Compound, light-emitting material, and delayed fluorescence material

Abstract

To provide a compound that is more useful as a compound for an organic light-emitting element.SOLUTION: The invention provides a compound represented by the general formula in the figure. (In the formula, one of X1 and X2 is N, and the other is C-Y3; one of Y1-Y3 is a cyano group, and each of the remaining two is an aryl group or a heteroaryl group; L1 is a single bond or a linking group; two to four of R1-R5 are donor groups; and one of R1-R3 is a cyano group, a diaryl cyanophenyl group, or the like.)SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound, a luminescent material, and a delayed fluorescence material using the same.

Background Art

[0002] Research on organic light-emitting devices has been actively conducted. For example, research on improving the luminous efficiency of light-emitting devices such as organic electroluminescence devices (organic EL devices) has been actively carried out. In particular, various efforts have been made to improve the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a luminescent material, etc., which constitute an organic electroluminescence device. Among them, research on organic electroluminescence devices using a delayed fluorescence material can also be seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after generating an inverse intersystem crossing from the excited triplet state to the excited singlet state in the excited state. Fluorescence by such a path 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, when a luminescent compound is excited by carrier injection, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, there is a limit to improving the luminous efficiency only with fluorescence from the directly generated excited singlet state. On the other hand, in a delayed fluorescence material, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the above-mentioned inverse intersystem crossing path, so that a higher luminous efficiency can be obtained compared with ordinary fluorescent materials.

[0004] Since such a principle was revealed, various delay fluorescence materials have been discovered through various studies, and their applications to organic light-emitting devices such as organic electroluminescence devices have been proposed. Among them, many compounds in which a donor group and an acceptor group are substituted on a benzene ring are included. For example, a compound having a skeleton in which a carbazol-9-yl group as a donor group, a cyano group as an acceptor group, and a substituted triazinyl group are substituted on a benzene ring has been proposed (see Patent Document 1).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

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

[0007] Under such circumstances, the present inventors have conducted repeated studies for the purpose of providing a more useful compound as a compound for an organic light-emitting device. Then, they have earnestly proceeded with in-depth studies for the purpose of deriving and generalizing a general formula of a more useful compound for an organic light-emitting device.

Means for Solving the Problems

[0008] As a result of intensive studies to achieve the above object, the present inventors have found that a compound having a structure satisfying specific conditions is useful as a compound for an organic light-emitting element. The present invention has been proposed based on such findings, and specifically has the following configuration. [1] A compound represented by the following general formula (1). General formula (1)

Chemical formula

Chemical formula

[10] R 1 ~R 5 Among these, at least one of the 2 to 4 donor groups is a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), and the compound according to any one of [1] to [9].

[11] R 1 ~R 5 Among these, at least one of the 2 to 4 donor groups is a substituted or unsubstituted carbazol-9-yl group which may be condensed, and the compound according to

[10] .

[12] R 1 ~R 5 Among these, 2 of them are the donor groups, and the compound according to any one of [1] to

[11] .

[13] R 1 ~R 5 Among these, 3 of them are the donor groups, and the compound according to any one of [1] to

[11] .

[14] The donor group and Y 1 ~Y 6 Among these, at least one of them contains a deuterium atom, and the compound according to any one of [1] to

[13] .

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

[14] .

[16] A delayed fluorescence material comprising the compound according to any one of [1] to

[14] .

Advantages of the Invention

[0009] The compound of the present invention represented by the general formula (1) exhibits excellent performance as a compound for an organic light-emitting device.

Embodiments for Carrying Out the Invention

[0010] Hereinafter, the content of the present invention will be described in detail. The description of the constituent elements described below may be 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 this specification, a 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. Further, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention can be substituted with deuterium atoms ( 2 H, deuterium D). In the chemical structural formulas in this specification, a hydrogen atom is represented as H or the representation is omitted. For example, when the representation of the atom bonded to the ring skeleton constituting carbon atom of the benzene ring is omitted, it is assumed that H is bonded to the ring skeleton constituting carbon atom at the position where the representation is omitted. In this specification, the term "substituent" means an atom or atomic group other than a hydrogen atom and a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

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

[0012] In general formula (1), X 1 and X 2 represent, one represents N and the other represents C-Y 3 . In one aspect of the present invention, X 1 is N and X 2 is C-Y 3 . In one aspect of the present invention, X 1 is C-Y 3 and X 2 is N. In general formula (1), X 1 and X 2 will not both be N. X 1 and X 2Compared with compounds where both are N, the compound represented by the general formula (1) exhibits excellent luminescence properties.

[0013] In the general formula (1), Y 1 ~Y 3 One of them represents a cyano group, and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. In one aspect of the present invention, Y 1 is a cyano group. In one aspect of the present invention, Y 2 is a cyano group. In one aspect of the present invention, Y 3 is a cyano group. In one aspect of the present invention, the remaining two other than the cyano group are each independently a substituted or unsubstituted aryl group, for example, the remaining two are the same. In one aspect of the present invention, the remaining two other than the cyano group are each independently a substituted or unsubstituted heteroaryl group, for example, the remaining two are the same. In one aspect of the present invention, one of the remaining two other than the cyano group is a substituted or unsubstituted aryl group, and one is a substituted or unsubstituted heteroaryl group.

[0014] Y 1 ~Y 3 The substituted or unsubstituted aryl group that Y 1 ~Y 3 can take may be a monocyclic ring or a condensed ring in which two or more rings are condensed. When it is a condensed ring, the number of condensed rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, pyrene ring. Specific examples of the aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group. The number of ring skeleton constituent atoms of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14 or within the range of 6 to 10. Y 1 ~Y 3 For specific examples of the substituted or unsubstituted aryl group that can be taken, reference can be made to the specific examples of the substituted or unsubstituted aryl group that R 1 ~R 5 can take. Y 1 ~Y 3 The substitutable or unsubstitutable heteroaryl group that can be taken may be a group bonded to a carbon atom constituting an aromatic heterocyclic ring or a group bonded to a nitrogen atom, but is preferably a group bonded to a nitrogen atom. Examples of the aromatic heterocyclic ring containing the carbon atom to which it is bonded include a pyridine ring, a pyrimidine ring, and a triazine ring. Examples of the aromatic heterocyclic ring containing the nitrogen atom to which it is bonded include a pyrrole ring. These aromatic heterocyclic rings may be substituted or may have another ring condensed thereto. Examples of the other ring include an aromatic hydrocarbon ring and an aromatic heterocyclic ring, and a ring in which these rings are further condensed may be condensed to the above-mentioned aromatic heterocyclic ring. In one embodiment of the present invention, Y 1 ~Y 3 Examples of the substitutable or unsubstitutable heteroaryl group that can be taken include a donor group represented by the general formula (a) described later, and further include a donor group represented by the general formula (b) described later. Further, for R 1 ~R 5 reference can be made to the description and specific examples of the donor groups that can be taken. In a preferred embodiment of the present invention, Y 1 ~Y 3 One of them is a cyano group, and the remaining two are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazol-9-yl group which may be condensed. In a preferred embodiment of the present invention, Y 3 represents a cyano group, Y 1 and Y 2 each independently represent a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group), or a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed). At this time, Y 1 and Y 2 may be different or the same. In a preferred embodiment of the present invention, Y 1 ~Y 3 At least one of them is a substituted aryl group. For example, Y 1is a substituted aryl group. For example, Y 2 is a substituted aryl group. For example, Y 1 and Y 2 are each independently a substituted aryl group. The substituent of the substituted aryl group herein is preferably an alkyl group which may be substituted with a deuterium atom, or an aryl group which may be substituted with a deuterium atom or an alkyl group, and more preferably an alkyl group which may be substituted with a deuterium atom. The number of carbon atoms of the alkyl group herein is preferably 1 to 10, for example, 3 to 10.

[0015] L in the general formula (1) 1 represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L 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. For the aryl moiety constituting the arylene group, reference can be made to the description and preferred range of the aryl group in the column of R 1 ~R 5 . Examples of the heteroarylene group include a linking group in which at least one of the ring-skeleton carbon atoms constituting the arylene group is replaced by a nitrogen atom. Hereinafter, specific examples of L 1 will be given. However, L 1 adoptable in the present invention should not be construed as being limited by these specific examples. In the following specific examples, the methyl group is omitted from the representation. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0016]

Chemical formula

[0017] Those in which all hydrogen atoms existing within the above L2 to L13 are replaced with deuterium atoms are disclosed as L14 to L25. In one aspect of the present invention, L 1 is selected from the group consisting of L1 to L25. In one aspect of the present invention, L 1 is selected from the group consisting of L1 to L7, L14 to L19. In one aspect of the present invention, L 1 is selected from the group consisting of L1, L8 to L13, L20 to L25. In one aspect of the present invention, L 1 is selected from the group consisting of L2 to L25. In one aspect of the present invention, L 1 is L1.

[0018] Two to four of R 1 to R 5 in the general formula (1) are each independently a donor group. The donor group referred to here does not include an alkyl group which may be substituted with a deuterium atom or an aryl group, and a deuterium atom, an alkyl group, or an aryl group which may be substituted with an alkyl group or an aryl group. The "donor group" can be selected from among groups having a negative Hammett σp value. The "acceptor group" can be selected from among groups having a positive Hammett σp value. The Hammett σp value was proposed by L.P. Hammett and quantifies the influence of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following formula established between the substituent and the reaction rate constant or equilibrium constant in a para-substituted benzene derivative: log(k / k0) = ρσp Or log(K / K0) = ρσp It is a constant (σp) specific to the substituent in []. In the above formula, k0 is the rate constant of a benzene derivative without a substituent, k is the rate constant of a benzene derivative substituted with a substituent, K0 is the equilibrium constant of a benzene derivative without a substituent, K is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ represents a reaction constant determined by the type and conditions of the reaction. For the description of the "Hammett's σp value" in the present invention and the numerical values of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0019] R 1 ~R 5 The donor group that can be adopted preferably has a σp of -0.3 or less, more preferably -0.5 or less, and even more preferably -0.7 or less. For example, it may be selected from the range of -0.9 or less, or from the range of -1.1 or less.

[0020] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or a group in which the substituted amino group is bonded via a linking group. For example, it may be an aryl group to which a substituted amino group is bonded, especially a phenyl group to which a substituted amino group is bonded, or an alkenylene group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0021] R 1 ~R 5 The donor groups that can be adopted are preferably groups represented by the following general formula (a), or groups in which the groups represented by the following general formula (a) are bonded via a linking group. The linking group mentioned here is preferably a π-conjugated linking group, and examples thereof include an arylene group and an alkenylene group, and specifically, L1 to L25 described above can be mentioned. General formula (a)

Chemical formula

[0022] In general formula (a), Z 1 represents C-R 14 or N, and Z 2 represents C-R 15 or N, and Z 3 represents C-R 16 or N, and Z 4 represents C-R 17 or N. Z 5 represents C or N, and 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.

[0023] Z 1 ~Z 4 Among them, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one aspect of the present invention, among Z 1 ~Z 4 the number of N is 1. In one aspect of the present invention, among Z 1 ~Z 4 the number of N is 0. R 14 ~R 17 each independently represents a hydrogen atom, a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from, for example, Group A described later, may be selected from Group B described later, may be selected from Group C described later, may be selected from Group D described later, may be selected from Group E described later, or may be selected from a plurality of each of Groups A to E. R 14 ~R 17 When two or more of them represent a deuterium atom or a substituent, these two or more deuterium atoms or substituents may be the same or different. R 14 ~R 17 The number of substituents among them is preferably 0 to 2. For example, R 14 ~R 17 The number of substituents among them may be 1, or R 14 ~R 17 The number of substituents among them may be 0 (R 14 ~R 17 being a hydrogen atom or a deuterium atom). R 14 ~R 17 When the number of substituents among them is 0, R 14 ~R 17 may all be hydrogen atoms, may all be deuterium atoms, or some may be hydrogen atoms and the rest may be deuterium atoms. R 14 and R 15 、R 15 and R 16 、R 16 and R 17They may be combined with each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring thereof. Preferably, it is an aromatic ring or a heteroaromatic ring. Examples of the aromatic ring include a substituted or unsubstituted benzene ring. Another benzene ring may be further condensed with the benzene ring, or a heterocyclic ring such as a pyridine ring may be condensed therewith. The heteroaromatic ring means a ring showing aromaticity containing a heteroatom as a ring skeleton constituent atom, and is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the heteroaromatic ring. In a preferred aspect of the present invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. Here, benzofuran, benzothiophene, and indole mentioned herein may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from group A described later, may be selected from group B described later, may be selected from group C described later, may be selected from group D described later, may be selected from group E described later, or may be selected from a plurality of each of groups A to E. It is preferable that a substituted or unsubstituted aryl group is bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the deuterium atom or substituent that can be substituted on the aryl group include a deuterium atom or a substituent selected from any of groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 in one set are combined with each other to form a cyclic structure. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17None of them are bonded to each other to form a cyclic structure.

[0024] In general formula (a), Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z 5 is C, and Ar 5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z 5 is N, and Ar 5 is a substituted or unsubstituted heteroaromatic ring. Ar 5 Examples of the aromatic ring that Ar can take include a benzene ring. Another benzene ring may be condensed with the benzene ring, or a heterocyclic ring such as a pyridine ring may be condensed. Ar 5 The heteroaromatic ring that Ar can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the heteroaromatic ring. In one aspect of the present invention, Z 5 is C, and the heteroaromatic ring is a furan ring of 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 aspect of the present invention, Z 5is N, and the complex aromatic ring is a pyrrole ring of an indole which is substituted or unsubstituted, or an imidazole ring of a benzimidazole which is substituted or unsubstituted. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole mentioned here may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from among the following Group A, may be selected from among the following Group B, may be selected from among the following Group C, may be selected from among the following Group D, may be selected from among the following Group E, or may be selected from among a plurality of each of Groups A to E.

