performed.

[0234] [Table 5]

[0235] As shown in Table 5, compared with comparative compounds A and B, the lifetime τ2 of the delayed fluorescence components of compounds A to J is shorter, thus indicating that they contribute to the stability of the device. Furthermore, the proportion of delayed fluorescence components in the total emission was calculated, and the results showed that the proportion of delayed fluorescence components in films using compounds A to H was greater than that in films using comparative compound B.

[0236] (Example 11) Fabrication and evaluation of organic electroluminescent devices Vacuum deposition was performed using a vacuum evaporation method at a vacuum level of 5.0 × 10⁻� -5 Pa stacked thin films on a glass substrate with an anode consisting of an indium / tin oxide (ITO) film with a thickness of 50 nm. First, HAT-CN was formed on the ITO with a thickness of 10 nm, followed by an NPD with a thickness of 30 nm, then TrisPCz with a thickness of 10 nm, and finally H1 with a thickness of 5 nm. Next, H1 and compound A were co-deposited from different evaporation sources to form a 40 nm thick layer as the light-emitting layer. The concentration of the compound in the light-emitting layer was set to 30% by weight. Then, SF3-TRZ was formed with a thickness of 10 nm, followed by co-depositing Liq and SF3-TRZ from different evaporation sources to form a 30 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were set to 30% by weight and 70% by weight, respectively. Furthermore, Liq was formed with a thickness of 2 nm, followed by aluminum (Al) deposition with a thickness of 100 nm to form the cathode, which served as the organic light-emitting element. Compound A was replaced by compounds B, C, E, F, G, H, comparative compound A, comparative compound B, and comparative compound C, respectively, and each organic electroluminescent element was fabricated using the same steps. The external quantum efficiency (EQE) of each organic electroluminescent element was measured. The results confirmed that, except for the organic electroluminescent element of compound C, all showed high values ​​of over 10%, and the compound represented by general formula (1) is useful. Furthermore, for organic electroluminescent devices using compounds A, E to H, and comparative compounds A to C, the time (LT95) during which the luminous intensity decreased to 95% of its initial value at 1000 nits was measured. The results are shown in Table 6. The "LT95" shown in Table 6 is a relative value when the LT95 of the device using comparative compound A is set to 1.

[0237] [Table 6]

[0238] As shown in Table 6, compared with the organic light-emitting elements of comparative compounds A to C, the organic light-emitting elements of compounds A, E to H all exhibited longer lifespans. In particular, it was confirmed that the organic light-emitting element of compound A had a lifespan 32.6 times that of the organic light-emitting element of comparative compound A. Furthermore, it was confirmed that even compared with other comparative compounds, for example, the organic light-emitting element of compound A had a lifespan 29.6 times that of comparative compound B and 673 times that of comparative compound C. Thus, it was confirmed that the organic light-emitting elements using compounds represented by general formula (1) have high durability.

[0239] (Example 12) Fabrication and evaluation of organic electroluminescent devices The light-emitting layer of Example 11 was modified by co-depositing H1, compound D and n-DABNA from different evaporation sources to form a 40 nm thick light-emitting layer with H1 concentration of 34.2 wt%, compound D concentration of 65.0 wt%, and n-DABNA concentration of 0.8 wt%. Otherwise, an organic electroluminescent element of compound D was fabricated using the same steps as in Example 11. At 12.6 mA / cm 2 The organic electroluminescent element driven by compound D showed an EQE exceeding 10%. Furthermore, it achieved an EQE of 12.6 mA / cm². 2 The LT95 was measured, and the results confirmed its long service life. Furthermore, the EQE and driving voltage of the organic electroluminescent elements of compounds A to H prepared in Examples 11 and 12, as well as the organic electroluminescent elements of comparative compounds A to C, are at practical levels.

[0240] [Chemical Formula 86]

[0241] [Chemical Formula 87] Industrial availability

[0242] By using the compound represented by general formula (1), it is possible to provide an organic light-emitting element with good light-emitting properties. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1), General formula (1) [Chemical Formula 1] In general formula (1), R 1 ~R 5 One to three of them are donor groups, R 1 ~R 5 The 0th to 1st group is a cyano group, R 1 ~R 5 The 0 to 3 atoms in R are hydrogen or deuterium atoms. 1 ~R 5 Of these, 0 to 2 are substituted or unsubstituted aryl groups, and the remaining R... 1 ~R 5 R is a substituted or unsubstituted alkyl group. 1 and R 2 R 2 and R 3 R 3 and R 4 R 4 and R 5 They can bond together to form a ring structure, where L represents a single bond or a linking group, and X... 1 Indicates N or CR 6 X 2 Indicates N or CR 7 R 6 and R 7 Each of these can independently represent a hydrogen atom, a deuterium atom, or a substituent, where Y represents a substituted or unsubstituted carbazole-9-yl or a substituted or unsubstituted aryl group. When Y is a substituted or unsubstituted aryl group, R 1 ~R 5 The 0 to 2 atoms are either hydrogen or deuterium atoms.

2. The compound according to claim 1, wherein, R 1 ~R 5 One of them is a cyano group.

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

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

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

6. The compound according to claim 5, wherein, R 1 It consists of hydrogen or deuterium atoms.

7. The compound according to claim 1, wherein, R 1 ~R 5 One or two of them are substituted or unsubstituted aryl groups.

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

9. The compound according to claim 1, wherein, Y represents carbazo-9-yl, which may or may not be substituted.

10. The compound according to claim 1, wherein, Y represents the aryl group, which may or may not be substituted.

11. The compound according to claim 1, wherein, L stands for a single bond.

12. The compound according to claim 1, wherein it has at least one deuterium atom.

13. A luminescent material comprising any one of the compounds according to claims 1 to 12.

14. A delayed phosphor, comprising the compound of any one of claims 1 to 12.

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

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

17. An organic light-emitting element comprising the compound of any one of claims 1 to 12.

18. The organic light-emitting element according to claim 17, wherein, The element has a layer containing the compound, and the layer further contains a host material.

19. The organic light-emitting element according to claim 18, wherein, The layer containing the compound includes the compound and the host material, as well as a luminescent material. The lowest excitation singlet energy of the compound is lower than that of the host material but higher than that of the luminescent material.

20. The organic light-emitting element according to claim 19, wherein, The layer also contains delayed fluorescence material.

21. The organic light-emitting element according to claim 17, wherein it is an organic electroluminescent element.

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

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