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

Abstract

The organic light-emitting element using the compound of the following general formula has excellent characteristics. R1-R5 are H, D, a cyano group, an alkyl group, an aryl group or a donor group, more than one is the cyano group, and more than one is the donor group; x1 to X3 are N or C (R); r is H, D or a substituent; one or more of Ar1 and Ar2 is a heteroaryl group bonded via N; and L1 represents a single bond or a linking group. # imgabs0 #

Description

Technical Field

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

[0002] Research is actively being conducted to improve the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, a lot of effort has been made to improve the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a luminescent material, etc. constituting an organic electroluminescent element. Among them, research related to an organic electroluminescent element using a delayed fluorescence material has also been seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after undergoing reverse intersystem crossing from the excited triplet state in the excited state. Fluorescence generated by this pathway is observed later than fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence), and thus is called delayed fluorescence. Here, for example, in the case of exciting a luminescent compound by injection of carriers, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, if only fluorescence from the directly generated excited singlet state is used, there is a limit to the improvement of luminous efficiency. On the other hand, in a delayed fluorescence material, in addition to the excited singlet state, the excited triplet state can also be used for fluorescence emission through the above-mentioned reverse intersystem crossing pathway, and thus higher luminous efficiency can be obtained compared with ordinary fluorescence materials.

[0004] After this principle was clarified, various delayed fluorescence materials were discovered through various studies. Among them, there are compounds in which multiple benzene rings are substituted with donor groups and acceptor groups. For example, a compound having the following skeleton in which a benzene ring is substituted with a carbazol-9-yl as a donor group, a cyano group as an acceptor group, and a substituted triazine group has been proposed (see Patent Document 1).

[0005] [Chemical Formula 1]

[0006]

[0007] Prior Art Documents

[0008] Non-Patent Documents

[0009] Non-Patent Document 1: WO2022 / 074122A1 Summary of the Invention

[0010] Technical Problem to be Solved by the Invention

[0011] So far, there has been no material that provides the following: a material that exhibits extremely good characteristics and has no practical problems even for a material that emits delayed fluorescence. For example, Patent Document 1 discloses that when the above-mentioned delayed fluorescence material is used, the element lifetime of an organic electroluminescent element can be improved, but the improvement effect of the element lifetime is not sufficient. Therefore, it is further useful if a delayed fluorescence material with more excellent characteristics can be provided. However, the improvement of delayed fluorescence materials is still in the trial stage, and it is not easy to generalize the chemical structures of useful luminescent materials.

[0012] Under such circumstances, the present inventors repeatedly conducted research to provide a compound that is more useful as a delayed fluorescence material for a light-emitting element. Moreover, they painstakingly explored to derive and generalize the general formula of a compound that is more useful as a delayed fluorescence material.

[0013] Means for Solving the Technical Problem

[0014] As a result of painstaking exploration to achieve the above object, the present inventors found that a compound having a structure that satisfies specific conditions can be used as a luminescent material. The present invention is proposed based on this finding, and specifically, it has the following structure.

[0015] [1] A compound represented by the following general formula (1).

[0016] [Chemical Formula 2]

[0017]

[0018] [In the general formula (1), R 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. And one or more of R 1 ~R 5 are cyano groups, one or more of R 1 ~R 5 are donor groups, 0 to 2 of R 1 ~R 5 are hydrogen atoms or deuterium atoms, 0 to 1 of R 1 ~R 5 is a substituted or unsubstituted aryl group. X 1 ~X 3 each independently represents N or C(R), provided that at least one of X 1 ~X 3 is N, and R represents a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring-skeleton constituting atom, provided that Ar 1 and Ar 2 at least one of which is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. L 1 represents a single bond or a divalent linking group.]

[0019] [2] The compound according to [1], wherein only one of R 1 to R 5 is a cyano group.

[0020] [3] The compound according to [2], wherein R 2 is a cyano group.

[0021] [4] The compound according to any one of [1] to [3], wherein only one of R 1 to R 5 is a substituted or unsubstituted aryl group.

[0022] [5] The compound according to [4], wherein R 4 is a substituted or unsubstituted aryl group.

[0023] [6] The compound according to any one of [1] to [5], wherein two of R 1 to R 5 are donor groups.

[0024] [7] The compound according to any one of [1] to [5], wherein three of R 1 to R 5 are donor groups.

[0025] [8] The compound according to any one of [1] to [7], wherein the donor group is a substituted or unsubstituted carbazol-9-yl.

[0026] [9] The compound according to any one of [1] to [8], wherein R 3 to R 5 are each independently a substituted or unsubstituted aryl group or a donor group.

[0027]

[10] The compound according to any one of [1] to [9], wherein X 1 to X 3 is N.

[0028]

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

[10] , wherein Ar 1 is a substituted or unsubstituted carbazol-9-yl, Ar 2is a substituted or unsubstituted aryl group.

[0029]

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

[10] , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted carbazol-9-yl group.

[0030]

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

[12] , wherein L 1 is a single bond.

[0031]

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

[13] , wherein R 1 is a hydrogen atom.

[0032]

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

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

[0033]

[16] A luminescent material composed of the compound according to any one of [1] to

[15] .

[0034]

[17] A delayed phosphor composed of the compound according to any one of [1] to

[15] .

[0035]

[18] A film containing the compound according to any one of [1] to

[15] .

[0036]

[19] An organic semiconductor element containing the compound according to any one of [1] to

[15] .

[0037]

[20] An organic light-emitting element containing the compound according to any one of [1] to

[15] .

[0038]

[21] The organic light-emitting element according to

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

[0039]

[22] The organic light-emitting element according to

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

[0040]

[23] The organic light-emitting element according to

[21] or

[22] , wherein the element has a layer containing the compound, and the layer further contains a luminescent material having a structure different from that of the compound.

[0041]

[24] The organic light-emitting element according to

[21] or

[22] , wherein the amount of light emission from the compound in the materials contained in the element is the largest.

[0042]

[25] The organic light-emitting element according to

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

[0043]

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

[20] to

[25] , which is an organic electroluminescent element.

[0044]

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

[20] to

[26] , which emits delayed fluorescence.

[0045] Advantages of the Invention

[0046] The compound of the present invention exhibits excellent light-emitting characteristics. The compound of the present invention can be used as a material for an organic light-emitting element. Detailed Description of the Invention

[0047] The content of the present invention will be described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, in the present specification, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. And, part or all of the hydrogen atoms in the molecule of the compound used in the present invention can be replaced by deuterium atoms ( 2 H, deuterium D). In the chemical structural formula of the present specification, a hydrogen atom is represented as H or its representation is omitted. For example, when omitting the representation of an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring, it is assumed that H is bonded to the carbon atom constituting the ring skeleton at the omitted position. In the present specification, the term "substituent" means an atom or a group of atoms other than a hydrogen atom and a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom can be replaced by a deuterium atom or a substituent.

[0048] [Compound represented by general formula (1)]

[0049] The compound represented by the following general formula (1) will be described.

[0050] [Chemical formula 3]

[0051]

[0052] In general formula (1), R 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. Ar 1 and Ar 2Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton constituting atom.

[0053] R 1 ~R 5 The alkyl group that can be used can be any one of straight chain, branched chain, and cyclic. In addition, two or more of the straight chain part, cyclic part, and branched chain part can be mixed. The number of carbon atoms of the alkyl group can be set to, for example, more than 1, more than 2, or more than 4. In addition, the number of carbon atoms can be set to less than 30, less than 20, less than 10, less than 6, or less than 4. As specific examples of alkyl groups, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isodecyl, cyclopentyl, cyclohexyl, and cycloheptyl can be cited. The alkyl group of the substituent can be further substituted by deuterium atoms, aryl groups, alkoxy groups, aryloxy groups, and halogen atoms, for example. In one embodiment of the present invention, the substituent of the alkyl group is one or more selected from the group consisting of aryl groups and deuterium atoms. In a preferred embodiment of the present invention, the alkyl group is unsubstituted, and can be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.

[0054] R 1 ~R 5 ,Ar 1 and Ar 2 The aryl group that can be used can be a single ring or a condensed ring formed by condensing two or more rings. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, for example, it can be selected from 2 to 4. As specific examples of rings, benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and triphenylene rings can be cited. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthalene-1-yl, or a substituted or unsubstituted naphthalene-2-yl, preferably a substituted or unsubstituted phenyl. Regarding the substituent of the aryl group, for example, it can be selected from the substituent group A, or from the substituent group B, or from the substituent group C, or from the substituent group D, or from the substituent group E. In one embodiment of the present invention, the substituent of the aryl group is selected from one or more of the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted by at least one deuterium atom. In one embodiment of the present invention, the aryl group is unsubstituted.

[0055] In the following, R 1 ~R 5 ,Ar 1 and Ar 2Specific examples of substituted or unsubstituted aryl groups that can be used. Among them, the aryl groups that can be used in the present invention should not be construed in a limiting manner by the following specific examples. In the following specific examples, * represents the bonding position. Also, the methyl group is omitted. Therefore, Ar2 to Ar7 represent structures substituted with a methyl group.

[0056] [Chemical formula 4-1]

[0057]

[0058] [Chemical formula 4-2]

[0059]

[0060] [Chemical formula 4-3]

[0061]

[0062] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar20 are replaced by deuterium atoms are exemplified here as Ar40 to Ar59 in sequence.

[0063] In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is Ar1 or Ar40. In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to 50. In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. In one embodiment of the present invention, R 1 ~R 5 The aryl group that can be used is selected from the group consisting of Ar21 to Ar59.

[0064] In one embodiment of the present invention, Ar 1 and Ar 2 The aryl group that can be used is Ar1 or Ar40. In one embodiment of the present invention, Ar 1 and Ar 2 The aryl group that can be used is selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to 50. In one embodiment of the present invention, Ar 1 and Ar2 The aryl groups that can be used are selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. In one embodiment of the present invention, Ar 1 and Ar 2 The aryl groups that can be used are selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. In one embodiment of the present invention, Ar 1 and Ar 2 The aryl groups that can be used are selected from the group consisting of Ar21 to Ar59.

[0065] At least one of R 1 to R 5 in the general formula (1) is a donor group. R 1 to R 5 The donor groups that can be used do not include substituted or unsubstituted aryl groups.

[0066] Regarding the "donor group", it can be selected from groups having a negative Hammett σp value. The Hammett σp value was proposed by L.P. Hammett and quantifies the influence of a substituent on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is the following formula established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0067] log(k / k0) = ρσp

[0068] or

[0069] log(K / K0) = ρσp

[0070] The constant (σp) specific to the substituent in. In the above formula, k0 represents the rate constant of the benzene derivative without a substituent, k represents the rate constant of the benzene derivative substituted with the substituent, K0 represents the equilibrium constant of the benzene derivative without a substituent, K represents the equilibrium constant of the benzene derivative substituted with the substituent, and ρ represents the reaction constant determined by the type and conditions of the reaction. Regarding the description related to the "Hammett σp value" in the present invention and the numerical values of each substituent, reference can be made to the description related to the σp value in Hansch, C. et al., Chem. Rev., 91, 165–195 (1991).

[0071] R 1 to R 5 The σp of the donor groups that can be used is preferably -0.3 or less, more preferably -0.5 or less, and further 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.

[0072] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or an aryl group formed by bonding of substituted amino groups, and a phenyl group formed by bonding of substituted amino groups among them. In a preferred embodiment of the present invention, the donor group is a substituted amino group.

[0073] The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group described herein may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0074] R 1 ~R 5 The donor group that can be used is preferably a group represented by the following general formula (a).

[0075] [Chemical formula 5]

[0076] General formula (a)

[0077]

[0078] In the general formula (a), Z 1 represents C-R 14 or N, Z 2 represents C-R 15 or N, Z 3 represents C-R 16 or N, Z 4 represents C-R 17 or N. Z 5 represents C or N, Ar 5 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. R 14 and R 15 , R 15 and R 16 , R 16 and R 17 may be bonded to each other to form a cyclic structure.

[0079] Z 1 ~Z 4 The number of N in Z 1 ~Z 4 is preferably 0 to 3, more preferably 0 to 2. In one embodiment of the present invention, the number of N in Z 1 ~Z 4 is one. In one embodiment of the present invention, the number of N in Z 1 ~Z 4 is zero.

[0080] R 14 ~R 17 Each independently represents a hydrogen atom, a deuterium atom or a substituent.

[0081] Regarding the substituent, for example, it can be selected from substituent group A, or it can be selected from substituent group B, or it can be selected from substituent group C, or it can be selected from substituent group D, or it can be selected from substituent group E. In R 14 ~R 17 When two or more of them represent substituents, these two or more substituents can be the same or different. R 14 ~R 17 Among them, 0 to 2 are preferably substituents. For example, one can be a substituent, or 0 can be a substituent (R 14 ~R 17 is a hydrogen atom or a deuterium atom).

[0082] R 14 and R 15 , R 15 and R 16 , R 16 and R 17 can bond to each other to form a cyclic structure. The cyclic structure can be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, and can also be a ring formed by fusing these. Preferably, it is an aromatic ring or a heteroaromatic ring. As the aromatic ring, an unsubstituted or substituted benzene ring can be mentioned. Another benzene ring can be further fused to the benzene ring, or a heteroaromatic ring such as a pyridine ring can be fused. The heteroaromatic ring represents a ring showing aromaticity containing heteroatoms as ring skeleton constituting atoms, preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, as the heteroaromatic ring, a furan ring, a thiophene ring, or a pyrrole ring can be adopted. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of unsubstituted or substituted benzofuran, a thiophene ring of unsubstituted or substituted benzothiophene, or a pyrrole ring of unsubstituted or substituted indole. The benzofuran, benzothiophene, and indole described herein can be unsubstituted, or can be substituted with a substituent selected from substituent group A, or can be substituted with a substituent selected from substituent group B, or can be substituted with a substituent selected from substituent group C, or can be substituted with a substituent selected from substituent group D, or can be substituted with a substituent selected from substituent group E. Preferably, an unsubstituted or substituted aryl is bonded to the nitrogen atom of the pyrrole ring constituting indole, and as its substituent, for example, a substituent selected from any one of substituent groups A to E can be mentioned. The cyclic structure can be an unsubstituted or substituted cyclopentadiene ring. In one embodiment of the present invention, R 14 and R 15, R 15 and R 16 , R 16 and R 17 One group among them bonds to each other to form a ring structure. In one embodiment of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 do not bond to each other to form a ring structure.

[0083] In the general formula (a), Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one embodiment of the present invention, Z 5 is C, and Ar 5 is a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. In one embodiment of the present invention, Z 5 is N, and Ar 5 is a substituted or unsubstituted heteroaromatic ring.

[0084] As the aromatic ring that can be adopted as Ar 5 , a benzene ring can be cited. Another benzene ring can be further fused to the benzene ring, or a heterocyclic ring such as a pyridine ring can be fused. As the heteroaromatic ring that Ar 5 can adopt, a 5- to 7-membered ring is preferred. For example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, as the heteroaromatic ring, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted. In one embodiment of the present invention, Z 5 is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. In one embodiment of the present invention, Z 5 is N, and the heteroaromatic ring is a pyrrole ring of a substituted or unsubstituted indole or an imidazole ring of a substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole described herein can be unsubstituted, or can be substituted with a substituent selected from substituent group A, or can be substituted with a substituent selected from substituent group B, or can be substituted with a substituent selected from substituent group C, or can be substituted with a substituent selected from substituent group D, or can be substituted with a substituent selected from substituent group E.

[0085] When Z 5 in the general formula (a) is C, it is preferably a group represented by the following general formula (b).

[0086] [Chemical Formula 6]

[0087] General formula (b)

[0088]

[0089] In general formula (b), Z 1 represents C-R 14 or N, Z 2 represents C-R 15 or N, Z 3 represents C-R 16 or N, Z 4 represents C-R 17 or N, Z 6 represents C-R 18 or N, Z 7 represents C-R 19 or N, Z 8 represents C-R 20 or N, Z 9 represents C-R 21 or N. R 14 and R 15 、R 15 and R 16 、R 16 and R 17 、R 18 and R 19 、R 19 and R 20 、R 20 and R 21 can be bonded to each other to form a cyclic structure.

[0090] Regarding Z in general formula (b) 1 ~Z 4 、R 14 ~R 17 , the description corresponding to general formula (a) can be referred to. Z in general formula (b) 6 ~Z 9 、R 18 ~R 21 corresponds to Z of general formula (a) in sequence 1 ~Z 4 、R 14 ~R 17 Regarding these, the description of Z of general formula (a) 1 ~Z 4 、R 14 ~R 17 can be referred to.

[0091] In one embodiment of the present invention, Z 1 ~Z 4 、Z 6~Z 9 The number of N in it is preferably 0 to 2, more preferably 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 、Z 6 ~Z 9 The number of N in it is one. In a preferred embodiment of the present invention, Z 1 ~Z 4 、Z 6 ~Z 9 The number of N in it is zero. When it is zero, it represents a substituted or unsubstituted carbazol-9-yl group.