[0025] Z in the general formula (a) 5 When it is C, it is preferably a group represented by the following general formula (b). General formula (b)

Chemical formula

[0026] In the general formula (b), Z 1 represents C-R 14 or N, and Z 2 represents C-R 15 or N, and Z 3 represents C-R 16 or N, and Z 4 represents C-R 17 or N, and Z 6 represents C-R 18 or N, and Z 7 represents C-R 19 or N, and Z 8 represents C-R 20 or N, and 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 R21 may be bonded to each other to form a cyclic structure. Z in the general formula (b) 1 ~Z 4 , R 14 ~R 17 For these, the corresponding description of the general formula (a) can be referred to. Z in the general formula (b) 6 ~Z 9 , R 18 ~R 21 is in correspondence with Z 1 ~Z 4 , R 14 ~R 17 in the general formula (a) in order, and for the details of these, the description of Z 1 ~Z 4 , R 14 ~R 17 in the general formula (a) can be referred to. In one aspect of the present invention, among Z 1 ~Z 4 , Z 6 ~Z 9 , the number of those which are N is preferably 0 to 2, and preferably 0 or 1. In one aspect of the present invention, among Z 1 ~Z 4 , Z 6 ~Z 9 , the number of those which are N is 1. In a preferred aspect of the present invention, among Z 1 ~Z 4 , Z 6 ~Z 9 , the number of those which are N is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0027] R 1 ~R 5The donor group that can be adopted is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group mentioned here may be unsubstituted or may be substituted with a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from Group A described below, may be selected from Group B described below, may be selected from Group C described below, may be selected from Group D described below, may be selected from Group E described below, or may be selected from a plurality of each of Groups A to E. For example, it may be substituted with at least a deuterium atom. For example, it may be substituted with at least a cyano group. For example, it may be substituted with an aryl group that may be substituted with at least a deuterium atom, an alkyl group, or an aryl group. For example, it may be substituted with an alkyl group that may be substituted with at least a deuterium atom. Further, one or more rings may be further condensed 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 adopted is a carbazol-9-yl group, which may be substituted with a deuterium atom or a substituent selected from Group E described below, and one or more rings may be further condensed. When a compound having a short emission wavelength is desired, it is preferable to adopt a carbazol-9-yl group substituted with an aryl group that may be substituted with a deuterium atom, an alkyl group, or an aryl group. When a carbazol-9-yl group having no condensed ring 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 still more preferably at the 3rd and 6th positions.

[0028] In one embodiment of the present invention, R 1 ~R 5 The donor group that can be adopted is a carbazol-9-yl group having one or more condensed rings, which is hereinafter referred to as a "ring-condensed carbazol-9-yl group". R 1 ~R 5The fused carbazol-9-yl group that can be adopted may be unsubstituted, or may be substituted with a deuterium atom or a substituent. The deuterium atom or substituent mentioned here may be selected from among the following Group A, may be selected from among the following Group B, may be selected from among the following Group C, may be selected from among the following Group D, may be selected from among the following Group E, or may be selected from among a plurality of each of Groups A to E. Preferably, it is unsubstituted or substituted with a deuterium atom or a substituent selected from Group E. In one aspect of the present invention, the fused carbazol-9-yl group is unsubstituted. In a preferred aspect of the present invention, the fused carbazol-9-yl group is substituted with an aryl group, and the aryl group mentioned here may be further substituted with one or more selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and a substituent having a structure in which two or more of these are bonded. For example, the fused carbazol-9-yl group is substituted with one or more selected from the group consisting of a deuterium atom; an alkyl group that may be substituted with a deuterium atom or an aryl group; and an aryl group that may be substituted with a deuterium atom, an alkyl group, or an aryl group.

[0029] The total number of fused rings in the fused carbazol-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred aspect of the present invention, the number of rings constituting the fused ring is 5. Here, the number of rings includes the number of rings of carbazole being fused (i.e., 3).

[0030] The ring-fused carbazol-9-yl group is a group bonded through a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a ring further fused with these. Preferably, it is 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 may be further fused to the benzene ring, or a heterocyclic ring such as a pyridine ring may be fused. The aromatic heterocyclic ring means a ring exhibiting aromaticity containing a hetero atom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring. For example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the aromatic heterocyclic ring. In one aspect of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. It should be noted that a deuterium atom or a substituent (except when it is only a deuterium atom) selected from Group E described later is preferably bonded to the nitrogen atom of the pyrrole ring, and it is more preferable that an aryl group which may be substituted with an alkyl group or an aryl group is bonded. In the present invention, it is preferable to adopt a carbazol-9-yl group in which a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton-constituting atoms is fused. Among them, a carbazol-9-yl group having a benzofuro structure fused, a carbazol-9-yl group having a benzothieno structure fused, and a carbazol-9-yl group having an indolo structure fused can be preferably adopted. In one aspect of the present invention, it has at least one carbazol-9-yl group having a benzofuro structure, for example, two or more. In one aspect of the present invention, it has at least one carbazol-9-yl group having a benzothieno structure, for example, two or more.

[0031] As the fused carbazole-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazole-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazole-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazole-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazole-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazole-8-yl group, a substituted or unsubstituted benzofuro[3,2-c]carbazole-5-yl group can be adopted. Further, as the fused carbazole-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazole-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazole-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazole-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazole-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazole-8-yl group, a substituted or unsubstituted benzothieno[3,2-c]carbazole-5-yl group can also be adopted. Further, as the fused carbazole-9-yl group, a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazole-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazole-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazole-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazole-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazole-8-yl group, a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazole-5-yl group can also be adopted.

[0032] When the ring-condensed carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, either the 3-position or the 6-position of the ring-condensed carbazol-9-yl group is substituted with a substituent. In a preferred embodiment of the present invention, at least one substituent is present at the para-position of the benzene ring as viewed from the heteroatom present in the ring-condensed carbazol-9-yl group. In a preferred embodiment of the present invention, at least one substituent is present only at the para-position of the benzene ring as viewed from the heteroatom present in the ring-condensed carbazol-9-yl group. In a preferred embodiment of the present invention, all of the substitutable para-positions of the benzene ring have substituents as viewed from the heteroatom present in the ring-condensed carbazol-9-yl group.

[0033] In the following, R in the general formula (1) 1 ~R 5 Specific examples of the donor groups that can be adopted are shown. The specific examples exemplified here are substituted or unsubstituted carbazol-9-yl groups (a ring may be further condensed to the carbazole ring), but the donor groups that can be adopted in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents the bonding position. Since the methyl group is omitted from the display, for example, D2 has one methyl group. However, the deuterated methyl group is represented as CD3. Also, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated (perdeuterated phenyl group). D represents a deuterium atom.

Chemical formula

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[0034] Disclosed are D815 to D1346, in which all hydrogen atoms existing in the above D1 to D532 are replaced with deuterium atoms.

[0035] R 1 ~R 5 Specific examples of those among the donor groups that R [Chemical formula] [Chemical formula] [Chemical formula]

[0036] Disclosed are D1399 to D1426, in which all hydrogen atoms existing in the above D1347 to D1374 are replaced with deuterium atoms. In one aspect of the present invention, R 1 ~R 5The donor groups that can be adopted are selected from the group consisting of D1 to D1426. In one aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D1 to D1346. In one aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D14 to D20, D24 to D87, D94 to D189, D256 to D369, D430 to D524, D545 to D606, D613 to D746, D797 to D803. In one aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D88 to D93, D130 to D255, D370 to D429, D526 to D532, D607 to D612, D623 to D628, D747 to D796, D805 to D814. In one aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D533 to D1346, D1375 to D1426. In one aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D533 to D1346. In a preferred aspect of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D1 to D20, D24 to D29, D44, D54 to D59, D84 to D93, D130 to D202, D205, D208, D211, D217, D220, D223, D226, D229, D232, D235, D238, D241, D244, D247, D250, D253, D269, D525, D539 to D558, D608 to D612, D636, D805 to D809, D815 to 834, D839 to D843, D858, D868 to D873, D898 to D907, D1004 to D1016, D1019, D1022, D1025, D1031, D1034, D1037, D1040, D1043, D1046, D1049, D1052, D1055, D1058, D1061, D1064, D1067, D1083, D1339. In a more preferred aspect of the present invention, R 1 ~R 5The donor groups that can be adopted are selected from the group consisting of D1, D6, D7, D8, D9, D14, D15, D18, D20, D26, D27, D44, D56, D57, D74, D84, D86, D88, D90, D130, D145, D178, D183, D190, D193, D540, D550, D552, D557, D558, D815, D820, D821, D822, D823, D828, D829, D832, D834, D840, D841, D858, D870, D871, D888, D898, D900, D902, D904, D944, D959, D992, D997, D1004, D1007.

[0037] In one aspect of the present invention, two of R 1 ~R 5 are donor groups. In one aspect of the present invention, three of R 1 ~R 5 are donor groups. In one aspect of the present invention, four of R 1 ~R 5 are donor groups. In one aspect of the present invention, two to four of R 1 ~R 5 are the same donor group. In one aspect of the present invention, all of the donor groups adopted by R 1 ~R 5 are the same. In one aspect of the present invention, two of R 1 ~R 5 are the same donor group, and one to two are different donor groups from this. In one aspect of the present invention, three of R 1 ~R 5 are the same donor group, and one is a different donor group from this. In one aspect of the present invention, at least R 5 is a donor group. In one aspect of the present invention, at least R 4 is a donor group. In one aspect of the present invention, at least R 3 is a donor group. In one aspect of the present invention, at least R 2 is a donor group. In one aspect of the present invention, at least R 1 is a donor group. In one aspect of the present invention, R 5 and R 4alone is the donor group. In one aspect of the present invention, R 5 and R 3 alone is the donor group. In one aspect of the present invention, R 5 and R 2 alone is the donor group. In one aspect of the present invention, R 5 and R 1 alone is the donor group. In one aspect of the present invention, R 4 and R 3 alone is the donor group. In one aspect of the present invention, R 4 and R 2 alone is the donor group. In one aspect of the present invention, R 4 and R 1 alone is the donor group. In one aspect of the present invention, R 3 and R 2 alone is the donor group. In one aspect of the present invention, R 3 and R 1 alone is the donor group. In one aspect of the present invention, R 2 and R 1 alone is the donor group. In one aspect of the present invention, R 5 and R 4 and R 3 alone is the donor group. In one aspect of the present invention, R 5 and R 4 and R 2 alone is the donor group. In one aspect of the present invention, R 5 and R 4 and R 1 alone is the donor group. In one aspect of the present invention, R 5 and R 3 and R 2 alone is the donor group. In one aspect of the present invention, R 5 and R 3 and R 1 alone is the donor group. In one aspect of the present invention, R 5 and R 2 and R 1 alone is the donor group. In one aspect of the present invention, R 4 and R 3 and R 2 alone is the donor group. In one aspect of the present invention, R 4 and R 3 and R 1Only R is the donor group. In one aspect of the present invention, R 4 and R 2 and R 1 Only R is the donor group. In one aspect of the present invention, R 3 and R 2 and R 1 Only R is the donor group. In one aspect of the present invention, R 5 and R 4 and R 3 and R 2 are donor groups. In one aspect of the present invention, R 5 and R 4 and R 3 and R 1 are donor groups. In one aspect of the present invention, R 5 and R 4 and R 2 and R 1 are donor groups. In one aspect of the present invention, R 5 and R 3 and R 2 and R 1 are donor groups. In one aspect of the present invention, R 4 and R 3 and R 2 and R 1 are donor groups. The donor group represented by R 1 to R 5 in the general formula (1) is preferably a group containing at least one (for example, only one) substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), for example, a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed. The donor group represented by R 1 to R 5 in the general formula (1) is also preferably a group containing all substituted or unsubstituted diarylamino groups (the two aryl groups may be bonded to each other), for example, a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other), for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed.

[0038] In general formula (1), R 1 ~R 3 One of them is a cyano group or a group represented by the following general formula (A). General formula (A)

Chemical formula

[0039] L in general formula (A) 2 represents a single bond or a divalent linking group. For details of L 2 , refer to the description, preferred range, and specific examples of L 1 in general formula (1). In a preferred embodiment of the present invention, L 2 is the same as L 1 . In one embodiment of the present invention, X 3 and X 4 in general formula (A), one represents N, and the other represents C-Y 6 , Y 4 ~Y 6 One of them represents a cyano group, and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. For details and specific examples of X 3 , X 4 , Y 4 ~Y 6 here, refer to the description, preferred range, and specific examples of X 1 , X 2 , Y 1 ~Y 3 in general formula (1). In a preferred embodiment of the present invention, L 2 , X 3 , X 4 , Y 4 ~Y 6 in general formula (A) are the same as L 1 , X 1 , X 2 , Y 1 ~Y 3 in general formula (1) in order. At this time, there will be two identical substituents represented by general formula (A) in the molecule of the compound. In another embodiment of the present invention, X 3and X 4 represents N, and Y 4 represents a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Y 5 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. As an example of the embodiment described here, when Y 4 is a cyano group and Y 5 is a substituted or unsubstituted aryl group, Y 4 is a cyano group and Y 5 is a substituted or unsubstituted heteroaryl group, Y 4 and Y 5 are each independently a substituted or unsubstituted aryl group (Y 4 and Y 5 may be the same or different), Y 4 and Y 5 are each independently a substituted or unsubstituted heteroaryl group (Y 4 and Y 5 may be the same or different), Y 4 is a substituted or unsubstituted aryl group and Y 5 is a substituted or unsubstituted heteroaryl group can be exemplified.

[0040] In one embodiment of the present invention, R 1 is a cyano group. In one embodiment of the present invention, R 2 is a cyano group. In one embodiment of the present invention, R 3 is a cyano group. In one embodiment of the present invention, R 1 is a group represented by the general formula (A), and at this time, for example, L 2 , X 3 , X 4 , Y 4 ~Y 6 are in order L 1 , X 1 , X 2 , Y 1 ~Y 3 are the same as each other. In one embodiment of the present invention, R 2 is a group represented by the general formula (A), and at this time, for example, L 2 , X 3 , X4 , Y 4 ~Y 6 are successively L 1 , X 1 , X 2 , Y 1 ~Y 3 and are the same. In one embodiment of the present invention, R 3 is a group represented by the general formula (A), and at this time, for example, L 2 , X 3 , X 4 , Y 4 ~Y 6 are successively L 1 , X 1 , X 2 , Y 1 ~Y 3 and are the same.