[0092] R 1 ~R 5 The donor group that can be used is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group described herein may be unsubstituted, or may be substituted with a substituent selected from substituent group A, or may be substituted with a substituent selected from substituent group B, or may be substituted with a substituent selected from substituent group C, or may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E. Further, one or more rings may be further fused to the two benzene rings constituting the carbazol-9-yl group. In a preferred embodiment of the present invention, R 1 ~R 5 The donor group that can be used is a carbazol-9-yl group that can be substituted with a group selected from substituent group E and can be fused with one or more rings. When the un-fused carbazol-9-yl group is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2nd to 7th positions, more preferably at least one of the 3rd and 6th positions, and further preferably the 3rd and 6th positions.

[0093] In one embodiment of the present invention, R 1 ~R 5 The donor group that can be used is a carbazol-9-yl group fused with one or more rings, which is hereinafter referred to as a "ring-fused carbazol-9-yl group". R 1 ~R 5The ring-fused carbazol-9-yl that can be employed may be unsubstituted, or may be substituted with a substituent selected from substituent group A, may be substituted with a substituent selected from substituent group B, may be substituted with a substituent selected from substituent group C, may be substituted with a substituent selected from substituent group D, or may be substituted with a substituent selected from substituent group E. It is preferably unsubstituted or substituted with a substituent selected from substituent group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl is substituted with an aryl group substituted with an atom or group selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group, or a group obtained by combining two or more thereof.

[0094] The total number of fused rings in the ring-fused carbazol-9-yl is 4 or more, preferably 5 or more, more preferably 5 to 9, and further preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused rings is five. In addition, the number of rings described herein includes the number of rings of the fused carbazole (i.e., three).

[0095] The ring-fused carbazol-9-yl is a group bonded to the nitrogen atom of the ring skeleton constituting carbazole and has a structure in which at least one of the two benzene rings constituting carbazole is fused to a ring. The fused ring can be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, and can also be a ring formed by further fusing these. It is preferably an aromatic hydrocarbon ring or an aromatic heterocyclic ring. Examples of the aromatic hydrocarbon ring include a substituted or unsubstituted benzene ring. Another benzene ring can be further fused to the benzene ring, or a heterocyclic ring such as a pyridine ring can be fused. An aromatic heterocyclic ring means a ring showing aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be used. In one embodiment of the present invention, as the aromatic heterocyclic ring, a furan ring, a thiophene ring, or a pyrrole ring can be used. In one embodiment of the present invention, the fused ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. Further, on the nitrogen atom of the pyrrole ring, a substituent selected from the substituent group E (wherein, except for the case of only deuterium atoms) is preferably bonded, and more preferably an aryl group which can be substituted by an alkyl group or an aryl group is bonded. In the present invention, it is preferable to use a carbazol-9-yl fused with a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton constituent atoms. Among them, a carbazol-9-yl fused with a benzofuran structure, a carbazol-9-yl fused with a benzothiophene structure, and a carbazol-9-yl fused with an indole structure can be preferably used. In one embodiment of the present invention, there is a carbazol-9-yl fused with at least one benzofuran structure, for example, two or more. In one embodiment of the present invention, there is a carbazol-9-yl fused with at least one benzothiophene structure, for example, two or more.

[0096] As the ring-fused carbazol-9-yl group, benzofuro[2,3-a]carbazol-9-yl, benzofuro[3,2-a]carbazol-9-yl, benzofuro[2,3-b]carbazol-9-yl, benzofuro[3,2-b]carbazol-9-yl, benzofuro[2,3-c]carbazol-9-yl, benzofuro[3,2-c]carbazol-9-yl can be used. Also, as the ring-fused carbazol-9-yl group, benzothieno[2,3-a]carbazol-9-yl, benzothieno[3,2-a]carbazol-9-yl, benzothieno[2,3-b]carbazol-9-yl, benzothieno[3,2-b]carbazol-9-yl, benzothieno[2,3-c]carbazol-9-yl, benzothieno[3,2-c]carbazol-9-yl can be used. Also, as the ring-fused carbazol-9-yl group, indolo[2,3-a]carbazol-9-yl, indolo[3,2-a]carbazol-9-yl, indolo[2,3-b]carbazol-9-yl, indolo[3,2-b]carbazol-9-yl, indolo[2,3-c]carbazol-9-yl, indolo[3,2-c]carbazol-9-yl can be used.

[0097] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 4. For example, it can be one, and for example, it can also be two. In a preferred embodiment of the present invention, either the 3-position or the 6-position of the ring-fused carbazol-9-yl group is substituted. In a preferred embodiment of the present invention, from the perspective of the heteroatoms present in the ring-fused carbazol-9-yl group, there is at least one substituent at the para-position of the benzene ring. In a preferred embodiment of the present invention, from the perspective of the heteroatoms present in the ring-fused carbazol-9-yl group, there is only at least one substituent at the para-position of the benzene ring. In a preferred embodiment of the present invention, from the perspective of the heteroatoms present in the ring-fused carbazol-9-yl group, there are substituents at all para-positions of the benzene ring where substitution is possible.

[0098] In the following, specific examples of the donor groups that can be adopted for R 1 ~R 5 are shown. Among them, the donor groups that can be adopted in the present invention should not be construed in a limiting sense by the following specific examples. In addition, in the following specific examples, Ph represents a phenyl group (C6H5), and * represents the bonding position. The methyl group is omitted, so for example, D2 has one methyl group. Among them, the deuterated methyl group is expressed as CD3. And C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0099] [Chemical formula 7-1]

[0100]

[0101] [Chemical formula 7-2]

[0102]

[0103] [Chemical Formula 7-3]

[0104]

[0105] [Chemical Formula 7-4]

[0106]

[0107] [Chemical Formula 7-5]

[0108]

[0109] [Chemical Formula 7-6]

[0110]

[0111] [Chemical Formula 7-7]

[0112]

[0113] [Chemical Formula 7-8]

[0114]

[0115] [Chemical Formula 7-9]

[0116]

[0117] [Chemical Formula 7-10]

[0118]

[0119] [Chemical Formula 7-11]

[0120]

[0121] [Chemical Formula 7-12]

[0122]

[0123] [Chemical Formula 7-13]

[0124]

[0125] [Chemical Formula 7-14]

[0126]

[0127] [Chemical Formula 7-15]

[0128]

[0129] [Chemical Formula 7-16]

[0130]

[0131] [Chemical Formula 7-17]

[0132]

[0133] [Chemical Formula 7-18]

[0134]

[0135] [Chemical Formula 7-19]

[0136]

[0137] [Chemical Formula 7-20]

[0138]

[0139] [Chemical Formula 7-21]

[0140]

[0141] [Chemical Formula 7-22]

[0142]

[0143] [Chemical Formula 7-23]

[0144]

[0145] [Chemical Formula 7-24]

[0146]

[0147] [Chemical Formula 7-25]

[0148]

[0149] [Chemical Formula 7-26]

[0150]

[0151] [Chemical Formula 7-27]

[0152]

[0153] [Chemical Formula 7-28]

[0154]

[0155] [Chemical Formula 7-29]

[0156]

[0157] [Chemical Formula 7-30]

[0158]

[0159] [Chemical Formula 7-31]

[0160]

[0161] [Chemical Formula 7-32]

[0162]

[0163] [Chemical Formula 7-33]

[0164]

[0165] [Chemical Formula 7-34]

[0166]

[0167] [Chemical Formula 7-35]

[0168]

[0169] [Chemical Formula 7-36]

[0170]

[0171] [Chemical Formula 7-37]

[0172]

[0173] [Chemical Formula 7-38]

[0174]

[0175] [Chemical Formula 7-39]

[0176]

[0177] [Chemical Formula 7-40]

[0178]

[0179] [Chemical Formula 7-41]

[0180]

[0181] The substances in which all the hydrogen atoms in the above D1 to D459 are replaced by deuterium atoms are disclosed as D717 to D1175. The phenyl groups bonded to the 3-position of the above D1 to D1175 (i.e., the meta-phenylene further bonded to the *-bonded group of D1 to D1175) are disclosed as D1(m) to D1175(m). The phenyl groups bonded to the 4-position of the above D1 to D1175 (i.e., the para-phenylene further bonded to the *-bonded group of D1 to D1175) are disclosed as D1(p) to D1175(p).

[0182] In a preferred embodiment of the present invention, R in the general formula (1) 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1 to D1175. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D460 to D1175. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1(m) to D1175(m). In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1(p) to D1175(p).

[0183] In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D1 to D13, D717 to D729. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D14 to D16, D730 to D732. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D17 to D87, D733 to D803. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D88 to D123, D804 to D839. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D124 to D189, D840 to D905. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, D1168 to D1175. In one embodiment of the present invention, R 1~R 5 The donor groups that can be used are selected from the group consisting of D364 to D451 and D1080 to D1167. In one embodiment of the present invention, R 1 ~R 5 The donor groups that can be used are selected from the group consisting of D460 to D716.

[0184] One or more of R in the general formula (1) 1 ~R 5 is a cyano group. In one embodiment of the present invention, R 1 ~R 5 One or two of them are cyano groups. In a preferred embodiment of the present invention, at least R 2 is a cyano group. In one embodiment of the present invention, at least R 1 is a cyano group. In one embodiment of the present invention, at least R 3 is a cyano group. In a preferred embodiment of the present invention, only R 2 is a cyano group. In one embodiment of the present invention, only R 1 is a cyano group. In one embodiment of the present invention, only R 3 is a cyano group. In one embodiment of the present invention, only R 2 and R 4 are cyano groups. In one embodiment of the present invention, only R 2 and R 5 are cyano groups. In one embodiment of the present invention, only R 1 and R 3 are cyano groups.

[0185] One or more of R in the general formula (1) 1 ~R 5 is a cyano group. In one embodiment of the present invention, R 1 ~R 5 1 to 3 of them are donor groups. In one embodiment of the present invention, R 1 ~R 5 Two or three of them are donor groups. In a preferred embodiment of the present invention, R 1 ~R 5 Two of them are donor groups. In a preferred embodiment of the present invention, R 1 ~R 5 Three of them are donor groups. In one embodiment of the present invention, at least R 3 is a donor group. In one embodiment of the present invention, at least R 4 is a donor group. In one embodiment of the present invention, at least R 5 is a donor group. In one embodiment of the present invention, only R 3 is a donor group. In one embodiment of the present invention, only R 4is a donor group. In one embodiment of the present invention, only R 5 is a donor group. In one embodiment of the present invention, only R 3 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 5 are donor groups. In one embodiment of the present invention, only R 2 and R 4 are donor groups. In one embodiment of the present invention, only R 3 、R 4 and R 5 are donor groups. In one embodiment of the present invention, only R 2 、R 4 and R 5 are donor groups. When two or more of R 1 to R 5 are donor groups, these may be the same or different.

[0186] The number of hydrogen atoms or deuterium atoms in R 1 to R 5 is 0 to 2, preferably zero or one, for example one, for example zero. Compounds in which the number of hydrogen atoms or deuterium atoms in R 1 to R 5 is three exhibit more excellent luminescence characteristics. The number of substituted or unsubstituted aryl groups in R 1 to R 5 is zero or one, preferably one. It may also be zero. The number of substituted or unsubstituted alkyl groups in R 1 to R 5 is 0 to 3, preferably 0 to 2, and may be one or zero.

[0187] In a preferred embodiment of the present invention, one of R 1 to R 5 is a cyano group, two are donor groups, one is a substituted or unsubstituted aryl group, and one is a hydrogen atom or deuterium atom. In one embodiment of the present invention, the two donor groups are the same. In one embodiment of the present invention, the two donor groups are different from each other. In one embodiment of the present invention, R 1 is a hydrogen atom or deuterium atom, and R 2 or R 3 is a cyano group. In a preferred embodiment of the present invention, R 1 is a hydrogen atom or deuterium atom, R 2 is a cyano group, R 3 and R 5 are donor groups, and R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1is a hydrogen atom or a deuterium atom, R 2 is a cyano group, R 4 and R 5 are donor groups, R 3 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, R 2 is a cyano group, R 4 and R 5 are donor groups, R 3 is a substituted or unsubstituted aryl group.

[0188] In a preferred embodiment of the present invention, one of R 1 to R 5 is a cyano group, three are donor groups, and one is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, the three donor groups are the same. In one embodiment of the present invention, two of the three donor groups are the same and one is different. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, R 2 is a cyano group, R 3 to R 5 are donor groups. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, R 3 is a cyano group, R 2 , R 4 and R 5 are donor groups.

[0189] In one embodiment of the present invention, one of R 1 to R 5 is a cyano group, one is a donor group, one is a substituted or unsubstituted aryl group, and two are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, R 1 and R 3 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, R 4 is a substituted or unsubstituted aryl group, R 5 is a donor group. In one embodiment of the present invention, R 1 and R 3 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, R 4 is a donor group, R 5 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1 and R 5 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, R 3 is a donor group, R 4 is a substituted or unsubstituted aryl group. In one embodiment of the present invention, R 1and R 4 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 is a donor group, and R 5 is a substituted or unsubstituted aryl group.

[0190] In one embodiment of the present invention, one of R 1 to R 5 is a cyano group, two are donor groups, and two are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, R 1 and R 4 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, and R 3 and R 5 are donor groups. In one embodiment of the present invention, R 1 and R 5 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, and R 3 and R 4 are donor groups. In one embodiment of the present invention, R 1 and R 3 are hydrogen atoms or deuterium atoms, R 2 is a cyano group, and R 4 and R 5 are donor groups. In one embodiment of the present invention, R 1 and R 4 are hydrogen atoms or deuterium atoms, R 3 is a cyano group, and R 2 and R 5 are donor groups.

[0191] The heteroaryl group that Ar 1 and Ar 2 in the general formula (1) can adopt can be a monocyclic ring or a fused ring formed by fusing two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from 2 to 4, for example. As specific examples of the ring, a pyridine ring, a pyrimidine ring, and a pyrrole ring can be cited, and these rings can be further fused with other rings. As specific examples of the heteroaryl group, 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazol-9-yl, carbazol-1-yl, carbazol-2-yl, carbazol-3-yl, and carbazol-4-yl can be cited. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and can be selected in the range of 5 to 16 or in the range of 5 to 12.

[0192] The Ar 1 and Ar 2At least one of them is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. That is, it is a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom and is a group bonded via a nitrogen atom which is one of the ring skeleton-constituting atoms. Typical examples of such a group are a substituted or unsubstituted pyrrol-1-yl group, preferably a substituted or unsubstituted fused-ring pyrrol-1-yl group, more preferably a substituted or unsubstituted carbazol-9-yl group, and the carbazole skeleton may be further fused with a ring. As Ar 1 and Ar 2 Specific examples of the substituted or unsubstituted heteroaryl group bonded via a nitrogen atom that at least one of them can adopt include the above D1 to D1176.

[0193] In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D1 to D13 and D717 to D729. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D14 to D16 and F730 to D732. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D17 to D87 and D733 to D803. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D88 to D123 and D804 to D839. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D124 to D189 and D840 to D905. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, and D1168 to D1175. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D364 to D451 and D1080 to D1167. In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2 is selected from the group consisting of D460 to D716.

[0194] In one embodiment of the present invention, the group adopted by at least one of Ar 1 and Ar 2Each independently is a substituted or unsubstituted heteroaryl bonded via a nitrogen atom. In one embodiment of the present invention, Ar 1 and Ar 2 are substituted or unsubstituted heteroaryls bonded via a nitrogen atom and have the same structure. In one embodiment of the present invention, only Ar 1 is a substituted or unsubstituted heteroaryl bonded via a nitrogen atom, and Ar 2 is a substituted or unsubstituted aryl.

[0195] L in the general formula (1) 1 represents a single bond or a divalent linking group. As the divalent linking group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group can be mentioned. In a preferred embodiment of the present invention, L 1 is a single bond. In one embodiment of the present invention, L 1 is a substituted or unsubstituted arylene group. In one embodiment of the present invention, L 1 is a substituted or unsubstituted heteroarylene group. Regarding the aryl moiety constituting the arylene group, reference can be made to the description and preferred range of the aryl in the description column of the above R 1 ~R 5 . As the heteroarylene group, a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is substituted with a nitrogen atom can be mentioned.

[0196] In the following, specific examples of L 1 are given. Among them, L 1 that can be adopted in the present invention should not be construed as being limited by these specific examples. In addition, in the following specific examples, the methyl group is omitted for representation. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0197] [Chemical formula 8]

[0198]

[0199] As L22 to L41, substances obtained by substituting all hydrogen atoms present in the above L2 to L21 with deuterium atoms are disclosed. In one embodiment of the present invention, L 1 is selected from the group consisting of L1 to L7, L22 to L27. In one embodiment of the present invention, L 1 is selected from the group consisting of L2 to L7, L22 to L27. In one embodiment of the present invention, L 1 is selected from the group consisting of L1, L8 to L13, L20, L21, L28 to L33, L40, L41. In one embodiment of the present invention, L 1is selected from the group consisting of L1, L8 to L13, L20, L21, L28 to L33, L40, and L41. In one embodiment of the present invention, L 1 is selected from the group consisting of L1, L14 to L19, L34 to L39. In one embodiment of the present invention, L 1 is selected from the group consisting of L14 to L19, L34 to L39.

[0200] X in the general formula (1) 1 ~X 3 each independently represents N or C(R). Among them, X 1 ~X 3 at least one of them is N. R represents a hydrogen atom, a deuterium atom, or a substituent. Regarding the substituents described herein, they can be selected from substituent group A, or can be selected from substituent group B, or can be selected from substituent group C, or can be selected from substituent group D, or can be selected from substituent group E. In a preferred embodiment of the present invention, X 1 ~X 3 is N. In one embodiment of the present invention, X 1 and X 3 are N, and X 2 is C(R). In one embodiment of the present invention, X 1 and X 2 are N, and X 3 is C(R). In one embodiment of the present invention, X 1 is N, and X 2 and X 3 are C(R). In one embodiment of the present invention, X 2 is N, and X 1 and X 3 are C(R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group that can be substituted by a deuterium atom. In one embodiment of the present invention, R is an aryl group that can be substituted by a deuterium atom, an alkyl group, or an aryl group.

[0201] In a preferred embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 and Ar 2 each independently is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl), R 2 is a cyano group, R 1 , R 3 ~R 5Two of them are donor groups (preferably a substituted or unsubstituted carbazol-9-yl), one is a substituted or unsubstituted aryl, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0202] In a preferred embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl), Ar 2 is a substituted or unsubstituted aryl, R 2 is a cyano group, R 1 , R 3 ~R 5 Two of them are donor groups (preferably a substituted or unsubstituted carbazol-9-yl), one is a substituted or unsubstituted aryl, and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0203] In a preferred embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl), R 2 is a cyano group, R 1 , R 3 ~R 5 Three of them are donor groups (preferably a substituted or unsubstituted carbazol-9-yl), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0204] In a preferred embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl), Ar 2 is a substituted or unsubstituted aryl, R 2 is a cyano group, R 1 , R 3 ~R 5 Three of them are donor groups (preferably a substituted or unsubstituted carbazol-9-yl), and one (preferably R 1 ) is a hydrogen atom or a deuterium atom.

[0205] In a preferred embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 and Ar 2 are each independently a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl group), R 3 is a cyano group, and 2 to 3 of R 1 , R 2 , R 4 , R 5 are donor groups (preferably a substituted or unsubstituted carbazol-9-yl group), 1 to 2 (preferably at least R 1 ) are hydrogen atoms or deuterium atoms, and 0 to 1 is a substituted or unsubstituted aryl group.

[0206] In one embodiment of the present invention, X 1 ~X 3 is N, L 1 is a single bond, Ar 1 is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom (preferably a substituted or unsubstituted carbazol-9-yl group), Ar 2 is a substituted or unsubstituted aryl group, R 3 is a cyano group, and 2 to 3 of R 1 , R 2 , R 4 , R 5 are donor groups (preferably a substituted or unsubstituted carbazol-9-yl group), 1 to 2 (preferably at least R 1 ) are hydrogen atoms or deuterium atoms, and 0 to 1 is a substituted or unsubstituted aryl group.

[0207] The compound represented by the general formula (1) preferably does not contain a metal atom and may 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 the 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. Further, the compound represented by the general formula (1) may 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 the general formula (1) may 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 the general formula (1) may 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 the general formula (1) may be a compound containing deuterium atoms and not containing hydrogen atoms.

[0208] In this specification, "substituent group A" means an atom or a group selected from the group consisting of a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton constituting atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton constituting atoms), a heteroarylthio group (e.g., having 5 to 30 ring skeleton constituting atoms), an acyl group (e.g., having 1 to 40 carbon atoms), an alkenyl group (e.g., having 1 to 40 carbon atoms), an alkynyl group (e.g., having 1 to 40 carbon atoms), an alkoxycarbonyl group (e.g., having 1 to 40 carbon atoms), an aryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (e.g., having 1 to 40 carbon atoms), a silyl group (e.g., a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group, or a group obtained by combining two or more of them.

[0209] In this specification, "substituent group B" means an atom or a group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton constituting atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton constituting atoms), and a diarylamino group (e.g., having 0 to 20 carbon atoms), or a group obtained by combining two or more of them.

[0210] In this specification, "substituent group C" means an atom or a group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring skeleton constituting atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms), or a group obtained by combining two or more of them.

[0211] In this specification, "substituent group D" means an atom or a group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton constituting atoms), or a group obtained by combining two or more of them.

[0212] In this specification, "substituent group E" means an atom or a group selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms), or a group obtained by combining two or more of them.

[0213] In this specification, when a substituent is described as "substituted or unsubstituted" or "may be substituted", it can be selected from substituent group A, or from substituent group B, or from substituent group C, or from substituent group D, or from substituent group E.

[0214] In Tables 1 to 4 below, specific examples of the compound represented by the general formula (1) are illustrated. However, the compound represented by the general formula (1) that can be used in the present invention should not be construed in a limiting manner by these specific examples.

[0215] In Table 1, for each compound, by determining R of the following general formula (1a) 3 ~R 5 the structure of each compound is shown individually. That is, Ar 1 and Ar 2 are deuterated carbazolyl (D717), X 1 ~X 3 are nitrogen atoms (N), L 1 is a single bond, R 1 is a hydrogen atom, R 2 is a cyano group, and the structures of R 3 ~R 5 determined in Table 1 are shown as the structures of Compounds 1 to 1175.

[0216] [Chemical formula 9]

[0217] General formula (1a)

[0218]

[0219] In Table 2, for each column, by collectively showing R of multiple compounds 3 ~R 5 the structures of Compounds 1 to 1015655 are shown. For example, for the column of Compounds 1 to 1175 in Table 2, the compounds in which R 4 is fixed as Ar1, and R 3 and R 5 are both D1 to D1175 are sequentially taken as Compounds 1 to 1175. R 3 and R 5 are the same. That is, the column of Compounds 1 to 1175 in Table 2 is a collective display of Compounds 1 to 1175 determined in Table 1 in one column. Similarly, for the column of Compounds 1176 to 2350 in Table 2, the compounds in which R 4 is fixed as Ar2, and R 3 and R 5The compounds D1 to D1175 are sequentially used as compounds 1176 to 2350. Based on the same principle, the compounds 2351 to 1015655 in Table 2 are also determined.

[0220] [Table 1-1]

[0221]

[0222] [Table 1-2]

[0223]

[0224] [Table 1-3]

[0225]

[0226] [Table 1-4]

[0227]

[0228] [Table 1-5]

[0229]

[0230] [Table 2-1]

[0231]

[0232] [Table 2-2]

[0233]

[0234] [Table 2-3]

[0235]

[0236] [Table 2-4]

[0237]

[0238] [Table 2-5]

[0239]

[0240] [Table 2-6]

[0241]

[0242] [Table 2-7]

[0243]

[0244] [Table 2-8]

[0245]

[0246] Next, specific examples of the compound having the structure represented by the following general formula (1b) are shown in Table 3. In Table 3, the structures of the respective compounds are shown based on the same principle as in Table 2.

[0247] [Chemical formula 10]

[0248]

[0249] [Table 3-1]

[0250]

[0251] [Table 3-2]

[0252]

[0253] [Table 3-3]

[0254]

[0255] [Table 3-4]

[0256]

[0257] [Table 3-5]

[0258]

[0259] [Table 3-6]

[0260]

[0261] [Table 3-7]

[0262]

[0263] [Table 3-8]

[0264]

[0265] In Tables 1 to 3, Ar of the general formula (1) 1 and Ar 2 with a deuterated carbazolyl group (D717) are determined as the structures of Compounds 1 to 2031310. In Table 4, for each of Compounds 1 to 2031310, the compounds with Ar 1 and Ar 2 changed as shown in Table 4 are sequentially shown in tabular form. In Table 4, for easy understanding of the correspondence, Compounds 1 to 2031310 are also shown in the first paragraph. In the second paragraph of Table 4, for example, Compound 1(1) represents having Ar of Compound 1 2Compounds with the structure where Ar is replaced by Ar1. And, Compound 2(1) represents having Ar of Compound 2 2 replaced by Ar1. Compound 2031310(1) represents having Ar of Compound 2031310 2 replaced by Ar1. Compounds 1(2) to 2031310(2) in the third paragraph of Table 4 or the compounds in subsequent paragraphs are also determined by the same principle. Additionally, for the compounds determined in Table 4, X 1 to X 3 are all nitrogen atoms (N), L 1 is a single bond, and R 1 is a hydrogen atom.

[0266] [Table 4-1]

[0267]

[0268] [Table 4-2]

[0269]

[0270] [Table 4-3]

[0271]

[0272] [Table 4-4]

[0273]

[0274] [Table 4-5]

[0275]

[0276] [Table 4-6]

[0277]

[0278] [Table 4-7]

[0279]

[0280] [Table 4-8]

[0281]

[0282] [Table 4-9]

[0283]

[0284] [Table 4-10]

[0285]

[0286] [Table 4-11]

[0287] No. <![CDATA[Ar 1 > <![CDATA[Ar 2 > 1(1771)～203131011771) D9 D735 1(1772)～2031310(1772) D9 D843 1(1773)～2031310(1773) D19 D37 1(1774)～2031310(1774) D19 D50 1(1775)～2031310(1775) D19 D77 1(1776)～2031310(1776) D19 D281 1(1777)～2031310(1777) D19 D459 1(1778)～2031310(1778) D19 D465 1(1779)～2031310(1779) D19 D466 1(1780)～2031310(1780) D19 D467 1(1781)～2031310(1781) D19 D471 1(1782)～2031310(1782) D19 D486 1(1783)～2031310(1783) D19 D520 1(1784)～2031310(1784) D19 D621 1(1785)～2031310(1785) D19 D711 1(1786)～2031310(1788) D19 D712 1(1787)～2031310(1787) D19 D713 1(1788)～2031310(1788) D19 D714 1(1789)～2031310(1789) D19 D715 1(1790)～2031310(1790) D19 D716 1(1791)～2031310(1791) D19 D725 1(1792)～2031310(1792) D19 D735 1(1793)～2031310(1793) D19 D843 1(1794)～2031310(1794) D37 D50 1(1795)～2031310(1795) D37 D77 1(1796)～2031310(1796) D37 D281 1(1797)～2031310(1797) D37 D459 1(1798)～2031310(1798) D37 D465 1(1799)～2031310(1799) D37 D466 1(1800)～2031310(1800) D37 D467 1(1801)～2031310(1801) D37 D471 1(1802)～2031310(1802) D37 D486 1(1803)～2031310(1803) D37 D520 1(1804)～2031310(1804) D37 D621 1(1805)～2031310(1805) D37 D711 1(1806)～2031310(1806) D37 D712 1(1807)～2031310(1807) D37 D713 1(1808)～2031310(1808) D37 D714 1(1809)～2031310(1809) D37 D715 1(1810)～2031310(1810) D37 D716 1(1811)～2031310(1811) D37 D725 1(1812)～2031310(1812) D37 D735 1(1813)～2031310(1813) D37 D843

[0288] The compounds determined by the above numbers are each disclosed separately. In addition, when there are rotational isomers in the specific examples of the above compounds, mixtures of rotational isomers and each separated rotational isomer are also disclosed in this specification.

[0289] In one embodiment of the present invention, a compound is selected from the group of compounds α consisting of Compounds 1 to 2031310 and Compounds 1(n) to 2031310(n) [where n is from 1 to 1813]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [4]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [5]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [6]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [7]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [8]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above [9]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above

[10] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above

[11] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds α that satisfy the above

[15] .

[0290] In one embodiment of the present invention, a compound is selected from the group of compounds β consisting of Compounds 1 to 1015655 and Compounds 1(n) to 1015655(n) [where n is from 1 to 1813]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [4]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [5]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [6]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [7]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [8]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above [9]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above

[10] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above

[11] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds β that satisfy the above

[15] .

[0291] In one embodiment of the present invention, a compound is selected from the group of compounds γ consisting of compounds 1015656 to 2031310 and compounds 1015656(n) to 2031310(n) [where n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above [4]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above [5]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above [6]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above [7]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above [8]. In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above

[10] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above

[11] . In one embodiment of the present invention, a compound is selected from the compounds in the group of compounds γ that satisfy the above

[15] .

[0292] In one embodiment of the present invention, the compound represented by the general formula (1) is selected from the following group of compounds.

[0293] [Chemical formula 11-1]

[0294]

[0295] [Chemical formula 11-2]

[0296]

[0297] [Chemical formula 11-3]

[0298]

[0299] In one embodiment of the present invention, the compound represented by the general formula (1) is selected from the following group of compounds.

[0300] [Chemical formula 12-1]

[0301]

[0302] [Chemical formula 12-2]

[0303]

[0304] [Chemical formula 12-3]

[0305]

[0306] Regarding the molecular weight of the compound represented by the general formula (1), for example, when attempting to form a film of an organic layer containing the compound represented by the general formula (1) by vapor deposition, it is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1).

[0307] The compound represented by the general formula (1) can be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, a film can be formed even for a compound with a relatively large molecular weight. The compound represented by the general formula (1) has advantages such as being easily soluble in organic solvents. Therefore, the compound represented by the general formula (1) is easily applicable to the coating method and is easily purified to improve the purity.

[0308] It is also possible to consider applying the present invention and using a compound containing a structure represented by the general formula (1) in the molecule as a light-emitting material.

[0309] For example, it is possible to consider using a polymer obtained by pre-existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is possible to consider preparing a monomer containing a polymerizable functional group at any position in the general formula (1), obtaining a polymer having a repeating unit by polymerizing it alone or copolymerizing it with other monomers, and using this polymer as a light-emitting material. Or, it is also possible to consider obtaining a dimer or trimer by coupling compounds having a structure represented by the general formula (1) and using these as light-emitting materials.

[0310] As an example of a polymer having a repeating unit containing a structure represented by the general formula (1), a polymer containing a structure represented by any one of the following two general formulas can be cited.

[0311] [Chemical formula 13]

[0312]

[0313] In the above general formula, Q represents a group containing a structure represented by the general formula (1), and L 1 and L 2 represent a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. The linking group is preferably a linking group having a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

[0314] In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represent a substituent. Preferably, they are a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom. More preferably, they are an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom. Further preferably, they are an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0315] L 1 and L 2 The linking groups represented can bond to any part in the general formula (1) constituting Q. Two or more linking groups can be connected to one Q to form a crosslinked structure or a network structure.

[0316] As a specific structural example of the repeating unit, the structure represented by the following formula can be cited.

[0317] [Chemical formula 14]

[0318]

[0319] A polymer having a repeating unit containing these formulas can be synthesized as follows: Hydroxyl groups are introduced into any part in the general formula (1), and the following compounds are reacted using them as linking groups to introduce polymerizable groups, and the polymerizable groups are polymerized.

[0320] [Chemical formula 15]

[0321]

[0322] The polymer containing the structure represented by the general formula (1) in the molecule can be a polymer composed only of repeating units having the structure represented by the general formula (1), or can be a polymer containing repeating units having other structures. Also, the repeating units having the structure represented by the general formula (1) contained in the polymer can be a single type or two or more types. As repeating units not having the structure represented by the general formula (1), repeating units derived from monomers usually used for copolymerization can be cited. For example, repeating units derived from monomers having an ethylenic unsaturated bond such as ethylene and styrene can be cited.

[0323] In one embodiment, the compound represented by the general formula (1) is a luminescent material.

[0324] In one embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence.

[0325] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the UV region, the blue, green, yellow, orange, red regions (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) of the visible spectrum, or the near-infrared region.

[0326] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the red or orange region (e.g., about 620 nm to about 780 nm, about 650 nm) of the visible spectrum.

[0327] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the orange or yellow region (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) of the visible spectrum.

[0328] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum.

[0329] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the blue region (e.g., about 400 nm to about 490 nm, about 475 nm) of the visible spectrum.

[0330] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the ultraviolet spectral region (e.g., 280 - 400 nm).

[0331] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the infrared spectral region (e.g., 780 nm to 2 μm).

[0332] In one embodiment of the present invention, an organic semiconductor element using the compound represented by the general formula (1) can be fabricated. The organic semiconductor element described herein can be an organic optical element involving light, or an organic element not involving light. 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 the compound represented by the general formula (1). In one embodiment of the present invention, a CMOS (complementary metal-oxide-semiconductor) or the like using the compound represented by the general formula (1) can be fabricated.