[0041] Of R 1 ~R 5 in the general formula (1), 0 to 2 are hydrogen atoms or deuterium atoms. For example, only 1 is a hydrogen atom or a deuterium atom, and for example, 2 are hydrogen atoms or deuterium atoms. None of R 1 ~R 5 needs to be a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, at least one of R 1 and R 5 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 1 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 2 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 3 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 4 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, at least R 5 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, only R 1 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, only R 2 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, only R 3 is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, only R 4is only a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 5 is only a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 2 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 3 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 4 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 5 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 3 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 4 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 5 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 3 and R 4 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 3 and R 5 are a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 4 and R 5 are a hydrogen atom or a deuterium atom.

[0042] R 1 to R 5Among them, those that are neither a hydrogen atom, a deuterium atom, a cyano group, a group represented by the general formula (A), nor a donor group are preferably a substituted or unsubstituted alkyl group (for example, having 1 to 20 carbon atoms) or a substituted or unsubstituted aryl group (for example, having 6 to 22 carbon atoms). Further, it may be an alkyl group substituted with a deuterium atom, an aryl group, or a substituent having a structure in which two or more of these are bonded; or more preferably, it may be an aryl group substituted with a deuterium atom, an alkyl group, an aryl group, a silyl group, or a substituent having a structure in which two or more of these are bonded. Still more preferably, it may be an aryl group substituted with a deuterium atom, an alkyl group, an aryl group, or a substituent having a structure in which two or more of these are bonded. In one aspect of the present invention, R 1 ~R 5 One to two (for example, one, for example, two) of them are each independently an aryl group which may be substituted with a deuterium atom, an alkyl group, an aryl group, or a substituent having a structure in which two or more of these are bonded, for example, a phenyl group which may be substituted with a deuterium atom, an alkyl group or an aryl group. The alkyl group may be linear, branched, or cyclic. Further, two or more of a linear portion, a cyclic portion, and a branched portion may be mixed. The number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, 4 or less. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group. The alkyl group may be further substituted with an aryl group or the like. The aryl group may be a monocyclic ring or a condensed ring in which two or more rings are condensed. When it is a condensed ring, the number of condensed rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, and pyrene ring. Specific examples of the aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group. The number of ring skeleton constituent atoms of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14 or within the range of 6 to 10. Hereinafter, R 1 ~R 5 Specific examples of the optionally substituted aryl group that can be adopted are given. However, the aryl group that can be adopted in the present invention is not construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position. Also, the methyl group is omitted from the display. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

Chemical formula

Chemical formula

Chemical formula

[0043] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar27 are replaced with deuterium atoms are exemplified here as Ar49 to Ar75 in order. In one aspect of the present invention, the aryl group that R 1 ~R 5 can adopt is selected from the group consisting of Ar1 to Ar75. In a preferred aspect of the present invention, R 1 ~R 5The aryl groups that can be adopted are selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar14, Ar15, Ar20, Ar21, Ar22, Ar49, Ar50, Ar53, Ar55, Ar58, Ar60, Ar62, Ar63, Ar68, Ar69, Ar70. In a preferred embodiment of the present invention, R 1 ~R 5 The aryl groups that can be adopted are selected from the group consisting of Ar28 to Ar75. In a preferred embodiment of the present invention, R 1 ~R 5 The aryl groups that can be adopted are selected from the group consisting of Ar49, Ar50, Ar53, Ar55, Ar58, Ar60, Ar62, Ar63, Ar68, Ar69, Ar70.

[0044] In the general formula (1), two of R 1 ~R 5 do not combine with each other to form a cyclic structure. That is, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 do not combine with each other to form a cyclic structure. The compound represented by the general formula (1) has a structure in which the benzene ring can rotate freely about a single bond between L 1 and the benzene ring. Therefore, the descriptions of R 1 , R 2 in this specification can be read as the descriptions of R 5 , R 4 respectively. Thus, for example, even if a compound in which R 4 is a group represented by the general formula (A), by rotating the benzene ring, it can be regarded as a compound in which R 2 is a group represented by the general formula (A), and if the compound also satisfies all other conditions of the general formula (1), it can be said that the compound is included in the general formula (1).

[0045] As the compound group 1 of the present invention, X 1 is N, and X2 is C-CN, and L 1 is a single bond, and R 3 Examples of the compound group of the general formula (1) where is a cyano group (CN) can be given. Compound group 1 has Y 1 and Y 2 each independently being a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from the following group E, for example, a phenyl group substituted with an alkyl group), Compound group 1a where Y 1 and Y 2 each independently being a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed), Compound group 1b where Y 1 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from the following group E, for example, a phenyl group substituted with an alkyl group), and Y 2 is a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed). Compound groups 1a to 1c each further include compounds that satisfy at least one of the following additional conditions. In one aspect of the present invention, R 1 , R 2 , R 4 , R 5 are donor groups. In one aspect of the present invention, R 1 , R 2 , R 4 are donor groups, and R 5 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 , R 2 , R 4 are donor groups, and R 5 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 2 , R 5 are donor groups, and R 4is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 , R 2 , R 5 is a donor group, and R 4 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 5 is a donor group, and R 2 , R 4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 4 is a donor group, and R 2 , R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 2 is a donor group, and R 4 , R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 , R 4 is a donor group, and R 1 , R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 2 , R 4 , R 5 adopt the same donor group. In one aspect of the present invention, R 1 , R 2 , R 4 , R 5 do not all adopt the same donor group, but are each different donor groups, or only some of the donor groups are the same. In one aspect of the present invention, three of R 1 , R 2 , R 4 , R 5 are donor groups. In one aspect of the present invention, two of R 1 , R 2 , R 4 , R 5 are donor groups. In one aspect of the present invention, R 1 , R 2 , R4 , R 5 The donor groups adopted by R contain deuterium atoms. R 1 , R 2 , R 4 , R 5 The donor groups adopted by R are perdeuterated. In one aspect of the present invention, R 1 , R 2 , R 4 , R 5 One or two of them are substituted or unsubstituted aryl groups. In one aspect of the present invention, R 1 , R 2 , R 4 , R 5 One or two of them are hydrogen atoms or deuterium atoms. Compound group 1 has X 1 being N and X 2 being C-CN, but changing this to a compound group where X 1 is C-CN and X 2 is N is defined as compound group 1'. Compound group 1' also includes compound groups 1'a to 1'c corresponding to compound groups 1a to 1c, and includes compounds that satisfy at least one of the additional conditions described for compound group 1.

[0046] As compound group 2 of the present invention, X 1 is N, X 2 is C-CN, L 1 is a single bond, R 3 is a group represented by general formula (A), X 3 is N, X 4 is C-CN, L 2 is a single bond, and the compound group of general formula (1) can be mentioned. Compound group 2 includes compound group 2a where Y 1 , Y 2 , Y 4 , Y 5 are substituted or unsubstituted aryl groups (for example, substituted or unsubstituted phenyl groups, for example, phenyl groups that may be substituted with deuterium atoms or substituents selected from group E described below, for example, phenyl groups substituted with alkyl groups), and in compound group 2a (for example, Y 1 , Y 2 , Y 4 , Y 5 are the same), Y 1, Y 2 , Y 4 , Y 5 wherein each of Y 1 , Y 2 , Y 4 , Y 5 is the same), Y 1 , Y 4 is a substituted or unsubstituted aryl group (e.g., a substituted or unsubstituted phenyl group, e.g., a phenyl group optionally substituted with a deuterium atom or a substituent selected from the following Group E, e.g., a phenyl group substituted with an alkyl group), and Y 2 , Y 5 is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused), including a compound group 2c (e.g., Y 1 and Y 4 are the same, Y 2 and Y 5 are the same). The compound groups 2a to 2c each further include a compound when satisfying at least one of the additional conditions described in the compound group 1. In the compound group 2, when X 1 is N and X 2 is C-CN, a compound group obtained by changing this such that X 1 is C-CN and X 2 is N is defined as a compound group 2'. The compound group 2' also includes compound groups 2'a to 2'c corresponding to the compound groups 2a to 2c, and includes a compound when satisfying at least one of the additional conditions described in the compound group 1. In the compound group 2', when X 3 is N and X 4 is C-CN, a compound group obtained by changing this such that X 3 is C-CN and X 4 is N is defined as a compound group 2''. The compound group 2'' also includes compound groups 2''a to 2''c corresponding to the compound groups 2a to 2c, and includes a compound when satisfying at least one of the additional conditions described in the compound group 1.

[0047] As compound group 3 of the present invention, X 1 is N, and X 2 is C-CN, L 1 is a single bond, and R 2 is a cyano group (CN), and a compound group of general formula (1) can be exemplified. Compound group 3 includes compound group 3a in which Y 1 and Y 2 are each independently a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group substituted with a deuterium atom or a substituent selected from the following group E, for example, a phenyl group substituted with an alkyl group), compound group 3b in which Y 1 and Y 2 are each independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed), and compound group 3c in which Y 1 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group substituted with a deuterium atom or a substituent selected from the following group E, for example, a phenyl group substituted with an alkyl group), and Y 2 is a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed). Compound groups 3a to 3c each further include compounds that satisfy at least one of the following additional conditions. In one aspect of the present invention, R 1 , R 3 , R 4 , R 5 are donor groups. In one aspect of the present invention, R 1 , R 3 , R 4 are donor groups, and R 5 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 , R 3 , R 4 are donor groups, and R 5 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R3 and R 5 is a donor group, and R 4 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 3 and R 5 are donor groups, and R 4 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 and R 4 and R 5 are donor groups, and R 3 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 4 and R 5 are donor groups, and R 3 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 and R 4 and R 5 are donor groups, and R 1 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 3 and R 4 and R 5 are donor groups, and R 1 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 and R 5 are donor groups, and R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 and R 4 are donor groups, and R 3 and R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 and R 3 are donor groups, and R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 and R 5 are donor groups, and R 1 and R 4is each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 , R 4 is a donor group, and R 1 , R 5 is each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 4 , R 5 is a donor group, and R 1 , R 3 is each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 1 , R 3 , R 4 , R 5 adopts the same donor group. In one aspect of the present invention, R 1 , R 3 , R 4 , R 5 do not all adopt the same donor group, but are each different donor groups, or only some of the donor groups are the same. In one aspect of the present invention, 3 of R 1 , R 3 , R 4 , R 5 are donor groups. In one aspect of the present invention, 2 of R 1 , R 3 , R 4 , R 5 are donor groups. In one aspect of the present invention, the donor group adopted by R 1 , R 3 , R 4 , R 5 contains a deuterium atom. The donor group adopted by R 1 , R 3 , R 4 , R 5 is perdeuterated. In one aspect of the present invention, 1 to 2 of R 1 , R 3 , R 4 , R 5 are substituted or unsubstituted aryl groups. In one aspect of the present invention, 1 to 2 of R 1 , R 3 , R 4 , R 5 are hydrogen atoms or deuterium atoms. Compound group 3 has X 1 being N, and X 2 being C-CN, but changing this to X 1 being C-CN and X 2 being N gives compound group 3'. Compound group 3' also includes compound groups 3'a to 3'c corresponding to compound groups 3a to 3c, and includes compounds that satisfy at least one of the additional conditions described for compound group 3.

[0048] As compound group 4 of the present invention, X 1 being N, X 2 being C-CN, L 1 being a single bond, R 2 being a group represented by general formula (A), X 3 being N, X 4 being C-CN, L 2 being a single bond, compounds of general formula (1) can be mentioned. Compound group 4 includes cases where Y 1 , Y 2 , Y 4 , Y 5 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group that may be substituted with a deuterium atom or a substituent selected from group E described below, for example, a phenyl group substituted with an alkyl group), compound group 4a (for example, Y 1 , Y 2 , Y 4 , Y 5 are the same), Y 1 , Y 2 , Y 4 , Y 5 are each independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group that may be condensed), compound group 4b (for example, Y 1 , Y 2 , Y 4 , Y 5 are the same), Y 1 , Y 4is a substituted or unsubstituted aryl group (e.g., a substituted or unsubstituted phenyl group, e.g., a phenyl group optionally substituted with a deuterium atom or a substituent selected from the group E described below, e.g., a phenyl group substituted with an alkyl group), and Y 2 , Y 5 is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused), and the compound group 4c is included (e.g., Y 1 and Y 4 are the same, Y 2 and Y 5 are the same). The compound groups 4a to 4c each further include a compound when satisfying at least one of the additional conditions described in the compound group 3. In the compound group 4, X 1 is N, and X 2 is C-CN, but this is changed to a compound group where X 1 is C-CN and X 2 is N, and this is defined as the compound group 4'. The compound group 4' also includes compound groups 4'a to 4'c corresponding to the compound groups 4a to 4c, and includes a compound when satisfying at least one of the additional conditions described in the compound group 3. In the compound group 4', X 3 is N, and X 4 is C-CN, but this is changed to a compound group where X 3 is C-CN and X 4 is N, and this is defined as the compound group 4''. The compound group 4'' also includes compound groups 4''a to 4''c corresponding to the compound groups 4a to 4c, and satisfies at least one of the additional conditions described in the compound group 3.