[0333] The electronic properties of a chemical library of small molecules can be calculated using quantum chemical calculations based on known ab initio methods. For example, as a basis set, time-dependent density functional theory using a functional group known as 6-31G* and Becke's three-parameter, Lee-Yang-Parr hybrid functional is used to analyze the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*), and molecular fragments (portions) having a HOMO above a specific threshold and a LUMO below a specific threshold can be screened.

[0334] Thus, for example, when there is a HOMO energy (e.g., ionization potential) of -6.5 eV or higher, a donor moiety ("D") can be selected. And, for example, when there is a LUMO energy (e.g., electron affinity) of -0.5 eV or lower, an acceptor moiety ("A") can be selected. The bridge moiety ("B") is, for example, a strong conjugated system that can strictly confine the acceptor and donor moieties to a unique three-dimensional structure, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties.

[0335] In one embodiment, the compound library is screened using one or more of the following properties.

[0336] 1. Emission near a specific wavelength

[0337] 2. Triplet state higher than a calculated specific energy level

[0338] 3. ΔE lower than a specific value ST Value

[0339] 4. Quantum yield higher than a specific value

[0340] 5. HOMO level

[0341] 6. LUMO level

[0342] In one embodiment, the difference (ΔE ST ) between the lowest excited singlet state and the lowest excited triplet state in 77K 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, the ΔE ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV.

[0343] In one embodiment, the compound represented by the general formula (1) exhibits a quantum yield of more than 25%, such as 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.

[0344] [Synthesis method of the compound represented by the general formula (1)]

[0345] The compound represented by the general formula (1) includes novel compounds.

[0346] The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, by reacting a substituted or unsubstituted aryl (e.g., phenyl) and a cyanobenzene having a halogen atom with a substituted ring-fused carbazol-9-yl, a compound of the general formula (1) substituted with a substituted ring-fused carbazol-9-yl can be synthesized. For the details of the reaction conditions, reference can be made to the synthesis examples described below.

[0347] [Structure using the compound represented by the general formula (1)]

[0348] In one embodiment, one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) that are dispersed in combination with the compound represented by the general formula (1), covalently bonded to the compound, coated with the compound, supported on the compound, or associated with the compound are used together to form a solid thin film or layer. For example, a thin film can be formed by combining the compound represented by the general formula (1) with an electroactive material. In some cases, the compound represented by the general formula (1) can be combined with a hole-transporting polymer. In some cases, the compound represented by the general formula (1) can be combined with an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can be combined with a copolymer having both a hole-transporting portion and an electron-transporting portion. Through the above embodiments, electrons and / or holes formed in the solid thin film or layer can interact with the compound represented by the general formula (1).

[0349] [Formation of thin film]

[0350] In one embodiment, a thin film containing the compound represented by the general formula (1) can be formed by a wet process. In the wet process, a solution obtained by dissolving a composition containing the compound of the present invention is coated on the surface, and after removing the solvent, a thin film is formed. Examples of the wet process include spin coating, slot coating, inkjet printing (spray coating), gravure printing, offset printing, and flexographic printing, but are not limited thereto. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected. In one embodiment, a substituent (such as an alkyl group) that improves the solubility in the organic solvent can be introduced into the compound contained in the composition.

[0351] In one embodiment, a thin film containing the compound of the present invention can be formed by a dry process. In one embodiment, as the dry process, a vacuum evaporation method can be employed, but it is not limited thereto. In the case of using the vacuum evaporation method, the compounds constituting the thin film can be co-evaporated from separate evaporation sources, or co-evaporated from a single evaporation source mixed with the compound. In the case of using a single evaporation source, a mixed powder containing the compound powder can be used, a compression molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating and melting each compound and then cooling can be used. In one embodiment, co-evaporation is performed under the condition that the evaporation rates (weight reduction rates) of the multiple compounds contained in the single evaporation source are the same or substantially the same, whereby a thin film having 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 as an evaporation source in the same composition ratio as the composition ratio of the formed thin film, a thin film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each compound for co-evaporation has the same weight reduction rate can be determined, and this temperature can be adopted as the temperature during co-evaporation.

[0352] [Example of use of the compound represented by the general formula (1)]

[0353] The compound represented by the general formula (1) is used as a material for an organic light-emitting element. In particular, it is preferably used in an organic light-emitting diode or the like.

[0354] Organic light-emitting diode:

[0355] One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention in the form of a light-emitting material of an organic light-emitting device. In one embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In one embodiment, the compound represented by the general formula (1) includes delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having the structure represented by the general formula (1). In one embodiment, the present invention relates to the use of the compound represented by the general formula (1) as a delayed phosphor. In one embodiment, the compound represented by the general formula (1) of the present invention can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF. In one embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by the 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 the compound represented by the general formula (1). In one embodiment, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high luminous efficiency.

[0356] In one embodiment, the light-emitting layer contains a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is the film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) on the film-forming surface affects or determines the propagation direction of the light emitted by the arranged compound. In one embodiment, by arranging in the propagation direction of the light emitted by the compound represented by the general formula (1), the light extraction efficiency from the light-emitting layer is improved.

[0357] One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes a light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by the general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called co-dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet state energy level, which is included 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.

[0358] In one embodiment, the organic photoluminescence device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device at least includes an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer at least includes a light-emitting layer. In one embodiment, the organic layer only includes a light-emitting layer. In one embodiment, the organic layer includes more than one organic layer other than the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer can be a hole injection and transport layer having a hole injection function, and the electron transport layer can be an electron injection and transport layer having an electron injection function.

[0359] Light-emitting layer:

[0360] In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and the cathode are re-bonded to form excitons. In one embodiment, the layer emits light.

[0361] In one embodiment, only a luminescent material is used as the light-emitting layer. In one embodiment, the light-emitting layer contains a luminescent material and a host material. In one embodiment, the luminescent material is one or more compounds represented by the general formula (1). In one embodiment, in order to enable an organic electroluminescent device and an organic photoluminescent device to exhibit high luminous efficiency, singlet excitons and triplet excitons generated in the luminescent material are confined in the luminescent material. In one embodiment, in addition to the luminescent material, a host material is also used in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has singlet excitation energy and triplet excitation energy, at least one of which is higher than those of the luminescent material of the present invention. In one embodiment, singlet excitons and triplet excitons generated in the luminescent material of the present invention are confined in the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are confined sufficiently to promote luminous efficiency. In one embodiment, the singlet excitons and triplet excitons are not confined sufficiently, but still a high luminous efficiency is 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, light emission occurs in the luminescent material in the light-emitting layer of the device of the present invention. In one embodiment, the emitted light contains both fluorescence and delayed fluorescence. In one embodiment, the emitted light contains 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 contains light emitted from the compound represented by the general formula (1) and light emitted from the host material. In one embodiment, a TADF molecule and a host material are used. In one embodiment, the TADF is a co-dopant, the singlet excitation energy of which is lower than that of the host material in the light-emitting layer and higher than that of the luminescent material in the light-emitting layer.

[0362] When a compound represented by the general formula (1) is used as a co-dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Such luminescent materials can be those using anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, Derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. These exemplified skeletons may or may not have substituents. Further, these exemplified skeletons may be combined with each other.

[0363] The following exemplifies luminescent materials that can be used in combination with a co-dopant having the structure represented by the general formula (1).

[0364] [Chemical Formula 16-1]

[0365]

[0366] [Chemical Formula 16-2]

[0367]

[0368] [Chemical Formula 16-3]

[0369]

[0370] [Chemical Formula 16-4]

[0371]

[0372] Further, it is particularly preferable to use the compound described in paragraphs 0220 to 0239 of WO2015 / 022974 as the luminescent material used in combination with the co-dopant having the structure represented by the general formula (1).

[0373] As a more preferable luminescent material, the compound represented by the following general formula (2) can also be mentioned.

[0374] [Chemical Formula 17]

[0375]

[0376] In the general formula (2), R 1 , R 3 ~R 16 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 2 represents a receptor group or R 1 and R 2 bond to each other to form a receptor group or R 2 and R3 bond to each other to form a receptor group. 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 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 can bond to each other to form a cyclic structure. X 1 represents O or NR, and R represents a substituent. X 2 ~X 4 in X 3 and X 4 in at least one of them can be O or NR and the remaining part can be O or NR, or they may not be connected. When not connected, each end independently represents a hydrogen atom, a deuterium atom or a substituent. C-R 1 、C-R 3 、C-R 4 、C-R 5 、C-R 6 、C-R 7 、C-R 8 、C-R 9 、C-R 10 、C-R 11 、C-R 12 、C-R 13 、C-R 14 、C-R 15 、C-R 16 can be substituted by N.

[0377] In one embodiment of the present invention, when X 2 is O or NR, R 7 is a receptor group, R 6 and R 7 bond to each other to form a receptor group or R 7 and R 8 bond to each other to form a receptor group. In one embodiment of the present invention, when X 3When X is O or NR, R 10 is a receptor group, R 9 and R 10 bond to each other to form a receptor group or R 10 and R 11 bond to each other to form a receptor group. In one embodiment of the present invention, when X 4 is O or NR, R 15 is a receptor group, R 14 and R 15 bond to each other to form a receptor group or R 15 and R 16 bond to each other to form a receptor group. In one embodiment of the present invention, when X 2 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 8 , at least one of the 3-position and 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 3 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 9 , at least one of the 3-position and 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 4 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 16 , at least one of the 3-position and 6-position of the carbazole ring is substituted with a receptor group. In one embodiment of the present invention, when X 1 is NR, R is a substituted or unsubstituted phenyl group, and a carbazole ring is formed by directly bonding to the carbon atom bonded to R 1 , the 3-position of the carbazole ring is substituted with a receptor group (wherein the 3-position is present on the phenyl group). In one embodiment of the present invention, it is a compound represented by the following general formula (2a).

[0378] [Chemical Formula 18]

[0379]

[0380] In the general formula (2a), R 1 , R 3 , R 6 ~R 11 , R 14 ~R 16 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 2 represents a receptor group or R 1 and R 2 bond to each other to form a receptor group or R 2 and R 3Bond to each other to form a receptor group.

[0381] R 6 and R 7 、R 7 and R 8 、R 9 and R 10 、R 10 and R 11 、R 14 and R 15 、R 15 and R 16 may bond to each other to form a cyclic structure. X 1 represents O or NR, and R represents a substituent. X 2 ~X 4 in X 3 and X 4 at least one of them may be O or NR and the remaining part may be O or NR, or may not be connected. When not connected, each end independently represents a hydrogen atom, a deuterium atom or a substituent. Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. C-R 1 、C-R 3 、C-R 6 、C-R 7 、C-R 8 、C-R 9 、C-R 10 、C-R 11 、C-R 14 、C-R 15 、C-R 16 may be substituted by N.

[0382] As a further preferred luminescent material, a compound represented by the following general formula (3) can also be cited.

[0383] [Chemical formula 19]

[0384]

[0385] In general formula (3), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, and R 3 ~R 16 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 1 and R 3 、R 3 and R 4 、R 4and R 5 、R 5 and R 6 、R 6 and R 7 、R 7 and R 8 、R 8 and R 9 、R 9 and R 2 、R 2 and R 10 、R 10 and R 11 、R 11 and R 12 、R 12 and R 13 、R 13 and R 14 、R 14 and R 15 、R 15 and R 16 、R 16 and R 1 may be bonded to each other to form a cyclic structure. C-R in the general formula (3) 3 、C-R 4 、C-R 5 、C-R 6 、C-R 7 、C-R 8 、C-R 9 、C-R 10 、C-R 11 、C-R 12 、C-R 13 、C-R 14 、C-R 15 、C-R 16 may be replaced by N.

[0386] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group which may be fused with other rings. In one embodiment of the present invention, R 3 and R 10 are each independently a substituted amino group. In one embodiment of the present invention, R 1 and R 3 and R 2 and R 10 at least one combination of which may be bonded to each other to form a cyclic structure. In one embodiment of the present invention, the cyclic structure contains a benzazaborane ring.

[0387] As a further preferred luminescent material, a compound represented by the following general formula (4) may also be mentioned.

[0388] [Chemical Formula 20]

[0389]

[0390] In the general formula (4), Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 ~R 9 each independently represents 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 may bond to each other to form a cyclic structure. Among them, the ring formed by Z 1 , Z 2 , R 1 and R 2 bonding to each other, the ring formed by R 2 and R 3 bonding to each other, the ring formed by R 4 and R 5 bonding to each other, and the ring formed by R 5 and R 6 bonding to each other, at least one of them is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyrrole ring of a substituted or unsubstituted indole, and at least one of R 1 ~R 9 is a substituted or unsubstituted aryl group or acceptor group, or at least one of Z 1 and Z 2 has an aryl group or acceptor group as a substituent. The carbon atoms in the benzene ring skeleton that make up the benzofuran ring, the benzothiophene ring, and the indole ring that can be substituted can be substituted by nitrogen atoms. C-R 1 , C-R 2 , C-R 3 , C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 can be substituted by N.

[0391] In one embodiment of the present invention, Z 1 and Z 2 are each independently an unsubstituted or substituted non-fused benzene ring, a furan ring fused by unsubstituted or substituted benzene rings, a thiophene ring fused by unsubstituted or substituted benzene rings, or a pyrrole ring fused by unsubstituted or substituted benzene rings. In one embodiment of the present invention, R 1 to R 9 are each independently an unsubstituted or substituted aryl group or acceptor group, or one or more rings selected from the group consisting of a ring formed by bonding R 1 and R 2 to each other, a ring formed by bonding R 2 and R 3 to each other, a ring formed by bonding R 4 and R 5 to each other, and a ring formed by bonding R 5 and R 6 to each other are a furan ring fused by unsubstituted or substituted benzene rings, a thiophene ring fused by unsubstituted or substituted benzene rings, or a pyrrole ring fused by unsubstituted or substituted benzene rings. In one embodiment of the present invention, R 8 is an unsubstituted or substituted aryl group or acceptor group. In one embodiment of the present invention, it contains two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0392] As a more preferred luminescent material, there can be mentioned a compound in which a carbon-carbon bond a having the following structure α is fused with a furan ring constituting an unsubstituted or substituted benzofuran ring, a thiophene ring constituting an unsubstituted or substituted benzothiophene ring, or a pyrrole ring constituting an unsubstituted or substituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting an unsubstituted or substituted dibenzofuran ring, a benzene ring constituting an unsubstituted or substituted dibenzothiophene ring, a benzene ring constituting an unsubstituted or substituted carbazole ring, or a benzene ring constituting an unsubstituted or substituted dibenzodioxane ring to form a fused ring structure A (the hydrogen atoms in the structure may be replaced by deuterium atoms or substituents).

[0393] [Chemical formula 21]

[0394]

[0395] In structure α, X 1 and X 2 each independently represent an unsubstituted or substituted aryl group, a nitrogen atom bonded by unsubstituted or substituted aryl groups, or an oxygen atom, Z represents an unsubstituted or substituted aromatic ring or an unsubstituted or substituted heteroaromatic ring, R 1represents a hydrogen atom, a deuterium atom or a substituent, Z and X 2 may be bonded to each other to form a cyclic structure.

[0396] In the fused ring structure A, the structure fused to b, the structure fused to X 1 , the structure fused to b, and Z, Z and X 2 may be bonded to each other to form a cyclic structure.

[0397] As a further preferred luminescent material, a compound represented by the following general formula (5) may also be cited.

[0398] [Chemical formula 22]

[0399]

[0400] In the general formula (5), Z 1 represents a furan ring fused by a substituted or unsubstituted benzene ring, a thiophene ring fused by a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused by a substituted or unsubstituted benzene ring. Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. R 1 represents a hydrogen atom, a deuterium atom or a substituent. R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure. Among them, R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 in at least one group are bonded to each other to form a cyclic structure.

[0401] As a further preferred luminescent material, a compound represented by the following general formula (6) may also be cited.

[0402] [Chemical formula 23]

[0403]

[0404] In the general formula (6), X 3 represents an oxygen atom or a sulfur atom, Z 2 and Z 3Each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 4 ~R 7 represent a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 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 can bond to each other to form a cyclic structure. Among them, at least one group of R 2 and Z 2 、Z 2 and Z 3 、Z 3 and R 3 bond to each other to form a cyclic structure.

[0405] As a further preferred luminescent material, a compound represented by the following general formula (7) can also be cited.

[0406] [Chemical formula 24]

[0407]

[0408] In the general formula (7), X 4 represents an oxygen atom or a sulfur atom, Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 4a ~R 7a represent a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 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 R7a , R 7a and R 1 can bond to each other to form a cyclic structure. Among them, R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 in at least one group of them bond to each other to form a cyclic structure.

[0409] As a further preferred luminescent material, a compound represented by the following general formula (8) can also be cited.

[0410] [Chemical formula 25]

[0411]

[0412] In the general formula (8), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring. R 1 and R 8 ~R 14 each independently represents a hydrogen atom, a deuterium atom or a substituent. R 3 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 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 can bond to each other to form a cyclic structure.

[0413] As a further preferred luminescent material, a compound represented by the following general formula (9) can also be cited.

[0414] [Chemical formula 26]

[0415]

[0416] In general formula (9), Z 1 and Z 4 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 15 ~R 17 each independently represent a hydrogen atom, a deuterium atom or a substituent, and R 3 represents 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 can bond to each other to form a cyclic structure.

[0417] As a further preferred luminescent material, a compound represented by the following general formula (10) can also be cited.

[0418] [Chemical formula 27]

[0419]

[0420] In general formula (10), Z 1 and Z 5 each independently represent a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring. Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , Z 3 and R 3 can bond to each other to form a cyclic structure. Among them, R 2and Z 2 、Z 2 and Z 3 、Z 3 and R 3 At least one group among them bonds to each other to form a cyclic structure.

[0421] As a further preferred luminescent material, a compound represented by the following general formula (11) can also be cited.

[0422] [Chemical formula 28]

[0423]

[0424] In the general formula (11), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 21 ~R 27 each independently represents a hydrogen atom, a deuterium atom, or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 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 R 26 、R 26 and R 27 can bond to each other to form a cyclic structure.

[0425] As a further preferred luminescent material, a compound represented by the following general formula (12) can also be cited.

[0426] [Chemical formula 29]

[0427]

[0428] In the general formula (12), Z 1 and Z 6Each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 28 ~R 30 each independently represents a hydrogen atom, a deuterium atom or a substituent, R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 1 and Z 1 、R 2 and Z 2 、Z 2 and R 28 、R 28 and R 29 、R 29 and R 30 、R 30 and Z 6 may be bonded to each other to form a cyclic structure.

[0429] As a further preferred luminescent material, a compound represented by the following general formula (13) can also be cited.

[0430] [Chemical formula 30]

[0431]

[0432] In the general formula (13), Z 1 and Z 7 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 represents a hydrogen atom, a deuterium atom or a substituent, R 2 and R 3 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 、R 2 and Z 2 、Z 2 and Z 7 、Z 7 and R 3 may be bonded to each other to form a cyclic structure. Among them, R 2 and Z 2 、Z 2 and Z7 , Z 7 , and R 3 in at least one set of Z, R, and R are bonded to each other to form a ring structure.

[0433] As a further preferred luminescent material, a compound represented by the following general formula (14) can also be mentioned.

[0434] [Chemical formula 31]

[0435]

[0436] In the general formula (14), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, and R 1 and R 31 to R 44 each independently represent 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 can be bonded to each other to form a ring structure.

[0437] As a further preferred luminescent material, a compound represented by the following general formula (15) can also be mentioned.

[0438] [Chemical formula 32]

[0439]

[0440] In the general formula (15), Z 1 , and Z8 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 51 ~R 60 each independently represents 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 R 58 、R 58 and R 59 、R 59 and R 60 、R 60 and Z 8 may bond to each other to form a cyclic structure.

[0441] As a further preferred luminescent material, a compound represented by the following general formula (16) can also be cited.

[0442] [Chemical formula 33]

[0443]

[0444] In the general formula (16), Z 1 、Z 8 and Z 9 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 61 ~R 66 each independently represents 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 R65 , R 65 and R 66 , R 66 and Z 8 can be bonded to each other to form a ring structure.

[0445] As a further preferred luminescent material, a compound represented by the following general formula (17) can also be cited.

[0446] [Chemical formula 34]

[0447]

[0448] In the general formula (17), Z 1 , Z 9 and Z 10 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 67 ~R 69 each independently represents a hydrogen atom, a deuterium atom or a substituent, R 70 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 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 can be bonded to each other to form a ring structure.

[0449] As a further preferred luminescent material, a compound represented by the following general formula (18) can also be cited.

[0450] [Chemical formula 35]

[0451]

[0452] In the general formula (18), Z 1 , Z 11 and Z 12 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring, R 1 and R 72 ~R 74Each independently represents a hydrogen atom, a deuterium atom or a substituent, R 71 represents an aryl group which may be substituted or unsubstituted or a heteroaryl group which may be substituted or unsubstituted. 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 may bond to each other to form a ring structure.

[0453] As a further preferred luminescent material, a compound represented by the following general formula (19) may also be cited.

[0454] [Chemical formula 36]

[0455]

[0456] In the general formula (19), Z 1 and Z 11 each independently represent a furan ring fused with a benzene ring which may be substituted or unsubstituted, a thiophene ring fused with a benzene ring which may be substituted or unsubstituted, or an N-substituted pyrrole ring fused with a benzene ring which may be substituted or unsubstituted, R 1 and R 76 ~R 82 each independently represent an aryl group which may be substituted or unsubstituted or a heteroaryl group which may be substituted or unsubstituted, R 75 represents an aryl group which may be substituted or unsubstituted or a heteroaryl group which may be substituted or unsubstituted. 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 may bond to each other to form a ring structure.

[0457] As a further preferred luminescent material, a compound represented by the following general formula (20) may also be cited.

[0458] [Chemical Formula 37]

[0459]

[0460] In general formula (20), X 5 represents an oxygen atom, a sulfur atom, or a nitrogen atom bonded by a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R 101 ~R 130 each independently represents a hydrogen atom, a deuterium atom, or a substituent, R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 104 and R 105 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 109 and R 110 , R 110 and R 111 , R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 114 and R 115 , R 115 and R 116 , R 116 and R 117 , R 117 and R 118 , R 118 and R 119 , R 119 and R 120 , R 120 and R 121 , R 121 and R 122 , 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 R128 , R 128 and R 129 , R 129 and R 130 , R 130 and R 101 may be bonded to each other to form a cyclic structure.

[0461] As a further preferred luminescent material, a compound represented by the following general formula (21) may also be cited.

[0462] [Chemical formula 38]

[0463]

[0464] In the general formula (21), R 1 and R 2 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Z 1 and Z 2 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 3 to R 9 each independently represent a hydrogen atom, a deuterium atom, or a substituent. Among them, at least one of R 1 , R 2 , Z 1 and Z 2 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 may be bonded to each other to form a cyclic structure. The carbon atoms in the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring that can be substituted can be substituted by nitrogen atoms. C-R in the general formula (21) 3, C-R 4 , C-R 5 , C-R 6 , C-R 7 , C-R 8 , C-R 9 can be replaced by N.

[0465] In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. In one embodiment of the present invention, Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. In one embodiment of the present invention, R 1 and Z 1 bond to each other to form a cyclic structure. In one embodiment of the present invention, R 1 and Z 1 bond to each other to form a pyrrole ring.

[0466] As a further preferred luminescent material, a compound represented by the following general formula (22) can also be mentioned.

[0467] [Chemical formula 39]

[0468]

[0469] In the general formula (22), one of X 1 and X 2 is a nitrogen atom and the other is a boron atom. R 1 ~R 26 , A 1 , A 2 each independently 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 , R6 and R 7 、R 7 and R 8 、R 8 and R 9 、R 9 and R 10 、R 10 and R 11 、R 11 and R 12 、R 13 and R 14 、R 14 and R 15 、R 15 and R 16 、R 16 and R 17 、R 17 and R 18 、R 18 and R 19 、R 19 and R 20 、R 20 and R 21 、R 21 and R 22 、R 22 and R 23 、R 23 and R 24 、R 24 and R 25 、R 25 and R 26 can be bonded to each other to form a cyclic structure. Among them, when X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form a single bond to form a pyrrole ring. When X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. Among them, when X 1 is a nitrogen atom, R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a 6-membered ring. When R 17 and R 18 are bonded to each other to form a single bond, at least one of R 1 ~R 6 is a substituted or unsubstituted aryl group or R 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R4 and R 5 、R 5 and R 6 Any one of them bonds to each other to form an aromatic ring or a heteroaromatic ring.

[0470] In one embodiment of the present invention, R 3 and R 6 At least one of them is a substituent. In one embodiment of the present invention, R 3 and R 6 Both are substituents. In one embodiment of the present invention, R 3 and R 6 The substituents represented are a group selected from the group consisting of an alkyl group and an aryl group or a group obtained by combining two or more thereof. In one embodiment of the present invention, R 8 and R 12 Both are substituents. In one embodiment of the present invention, it is represented by the following general formula (22a).

[0471] [Chemical formula 40]

[0472]

[0473] In the general formula (22a), Ar 1 ~Ar 4 Each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. R 41 and R 42 Each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represent an integer from 0 to 5, n1 and n3 each independently represent an integer from 0 to 4, and n2 and n4 each independently represent an integer from 0 to 3. A 1 、A 2 Each independently represents a hydrogen atom, a deuterium atom or a substituent.

[0474] In one embodiment of the present invention, A 1 and A 2 Each independently is a group with a Hammett σp value greater than 0.2. In one embodiment of the present invention, A 1 and A 2 Both are cyano groups. In one embodiment of the present invention, A 1 and A 2 Both are halogen atoms. In one embodiment of the present invention, it has a rotationally symmetric structure.

[0475] Hereinafter, preferred specific examples of the compound having the fused ring structure A and the compound represented by any one of the general formulas (5) to (22) are given.

[0476] [Chemical formula 41-1]

[0477]

[0478] [Chemical Formula 41-2]

[0479]

[0480] [Chemical Formula 41-3]

[0481]

[0482] [Chemical Formula 41-4]

[0483]

[0484] [Chemical Formula 41-5]

[0485]

[0486] [Chemical Formula 41-6]

[0487]

[0488] [Chemical Formula 41-7]

[0489]

[0490] [Chemical Formula 41-8]

[0491]

[0492] [Chemical Formula 41-9]

[0493]

[0494] [Chemical Formula 42-1]

[0495]

[0496] [Chemical Formula 42-2]

[0497]

[0498] [Chemical Formula 43-1]

[0499]

[0500] [Chemical Formula 43-2]

[0501]

[0502] In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 20% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 10% by weight or less.

[0503] In one embodiment, the host material in the light-emitting layer is an organic compound having a hole-transporting function and an electron-transporting function. In one 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 one embodiment, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0504] In some embodiments, the host material is selected from the group consisting of:

[0505] [Chemical formula 44-1]

[0506]

[0507] [Chemical formula 44-2]

[0508]

[0509] In one embodiment, the light-emitting layer contains two or more TADF molecules having different structures. For example, a light-emitting layer can be provided that contains these three materials in which the singlet excitation energy levels are high in the order of the host material, the first TADF molecule, and the second TADF molecule. At this time, the difference δE between the lowest singlet excitation energy level of the first TADF molecule and the second TADF molecule and the lowest triplet excitation energy level at 77K STThey are all preferably below 0.3 eV, more preferably below 0.25 eV, still more preferably below 0.2 eV, even more preferably below 0.15 eV, further preferably below 0.1 eV, still further preferably below 0.07 eV, yet further preferably below 0.05 eV, and even further preferably below 0.03 eV, and particularly preferably below 0.01 eV. The concentration of the first TADF molecule in the light-emitting layer is preferably greater than that of the second TADF molecule. Also, the concentration of the host material in the light-emitting layer is preferably greater than that of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition in the light-emitting layer may be set as follows: the host material is 10 to 70% by weight, the first TADF molecule is 10 to 80% by weight, and the second TADF molecule is 0.1 to 30% by weight. In one embodiment, the composition in the light-emitting layer may be set as follows: the host material is 20 to 45% by weight, the first TADF molecule is 50 to 75% by weight, and the second TADF molecule is 5 to 20% by weight. In one embodiment, the photoluminescence quantum yield φPL1(A) based on photoexcitation of the co-evaporated film of the first TADF molecule and the host material (the concentration of the first TADF molecule in this co-evaporated film = A% by weight) and the photoluminescence quantum yield φPL2(A) based on photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-evaporated film = A% by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photoluminescence quantum yield φPL2(B) based on photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the concentration of the second TADF molecule in this co-evaporated film = B% by weight) and the photoluminescence quantum yield φPL2(100) based on photoexcitation of the single film of the second TADF molecule satisfy the relationship φPL2(B) > φPL2(100). 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 the multiple TADF compounds contained in the light-emitting layer.

[0510] In one embodiment, the light-emitting layer can be composed of materials selected from the group consisting of a host material, a co-dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain a metal element. In one embodiment, the light-emitting layer can be composed of materials 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 materials 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 materials consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0511] When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescence material. Preferred delayed fluorescence materials may include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, paragraphs 0008 to 0071 and 0118 to 0133 of WO2013 / 081088, paragraphs 0009 to 0046 and 0093 to 0134 of JP-A 2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of JP-A 2013-116975, paragraphs 0007 to 0032 and 0079 to 0084 of WO2013 / 133359, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013 / 161437, paragraphs 0007 to 0041 and 0060 to 0069 of JP-A 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of JP-A 2014-9224, paragraphs 0013 to 0025 of JP-A 2017-119663, paragraphs 0013 to 0026 of JP-A 2017-119664, paragraphs 0012 to 0025 of JP-A 2017-222623, paragraphs 0010 to 0050 of JP-A 2017-226838, paragraphs 0012 to 0043 of JP-A 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, especially exemplified compounds and compounds capable of emitting delayed fluorescence included in the general formulas described therein.Moreover, it is preferable to use a luminescent material that can emit delayed fluorescence and is described in Japanese Patent Application Laid-Open No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Laid-Open No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, WO2015 / 159541. Additionally, the above-mentioned gazettes described in this paragraph are incorporated herein by reference as part of this specification.

[0512] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0513] Substrate:

[0514] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, where the substrate is not particularly limited and can be any of those substrates that have been commonly used in organic electroluminescent elements, such as those substrates formed of glass, transparent plastic, quartz, and silicon.

[0515] Anode:

[0516] In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a large work function (above 4 eV). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material can be selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material such as IDIXO (In2O3-ZnO) capable of forming a transparent conductive film is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by evaporation or sputtering. In some embodiments, the thin film is patterned by photolithography. In some embodiments, when high precision of the pattern is not required (e.g., above about 100 μm), the pattern can be formed using a mask having a desired shape during evaporation or sputtering of the electrode material. In some embodiments, when a coating material (such as an organic conductive compound) can be coated, wet film forming methods such as printing and coating methods are used. In some embodiments, when the emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is several hundred ohms per square or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0517] Cathode:

[0518] In some embodiments, the cathode is made of an electrode material such as a metal with a small work function (below 4 eV) (referred to as an electron injection metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth metals. In some embodiments, a mixture of an electron injection metal and a second metal is used, where the second metal is a stable metal with a larger work function than the electron injection metal. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture increases electron injection characteristics and durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by evaporation or sputtering. In some embodiments, the sheet resistance of the cathode is several hundred ohms per square or less. 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, in order to transmit the emitted light, either the anode or the cathode of the organic electroluminescent element is transparent or semi-transparent. In some embodiments, the transparent or semi-transparent electroluminescent element enhances the emission brightness.

[0519] In some embodiments, the cathode is formed of a conductive transparent material as described for the anode to form a transparent or semi-transparent cathode. In some embodiments, the element includes both a transparent or semi-transparent anode and a cathode.

[0520] Injection layer:

[0521] The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the emission brightness. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light-emitting layer or the hole transport layer, and between the cathode and the light-emitting layer or the electron transport layer. In some embodiments, there is an injection layer. In some embodiments, there is no injection layer.

[0522] The following includes preferred compound examples that can be used as hole injection materials.

[0523] [Chemical formula 45]

[0524]

[0525] Next, preferred compound examples that can be used as electron injection materials are given.

[0526] [Chemical Formula 46]

[0527]

[0528] Blocking layer:

[0529] The blocking layer is a layer that can inhibit the diffusion of charges (electrons or holes) and / or excitons in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, the electron blocking layer is between the light-emitting layer and the hole transport layer and inhibits electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron transport layer and inhibits holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer inhibits the diffusion of excitons to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer form an exciton blocking layer. The term "electron blocking layer" or "exciton blocking layer" as used in this specification includes a layer having the functions of both an electron blocking layer and an exciton blocking layer.

[0530] Hole blocking layer:

[0531] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer inhibits holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer increases the probability of rebonding of electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material as that described for the electron transport layer.

[0532] The following includes preferred compound examples that can be used for the hole blocking layer.

[0533] [Chemical Formula 47]

[0534]

[0535] Electron blocking layer:

[0536] Holes are transported by the electron blocking layer. In some embodiments, the electron blocking layer inhibits electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer increases the probability of rebonding of electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material as that described for the hole transport layer.

[0537] The following includes specific examples of preferred compounds that can be used as electron blocking materials.