[0049] As the compound group 5 of the present invention, a compound group of the general formula (1) can be exemplified in which X 1 is N, X 2 is C-CN, L 1 is a single bond, and R 1 is a cyano group (CN). The compound group 5 includes Y 1 and Y 2Compound group 5a, Y, wherein each is independently a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from the group E described below, for example, a phenyl group substituted with an alkyl group) 1 and Y 2 Compound group 5b, Y, wherein each is independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed) 1 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from the group E described below, for example, a phenyl group substituted with an alkyl group), and Y 2 is a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed). Compound group 5c is included. Compound groups 5a to 5c each further include a compound that satisfies at least one of the following additional conditions. In one aspect of the present invention, R 2 and R 3 and R 4 and R 5 are donor groups. In one aspect of the present invention, R 2 and R 3 and R 4 are donor groups, and R 5 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 3 and R 4 are donor groups, and R 5 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 and R 3 and R 5 are donor groups, and R 4 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 3 and R 5 are donor groups, and R 4 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 and R4 and R 5 is a donor group, and R 3 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 2 and R 4 and R 5 are donor groups, and R 3 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 and R 4 and R 5 are donor groups, and R 2 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 3 and R 4 and R 5 are donor groups, and R 2 is a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 and R 5 are donor groups, and R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 and R 4 are donor groups, and R 3 and R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 and R 3 are donor groups, and R 4 and R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 and R 5 are donor groups, and R 2 and R 4 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 3 and R 4 are donor groups, and R 2 and R 5 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 4 and R 5 are donor groups, and R 2 and R 3is each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, R 2 , R 3 , R 4 , R 5 adopt the same donor group. In one aspect of the present invention, R 2 , R 3 , R 4 , R 5 do not all adopt the same donor group, but rather are each different donor groups, or only some of the donor groups are the same. In one aspect of the present invention, 3 of R 2 , R 3 , R 4 , R 5 are donor groups. In one aspect of the present invention, 2 of R 2 , R 3 , R 4 , R 5 are donor groups. In one aspect of the present invention, the donor groups adopted by R 2 , R 3 , R 4 , R 5 include a deuterium atom. R 2 , R 3 , R 4 , R 5 are perdeuterated. In one aspect of the present invention, 1 to 2 of R 2 , R 3 , R 4 , R 5 are substituted or unsubstituted aryl groups. In one aspect of the present invention, 1 to 2 of R 2 , R 3 , R 4 , R 5 are hydrogen atoms or deuterium atoms. Compound group 5 has X 1 being N and X 2 being C-CN. However, a compound group where X 1 is C-CN and X 2 is N is defined as compound group 5'. Compound group 5' also includes compound groups 5'a to 5'c corresponding to compound groups 5a to 5c, and includes compounds that satisfy at least one of the additional conditions described for compound group 5.

[0050] As compound group 6 of the present invention, X 1 is N, and X 2 is C-CN, L 1 is a single bond, R 1 is a group represented by general formula (A), and X 3 is N, and X 4 is C-CN, L 2 is a single bond, and a compound group of general formula (1) can be exemplified. Compound group 4 is Y 1 , Y 2 , Y 4 , Y 5 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from group E described below, for example, a phenyl group substituted with an alkyl group), and compound group 6a (for example, Y 1 , Y 2 , Y 4 , Y 5 are the same), Y 1 , Y 2 , Y 4 , Y 5 is each independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed), and compound group 6b (for example, Y 1 , Y 2 , Y 4 , Y 5 are the same), Y 1 , Y 4 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from group E described below, for example, a phenyl group substituted with an alkyl group), and Y 2 , Y 5 is a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be condensed), and includes compound group 6c (for example, Y 1 and Y 4 are the same, Y 2 and Y 5(are the same). The compound groups 6a to 6c each contain compounds when satisfying at least one of the additional conditions described in the compound group 5. The compound group 6 has X 1 being N, and X 2 being C-CN, but changing this to X 1 being C-CN and X 2 being N, the resulting compound group is designated as compound group 6'. The compound group 6' also includes compound groups 6'a to 6'c corresponding to the compound groups 6a to 6c, and contains compounds when satisfying at least one of the additional conditions described in the compound group 5. The compound group 6' has X 3 being N, and X 4 being C-CN, but changing this to X 3 being C-CN and X 4 being N, the resulting compound group is designated as compound group 6''. The compound group 6'' also includes compound groups 6''a to 6''c corresponding to the compound groups 6a to 6c, and contains compounds when satisfying at least one of the additional conditions described in the compound group 5.

[0051] When a compound having a short emission wavelength is provided, it is preferable to employ a compound having a carbazole-9-yl group substituted with an aryl group which may be substituted with a deuterium atom, an alkyl group or an aryl group in the molecule.

[0052] 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 a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. 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 a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Further, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and a sulfur atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, and a nitrogen atom. The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, and a nitrogen atom. Furthermore, the compound represented by the general formula (1) may not contain a hydrogen atom and may be a compound containing a deuterium atom.

[0053] As used herein, "Group A" means a 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 a ring skeleton composed of 5 to 30 atoms), a heteroaryloxy group (e.g., having a ring skeleton composed of 5 to 30 atoms), a heteroarylthio group (e.g., having a ring skeleton composed of 5 to 30 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. The alkyl group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, heteroaryl group, heteroaryloxy group, heteroarylthio group, acyl group, alkenyl group, alkynyl group, alkoxycarbonyl group, aryloxycarbonyl group, heteroaryloxycarbonyl group, silyl group, and nitro group referred to herein may be substituted with a substituent having a structure in which any one or two or more of the deuterium atom and the above substituents constituting Group A are bonded. As used herein, "Group B" means a 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 a ring skeleton composed of 5 to 30 atoms), a heteroaryloxy group (e.g., having a ring skeleton composed of 5 to 30 atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). The alkyl group, alkoxy group, aryl group, aryloxy group, heteroaryl group, heteroaryloxy group, and diarylaminoamino group referred to herein may be substituted with a substituent having a structure in which any one or two or more of the deuterium atom and the above substituents constituting Group B are bonded. As used herein, "Group C" is a 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 a ring skeleton composed of 5 to 20 atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). The alkyl group, aryl group, heteroaryl group, and diarylamino group mentioned herein may be substituted with a substituent having a structure in which one or more of the deuterium atom constituting Group C and the above-mentioned substituents are bonded. As used herein, "Group D" is a 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 a ring skeleton composed of 5 to 20 atoms). The alkyl group, aryl group, and heteroaryl group mentioned herein may be substituted with a substituent having a structure in which one or any two or more of the deuterium atom constituting Group D and the above-mentioned substituents are bonded. As used herein, "Group E" is a 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). The alkyl group and aryl group mentioned herein may be substituted with a substituent having a structure in which one or any two or more of the deuterium atom constituting Group E and the above-mentioned substituents are bonded. When it is described as "substituted or unsubstituted" or "optionally substituted" in this specification, the deuterium atom or substituent to be substituted may be selected, for example, from among Group A, from among Group B, from among Group C, from among Group D, or from among Group E.

[0054] 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 as being limited by these specific examples. In Table 1, among the compounds represented by the general formula (1), Y 1 and Y 2 are phenyl groups (Ar1), X 1 is N, X 2is C-CN, and L 1 is a single bond, and R 3 is a cyano group (CN), and R 1 , R 2 , R 4 , R 5 shows specific examples of compounds in which are the same and are any of D1 to D1426. That is, the R of the compounds having the following structure 1 , R 2 , R 4 , R 5 are shown in Table 1 in order to individually specify the structures of Compounds 1 to 1426.

Chemical formula

Table 1-1

Table 1-2

Table 1-3

Table 1-4

Table 1-5

[0055] In Table 2, the structures of Compounds 1 to 18848500 are shown as variations of the structure represented by General Formula (1). In Table 2, among the compounds represented by General Formula (1), Y 1 and Y 2 are phenyl groups (Ar1), X 1 is N, X 2 is C-CN, L 1 is a single bond, and R 1 to R 5 are specific examples of compounds in which the groups specified in Table 2. That is, the R of the compounds having the following structure 1 to R 5The structures of Compounds 1 to 18848500 are individually specified by sequentially showing them in Table 2. The rows of Compounds 1 to 1426 in Table 2 indicate that Y 1 and Y 2 are fixed to the phenyl group (Ar1), X 1 is fixed to N, X 2 is fixed to C-CN, L 1 is fixed to a single bond, R 3 is fixed to the cyano group (CN), R 1 , R 2 , R 4 , R 5 are the same and are D1 to D1426, and they are sequentially specified as Compounds 1 to 1426. That is, the rows of Compounds 1 to 1426 in Table 2 show the structures of Compounds 1 to 1426 in Table 1 in one row. The rows of Compounds 1427 to 2852 in Table 2 indicate that Y 1 and Y 2 are fixed to the phenyl group (Ar1), X 1 is fixed to N, X 2 is fixed to C-CN, L 1 is fixed to a single bond, R 1 is fixed to a hydrogen atom, R 3 is fixed to the cyano group (CN), R 2 , R 4 , R 5 are the same and are D1 to D1426, and they are sequentially specified as Compounds 1427 to 2852. The rows of Compounds 2853 to 4278 in Table 2 indicate that Y 1 and Y 2 are fixed to the phenyl group (Ar1), X 1 is fixed to N, X 2 is fixed to C-CN, L 1 is fixed to a single bond, R 2 is fixed to a hydrogen atom, R 3 is fixed to the cyano group (CN), R 1 , R 4 , R 5 are the same and are D1 to D1426, and they are sequentially specified as Compounds 2853 to 4278. The structures of the compounds are specified in the same way for the subsequent rows. The rows of Compounds 9979 to 116853 in Table 2 indicate that Y 1 and Y 2 are fixed to the phenyl group (Ar1), X1 is fixed to N, X 2 is fixed to C-CN, L 1 is fixed to a single bond, R 2 and R 5 is fixed to D57, R 3 is fixed to CN, R 1 varies among Ar1~Ar75, R 4 varies among D1~D56, D58~D1426. When there are two types of such variables, first fix Ar1~Ar75 and vary D1~D56, D58~D1426 to assign compound numbers in order. That is, first fix R 1 to Ar1 and identify the compounds with R 4 being D1~D56, D58~D1426 in order as compounds 9979~11403. Next, fix R 1 to Ar2 and identify the compounds with R 4 being D1~D56, D58~D1426 in order as compounds 11404~12828. Next, fix R 1 to Ar3 and identify the compounds with R 4 being D1~D56, D58~D1426 in order as compounds 12829~14253. Proceed with the identification in the same manner. Finally, fix R 1 to Ar75 and identify the compounds with R 4 being D1~D56, D58~D1426 in order as compounds 115429~116853. In the rightmost column of Table 2, the identical ones among R 1 ~R 5 are identified. For example, for the compounds 1~1426 in the uppermost row, R 1 and R 2 and R 4 and R 5 are the same. In Table 2, those marked with "(A)" represent groups represented by the general formula (A), where Y 4 and Y 5 are phenyl groups (Ar1), X 3 is N, X 4 is C-CN, and L 2 is a single bond. Also, those marked with "D" in Table 2 represent deuterium atoms.

Chem.

Table 2-1

Table 2-2

Table 2-3

Table 2-4

Table 2-5

Table 2-6

Table 2-7

Table 2-8

Table 2-9

Table 2-10

Table 2-11

Table 2-12

Table 2-13

Table 2-14

Table 2-15

Table 2-16

Table 2-17

Table 2-18

Table 2-19

Table 2-20

Table 2-21

Table 2-22

Table 2-23

Table 2-24

Table 2-25

Table 2-26

Table 2-27

Table 2-28

Table 2-29

Table 2-30

Table 2-31

Table 2-32

Table 2-33

Table 2-34

Table 2-35

Table 2-36

Table 2-37

Table 2-38

Table 2-39

Table 2-40

Table 2-41

Table 2-42

Table 2-43

Table 2-44

Table 2-45

Table 2-46

Table 2-47

Table 2-48

Table 2-49

Table 2-50

Table 2-51

Table 2-52

Table 2-53

[0056] In Table 2, Y of the general formula (1) 1 and Y 2 are phenyl groups (Ar1), X 1 is N, X 2 is C-CN, L 1 is fixed to a group where it is a single bond, and compounds 1 to 10554355 were specified as those in which groups represented by the general formula (A) do not exist as R 1 to R 5 . In Table 3, for each of compounds 1 to 10554355, compounds in which Y 1 and Y 2 were changed from phenyl groups (Ar1) as shown in Table 3 were successively displayed in tabular form. In Table 3, for the sake of clarity of the correspondence, compounds 1 to 10554355 in which Y 1 and Y 2 are phenyl groups (Ar1) are shown in the first row. In the second row of Table 3, for example, compound 1(1) shows a compound having a structure in which Y 1 and Y 2 of compound 1 were changed to Ar2. Also, compound 2(1) shows a compound having a structure in which Y 1 and Y 2 of compound 2 were changed to Ar2. In the same manner, compound 10554355(1) shows a compound having a structure in which Y 1 and Y 2 of compound 10554355 were changed to Ar2. The structures after compound 1(2) to 10554355(2) in the third row are also specified in the same way as in the second row.

Table 3-1

Table 3-2

Table 3-3

Table 3-4

Table 3-5

Table 3-6

Table 3-7

Table 3-8

Table 3-9

[0057] In Table 2, Y in the general formula (1) 1 and Y 2 are phenyl groups (Ar1), X 1 is N, X 2 is C-CN, L 1 is fixed to a group where it is a single bond, and any one of R 1 to R 3 is a group represented by the general formula (A), and those where Y 3 and Y 4 are phenyl groups (Ar1) were specified as Compounds 10554356 to 18848500. In Table 4, for each of Compounds 10554356 to 18848500, compounds in which Y 4 and Y 5 were changed from phenyl groups (Ar1) as shown in Table 4 were successively shown in tabular form. In Table 4, for the sake of clarity of the correspondence, Y 4 and Y 5Compounds 10554356 to 18848500 where it is a phenyl group (Ar1) are shown in the first row. In the second row of Table 4, for example, compound 10554356(1) shows a compound having a structure in which Y 4 and Y 5 of compound 10554356 are replaced with Ar2. Also, compound 10554357(1) shows a compound having a structure in which Y 4 and Y 5 of compound 10554357 are replaced with Ar2. In the same manner, compound 18848500(1) shows a compound having a structure in which Y 4 and Y 5 of compound 18848500 are replaced with Ar2. The structures after compound 10554356(2) to 18848500(2) in the third row are also specified in the same way as in the second row.