[0538] [Chemical Formula 48]

[0539]

[0540] Exciton blocking layer:

[0541] The exciton blocking layer suppresses the diffusion of excitons generated by the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables the effective confinement of excitons in the light-emitting layer. In some embodiments, the light-emitting efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side and the cathode side or on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or the same layer is between the anode and the exciton blocking layer, and the exciton blocking layer is 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 the same layer is between the cathode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes singlet excitation energy and triplet excitation energy, at least one of which is higher than the singlet excitation energy and the triplet excitation energy of the light-emitting material, respectively.

[0542] Hole transport layer:

[0543] The hole transport layer includes 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.

[0544] 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 the present invention include (but are not limited to) triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, chalcone derivatives substituted with amino groups, oxazole derivatives, styryl 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 styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. The following includes specific examples of preferred compounds that can be used as hole transport materials.

[0545] [Chemical formula 49]

[0546]

[0547] Electron transport layer:

[0548] The electron transport layer contains 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.

[0549] In some embodiments, the electron transport material only needs to have the function of transporting electrons, which are 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 the electron transport layer that can be used in the present invention include (but are not limited to) fluorene derivatives substituted with nitro groups, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenediylmethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, or combinations or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. The following includes specific examples of preferred compounds that can be used as electron transport materials.

[0550] [Chemical formula 50]

[0551]

[0552] In addition, examples of compounds that are more preferably used as materials that can be added to each organic layer are included. For example, addition as a stabilizing material can be considered.

[0553] [Chemical formula 51]

[0554]

[0555] Specific examples of preferred materials that can be used in the organic electroluminescent element are illustrated, but the materials that can be used in the present invention should not be construed as being limited to the following exemplified compounds. Moreover, even compounds exemplified as materials having specific functions can be used as materials having other functions.

[0556] Device:

[0557] In some embodiments, a light-emitting layer is incorporated into the device. For example, the device includes an OLED bulb, an OLED lamp, a television screen, a computer monitor, a mobile phone, and a tablet computer, but is not limited to these.

[0558] 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.

[0559] In some embodiments, the compositions described in this specification can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be suitable for promoting charge transfer or energy transfer within the device and / or can be used as hole transport materials. The devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0560] Light bulb or lamp:

[0561] In some embodiments, the electronic device includes an OLED, which includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode.

[0562] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, or blue (e.g., orange and yellowish green). In some embodiments, the combination of OLEDs is a combination of two, four, or more than four colors.

[0563] In some embodiments, the device is an OLED lamp, which includes:

[0564] A circuit board having a first surface with a mounting surface and a second surface opposite thereto, and defining at least one opening;

[0565] At least one OLED disposed on the mounting surface and having a structure in which the at least one OLED includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode and emits light;

[0566] A housing for the circuit board; and

[0567] At least one connector disposed at an end of the housing, and the housing and the connector define a package suitable for being mounted on a lighting device.

[0568] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board such that light is emitted 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.

[0569] Display or screen:

[0570] In some embodiments, the light-emitting layer of the present invention can be used in a screen or a 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 unique aspect ratio pixels. A screen (which can also be referred to as a mask) is used in the method for manufacturing an OLED display. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and larger sweep angle openings in the horizontal direction. Thereby, it allows for tight patterning of pixels required for a high-definition display while optimizing chemical vapor deposition onto the TFT substrate.

[0571] Internal patterning of the pixels allows for the construction of three-dimensional pixel openings with aspect ratio variations in the horizontal and vertical directions. Additionally, "strips" or halftone circles using imaging are used within the pixel area to inhibit etching in specific areas until these specific patterns are undercut and removed from the substrate. At this time, all pixel areas are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone pattern allows etching to be inhibited at different rates within the pixel, allowing for local deeper etching required to form steep vertical chamfers.

[0572] A preferred material for the evaporation mask is invar. Invar is a metal alloy cold-rolled into long thin sheets in a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming an opening area within the evaporation mask is a wet chemical etching-based method.

[0573] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is manufactured using lithography (such as photolithography and e-beam lithography). In some embodiments, the screen or display pattern is manufactured using wet chemical etching. In additional embodiments, the screen or display pattern is manufactured using plasma etching.

[0574] Method for manufacturing the device:

[0575] OLED displays are generally manufactured by forming a large mother board and then cutting the mother board into unit board units. Generally, each unit board on the mother board is formed by: forming a thin film transistor (TFT) including an active layer and source / drain electrodes on a substrate, coating a planarization film on the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting from the mother board.

[0576] In another aspect of the present invention, there is provided a method of manufacturing an organic light-emitting diode (OLED) display, the method comprising:

[0577] a step of forming a barrier layer on a substrate of a mother board;

[0578] a step of forming a plurality of display units in unit board units on the barrier layer;

[0579] a step of forming an encapsulation layer on each of the display units of the unit board; and

[0580] a step of coating an organic film on an interface portion between the unit boards.

[0581] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryloyl. In some embodiments, the organic film helps to gently cut the mother board into unit board units.

[0582] In some embodiments, the thin film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may 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 material of the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer, 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 does not contact either the display unit or the encapsulation layer.

[0583] Each of the organic film and the planarization film may include either polyimide or acryloyl. 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 a glass material onto the other surface of the substrate formed of polyimide before forming a 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.

[0584] 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 acryloyl, such as the organic film formed on the edge portion of the barrier layer. In some embodiments, when manufacturing the OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film may be formed on the edge portion of the barrier layer such that a part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0585] 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 electrode / drain electrode of the TFT layer.

[0586] 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 counter electrode, whereby the organic light-emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.

[0587] In some embodiments, an encapsulation layer that covers the display unit and prevents external moisture from penetrating may be formed to have a thin film encapsulation structure in which an organic film and an inorganic film are alternately laminated. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film 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 part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0588] 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.

[0589] In some embodiments, a barrier layer is formed on a surface of the substrate on a side opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit panel. For example, while the substrate is formed over the entire surface of the mother board, the barrier layer is formed according to the size of each unit panel, thereby forming a groove at an interface portion between the unit panel barrier layers. Each unit panel can be cut along the groove.

[0590] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, where a groove is formed in the barrier layer, at least a part of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, the TFT layer of each unit panel is formed, 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. While forming the planarization film formed of, for example, polyimide or acryloyl, the groove at the interface portion is covered with an organic film formed of, for example, polyimide or acryloyl. This is when cracking is prevented from occurring by allowing the organic film to absorb the impact, which is 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 impact 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, since the groove at the interface portion between the barrier layers is covered with the organic film and the organic film absorbs the impact that would otherwise be transferred to the barrier layer, each unit panel can be gently cut and cracking in the barrier layer can be prevented. In one embodiment, the organic film covering the groove at the interface portion is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected to each other as a single layer, since external moisture may penetrate into the display unit via the planarization film and a part where the organic film remains, the organic film is spaced apart from the planarization film so that the organic film is spaced apart from the display unit.

[0591] In some embodiments, a display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother board is completely manufactured, the 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 is separated from the substrate due to a difference in the coefficient of thermal expansion between the carrier substrate and the substrate.

[0592] In some embodiments, the mother board is cut into unit board units. In some embodiments, the mother board is cut along the interface portion between the unit boards by using a cutting machine. In some embodiments, since the groove at the interface portion along which the mother board is cut is covered with an organic film, the organic film absorbs impacts during cutting. In some embodiments, cracking can be prevented from occurring in the barrier layer during cutting.

[0593] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0594] Another aspect 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 an edge portion of the barrier layer.

[0595] Examples

[0596] The following presents synthesis examples and examples to further specifically illustrate the features of the present invention. Materials, processing contents, processing steps, etc. shown below can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed in a limiting manner by the specific examples shown below. In addition, for the evaluation of luminescence characteristics, a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies Japan, Ltd.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), a spectrometer (manufactured by Ocean Optics: USB2000), a spectroradiometer (manufactured by TOPCON CORPORATION: SR-3), and a streak camera (type C4334 manufactured by Hamamatsu Photonics K.K.) are used. And, for the measurement of the energies of HOMO and LUMO, it is carried out by an atmospheric photoelectron spectrometer (such as AC-3 manufactured by RIKEN KEIKI CO., LTD.).

[0597] In the following synthesis examples, the compounds contained in the general formula (1) were synthesized.

[0598] (Synthesis Example 1) Synthesis of Compound 46542

[0599] [Chemical Formula 52]

[0600]

[0601] Compound a

[0602] Under a nitrogen stream, at -78 °C, a solution of 2.0 M isopropylmagnesium chloride in tetrahydrofuran (THF) (8.2 mL, 16.4 mmol) was slowly added dropwise to a solution of 5-bromo-2,4-difluorobenzonitrile (3.35 g, 15.3 mmol) in tetrahydrofuran (THF) (150 mL). After stirring for 1 hour after the addition was complete, tributyltin chloride (5.92 g, 18.2 mmol) was added, the temperature was raised to room temperature, and stirring was continued for 3 hours. The reaction vessel was cooled to 0 °C, and saturated ammonium chloride solution was added. The resulting reaction solution was extracted with toluene, the organic layer was washed with saturated brine, and then dried over anhydrous magnesium. The solvent was removed, and the resulting yellow liquid was dissolved in dehydrated toluene (150 mL). Bis(triphenylphosphine)palladium(II) dichloride (1.05 g, 1.50 mmol) and 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (6.3 g, 13.6 mmol) were added, and the mixture was heated at 120 °C for 18 hours. The reaction solution was returned to room temperature, and the resulting gray solid was filtered out. The solid was washed with toluene, tetrahydrofuran, and hexane to obtain 5.61 g (9.93 mmol, 73% yield) of the gray solid compound a.

[0603] ASAP MS spectral analysis: C 34 H2D 16 F2N6: Theoretical value 564.26, Observed value 565.50 [M+H +

[0604] [Chemical formula 53]

[0605]

[0606] Compound b

[0607] Under a nitrogen stream, to a solution of compound a (5.61 g, 9.93 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.33 g, 0.50 mmol), tricyclohexylphosphine (0.28 g, 1.00 mmol), and potassium carbonate (2.77 g, 20 mmol) in dehydrated xylene (100 mL) were added 2-ethylhexanoic acid (0.30 g, 2.00 mmol) and bromobenzene-d5 (1.77 g, 10.9 mmol), and the mixture was stirred at 120 °C for 18 hours. The reaction solution was returned to room temperature, and the resulting gray solid was filtered out. After washing the solid with toluene, ion-exchanged water, and methanol, the solid was dissolved in hot toluene. The toluene solution was passed through a silica pad, and the filtrate was concentrated to obtain 2.80 g (4.33 mmol, 44% yield) of the white compound b. ​

[0608] ASAP MS spectroscopy: C 40 HD 21 F2N6: Theoretical value 645.32, Observed value 646.49 [M+H +

[0609] [Chemical formula 54]

[0610]

[0611] Compound 46542

[0612] To a solution of compound b (1.62 g, 2.50 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.96 g, 5.50 mmol) in N-methyl-2-pyrrolidone (50 mL) was added potassium carbonate (0.87 g, 6.29 mmol), and the mixture was stirred at 100 °C for 4 hours. The reaction solution was cooled to 0 °C, ion-exchanged water was added, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The obtained reaction mixture was purified by silica gel chromatography (toluene:hexane = 2:1). The obtained solid was reprecipitated with ethyl acetate / hexane to obtain 0.90 g (0.94 mmol, yield 38%) of light green compound 46542.

[0613] 1 H-NMR (400 MHz, DMSO-d6): δ 9.03 (s, 1H).

[0614] ASAP MS spectroscopy: C 64 HD 37 N8: Theoretical value 955.55, Observed value 956.99 [M+H +

[0615] (Synthesis Example 2) Synthesis of compound 46542 (40)

[0616] [Chemical formula 55]

[0617]

[0618] Compound c

[0619] ​​Under a nitrogen stream and at -78 °C, a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (16.5 mL, 33.0 mmol) was slowly added dropwise to a solution of 5-bromo-2,4-difluorobenzonitrile (6.54 g, 30.0 mmol) in tetrahydrofuran (300 mL). After stirring for 1 hour after the addition was complete, tributyltin chloride (11.7 g, 35.9 mmol) was added, the temperature was raised to room temperature, and the mixture was stirred for 3 hours. The reaction vessel was cooled to 0 °C, and saturated ammonium chloride solution was added. The resulting reaction solution was extracted with toluene, the organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was removed, and the resulting yellow liquid was dissolved in dehydrated toluene (300 mL). Bis(triphenylphosphine)palladium(II) dichloride (2.11 g, 3.00 mmol) and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (11.0 g, 29.67 mmol) were added, and the mixture was stirred at 120 °C for 18 hours. The reaction solution was returned to room temperature and filtered through diatomaceous earth. The filtrate was concentrated, and the resulting solid was washed with hexane, toluene, and tetrahydrofuran to obtain 8.1 g (17.1 mmol, 57% yield) of the light orange solid compound c.

[0620] 1 1H-NMR (400 MHz, DMSO-d6): δ 9.61 (t, J = 9.2 Hz, 1H), 7.98 (t, J = 10.0 Hz, 1H).

[0621] ASAP MS spectral analysis: C 28 H2D 13 F2N5: Theoretical value 472.21, Observed value 473.41 [M+H +

[0622] [Chemical formula 56]

[0623]

[0624] Compound d

[0625] Under a nitrogen stream, 2-ethylhexanoic acid (0.49 g, 3.40 mmol) and bromobenzene-d5 (3.32 g, 20.5 mmol) were added to a solution of compound c (8.08 g, 17.1 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.60 g, 0.85 mmol), tricyclohexylphosphine (0.49 g, 1.75 mmol), and potassium carbonate (4.75 g, 34.4 mmol) in dehydrated xylene (340 mL), and the mixture was heated at 120 °C for 20 h. The reaction solution was returned to room temperature, and the obtained white solid was filtered out. After washing the solid with toluene, ion-exchanged water, and methanol, the solid was dissolved in hot toluene. The toluene solution was passed through a silica pad, and the filtrate was concentrated to obtain 4.2 g (7.59 mmol, 44% yield) of white compound d.

[0626] ASAP MS spectral analysis: C 34 HD 16 F2N5: theoretical value 553.27, observed value 554.50 [M+H +

[0627] [Chemical formula 57]

[0628]

[0629] Compound 46542(40)

[0630] Potassium carbonate (1.38 g, 9.98 mmol) was added to a solution of compound d (2.21 g, 3.99 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.47 g, 8.39 mmol) in N-methyl-2-pyrrolidone (80 mL), and the mixture was stirred at 100 °C for 6 h. The reaction solution was cooled to 0 °C, ion-exchanged water and methanol were added, and the solid was filtered out. After washing the solid with a mixed solution of ethyl acetate / hexane, purification was carried out by silica gel chromatography (toluene:hexane = 4:1). The obtained solid was reprecipitated with ethyl acetate / hexane to obtain 2.77 g (3.21 mmol, 80% yield) of light green compound 46542(40).

[0631] 1 1H-NMR (400 MHz, DMSO-d6): δ 8.85 (s, 1H).

[0632] ASAPMS spectral analysis: C 58 HD 34 N7: theoretical value 863.50, observed value 864.87 [M+H +

[0633] ​​(Synthesis Example 3) Synthesis of Compound 38317

[0634] [Chemical Formula 58]

[0635]

[0636] Compound e

[0637] Under a nitrogen stream, 2-ethylhexanoic acid (0.20 g, 1.42 mmol) and 5'-bromo-1,1':3',1''-terphenyl-2,2'',3,3'',4,4'',5,5'',6,6''-d 10 (2.50 g, 7.79 mmol) were added to a solution of Compound a (4.00 g, 7.08 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.24 g, 0.35 mmol), tricyclohexylphosphine (0.20 g, 0.71 mmol), and potassium carbonate (1.95 g, 34.4 mmol) in dehydrated xylene (71 mL), and the mixture was heated at 120 °C for 20 hours. The reaction solution was returned to room temperature, and the obtained white solid was filtered out. After washing the solid with toluene, ion-exchanged water, and methanol, the solid was dissolved in hot toluene. The toluene solution was passed through a silica pad, and the filtrate was concentrated to obtain 1.36 g (1.69 mmol, 24% yield) of white Compound e.

[0638] ASAP MS spectroscopic analysis: C 52 H4D 26 F2N6: Theoretical value 802.41, Observed value 803.82 [M+H +

[0639] [Chemical Formula 59]

[0640]

[0641] Compound 38317

[0642] ​To a solution of compound e (1.06 g, 1.32 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.49 g, 2.80 mmol) in N-methyl-2-pyrrolidone (26 mL) was added potassium carbonate (0.46 g, 6.29 mmol), and the mixture was stirred at 130 °C for 4 hours. The reaction solution was cooled to room temperature and diluted with ethyl acetate. The solution was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed. The solid was reprecipitated with a mixed solvent of ethyl acetate / hexane, and the solid was filtered out. The crude product was purified by silica gel chromatography (toluene:hexane = 2:1). The obtained solid was reprecipitated with ethyl acetate / hexane to give 0.46 g (0.41 mmol, yield 31%) of pale yellow compound 38317.

[0643] 1 1H-NMR (400 MHz, DMSO-d6): δ 9.13 (s, 1H), 7.02 (t, J = 1.6 Hz, 1H), 6.90 (d, J = 1.6 Hz, 2H).

[0644] ASAP MS spectral analysis: C 76 H4D 42 N8: calculated value 1112.64, observed value 1113.21 [M+H +

[0645] (Synthesis Example 4) Synthesis of compound 38317 (40)

[0646] [Chemical formula 60]

[0647]

[0648] Compound f

[0649] Under a nitrogen stream, to a solution of compound c (4.21 g, 8.90 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.48 g, 0.68 mmol), tricyclohexylphosphine (0.39 g, 1.39 mmol), and potassium carbonate (2.46 g, 34.4 mmol) in dehydrated xylene (180 mL) were added 2-ethylhexanoic acid (0.39 g, 2.70 mmol) and 5’-bromo-1,1’:3’,1”-terphenyl-2,2”,3,3”,4,4”,5,5”,6,6”-d 10 ​(3.13 g, 9.80 mmol), and heated at 120 °C for 20 h. The reaction solution was returned to room temperature, and the obtained white solid was filtered out. After washing the solid with toluene, ion-exchanged water, and methanol, the solid was dissolved in hot toluene. The toluene solution was passed through a silica gel pad, and the filtrate was concentrated to obtain 2.90 g (4.08 mmol, yield 46%) of white compound f.

[0650] ASAP MS spectral analysis: C 46 H4D 23 F2N5: theoretical value 710.36, observed value 711.78 [M+H +

[0651] [Chemical formula 61]

[0652]

[0653] Compound 38317(40)

[0654] To a solution of compound f (2.13 g, 3.00 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.10 g, 6.28 mmol) in N-methyl-2-pyrrolidone (60 mL) was added potassium carbonate (1.04 g, 7.52 mmol), and the mixture was stirred at 100 °C for 6 h. The reaction solution was cooled to 0 °C, and ion-exchanged water and methanol solution were added. The solid was filtered out, washed with water, and then dissolved in ethyl acetate. The solution was washed with saturated brine, dried over anhydrous magnesium sulfate, the solvent was removed, and the obtained solid was reprecipitated with a mixed solvent of ethyl acetate / hexane, and the solid was filtered out. The crude product was purified by silica gel chromatography (toluene:hexane = 2:1). The obtained solid was reprecipitated with toluene / hexane to obtain 2.10 g (2.05 mmol, yield 68%) of light yellow compound 38317(40).

[0655] 1 1H-NMR (400 MHz, DMSO-d6): δ 9.19 (s, 1H), 7.07 (t, J = 1.6 Hz, 1H), 6.98 (d, J = 1.6 Hz, 2H).

[0656] ASAP MS spectral analysis: C 70 H4D 39 N7: theoretical value 1020.60, observed value 1021.21 [M+H +

[0657] (Synthesis Example 5) Synthesis of compound 937647(40)

[0658] ​​[Chemical Formula 62]

[0659]

[0660] Compound g

[0661] Under a nitrogen stream and at -78 °C, a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (4.6 mL, 9.32 mmol) was slowly added dropwise to a solution of 3-bromo-4,5,6-trifluorobenzonitrile (2.00 g, 8.47 mmol) in tetrahydrofuran (85 mL). After stirring for 0.5 h after the addition was complete, tributyltin chloride (3.31 g, 10.17 mmol) was added, the temperature was raised to room temperature, and the mixture was stirred for 3 h. The reaction vessel was cooled to 0 °C, and saturated ammonium chloride solution was added. The resulting reaction solution was extracted with toluene, the organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was removed, and the resulting yellow liquid was dissolved in dehydrated toluene (85 mL). Bis(triphenylphosphine)palladium(II) dichloride (0.48 g, 0.68 mmol) and 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8) (3.91 g, 8.47 mmol) were added, and the mixture was heated at 120 °C for 14 h. The reaction solution was returned to room temperature, the resulting liquid was filtered through silica gel and diatomaceous earth, and then dried. The resulting cream-colored solid was recrystallized from toluene to obtain 2.05 g (4.18 mmol, 49% yield) of the white solid compound g.

[0662] 1 1H-NMR (400 MHz, CDCl3): δ 8.67 (td, J = 7.2, 2.4 Hz, 1H),

[0663] ASAP MS spectral analysis: C 28 HD 13 F4N5: theoretical value 490.20, observed value 491.4 [M+H +

[0664] [Chemical Formula 63]

[0665]

[0666] Compound 937647(40)

[0667] ​To a solution of compound g (1.0 g, 2.03 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.23 g, 7.03 mmol) in N,N-dimethylformamide (34 mL) was added potassium carbonate (1.13 g, 8.15 mmol), and the mixture was stirred at 110 °C for 16 h. Ion-exchanged water and methanol were added to the reaction solution, and filtration was carried out. The obtained yellow solid was purified by silica gel chromatography (toluene:hexane:chloroform = 6:3.5:0.5). The obtained solid was reprecipitated with toluene / methanol to obtain 1.40 g (1.46 mmol, yield 72%) of dark orange compound 937647(40).

[0668] 1 1H-NMR (400 MHz, CHCl3-d): δ 8.96 (s, 1H).

[0669] ASAPMS spectral analysis: C 64 HD 37 N8: theoretical value 955.55, observed value 957.07 [M+H +

[0670] (Synthesis Example 6) Synthesis of compound 935051(866)

[0671] [Chemical formula 64]

[0672]

[0673] Using the same starting materials as in Synthesis Example 5, the reaction substances were changed as shown in the above reaction formula, and the reaction and purification were carried out in the same manner as in Synthesis Example 5. Compound h with a yield of 62% and compound 935051(866) with a yield of 54% were obtained.

[0674] Compound h

[0675] 1 1H-NMR (400 MHz, CHCl3-d): δ 9.11 (d, J = 8.4 Hz, 1H), 9.06 (d, J = 8.4 Hz, 1H), 8.68 (td, J = 6.0 Hz and 2.4 Hz, 1H), 7.61 (t, J = 8.4 Hz, 1H), 7.50 (t, J = 8.4 Hz, 1H), 7.30 (d, J = 7.6 Hz, 1H), 7.27 - 7.25 (m, 1H), 7.14 (t, J = 8.4 Hz, 1H).

[0676] ASAPMS spectral analysis: C 64 HD 37 ​N8: Theoretical value 563.21, Observed value 564.43[M + H +

[0677] Compound 935051(866)

[0678] 1 H-NMR(400 MHz, CHCl3-d): δ 9.03 (s, 1H), 8.87 - 8.83 (m, 2H), 7.51 - 7.46 (m, 1H), 7.42 - 7.33 (m, 3H), 7.27 - 7.23 (m, 2H), 7.16 - 6.53 (m, 20H).

[0679] (Synthesis Example 7) Synthesis of Compound 937647(866)

[0680] [Chemical Formula 65]

[0681]

[0682] Compound 937647(866)

[0683] Using Compound h and carbazole-1,2,3,4,5,6,7,8-d8, the reaction was carried out in the same manner as in Synthesis Example 5 to obtain Compound 937647(866) with a yield of 32%.

[0684] ASAP MS Spectral Analysis: C 70 H8D 34 N8: Theoretical value 1028.57, Observed value 1030.01[M+H +

[0685] (Synthesis Example 8) Synthesis of Compound 992174

[0686] [Chemical Formula 66]

[0687]

[0688] Compound n

[0689] ​​Under a nitrogen stream, at -78 °C, a 1.0 M solution of lithium diisopropylamide in tetrahydrofuran / hexane (8.5 mL, 8.5 mmol) was slowly added dropwise to a solution of compound j (1.7 g, 8.40 mmol) in tetrahydrofuran (THF) (35 mL). After stirring for 30 minutes after the addition was complete, isopropoxyboronic acid pinacol ester (1.5 g, 8.40 mmol) was added, and stirring was continued for 30 minutes. The reaction vessel was cooled to -60 °C, 7 mL of ion-exchanged water was added, and then the temperature was raised to room temperature. Tris(dibenzylideneacetone)dipalladium(0) (0.19 g, 0.21 mmol), compound m (3.8 g, 8.4 mmol), sodium carbonate (1.7 g, 16.8 mmol), SPhos (0.35 g, 0.84 mmol), and 1,4-dioxane (35 mL) were added, and the mixture was heated at 100 °C for 14 hours.

[0690] The obtained gray solid was filtered out and washed with ion-exchanged water, methanol, ethyl acetate, and hexane. The solid was dissolved in THF, the THF solution was passed through a silica pad, and the filtrate was concentrated to obtain 0.96 g (1.5 mmol, 18% yield) of the gray solid compound n.

[0691] ASAP MS spectrum analysis: C 40 H2D 21 FN6: Theoretical value 627.33, Observed value 628.55 [M+H +

[0692] [Chemical formula 67]

[0693]

[0694] Compound 992174

[0695] Under a nitrogen stream, at room temperature, 5H-benzo[f]chromeno[3,2-c]carbazole (0.44 g, 1.72 mmol) and a solution of sodium hydride (60%, 0.086 g, 2.15 mmol) in N-methyl-2-pyrrolidone (5 mL) were added to a solution of compound X4 (0.90 g, 1.43 mmol) in N-methyl-2-pyrrolidone (40 mL), and the mixture was stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride solution was added to the reaction solution, the obtained solid was filtered out and washed with ion-exchanged water and methanol. The obtained reaction mixture was purified by silica gel chromatography (toluene:hexane = 1:1) to obtain 0.39 g (0.45 mmol, 31% yield) of the yellow solid compound 992174.

[0696] ASAP MS spectrum analysis: C 58 H​12 D 21 N7O: Theoretical value 864.41, Observed value 865.72 [M+H +

[0697] (Synthesis Example 9) Synthesis of Compound 46542(1456)

[0698] [Chemical Formula 68]

[0699]

[0700] Compound o

[0701] Under a nitrogen atmosphere, a mixture of 3-(phenyl-d5)-9H-carbazole-1,2,4,5,6,7,8-d7 (5.36 g, 21.8 mmol), 60 wt% sodium hydride (0.98 g, 24.5 mmol), and THF (100 mL) was stirred at room temperature for 1 hour. The resulting light brown solution was slowly added dropwise to a THF solution (100 mL) of 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (5.04 g, 21.8 mmol) cooled to -5 °C. After stirring for 1 hour after warming to room temperature, it was cooled to 0 °C, and ion-exchanged water was added. After filtering the white solid, it was washed in the order of ion-exchanged water, methanol, ethyl acetate, and hexane to obtain 8.9 g (19.8 mmol, yield 91%) of the white solid compound o.

[0702] ASAP MS Spectral Analysis: C 27 D 17 CLN4: Theoretical value 449.22, Observed value 450.31 [M+H +

[0703] [Chemical Formula 69]

[0704]

[0705] Compound p

[0706] ​​Under a nitrogen stream, at -78 °C, a 1.0 M solution of lithium diisopropylamide (LDA) in THF (30 mL, 30.0 mmol) was slowly added dropwise to a solution of 5-bromo-2,4-difluorobenzonitrile (6.58 g, 30.1 mmol) in THF (100 mL). After stirring for 1 hour, iodine (11.4 g, 45.0 mmol) was added, and the temperature was raised to room temperature. After stirring for 17 hours, it was cooled to 0 °C, and ion-exchanged water and saturated brine were added. After returning to room temperature, after separating into an organic phase and an aqueous phase, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated, and the obtained crude product was purified by silica gel chromatography (hexane / ethyl acetate = 5:1) to obtain 9.81 g (28.5 mmol, yield 95%) of the compound p as a brown solid.

[0707] 1 H NMR (400 MHz, CDCl3): δ 7.86 (t, J = 6.8 Hz, 1H).

[0708] [Chemical formula 70]

[0709]

[0710] Compound q

[0711] To a mixed solution of toluene (75 mL) and ion-exchanged water (30 mL) of compound p (9.80 g, 28.5 mmol), phenyl-d5-boronic acid (3.8 g, 29.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (1.0 g, 1.42 mmol), and potassium carbonate (7.88 g, 57.2 mmol) were added, and it was stirred at 110 °C for 18 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, saturated brine was added, and the organic phase and the aqueous phase were separated. After extracting the aqueous phase with toluene, the combined organic phases were dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated. The crude product was purified by silica gel chromatography (hexane / toluene = 1:1) to obtain 6.1 g (20.4 mmol, yield 71%) of the compound q as a white solid.

[0712] 1 H NMR (400 MHz, CDCl3): δ 7.84 (t, J = 6.8 Hz, 1H).

[0713] [Chemical formula 71]

[0714]

[0715] Compound r

[0716] To a solution of compound q (6.10 g, 20.4 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (7.88 g, 45.0 mmol) in N,N-dimethylformamide (DMF, 200 mL) was added potassium carbonate (8.46 g, 61.2 mmol), and the mixture was stirred at 30 °C for 25 h under a nitrogen atmosphere. Ion-exchanged water was added, the resulting solid was filtered, and washed with ion-exchanged water, methanol, and hexane. The obtained solid was purified by silica gel chromatography (toluene / hexane = 2:1). The obtained solid was washed with methanol to give 10.3 g (16.1 mmol, 83% yield) of white solid compound r.

[0717] 1 H NMR (400 MHz, DMSO-d6): δ 8.98 (s, 1H).

[0718] ASAPMS spectral analysis: C 37 HD 21 BrN3: theoretical value 608.23, observed value 609.35 [M+H +

[0719] [Chemical formula 72]

[0720]

[0721] Compound 46542(1456)

[0722] Under a nitrogen stream at -78 °C, a 2.0 M solution of isopropylmagnesium chloride in THF (5.5 mL, 11.0 mmol) was slowly added dropwise to a solution of compound r (6.11 g, 10.0 mmol) in THF (65 mL). After stirring for 90 min, a 1.0 M solution of zinc chloride in THF (30.0 mL, 30.0 mmol) was added and stirred for 30 min. After returning to room temperature, it was further stirred for 1 h. Compound o (3.0 g, 6.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.38 g, 0.19 mmol) were added, and the mixture was stirred at 80 °C for 20 h. The reaction vessel was returned to room temperature, saturated brine and ethyl acetate were added, and the organic and aqueous phases were separated. The obtained crude product was reprecipitated with ethyl acetate / hexane, and the resulting solid was filtered out. After purifying the obtained solid by flash column chromatography (toluene / hexane = 2:1), it was reprecipitated with ethyl acetate / hexane, and the solid was filtered out to give 1.93 g (2.04 mmol, 31% yield) of light green solid compound 46542(1456).

[0723] 1 ​1H NMR (400 MHz, DMSO-d6): δ 9.08 (s, 1H).

[0724] ASAPMS spectral analysis: C 64 HD 38 N7: Theoretical value 943.56, Observed value 944.66 [M+H +

[0725] (Synthesis Example 10) Synthesis of Compound 984647 (40)

[0726] [Chemical Formula 73]

[0727]

[0728] Compound s

[0729] Dissolve 4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.85 g, 7.49 mmol) in a mixed solvent of 50 mL of THF and ion-exchanged water, add 5'-bromo-1,1':3',1''-terphenyl-2,2'',3,3'',4,4'',5,5'',6,6''-d10 (2.8 g, 8.61 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.26 g, 0.37 mmol), and sodium carbonate (2.38 g, 22.5 mmol), and stir overnight at 100 °C. Cool the reaction solution to room temperature, add saturated brine, and separate the organic phase and the aqueous phase. Dry the organic phase with anhydrous magnesium sulfate and filter, and concentrate the filtrate. Purify the crude product by silica gel chromatography to obtain 2.2 g (6.2 mmol, yield 82%) of Compound s.

[0730] ASAPMS spectral analysis: C 25 H6D 10 FN: Theoretical value 359.19, Observed value 359.24 [M]

[0731] [Chemical Formula 74]

[0732]

[0733] Compound t

[0734] ​Under a nitrogen atmosphere and at -85 °C, a 1.0 M solution of LDA in THF (2.8 mL, 2.80 mmol) was slowly added dropwise to a solution of compound s (1.0 g, 2.78 mmol) in THF (20 mL). After stirring for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.57 g, 3.06 mmol) was added at -78 °C and stirred for 1 hour. After adding deionized water, the temperature was raised to room temperature, and 9-(4-chloro-6-(phenyl-d5)

[0735] -1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.13 g, 3.06 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.05 g, 0.08 mmol), and sodium carbonate (0.44 g, 4.17 mmol) were added, and the mixture was stirred overnight at 60 °C. The reaction solution was cooled to room temperature, the solid was filtered out, and washed with deionized water to obtain 1.4 g (2.02 mmol, 73% yield) of compound t.