[0058]

Table 4-1

Table 4-2

Table 4-3

Table 4-4

Table 4-5

Table 4-6

Table 4-7

Table 4-8

Table 4-9

[0059] In Table 4, Y of the general formula (1)1 and Y 2 Specific examples of the compound in which Y 1 and Y 2 is a phenyl group (Ar1) are shown as Compounds 10554356 to 18848500, Compounds 10554356(n) to 18848500(n) [where n is 1 to 898]. In Table 5 below, Y 1 and Y 2 of these compounds are sequentially changed to the groups shown in Table 5. In Table 5, each compound is specified by showing the relationship between n and Y 1 and Y 2 of Compounds 1(n) to 6714537752(n). For clarity, in the first row of Table 5, it is indicated that both Y 1 and Y 2 are Ar1. The second row of Table 5 shows the compounds in which both Y 1 and Y 2 of Compounds 10554356 to 18848500, Compounds 10554356(n) to 18848500(n) [where n is 1 to 898] are changed to Ar2, shown sequentially as Compounds 10554356(n) to 18848500(n) [where n is 899 to 1797]. The third row of Table 5 shows the compounds in which both Y

[0060]

Table 5-1

Table 5-2

Table 5-3

Table 5-4

Table 5-5

Table 5-6

[0061] As shown in Table 2, Compounds 1 to 10554355 are compounds in which any one of R 1 ~R 3 is a cyano group. Instead of the cyano group, a variation of a compound in which X 3 and X 4 are N and a group of General Formula (A) in which L 2 is a single bond is bonded is shown in Table 6. That is, in Table 6, variations of compounds having a structure represented by any of the following general formulas are shown. In Table 6, for each of Compounds 1 to 10554355, the cyano group is replaced in order with a group of General Formula (A) having Y 4 and Y 5 shown in Table 6 [X 3 and X 4 are N and L 2 is a single bond]. In the first row of Table 6, for example, Compound 1 (808201) shows a compound having a structure in which the cyano group of Compound 1 is replaced with a group of General Formula (A) in which Y 4 and Y 5 are Ar1, X 3 and X 4 are N, and L 2 is a single bond. Also, Compound 2 (808201) shows a compound having a structure in which the cyano group of Compound 2 is replaced with a group of General Formula (A) in which Y 4 and Y 5 are Ar1, X 3 and X 4 are N, and L 2 is a single bond. Similarly, Compound 10554355 (808201) has the cyano group of Compound 10554355 replaced with Y 4 and Y 5 are Ar1, X3 and X 4 is N, and L 2 represents a compound having a structure in which is a single bond and is a group of general formula (A). The following structures are specified in the same way as in the first row. [Chemical formula] [Table 6-1] [Table 6-2] [Table 6-3] [Table 6-4] [Table 6-5] [Table 6-6] [Table 6-7] [Table 6-8] [Table 6-9]

[0062] In Table 6, specific examples of compounds in which Y 1 and Y 2 are Ar1 are shown as Compound 1(n) to Compound 10554355(n) [where n is from 808201 to 809099]. In Table 7 below, Y 1 and Y 2Compounds in which the groups shown in Table 7 are sequentially changed are shown. For clarity, in the first row of Table 7, Y of Compound 1(n) to Compound 10554355(n) [where n is from 809100 to 809998] 1 and Y 2 are both shown as Ar1. In the second row of Table 7, Y of the compounds in this first row 1 and Y 2 are both changed to Ar2, and the compounds are sequentially shown as Compound 1(n) to Compound 10554355(n) [where n is from 809999 to 810897]. In the third row of Table 5, Y of the compounds in the first row 1 and Y 2 are both changed to Ar3, and the compounds are sequentially shown as Compound 1(n) to Compound 10554355(n) [where n is from 810898 to 811796]. The structure of the compounds is specified in the same manner hereinafter.

[0063]

Table 7-1

Table 7-2

Table 7-3

Table 7-4

Table 7-5

Table 7-6

[0064] All compounds identified by the above numbers are assumed to be individually disclosed. Among the above specific examples of compounds, when there are rotational isomers, the mixture of rotational isomers and each separated rotational isomer are also assumed to be disclosed in this specification. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1 to 18848500, Compounds 1(n) to 18848500(n) where n is from 1 to 898, Compounds 10554356(n) to 18848500(n) where n is from 899 to 808200, and Compounds 1(n) to 10554355(n) where n is from 808201 to 1617300. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1 to 18848500 and Compounds 1(n) to 18848500(n) where n is from 1 to 74. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 18848500(n) where n is from 75 to 746. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 18848500(n) where n is from 747 to 870. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 18848500(n) where n is from 871 to 898. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 758641 to 758715. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 808201 to 808275. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 808276 to 809071. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 809072 to 809099. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 809100 to 876524. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 876525 to 1480652. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 1480653 to 1592128. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 10554355(n) where n is from 1592129 to 1617300.In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compound 1(n) to 10554355(n) [where n is from 1 to 808200].

[0065] Examples of the group of compounds represented by General Formula (1) are given below.

Chemical formula

Chemical formula

[0066] Examples of another group of compounds represented by General Formula (1) are given below.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0067] Examples of another group of compounds represented by General Formula (1) are given below.

Chemical formula

[0068] Examples of another group of compounds represented by General Formula (1) are given below.

Chemical formula

Chemical formula

Chemical formula

[0069] Examples of another group of compounds represented by the general formula (1) are given below.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

Chem.

[0070] Examples of another group of compounds represented by the general formula (1) are given below.

Chem.

[0071] Examples of another group of compounds represented by the general formula (1) are given below.

Chem.

[0072] Examples of another group of compounds represented by the general formula (1) are given below.

Chem.

[0073] When it is intended to use, for example, an organic layer containing the compound represented by the general formula (1) to form a film by a vapor deposition method, the molecular weight of the compound represented by the general formula (1) is preferably 1500 or less, more preferably 1200 or less, and still more preferably 1000 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1). The compound represented by the general formula (1) is useful as a luminescent material and can be used as a delayed fluorescence material. For example, among the compounds represented by the general formula (1), there are compounds containing a large amount of delayed fluorescence components. The organic light-emitting device using the compound represented by the general formula (1) has good light-emitting characteristics. For example, among the compounds represented by the general formula (1), there are compounds that can extend the device life when used in an organic light-emitting device. For example, among the compounds represented by the general formula (1), there are compounds that can increase the light-emitting efficiency when used in an organic light-emitting device. For example, among the compounds represented by the general formula (1), there are compounds that can lower the driving voltage when used in an organic light-emitting device. The compound represented by the general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using the coating method, it is possible to form a film even with a compound having a relatively large molecular weight. The compound represented by the general formula (1) has the advantage of being easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify and increase the purity.

[0074] By applying the present invention, it is also conceivable to use a compound containing a plurality of structures represented by the general formula (1) in the molecule as a luminescent material. For example, it is conceivable to use, as a light-emitting material, a polymer obtained by previously introducing a polymerizable group into the structure represented by the general formula (1) and polymerizing the polymerizable group. For example, a monomer containing a polymerizable functional group is prepared at any site of the general formula (1), and this monomer is polymerized alone or copolymerized with other monomers to obtain a polymer having a repeating unit, and it is conceivable to use the polymer as a light-emitting material. Alternatively, it is also conceivable to obtain dimers or trimers by coupling compounds having the structure represented by the general formula (1) and use them as light-emitting materials.

[0075] Examples of the polymer having a repeating unit containing the structure represented by the general formula (1) include polymers containing the structure represented by any of the following two general formulas.

Chemical formula

[0076] In the above general formula, Q represents a group containing the structure represented by the general formula (1), and L 1 and L 2 represent linking groups. The number of carbon atoms of the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group preferably has a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L 11 represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. In the above general formula, R 101 , R 102 , R 103 and R 104Each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent herein is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L 1 and L 2 The linking group represented by can be bonded to any site of the general formula (1) constituting Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.

[0077] As specific structural examples of the repeating unit, the structures represented by the following formulas can be cited.

Chemical formula

[0078] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of the general formula (1), reacting the following compound using it as a linker to introduce a polymerizable group, and polymerizing the polymerizable group.

Chemical formula

[0079] A polymer containing a structure represented by the general formula (1) in the molecule may be a polymer consisting only of repeating units having the structure represented by the general formula (1), or may be a polymer containing repeating units having other structures. Further, the repeating units having the structure represented by the general formula (1) contained in the polymer may be of a single type or two or more types. Examples of the repeating units having no structure represented by the general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene can be mentioned.

[0080] In one embodiment, the compound represented by the general formula (1) is a light-emitting material. Among the compounds represented by the general formula (1), there are compounds having a long emission lifetime. When the compound represented by the general formula (1) is used in an organic light-emitting device, the light-emitting characteristics can be improved. For example, among the compounds represented by the general formula (1), there are compounds that can extend the device lifetime when used in an organic light-emitting device. In one embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence. Among the compounds represented by the general formula (1), there are compounds having a large ratio of the delayed fluorescence component. For example, compounds in which 80% or more of the total emission is the delayed fluorescence component, for example, 90% or more of the total emission is the delayed fluorescence component are included. In one embodiment of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the UV region, the blue, green, yellow, orange, or red region (for example, 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. In one embodiment of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the red or orange region (for example, about 620 nm to about 780 nm, about 650 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, 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. In certain embodiments of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the blue region (e.g., about 400 nm to about 490 nm, about 475 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the ultraviolet spectral region (e.g., 280 - 400 nm). In certain embodiments of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the infrared spectral region (e.g., 780 nm to 2 μm).

[0081] The electronic properties of the small molecule chemical substance library can be calculated using known ab initio quantum chemical calculations. For example, using time-dependent density functional theory with 6-31G* as the basis and a function group known as the Becke three-parameter, Lee-Yang-Parr hybrid functional, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) is analyzed to screen for molecular fragments (portions) having a HOMO above a specific threshold and a LUMO below a specific threshold. Thereby, 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. Also, 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 severely restrict the acceptor and donor moieties to a specific three-dimensional configuration, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties. In certain embodiments, the compound library is selected using one or more of the following properties. 1. Emission near a specific wavelength 2. Calculated triplet state above a specific energy level 3. ΔE below a specific value ST Value 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In certain embodiments, the difference (ΔE ST ) between the lowest singlet excited state and the lowest triplet excited state at 77 K 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 certain embodiments, 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. In certain embodiments, the compound represented by general formula (1) exhibits a quantum yield of greater 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.

[0082] [Synthesis method of the compound represented by general formula (1)] The compound represented by general formula (1) includes novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. The compound represented by general formula (1) has R 1~R 5 Among 2 to 4 of them, each is independently a donor group. For example, by reacting a substituted or unsubstituted carbazole with a precursor in which the site of the donor group is a fluorine atom, a compound of general formula (1) in which the substituted or unsubstituted carbazol-9-yl group is a donor group can be synthesized. For details of the reaction conditions, the examples described later can be referred to.

[0083] [Composition using the compound represented by general formula (1)] In one embodiment, it is combined with the compound represented by general formula (1), the compound is dispersed, covalently bonded to the compound, coated with the compound, supported by the compound, or used together with one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) that associate with the compound to form a solid film or layer. For example, a film can be formed by combining the compound represented by general formula (1) with an electroactive material. In some cases, the compound represented by general formula (1) may be combined with a hole-transporting polymer. In some cases, the compound represented by general formula (1) may be combined with an electron-transporting polymer. In some cases, the compound represented by general formula (1) may be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by general formula (1) may be combined with a copolymer having both a hole-transporting part and an electron-transporting part. According to the above embodiments, electrons and / or holes formed in the solid film or layer can be made to interact with the compound represented by general formula (1).

[0084] [Formation of film] In one embodiment, a film containing the compound represented by the general formula (1) can be formed by a wet process. In the wet process, a solution in which a composition containing the compound represented by the general formula (1) is dissolved is applied to a surface, and a film is formed after removing the solvent. Examples of the wet process include, but are not limited to, the spin coating method, the slit coating method, the inkjet method (spray method), the gravure printing method, the offset printing method, and the flexographic printing method. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound represented by the general formula (1) is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that increases the solubility of the compound contained in the composition in the organic solvent can be introduced into the compound. In one embodiment, a film containing the compound represented by the general formula (1) can be formed by a dry process. In one embodiment, a vacuum evaporation method can be employed as the dry process, but it is not limited thereto. When the vacuum evaporation method is employed, the compounds constituting the film may be co-evaporated from individual evaporation sources, or may be co-evaporated from a single evaporation source in which the compounds are mixed. When using a single evaporation source, a mixed powder obtained by mixing the powders of the compounds may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting each compound and then cooling it may be used. In one embodiment, by performing co-evaporation under the condition that the evaporation rates (weight loss rates) of the plurality of compounds contained in a single evaporation source are identical or substantially identical, a film having a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the evaporation source can be formed. If a plurality of compounds are mixed at the same composition ratio as the composition ratio of the film to be formed to form an evaporation source, a film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-evaporated compound has the same weight loss rate can be specified and adopted as the temperature during co-evaporation.

[0085] [Examples of Use of the Compound Represented by the General Formula (1)] By using the compound represented by the general formula (1), an organic light-emitting device with excellent performance can be fabricated. In certain embodiments of the present invention, an organic electroluminescence device can be fabricated using the compound represented by the general formula (1). In certain embodiments of the present invention, a CMOS (complementary metal-oxide-semiconductor) can be fabricated using the compound represented by the general formula (1). In certain embodiments of the present invention, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using the compound represented by the general formula (1). The compound represented by the general formula (1) is useful as a material for organic light-emitting devices. It is particularly preferably used for organic light-emitting diodes and the like. Organic light-emitting diode: One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In certain embodiments, 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 certain embodiments, the compound represented by the general formula (1) includes a delayed fluorescence (delayed fluorescence material) that emits delayed fluorescence. In certain embodiments, the present invention provides a delayed fluorescence material having the structure represented by the general formula (1). In certain embodiments, the present invention relates to the use of the compound represented by the general formula (1) as a delayed fluorescence material. In certain embodiments, the compound represented by the general formula (1) can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF (delayed fluorescence materials). In certain embodiments, the compound represented by the general formula (1) can also be used as a hole-transporting material. In certain embodiments, the compound represented by the general formula (1) can be used as an electron-transporting material. In certain embodiments, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In certain embodiments, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. 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 a film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) with respect to the film-forming surface affects or determines the propagation direction of the light emitted by the aligning compound. In one embodiment, by aligning 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. For details of the use in the organic light-emitting device, reference can be made to

[0063] to

[0099] of WO2022 / 168956A1, which is incorporated herein by reference as part of this specification. For example, the compound represented by the general formula (1) can be used in combination with the host material described in

[0123] to

[0145] of WO2022 / 270602A1, which is incorporated herein by reference as part of this specification, or in combination with the dopant described in

[0006] to

[0129] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification.