[0736] ASAPMS spectral analysis: C 46 H5D 23 FN5: Theoretical value 692.38, Observed value 692.47 [M]

[0737] [Chemical formula 75]

[0738]

[0739] Compound 984647(40)

[0740] To a mixture of compound t (0.80 g, 1.15 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (0.30 g, 1.73 mmol), and DMF (70 mL) was added potassium carbonate (0.32 g, 2.31 mmol), and the mixture was stirred under a nitrogen atmosphere at 140 °C. After confirming the disappearance of the starting material, the reaction vessel was cooled to room temperature and deionized water was added. The resulting solid was filtered and washed with deionized water and methanol. The obtained solid was purified by silica gel chromatography to obtain 0.60 g (0.71 mmol, 62% yield) of compound 984647(40).

[0741] 1 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 1.6 Hz, 1H), 7.46 (t, J = 1.6 Hz, 1H), 7.23 (d, J = 1.2 Hz, 1H).

[0742] ASAP MS spectrum analysis: C 58 H6D 30 N6: Theoretical value 846.49, Observed value 847.65 [M+H +

[0743] (Synthesis Example 11) Synthesis of Compound 937647(33)

[0744] [Chemical Formula 76]

[0745]

[0746] Compound u

[0747] Under a nitrogen atmosphere and at room temperature, magnesium (0.0962 g, 3.95 mmol) was added dropwise to a 10 mL THF solution of 5'-bromo-1,1':3',1''-terphenyl-2,2'',3,3'',4,4'',5,5'',6,6''-d10 (1.01 g, 3.16 mmol). After that, the temperature was raised to 60 °C and stirred for 3 hours. The resulting solution was slowly added dropwise to a THF solution (10 mL) of 2,4,6-trichloro-1,3,5-triazine (0.596 g, 3.23 mmol) cooled to 0 °C. After stirring at 0 °C for 30 minutes, the temperature was raised to room temperature and then stirred for 23 hours. It was cooled to 0 °C, 100 mL of saturated aqueous ammonium chloride solution was added, and extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated. The obtained solid was purified by silica gel chromatography (hexane / methylene chloride = 5:1). The obtained solid was washed with hexane to obtain 0.443 g (1.14 mmol, yield 36%) of white solid Compound u.

[0748] 1 H NMR (400 MHz, CDCl3): δ 8.72 (d, J = 1.6 Hz, 2H), 8.09 (t, J = 1.6 Hz, 1H).

[0749] ASAP MS spectrum analysis: C 21 H3D 10 CL2N3: Theoretical value 387.11, Observed value 388.05 [M+H +

[0750] [Chemical Formula 77]

[0751]

[0752] Compound v

[0753] ​​Under a nitrogen atmosphere, a mixture of carbazole-1,2,3,4,5,6,7,8-d8 (0.201 g, 0.507 mmol), 60 wt% sodium hydride (0.0303 g, 0.757 mmol), and THF (2.5 mL) was stirred at room temperature for 1 hour. The resulting solution was slowly added dropwise to a THF solution (2.5 mL) of compound u (0.201 g, 0.517 mmol) cooled to 0 °C. After stirring for 1 hour after warming to room temperature, it was cooled to 0 °C, and a saturated aqueous ammonium chloride solution was added. After filtering the white solid, it was washed with ion-exchanged water and methanol to obtain 0.212 g (0.402 mmol, yield 79.3%) of the white solid compound v.

[0754] 1 H NMR (400 MHz, CDCl3): δ 8.84 (d, J = 2.0 Hz, 2H), 8.12 (t, J = 2.0 Hz, 1H).

[0755] ASAPMS spectral analysis: C 33 H3D 18 CLN4: Theoretical value 526.26, Observed value 527.30 [M+H +

[0756] [Chemical formula 78]

[0757]

[0758] Compound w

[0759] Under a nitrogen stream, at -78 °C, a 2.0 M THF solution of isopropylmagnesium chloride (0.4 mL, 0.8 mmol) was slowly added dropwise to a THF solution (2.4 mL) of 5-bromo-2,3,4-trifluorobenzonitrile (0141 g, 0.600 mmol). After stirring for 30 minutes, a 1.0 M THF solution of zinc chloride (1.8 mL, 1.8 mmol) was added and stirred for 1 hour. After returning to room temperature, it was further stirred for 30 minutes. Compound v (0.201 g, 0.381 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0216 g, 0.0186 mmol) were added and stirred at 70 °C for 16 hours. The reaction vessel was returned to room temperature, and after filtering the precipitated solid, it was washed with ion-exchanged water, methanol, ethyl acetate, and hexane to obtain 0.168 g (0.259 mmol, yield 67.9%) of the white solid compound w.

[0760] ASAP MS spectral analysis: C 40 H4D 18 ​F3N5: Theoretical value 647.30, Observed value 648.35 [M+H +

[0761] [Chemical formula 79]

[0762]

[0763] Compound 937647(33)

[0764] To a solution of compound w (0.763 g, 1.17 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.719 g, 4.10 mmol) in DMF (20 mL) was added potassium carbonate (0.646 g, 4.67 mmol), and the mixture was stirred at 110 °C for 17 hours under a nitrogen atmosphere. Ion-exchanged water was added, and after extraction with methyl chloride, the organic phase was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated, and the obtained solid was purified by silica gel chromatography (hexane / methyl chloride = 2:1) to obtain 0.63 g (0.565 mmol, yield 48.3%) of the yellow solid compound 937647(33).

[0765] 1 H NMR (400 MHz, CDCl3): δ 8.94 (s, 1H), 8.17 (d, J = 2.0 Hz, 1H), 7.93 (t, J = 2.0 Hz, 1H).

[0766] ASAP MS spectral analysis: C 76 H4D 42 N8: Theoretical value 1112.65, Observed value 1113.76 [M+H +

[0767] (Synthesis Example 11) Synthesis of compound 937647(512)

[0768] [Chemical formula 80]

[0769]

[0770] Compound x

[0771] ​​Under a nitrogen atmosphere, a mixture of 5,12-dihydro-5-phenylindolo[3,2-a] (8.6 g, 25.8 mmol), 60 wt% sodium hydride (1.2 g, 51.7 mmol), and THF (100 mL) was stirred at room temperature for 1 hour. The resulting light brown solution was slowly added dropwise to a THF solution (100 mL) of 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (6.0 g, 25.9 mmol) cooled to 0 °C. After stirring for 1 hour after warming to room temperature, it was cooled to 0 °C, and ion-exchanged water was added. After filtering the resulting white solid, it was washed in the order of ion-exchanged water, methanol, ethyl acetate, and hexane to obtain 11.18 g (21.2 mmol, yield 82%) of the white solid compound x.

[0772] 1 H NMR (400 MHz, CDCl3): δ 8.83 (dd, J = 7.2, 0.6 Hz, 1H). 8.03 - 8.06 (m, 2H), 7.67 (m, 4H), 7.40 - 7.57 (m, 5H), 7.27 - 7.31 (m, 1H), 6.98 - 7.04 (m, 2H)

[0773] ASAP MS spectral analysis: C 33 H 15 D5CLN5: Theoretical value 526.17, Observed value 527.62 [M + H +

[0774] [Chemical formula 81]

[0775]

[0776] Compound y

[0777] ​Under a nitrogen atmosphere, at -78 °C, a 2.0 M solution of isopropylmagnesium chloride in THF (11.1 mL, 22.2 mmol) was slowly added dropwise to a solution of 5-bromo-2,3,4-trifluorobenzonitrile (5.0 g, 21.9 mmol) in THF (423 mL). After stirring for 1 hour, tributyltin chloride (6.8 mL, 25.42 mmol) was added and stirred for 30 minutes. After returning to room temperature, it was further stirred for 3 hours. Saturated aqueous ammonium chloride (25 mL) was added, extracted with toluene, dried over saturated brine, dehydrated with magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure. The obtained crude product was dissolved in toluene (211 mL), compound x (11.18 g, 21.18 mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.19 g, 1.69 mmol) were added, and stirred at 120 °C for 14 hours. The reaction vessel was returned to room temperature, saturated brine and ethyl acetate were added, and the organic and aqueous phases were separated. The obtained crude product was dissolved in toluene and passed through a silica pad. The silica was washed with toluene and the filtrate was concentrated. After washing the obtained solid with ethyl acetate, it was reprecipitated with chloroform / methanol. The solid was filtered out to obtain 1.96 g (3.0 mmol, yield 14.2%) of the yellow solid compound y.

[0778] 1 H NMR (400 MHz, CDCl3): δ 9.92 (d, J = 7.6 Hz, 1H), 7.65 - 7.73 (m, 5H), 7.45 - 7.57 (m, 6H), 7.27 - 7.31 (m, 2H), 6.99 - 7.00 (m, 1H), 6.80 (t, J = 7.6 Hz, 1H)

[0779] ASAP MS spectral analysis: C 40 H 16 D5F3N6: Theoretical value 647.21, Observed value 647.38 [M+H +

[0780] [Chemical formula 82]

[0781]

[0782] Compound 937647(512)

[0783] ​To a solution of compound y (1.1 g, 1.69 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.92 g, 5.26 mmol) in DMF (34 mL) was added potassium carbonate (0.93 g, 6.79 mmol), and the mixture was stirred at 110 °C for 21 h. Ion-exchanged water and methanol were added, the resulting solid was filtered, and washed with methanol and hexane. The obtained solid was purified by silica gel chromatography (hexane / toluene / chloroform = 6:3.5:0.5). The obtained solid was washed with methanol to afford 1.07 g (0.96 mmol, 53% yield) of the yellow solid compound 937647(512).

[0784] 1 H NMR (400 MHz, CDCl3): δ 8.47 (d, J = 7.2 Hz, 1H), 8.06 - 8.10 (m, 3H), 7.61 - 7.70 (m, 4H), 7.39 - 7.56 (m, 6H), 6.98 - 7.02 (m, 1H), 6.72 (d, J = 8.4 Hz, 1H).

[0785] ASAP MS spectral analysis: C 76 H 16 D 29 N9: calculated 1112.56, found 1112.95 [M + H +

[0786] (Example 1) Fabrication and evaluation of thin films

[0787] By vacuum evaporation method, compound 46542 was evaporated onto a quartz substrate under a vacuum of less than 1×10 -3 Pa to form a pure thin film of compound 46542 with a thickness of 100 nm.

[0788] In contrast, by vacuum evaporation method, compound 46542 and H1 with the following structure were evaporated from different evaporation sources onto a quartz substrate under a vacuum of less than 1×10 -3 Pa to form a doped thin film with a concentration of 30 wt% of compound 46542 with a thickness of 100 nm.

[0789] ​Compound 46542 (40), Compound 38317, Compound 38317 (40), Compound 46542 (1456), Compound 984647 (40), Compound 937647 (40), Compound 935051 (866), Compound 937647 (512), Compound 937647 (33), and Comparative Compound A were used to replace Compound 46542, and pure films and doped films were formed in the same manner. Among them, the concentrations in the doped films of Compound 937647 (512) and Compound 937647 (33) were set to 35 wt%.

[0790] Photoluminescence was analyzed when 300 nm excitation light was irradiated to each of the formed doped films, and the ratio of the delayed fluorescence component and the lifetime (τ2) of the delayed fluorescence component were measured. Also, using each of the formed pure films, the energy of the HOMO and the energy of the LUMO were measured. The results are shown in the following table.

[0791] [Table 5]

[0792]

[0793] [Chemical formula 83]

[0794]

[0795] (Example 2) Fabrication and evaluation of organic electroluminescent element

[0796] By vacuum evaporation method, on a glass substrate on which an anode composed of indium tin oxide (ITO) with a film thickness of 50 nm was formed, each film was laminated at a vacuum degree of 5.0×10 -5 Pa. First, HAT-CN with a thickness of 10 nm was formed on the ITO, NPD with a thickness of 30 nm was formed thereon, TrisPCz with a thickness of 10 nm was further formed thereon, and H1 with a thickness of 5 nm was formed thereon. Then, H1 and Compound 46542 were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm, which was set as the light-emitting layer. The concentration of Compound 46542 in the light-emitting layer was set to 30 wt%. Then, after SF3-TRZ was formed to a thickness of 10 nm, Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30 wt% and 70 wt%, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, which was set as the organic electroluminescent element.

[0797] Compound 46542 (40), Compound 38317 (40), Compound 46542 (1456), and Comparative Compound A were used to replace Compound 46542, respectively, and each organic electroluminescent element was fabricated through the same steps.

[0798] The elapsed time (LT95) until the luminous intensity became 95% of that at the start of the test was measured when driving each organic electroluminescent element at 2.0 mA / cm 2 The results are shown in the following table. The LT95 in the table is represented as a relative value when taking the LT95 of Comparative Compound A as the reference (1). It was confirmed that: the LT95 of each organic electroluminescent element using the compound represented by the general formula (1) was long, and the element lifetime was improved.

[0799] [Table 6]

[0800] LT95 Compound 46542 6.7 Compound 46542(40) 7.0 Compound 38317(40) 8.0 Compound 46542(1456) 12.2 Comparative Compound A 1

[0801] (Example 3) Fabrication and Evaluation of Organic Electroluminescent Element Using a Co - dopant

[0802] An organic electroluminescent element was fabricated through the same steps as in Example 2, except that the viewpoint of forming a 40 - nm - thick light - emitting layer by sequentially evaporating H1, Compound 937647 (40), and EM1 as a light - emitting material from different evaporation sources at 69.5 wt%, 30.0 wt%, and 0.5 wt% respectively was only changed.

[0803] Moreover, Compound 935051 (866) and Comparative Compound A were used to replace Compound 937647 (40) respectively, and each organic electroluminescent element was fabricated through the same steps.

[0804] When the compound represented by the general formula (1) was used as the co - dopant, the element lifetime was also improved.

[0805] [Chemical Formula 84]

[0806]

[0807] Industrial Applicability

[0808] By using the compound represented by the general formula (1), an organic light - emitting element with good luminous characteristics can be provided. Therefore, the industrial applicability of the present invention is high.

Claims

1. A compound represented by the following general formula (1), [Chemical formula 1] In general formula (1), R 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group, and one or more of R 1 ~R 5 are cyano groups, one or more of R 1 ~R 5 are donor groups, 0 to 2 of R 1 ~R 5 are hydrogen atoms or deuterium atoms, 0 to 1 of R 1 ~R 5 is a substituted or unsubstituted aryl group, X 1 ~X 3 each independently represents N or C(R), provided that at least one of X 1 ~X 3 is N, R represents a hydrogen atom, a deuterium atom, or a substituent, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-forming atom, provided that at least one of Ar 1 and Ar 2 is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom, and L 1 represents a single bond or a divalent linking group.

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

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

4. The compound according to claim 1, wherein, R 1 ~R 5 Only one of them is a substituted or unsubstituted aryl group.

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

6. The compound according to claim 1, wherein, R 1 ~R 5 Two of them are donor groups.

7. The compound according to claim 1, wherein, R 1 ~R 5 Three of them are donor groups.

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

9. The compound according to claim 1, wherein, R 3 ~R 5 Each independently is a substituted or unsubstituted aryl group, or a donor group.

10. The compound according to claim 1, wherein, X 1 ~X 3 is N.

11. The compound according to claim 1, wherein, Ar 1 is a substituted or unsubstituted carbazol-9-yl, and Ar 2 is a substituted or unsubstituted aryl group.

12. The compound according to claim 1, wherein, Ar 1 and Ar 2 are each independently a substituted or unsubstituted carbazol-9-yl group.

13. The compound according to claim 1, wherein, L 1 is a single bond.

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

15. The compound according to claim 1, which has at least one deuterium atom.

16. A luminescent material composed of the compound according to any one of claims 1 to 15.

17. A delayed phosphor composed of the compound according to any one of claims 1 to 15.

18. A film containing the compound according to any one of claims 1 to 15.

19. An organic semiconductor element containing the compound according to any one of claims 1 to 15.

20. An organic light-emitting element containing the compound according to any one of claims 1 to 15.

21. The organic light-emitting element according to claim 20, wherein, The element has a layer containing the compound, and the layer further contains a host material.

22. The organic light-emitting element according to claim 21, wherein, The layer containing the compound further contains a delayed fluorescence material in addition to the compound and the host material, and the lowest excited singlet state energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound.

23. The organic light-emitting element according to claim 21, wherein, The element has a layer containing the compound, and the layer further contains a luminescent material having a structure different from that of the compound.

24. The organic light-emitting element according to claim 21, wherein, The amount of light emission from the compound in the materials contained in the element is the largest.

25. The organic light-emitting element according to claim 23, wherein, The amount of light emission from the luminescent material is more than that from the compound.

26. The organic light-emitting element according to claim 20, which is an organic electroluminescent element.

27. The organic light-emitting element according to claim 20, which emits delayed fluorescence.

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