Examples

[0086] The features of the present invention will be described more specifically with reference to the following examples. The materials, treatment contents, treatment procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The evaluation of the light-emitting characteristics was performed using a source meter (manufactured by Keithley Instruments, Inc.: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies, Inc.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), an optical spectrometer (manufactured by Ocean Optics, Inc.: USB2000), a spectro-radiometer (manufactured by Topcon Corporation: SR-3), and a streak camera (model C4334 manufactured by Hamamatsu Photonics K.K.). The measurement of the HOMO and LUMO energies was performed by atmospheric photoelectron spectroscopy (AC-3 manufactured by Riken Keiki Co., Ltd., etc.).

[0087] (Example 1) Synthesis of Compound A

Chemical formula

[0088] Synthesis of Intermediate a Under a nitrogen atmosphere, a degassed mixed solution of tetrahydrofuran (500 mL) / water (250 mL) was added to a mixture of 2,3,4-trifluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile (11.5 g, 48.8 mmol), 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (14.9 g, 51.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.42 g, 4.87 mmol), and sodium carbonate (10.3 g, 97.5 mmol). The temperature was raised to 75 °C and stirred overnight. After completion of the reaction, it was cooled to room temperature, water was added, and the precipitate was filtered. The obtained precipitate was washed with hot 1,2-dichlorobenzene and ethyl acetate to obtain Intermediate a (6.73 g, 16.3 mmol, yield 33.4%). ASAP mass spectrum analysis: Theoretical value 412.38, Observed value 413.55.

[0089] Synthesis of Compound A Under a nitrogen atmosphere, dimethylformamide (350 mL) was added to a mixture of Intermediate a (6.73 g, 16.3 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (14.3 g, 81.6 mmol), and potassium carbonate (13.5 g, 97.9 mmol). The temperature was raised to 100 °C and stirred overnight. After completion of the reaction, it was cooled to room temperature, water was added, the precipitated precipitate was filtered, and washed with methanol. The obtained precipitate was purified by silica gel column chromatography and then recrystallized to obtain Compound A (4.55 g, 5.18 mmol, yield 31.8%). 1 H-NMR (400 MHz, CDCl3): δ 8.82 (s, 1H), 7.50 - 7.41 (m, 6H), 7.35 - 7.31 (m, 4H). ASAP mass spectrum analysis: Theoretical value 878.14, Observed value 878.98. On a quartz substrate, the vacuum degree is 1×10-3 When measured using a neat thin film obtained by vapor-depositing Compound A at less than Pa, the energy of the HOMO of Compound A was 5.96 eV and the energy of the LUMO was 3.49 eV.

[0090] (Example 2) Synthesis of Compounds B and C [Chemical formula]

[0091] Synthesis of Intermediate b Under a nitrogen atmosphere, dimethylformamide (500 mL) was added to a mixture of 2,5-difluoro-1,4-benzenedicarbonitrile (9.30 g, 51.1 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (22.4 g, 128 mmol), and potassium carbonate (21.8 g, 153 mmol), and the temperature was raised to 100 °C and stirred for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitated precipitate was filtered and washed with methanol. The obtained precipitate was washed with hot toluene and methanol to obtain Intermediate b (21.6 g, 45.4 mmol, yield 89.0%). 1 1H-NMR (400 MHz, CDCl3): δ 8.28 (s, 2H). ASAP mass spectrum analysis: Theoretical value 474.62, Observed value 475.33.

[0092] Synthesis of Intermediate c Under a nitrogen atmosphere, anhydrous tetrahydrofuran (80 mL) was added to Intermediate b (12.0 g, 25.3 mmol), and the mixture was cooled to 0 °C. Then, lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 30 mL, 39 mmol) was added, and the temperature was raised to room temperature and stirred overnight. Subsequently, after the reaction solution was cooled to 0 °C again, hydrogen chloride (about 6 M ethanol-diluted solution, 100 mL) was added, the temperature was raised to room temperature, and the mixture was stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitated precipitate was filtered. The obtained precipitate was washed with water to obtain Intermediate c (10.2 g, 20.8 mmol, yield 79.5%). ASAP Mass Spectrum Analysis: Theoretical value 528.11, Observed value 491.65 (-HCl).

[0093] Synthesis of Compound B Under a nitrogen atmosphere, dimethylformamide (120 mL) was added to a mixture of intermediate c (6.20 g, 12.6 mmol), benzoylacetonitrile (3.66 g, 25.2 mmol), benzaldehyde (2.68 g, 25.2 mmol), and sodium carbonate (4.01 g, 37.8 mmol). The temperature was raised to 80 °C and stirred overnight. After completion of the reaction, the reaction mixture was cooled to room temperature, water was added, and the precipitated solid was filtered and washed with methanol. The obtained solid was purified by silica gel column chromatography and then recrystallized to obtain compound B (2.75 g, 3.90 mmol, yield 30.9%). 1 1H-NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 8.33 (s, 1H), 7.46 - 7.40 (m, 6H), 7.33 - 7.29 (m, 4H). ASAP Mass Spectrum Analysis: Theoretical value 704.89, Observed value 705.69. The measurement was carried out using a neat film obtained by vapor-depositing compound B on a quartz substrate under a vacuum of less than 1×10 -3 Pa. The energy of the HOMO of compound B was 6.02 eV and the energy of the LUMO was 3.64 eV.

[0094] Synthesis of Intermediate d Under a nitrogen atmosphere, anhydrous tetrahydrofuran (80 mL) was added to intermediate b (12.0 g, 25.3 mmol), and the mixture was cooled to 0 °C. Then, lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 60 mL, 78 mmol) was added, and the temperature was raised to room temperature and stirred overnight. Subsequently, the reaction solution was cooled to 0 °C again, and a hydrogen chloride solution (approx. 6 M ethanol-diluted solution, 200 mL) was added. The temperature was raised to room temperature and stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitated solid was filtered. The obtained solid was washed with water to obtain intermediate d (10.1 g, 17.4 mmol, yield 63.4%).

[0095] Synthesis of Compound C Under a nitrogen atmosphere, dimethylformamide (30 mL) was added to a mixture of intermediate d (3.00 g, 5.16 mmol), benzoylacetonitrile (2.25 g, 15.5 mmol), benzaldehyde (1.64 g, 15.5 mmol), and sodium carbonate (3.28 g, 31.0 mmol). The temperature was raised to 80 °C and the mixture was stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitated solid was filtered and washed with methanol. The obtained solid was purified by silica gel column chromatography and then recrystallized to obtain compound C (0.789 g, 3.90 mmol, yield 21.7%). 1 H-NMR (400 MHz, CDCl3): δ 9.05 (s, 1H), 7.43 - 7.29 (m, 6H), 7.22 - 7.10 (m, 4H). ASAP mass spectrum analysis: Theoretical value 935.16, Observed value 935.63. On a quartz substrate, a neat film obtained by vapor-depositing compound C under a vacuum of less than 1×10 -3 Pa was used for measurement. The energy of the HOMO of compound C was 6.19 eV and the energy of the LUMO was 3.36 eV.

[0096] (Example 3) Synthesis of Compound D

Chemical formula

[0097] Synthesis of Intermediate e Under a nitrogen atmosphere, anhydrous xylene (60 mL) was added to a mixture of 2,5-difluoro-1,4-benzenedicarbonitrile (4.70 g, 28.6 mmol), bromobenzene-d5 (2.32 g, 14.3 mmol), palladium(II) acetate (0.321 g, 1.43 mmol), tricyclohexylphosphine (1.21 g, 4.30 mmol), 2-ethylhexanoic acid (0.23 mL, 1.4 mmol), and potassium carbonate (2.97 g, 21.5 mmol). The temperature was raised to 110 °C and the mixture was stirred overnight. After completion of the reaction, the precipitate was filtered off, the solution was recovered, and concentrated under reduced pressure. The resulting mixture was purified by silica gel column chromatography to obtain intermediate e (4.55 g, 1.03 mmol, crude yield 130%). Further purification was not performed, and it was used directly in the next reaction. 1 1H-NMR (400 MHz, CDCl3): δ 7.49 (dd, J = 7.1, 4.6 Hz, 1H). ASAP mass spectrum analysis: theoretical value 245.24, observed value 246.18.

[0098] Synthesis of Intermediate f Under a nitrogen atmosphere, dimethylformamide (190 mL) was added to a mixture of intermediate e (4.55 g, 18.6 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (7.15 g, 40.8 mmol), and potassium carbonate (7.69 g, 55.7 mmol). The temperature was raised to 100 °C and the mixture was stirred for 3 hours. After completion of the reaction, it was cooled to room temperature, water was added, and the precipitated solid was filtered off and washed with methanol. The resulting solid was purified by silica gel column chromatography and then recrystallized to obtain intermediate f (3.48 g, 6.26 mmol, yield 34.0%). 1 1H-NMR (400 MHz, CDCl3): δ 8.17 (s, 1H). ASAP mass spectrum analysis: theoretical value 555.75, observed value 556.62.

[0099] Synthesis of Intermediate g Under a nitrogen atmosphere, anhydrous tetrahydrofuran (40 mL) was added to intermediate f (1.92 g, 3.45 mmol) and cooled to 0 °C. Then, lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 3.9 mL, 5.1 mmol) was added, and the temperature was raised to room temperature and stirred overnight. Subsequently, after the reaction solution was cooled to 0 °C again, hydrogen chloride (about 6 M ethanol-diluted solution, 14 mL) was added, the temperature was raised to room temperature, and the mixture was stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitated precipitate was filtered. The obtained precipitate was washed with water and methanol to obtain intermediate g (2.15 g, 3.75 mmol, crude yield 109%). No further purification was performed, and it was used directly in the next reaction. ASAP mass spectrum analysis: Theoretical value 609.24, Observed value 573.66 (-HCl).

[0100] Synthesis of Compound D Under a nitrogen atmosphere, dimethylformamide (40 mL) was added to a mixture of intermediate g (2.15 g, 3.75 mmol), benzoylacetonitrile (0.590 g, 4.12 mmol), benzaldehyde (0.430 g, 4.12 mmol), and sodium carbonate (1.19 g, 11.3 mmol). The temperature was raised to 80 °C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, the precipitated precipitate was filtered, and washed with methanol. The obtained precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound D (0.900 g, 1.14 mmol, yield 31%). 1 H-NMR (400 MHz, CDCl3): δ 8.38 (s, 1H), 7.46 - 7.43 (m, 2H), 7.34 - 7.32 (m, 8H). ASAP mass spectrum analysis: Theoretical value 786.02, Observed value 786.84. The measurement was carried out using a neat thin film obtained by vapor-depositing compound D on a quartz substrate under a vacuum of less than 1×10 -3 Pa. The energy of the HOMO of compound D was 6.15 eV, and the energy of the LUMO was 3.82 eV.

[0101] (Example 4) Synthesis of Compound E [Chemical formula]

[0102] Synthesis of Intermediate h Under a nitrogen atmosphere, dimethylformamide (60 mL) was added to a mixture of 2,5-difluoro-1,4-benzenedicarbonitrile (1.00 g, 6.09 mmol), 12H-[1]benzothieno[2,3-a]carbazole (3.83 g, 14.0 mmol), and cesium carbonate (4.37 g, 13.4 mmol). The temperature was raised to 100 °C and the mixture was stirred for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitated solid was filtered and washed with methanol. The obtained solid was washed with hot toluene and methanol to obtain Intermediate h (3.67 g, 5.47 mmol, 89.7% yield). 1 H-NMR (400 MHz, DMSO-d6): δ 9.23 (s, 1H), 8.59 - 8.44 (m, 4H), 8.15 (d, J = 7.1 Hz, 1H), 7.78 - 7.51 (m, 5H). ASAP mass spectrum analysis: Theoretical value 670.81, Observed value 671.44.

[0103] Synthesis of Intermediate i Under a nitrogen atmosphere, anhydrous tetrahydrofuran (60 mL) was added to Intermediate h (3.66 g, 5.47 mmol), and the mixture was cooled to 0 °C. Then, lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 12 mL, 15 mmol) was added, and the temperature was raised to room temperature and stirred overnight. Subsequently, the reaction solution was cooled to 0 °C again, and a hydrogen chloride solution (about 6 M ethanol-diluted solution, 22 mL) was added. The temperature was raised to room temperature and stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitated solid was filtered. The obtained solid was washed with water and methanol to obtain Intermediate i (2.38 g, 3.29 mmol, 60.1% yield). 1H-NMR (400 MHz, DMSO-d6): δ 9.07 (s, 1H), 8.81 (s, 1H), 8.63 - 8.41 (m, 9H), 7.94 - 7.82 (m, 2H), 7.79 - 7.44 (m, 12H).

[0104] Synthesis of Compound E Under a nitrogen atmosphere, dimethylformamide (30 mL) was added to a mixture of intermediate i (2.38 g, 3.29 mmol), benzoylacetonitrile (0.888 g, 6.12 mmol), benzaldehyde (0.649 g, 6.12 mmol), and sodium carbonate (3.89 g, 36.7 mmol). The temperature was raised to 80 °C and stirred overnight. After completion of the reaction, it was cooled to room temperature, water was added, and the precipitated precipitate was filtered and washed with methanol. The obtained precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound E (1.70 g, 1.89 mmol, yield 61.7%). 1 H-NMR (400 MHz, CDCl3): δ 8.88 (s, 1H), 8.45 (s, 1H), 8.35 - 8.21 (m, 5H), 8.19 - 8.07 (m, 4H), 7.88 - 7.75 (m, 2H), 7.69 - 7.23 (m, 15H), 7.22 - 7.14 (m, 4H). ASAP mass spectrum analysis: Theoretical value 901.08, Observed value 901.65. On a quartz substrate, a neat thin film obtained by depositing compound E under a vacuum of less than 1 × 10 -3 Pa was used for measurement. The energy of the HOMO of compound E was 6.03 eV and the energy of the LUMO was 3.69 eV.

[0105] (Example 5) Synthesis of Compound F

Chemical formula

[0106] Synthesis of Intermediate j Under a nitrogen atmosphere, a degassed mixed solution of tetrahydrofuran (300 mL) / water (100 mL) was added to a mixture of 2,2′-(2,5-difluoro-1,4-phenylene)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborolane] (2.67 g, 7.29 mmol), 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (4.47 g, 15.3 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.51 g, 0.73 mmol), and sodium carbonate (3.87 g, 36.5 mmol). The temperature was raised to 75 °C and stirred overnight. After completion of the reaction, it was cooled to room temperature, water was added, and the precipitate was filtered. The obtained precipitate was washed with hot 1,2-dichlorobenzene and ethyl acetate to obtain intermediate j (3.40 g, 5.44 mmol, yield 74.6%). ASAP mass spectrum analysis: Theoretical value 624.65, Observed value 625.63.

[0107] Synthesis of Compound F Under a nitrogen atmosphere, dimethylformamide (500 mL) was added to a mixture of intermediate j (3.40 g, 5.44 mmol), 12H-[1]benzothieno[2,3-a]carbazole (4.46 g, 16.3 mmol), and cesium carbonate (5.32 g, 16.3 mmol). The temperature was raised to 150 °C and stirred overnight. After completion of the reaction, it was cooled to room temperature, water was added, the precipitated precipitate was filtered, and washed with methanol. The obtained precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound F (1.16 g, 1.03 mmol, yield 18.8%). 1 H-NMR (400 MHz, CDCl3): δ 9.07 (s, 1H), 8.26 (d, J = 7.3 Hz, 1H), 8.16 - 8.07 (m, 3H), 7.75 (d, J = 7.8 Hz, 1H), 7.53 - 7.30 (m, 11H), 7.24 - 7.18 (m, 4H). ASAP mass spectrum analysis: Theoretical value 1131.75, Observed value 1131.90. On a quartz substrate, the vacuum degree is 1×10 -3When measured using a neat thin film obtained by vapor-depositing Compound F at less than Pa, the energy of the HOMO of Compound F was 6.01 eV and the energy of the LUMO was 3.80 eV.

[0108] (Example 6) Synthesis of Compound G [Chemical formula]

[0109] Synthesis of Intermediate k Phenyl-d5-boronic acid (6.61 g, 52.1 mmol), tetrakis(triphenylphosphine)palladium(0) (2.74 g, 2.37 mmol), and potassium carbonate (13.1 g, 94.8 mmol) were added to a reaction vessel, followed by nitrogen substitution. Then, 1-bromo-3,4,5-trifluorobenzene (10 g, 47.4 mmol), tetrahydrofuran (THF, 150 mL), and water (75 mL) were added. After stirring at 80 °C, the mixture was heated and stirred overnight. The reaction vessel was cooled to room temperature, filtered through celite, and the solid was washed with water and methanol. After recrystallization from methanol, a white solid intermediate k was obtained (7.2 g, 33.8 mmol, yield 71%).

[0110] Synthesis of Intermediate m Put the intermediate k (4.33 g, 20.3 mmol) into a 1 L three-necked flask, replace the air with nitrogen, add 500 mL of THF, and cool it to -80 °C. After dropping 1.0 mol / L lithium diisopropylamide n-hexane-tetrahydrofuran solution (22.3 mL, 22.3 mmol), stir for 15 minutes, add iodine (5.67 g, 22.3 mmol), and stir for 30 minutes. Then, after dropping 1.0 mol / L lithium diisopropylamide n-hexane-tetrahydrofuran solution (22.3 mL, 22.3 mmol), stir for 20 minutes, and add iodine (6.19 g, 24.4 mmol). After warming to room temperature, add saturated aqueous ammonium chloride solution and ethyl acetate, extract the organic layer, and then wash the organic layer with saturated brine. Dry over magnesium sulfate, filter, and concentrate. The obtained crude product was recrystallized from methanol to obtain intermediate m (6.98 g, 15.0 mmol, yield 74%).

[0111] Synthesis of Intermediate n Put the intermediate m (7.1 g, 15.3 mmol) and copper(I) cyanide (2.05 g, 22.9 mmol) into a 100 mL three-necked flask, replace the air with nitrogen, add N,N-dimethylformamide (DMF, 35 mL), heat to 100 °C, and stir for 19 hours. Add toluene, filter through celite, add aqueous ammonia, extract the organic layer, and wash the organic layer with saturated brine. Dry over magnesium sulfate, filter, and concentrate. The obtained crude product was purified by silica gel chromatography to obtain white solid intermediate n (3.6 g, 9.89 mmol, yield 65%). ASAP mass spectrum analysis: C 13 D5F3IN: Theoretical value 364.0, Observed value 365.1.

[0112] Synthesis of Intermediate p Place the intermediate n (2.66 g, 7.3 mmol) into a 500 mL three-necked flask, replace the air with nitrogen, then add 65 mL of THF, cool it to -78 °C, and dropwise add a 2 M solution of isopropylmagnesium chloride in THF (10 mL, 20 mmol). Stir for 30 minutes. Add 1 M zinc chloride solution in THF (50 mL, 50 mmol) and stir for 1 hour. Warm up to room temperature, add tetrakis(triphenylphosphine)palladium(0) (0.95 g, 0.82 mmol), 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (4.79 g, 16.42 mmol), and 65 mL of THF, heat to 70 °C, and stir for 15 hours. Cool to room temperature, add ethyl acetate and water, and extract the organic layer. Wash the organic layer with saturated brine, dry over magnesium sulfate, and filter. Concentrate the filtrate and purify it by silica gel column chromatography to obtain the white solid intermediate p (2.52 g, 5.10 mmol, yield 70%). 1 1H-NMR (400 MHz, CDCl3): δ 7.73 - 7.77 (m, 4H), 7.56 - 7.62 (m, 2H), 7.48 - 7.55 (m, 4H). ASAP MS spectrum analysis: C 30 H 10 D5F3N4: Theoretical value 493.2, Observed value 494.4.

[0113] Synthesis of Compound G Place the intermediate p (2.2 g, 4.46 mmol), carbazole-1,2,3,4,5,6,7,8-d8 (3.13 g, 17.8 mmol), and potassium carbonate (3.08 g, 22.3 mmol) into a 100 mL three-necked flask, replace the air with nitrogen, and then add 15 mL of DMF. Heat to 120 °C, stir for 13 hours, cool to room temperature, add water, filter the precipitated solid, and wash it with methanol. Purify the obtained solid by silica gel chromatography to obtain the yellow solid compound G (3.47 g, 3.61 mmol, yield 81%). 1H-NMR (400 MHz, CDCl3): δ 7.41 - 7.46 (m, 2H), 7.24 - 7.30 (m, 4H), 6.94 - 6.98 (m, 4H) ASAP mass spectrum analysis: C 66 H 10 D 29 N7 theoretical value 958.51, observed value 960.0.

[0114] (Example 7) Synthesis of Compound H

Chemical Structure

[0115] Synthesis of Intermediate 3a The mixed solvent of THF (100 mL) and water (50 mL) of Compound 1a (3.97 g, 10.3 mmol) was purged with nitrogen bubbling. Then, under a nitrogen stream, Compound 2a (6.34 g, 21.7 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.43 g, 0.62 mmol), and sodium carbonate (4.38 g, 41.3 mmol) were added to this solution, and the mixture was heated and stirred at 75 °C for 18 hours. The reaction vessel was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water, dichloromethane, ethyl acetate, and methanol. The obtained solid was filtered and dried to give a light gray solid intermediate 3a (6.46 g, 10.0 mmol, yield 97%). ASAP MS spectrum analysis: C 40 H 21 F3N6: theoretical value 642.18, observed value 643.53.

[0116] Synthesis of Compound H Under a nitrogen stream, potassium carbonate (6.91 g, 50.0 mmol) was added to a solution of intermediate 3a (6.46 g, 10.0 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (7.01 g, 40.0 mmol) in DMF (100 mL), and the mixture was stirred at 150 °C for 15 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:hexane = 7:3) to obtain a yellow solid compound H (3.46 g, 3.12 mmol, yield 31%). 1 1H-NMR (400 MHz, CDCl3): δ 8.99 (s, 1H), 7.46 (m, 12H), 7.32(m, 8H) 7.59 - 7.52(m, 4H), 7.38 - 7.26 (m, 8H), 7.10 - 7.12(m, 4H). ASAP MS spectrum analysis: C 76 H 21 D 24 N9: Theoretical value 1107.53, Observed value 1108.23.

[0117] (Example 8) Synthesis of Compound I

Chemical Structure

[0118] Synthesis of Intermediate 1b Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (20.0 g, 90.8 mmol), phenyl-d5-boronic acid (24.1 g, 190 mmol), sodium carbonate (28.8 g, 272 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.18 g, 4.54 mmol), THF (180 mL), and degassed water (90 mL) were added to a reaction vessel and stirred at 80 °C overnight. The reaction solution was cooled to room temperature, filtered, dissolved in dichloromethane, and the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution was filtered, and the resulting solution was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain white solid intermediate 1b (27.7 g, 88.3 mmol, 80% yield). 1 H-NMR (400 MHz, CDCl3): δ 2.70 (s, 3H). ASAP MS spectrum analysis: C 18 H3D 10 N3S: calculated value 313.44, observed value 314.38.

[0119] Synthesis of Intermediate 2b Under a nitrogen stream, a dichloromethane solution (380 mL) of intermediate 1b (30.00 g, 95.7 mmol) was placed, cooled to 0 °C, and sulfuryl chloride (19.3 mL, 239 mmol) was added dropwise. The temperature was raised to room temperature, acetonitrile was added, and then saturated sodium bicarbonate solution was added until the reaction solution became a basic solution. Dichloromethane and water were added, and the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution obtained after filtration was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain white solid intermediate 2b (23.9 g, 79.1 mmol, 83% yield). ASAP MS spectrum analysis: C 17 D 10 N3Cl: calculated value 301.80, observed value 302.28.

[0120] Synthesis of Intermediate 3b A mixed solvent of THF (78 mL) and water (39 mL) of Compound 1a (3.0 g, 7.85 mmol) was purged with nitrogen. Under a nitrogen stream, to this solution were added Intermediate 2b (5.00 g, 16.5 mol), (triphenylphosphine)palladium(II) dichloride (0.55 g, 0.78 mmol), and sodium carbonate (3.32 g, 31.4 mmol), and the mixture was heated and stirred at 75 °C for 18 hours. The reactor was cooled to room temperature. The solution was filtered, toluene was added to the solid remaining in the funnel, and the mixture was stirred at 100 °C for 1 hour. The reactor was cooled to room temperature. The solution was filtered, and the solid remaining in the funnel was dried under reduced pressure to obtain a light gray solid of Compound 3b (4.76 g, 7.18 mmol, yield 92%). ASAP MS spectrum analysis: C 40 HD 20 F3N6: Theoretical value 662.77, Observed value 664.08

[0121] Synthesis of Compound I Under a nitrogen stream, potassium phosphate (28.6 g, 135 mmol) was added to a solution of Intermediate 3b (12.9 g, 19.4 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (20.3 g, 116 mmol) in dimethyl sulfoxide (DMSO, 194 mL), and the mixture was stirred at 150 °C for 4.5 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:hexane:chloroform = 8:1:1) to obtain a yellow Compound I (12.5 g, 13.8 mmol, yield 71%). 1 1H-NMR (400 MHz, CDCl3): δ 9.00 (s, 1H), ASAP MS spectrum analysis: C 76 HD 44 N9: Theoretical value 1127.66, Observed value 1129.08

[0122] (Example 9) Synthesis of Compound J

Chemical formula

[0123] Synthesis of Intermediate 1c Under a nitrogen stream, potassium carbonate (0.96 g, 6.98 mmol) was added to a solution of compound 3a (1.50 g, 2.33 mmol) and 9H-carbazole-3-carbonitrile (0.98 g, 5.12 mmol) in NMP (46 mL), and the mixture was stirred at 50 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane and purified by column chromatography (dichloromethane) to obtain yellow solid intermediate 1c (1.72 g, 1.74 mmol, 75% yield). 1 H-NMR (400 MHz, CDCl3): δ 9.35 (d, J = 1.6 Hz, 1H), 8.21 (d, J = 0.8 Hz, 2H), 7.97 (d, J = 7.6 Hz, 2H), 7.65 (dd, J = 8.4 Hz, J = 2.4 Hz, 2H), 7.56-7.23 (m, 28H).

[0124] Synthesis of Compound J Under a nitrogen stream, potassium carbonate (1.24 g, 9.1 mmol) was added to a solution of intermediate 1c (2.97 g, 3.00 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.31 g, 7.5 mmol) in N-methyl-2-pyrrolidone (NMP, 60 mL), and the mixture was stirred at 150 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane and purified by column chromatography (dichloromethane) to obtain yellow solid compound J (1.95 g, 1.75 mmol, 57% yield). 1H-NMR (400 MHz, CDCl3): δ 9.23 (s, 1H, rotamer 1), 9.21 (s, 1H, rotamer 2), 7.84 - 7.75 (m, 2H), 7.64 - 7.58 (m, 2H), 7.52 - 7.29 (m, 22H), 7.26 - 7.00 (m, 8H). ASAP MS spectrum analysis: C 78 H 35 D8N 11 : Theoretical value 1142.33, observed value 1143.15.

[0125] (Example 10) Synthesis of compound K

Chemical Structure

[0126] Synthesis of Intermediate 1d Under a nitrogen stream, potassium carbonate (0.64 g, 4.65 mmol) was added to a solution of compound 3a (1.00 g, 1.55 mmol) and carbazole - 1,2,3,4,5,6,7,8 - d8 (0.67 g, 3.87 mmol) in NMP (31 mL), and the mixture was stirred at 50 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in o - dichlorobenzene and purified by column chromatography (toluene:hexane = 1:1) to obtain the yellow solid intermediate 1d (1.00 g, 1.04 mmol, yield 68%). ASAP MS spectrum analysis: C 64 H 21 D 16 N8F: Theoretical value 952.41, observed value 953.62.

[0127] Synthesis of Compound K Under a nitrogen stream, potassium carbonate (0.49 g, 3.18 mmol) was added to a solution of intermediate 1d (1.00 g, 1.04 mmol) and 9H-carbazole-3,6-dicarbonitrile (0.45 g, 2.08 mmol) in NMP (35 mL), and the mixture was stirred at 150 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in o-dichlorobenzene and purified by column chromatography (dichloromethane:hexane = 9:7) to obtain a yellow solid compound K (0.47 g, 0.40 mmol, 39% yield). 1 1H-NMR (400 MHz, CDCl3): δ 9.19 (s, 1H), 7.74 (dd, J = 1.6 Hz, J = 0.8 Hz, 2H), 7.48 - 7.37 (m, 12H) 7.32 - 7.27 (m, 8H), 7.18 (dd, J = 8.8 Hz, J = 0.4 Hz, 2H), 7.00 (dd, J = 8.4 Hz, J = 1.6 Hz, 2H). ASAP MS spectrum analysis: C 78 H 27 D 16 N 11 : Theoretical value 1149.47, Observed value 1150.72.

[0128] (Example 11) Synthesis of compound L

Chemical formula

[0129] Synthesis of Intermediate 1e Under a nitrogen stream, tripotassium phosphate (3.54 g, 16.7 mmol) was added to a solution of compound 3b (3.70 g, 5.58 mmol) and 9H-carbazole-1,2,4,5,6,7,8-d7-3-carbonitrile (2.43 g, 12.2 mmol) in NMP (55 mL), and the mixture was stirred at 50 °C for 15 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane, adsorbed onto silica gel, and purified by column chromatography (dichloromethane:hexane = 9:1) to obtain yellow solid intermediate 1e (2.41 g, 2.35 mmol, 42.3% yield). 1 1H-NMR (400 MHz, CDCl3): δ 9.34 (d, J = 1.6 Hz, 1H, rotamer 1), 9.33 (d, J = 1.6 Hz 1H, rotamer 2). ASAP MS spectrum analysis: C 84 H 21 D 28 N9O2: calculated value 1020.52, observed value 1021.80.

[0130] Synthesis of Compound L Under a nitrogen stream, tripotassium phosphate (0.99 g, 4.68 mmol) was added to a solution of intermediate 1e (2.40 g, 2.34 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.61 g, 3.51 mmol) in NMP (23 mL), and the mixture was stirred at 140 °C for 3 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane, adsorbed onto silica gel, and purified by column chromatography (dichloromethane:hexane = 9:1) to obtain yellow solid compound L (2.02 g, 1.71 mmol, 73.4% yield). 1 1H-NMR (400 MHz, CDCl3): δ 9.23 (s, 1H, rotamer 1), 9.21 (s, 1H, rotamer 2). ASAP MS spectrum analysis: C 78 HD 42 N11 : Theoretical value 1175.63, Observed value 1176.91.

[0131] (Example 12) Synthesis of Compound M

Chemical Structure

[0132] Synthesis of Intermediate 1f Under a nitrogen stream, potassium carbonate (2.18 g, 15.80 mmol) was added to a solution of compound 3b (3.00 g, 4.52 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.96 g, 11.20 mmol) in NMP (90 mL), and the mixture was stirred at 60 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:dichloromethane = 9:1) to obtain yellow compound 1f (3.72 g, 3.81 mmol, 84% yield). 1 1H-NMR (400 MHz, CDCl3): δ 9.02 (s, 1H). ASAP MS spectrum analysis: C 64 HD 36 FN8: Theoretical value 972.54, Observed value 974.30.

[0133] Synthesis of Compound M Under a nitrogen stream, potassium carbonate (1.52 g, 11.0 mmol) was added to a solution of intermediate 1f (4.32 g, 4.43 mmol) and 9H-carbazole-1,2,4,5,6,7,8-d7-3-carbonitrile (1.32 g, 6.64 mmol) in NMP (45 mL), and the mixture was stirred at 130 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in o-dichlorobenzene and purified by column chromatography (dichloromethane:toluene = 1:1) to obtain yellow solid compound M (2.31 g, 2.00 mmol, 45% yield). 1H-NMR (400 MHz, CDCl3): δ 9.10 (s, 1H).

[0134] (Example 13) Synthesis of Compound N

Chemical formula

[0135] Synthesis of Intermediate 1g Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (10.0 g, 45.4 mmol), (3,5-di-tert-butylphenyl)boronic acid (22.3 g, 95.3 mmol), potassium carbonate (18.7 g, 136 mmol), tetrakis(triphenylphosphine)palladium (2.62 g, 2.27 mmol), THF (151 mL), and degassed water (50 mL) were added to a reaction vessel and stirred at 70 °C overnight. The reaction solution was cooled to room temperature, filtered, dissolved in dichloromethane, the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution was filtered, and the resulting solution was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain 1 g of a transparent liquid intermediate (12.84 g, 24.3 mmol, 53% yield). 1 H-NMR(400 MHz, CDCl3): δ 7.86 (d, J=1.6 Hz, 4H), 7.63 (t, J = 1.6 Hz, 2H), 2.70 (s, 3H), 1.40 (s, 36H). ASAP MS spectrum analysis: C 34 H 45 N3S: Theoretical value 527.33, Observed value 528.64.

[0136] Synthesis of Intermediate 2g Under a nitrogen stream, a methylene chloride solution (242 mL) of Intermediate 1g (12.84 g, 24.2 mmol) was placed, cooled to 0 °C, and sulfuryl chloride (5.87 mL, 72.6 mmol) was added dropwise. The temperature was raised to room temperature, acetonitrile was added, and then a saturated sodium hydrogen carbonate solution was added until the reaction solution became a basic solution. Methylene chloride and water were added, the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution obtained after filtration was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain Intermediate 2g as a white solid (10.97 g, 21.2 mmol, yield 88%). 1 1H-NMR (400 MHz, CDCl3): δ 7.86 (d, J = 1.6 Hz, 4H), 7.67 (t, J = 1.6 Hz, 2H), 1.40 (s, 36H). ASAP MS spectrum analysis: C 33 H 42 ClN3: Theoretical value 515.31, Observed value 516.60.

[0137] Synthesis of Intermediate 3g A mixed solvent of THF (52 mL) and water (17 mL) of Compound 1a (2.0 g, 5.20 mmol) was purged with nitrogen. Under a nitrogen stream, Intermediate 2g (5.62 g, 10.9 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.36 g, 0.52 mmol), and sodium carbonate (1.65 g, 15.6 mmol) were added to this solution and stirred at 75 °C overnight. The reactor was cooled to room temperature. The solution was filtered, the solid remaining in the funnel was washed with toluene and methanol, and the remaining solid was dried under reduced pressure to obtain Intermediate 3g as a white solid (3.37, 3.08 mmol, yield 59%). 1 1H-NMR (400 MHz, CDCl3): δ 9.32 (dt, J = 8.4 Hz, 2Hz 1H), 7.99 (d, J = 2.0 Hz, 8H), 7.64 (t, J = 2.0 Hz, 4H), 1.400 - 1.353 (m, 72H). ASAP MS Spectrum Analysis: C 72 H 85 F3N6: Theoretical value 1090.68, Observed value 1092.32.

[0138] Synthesis of Compound N Under a nitrogen stream, potassium phosphate (1.06 g, 5.03 mmol) was added to a solution of 3 g (1.0 g, 0.92 mmol) of the intermediate and carbazole-1,2,3,4,5,6,7,8-d8 (0.72 g, 4.12 mmol) in NMP (18 mL), and the mixture was stirred at 130 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:hexane = 6:4) to obtain yellow solid Compound N (0.57 g, 0.36 mmol, 40% yield). 1 H-NMR (400 MHz, CDCl3): δ 8.88 (s, 1H), 7.48 (t, J = 1.6 Hz, 4H), 7.36 (d, J = 1.6Hz, 8H), 1.26 (s, 72H). ASAP MS Spectrum Analysis: C 108 H 85 D 24 N9: Theoretical value 1556.03, Observed value 1557.95.

[0139] (Example 14) Synthesis of Compound O

Chemical Structure

[0140] Synthesis of Intermediate 1h Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (10.0 g, 45.5 mmol), (4-tert-butylphenyl)boronic acid (16.9 g, 95.3 mmol), potassium carbonate (18.7 g, 136 mmol), tetrakis(triphenylphosphine)palladium (2.62 g, 2.27 mmol), THF (151 mL), and degassed water (50 mL) were added to a reaction vessel and stirred at 70 °C overnight. The reaction solution was cooled to room temperature, filtered, dissolved in dichloromethane, the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution was filtered, the resulting solution was concentrated under reduced pressure using an evaporator, and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain Intermediate 1h as a white solid (11.96 g, 28.5 mmol, yield 63%). 1 1H-NMR (400 MHz, CDCl3): δ 8.01 (dt, J = 8.4 Hz, J = 2.0 Hz, 4H), 7.57 (d, J = 8.0 Hz, J = 1.6 Hz, 4H), 2.69 (s, 3H), 1.38 (s, 18H). ASAP MS spectrum analysis: C 26 H 29 N3S: calculated value 415.21, observed value 416.44.

[0141] Synthesis of Intermediate 2h Under a nitrogen stream, a dichloromethane solution (285 mL) of Intermediate 1h (11.95 g, 28.6 mmol) was placed in a reaction vessel, cooled to 0 °C, and sulfuryl chloride (11.5 g, 85.8 mmol) was added dropwise. The temperature was raised to room temperature, acetonitrile was added, and then saturated sodium bicarbonate solution was added until the reaction solution became a basic solution. Dichloromethane and water were added, the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution obtained after filtration was concentrated under reduced pressure using an evaporator, and then purified by column chromatography (methylene chloride:hexane = 1:1) to obtain Intermediate 2h as a white solid (11.3 g, 27.9 mmol, yield 98%). 11H-NMR (400 MHz, CDCl3): δ 8.04 (dt, J = 8.8 Hz, J = 2.0 Hz 4H), 7.59 (dt, J = 8.8 Hz, J = 2.0 Hz, 4H), 1.38 (s, 18H). ASAP MS spectrum analysis: C 25 H 26 ClN3: Theoretical value 403.18, Observed value 404.40.

[0142] Synthesis of Intermediate 3h The mixed solvent of THF (81 mL) and water (27 mL) of compound 1a (2.5 g, 6.51 mmol) was purged with nitrogen. Under a nitrogen stream, to this solution were added intermediate 2h (5.77 g, 14.3 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.46 g, 0.65 mmol), and sodium carbonate (2.06 g, 19.2 mmol), and the mixture was heated with stirring at 75 °C for 18 hours. The reaction solution was cooled to room temperature, filtered, then dissolved in dichloromethane, and the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. The solution was filtered, and the resulting solution was concentrated under reduced pressure using an evaporator and then purified by column chromatography (toluene:hexane = 2:8) to obtain white solid intermediate 3h (3.82 g, 4.40 mmol, yield 68%). 1 1H-NMR (400 MHz, CDCl3): δ 9.20 (td, J = 8 Hz, J = 2 Hz, 1H), 8.17 (dt, J = 8.8 Hz, 2.0 Hz, 8H), 7.62 (dt, J = 8.8, 2.0 Hz, 8H), 1.40 (s, 36H). ASAP MS spectrum analysis: C 56 H 53 F3N6: Theoretical value 866.43, Observed value 867.86.

[0143] Synthesis of Compound O Under a nitrogen stream, tripotassium phosphate (5.11 g, 24.1 mmol) was added to a solution of intermediate 3h (3.81 g, 4.39 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (3.45 g, 19.7 mmol) in NMP (73 mL), and the mixture was stirred at 150 °C for 4 hours. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane and purified by column chromatography (dichloromethane:hexane = 3:7) to obtain yellow solid compound O (1.00 g, 0.75 mmol, yield 17%). 1 1H-NMR (400 MHz, CDCl3): δ 8.98 (s, 1H), 7.37 - 7.27 (m, 16H), 1.29(s, 36H). MALDI-TOF MS spectrum analysis: C 92 H 53 D 24 N9: Theoretical value 1331.78, Observed value 1332.71.

[0144] (Example 15) Synthesis of compound P

Chemical formula

[0145] Synthesis of Compound 1k Under a nitrogen stream, potassium carbonate (1.24 g, 9.03 mmol) was added to a solution of compound 3b (2.0 g, 3.01 mmol) and 2-phenyl-5H-[1]benzofuro[3,2-c]carbazole (2.50 g, 7.52 mmol) in NMP (30 mL), and the mixture was stirred at 90 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The obtained solid was purified by column chromatography (toluene) to obtain yellow solid compound 1k (3.50 g, 2.50 mmol, yield 83%). 11H-NMR (400 MHz, CDCl3): δ 9.30 (d, J = 1.6 Hz, 1H), 8.59-8.58 (m, 2H), 8.00-7.97 (m, 2H), 7.95 (dd, J = 8.4 Hz, J = 3.6 Hz, 2H), 7.80-7.69 (m, 8H), 7.56-7.28 (m, 14H). ASAP MS spectrum analysis: C 88 H 29 D 20 FN8O2: Theoretical value 1288.52, Observed value 1290.19.

[0146] Synthesis of Compound P Under a nitrogen stream, potassium carbonate (1.02 g, 7.44 mmol) was added to a solution of compound 1k (3.20 g, 2.48 mmol) and 4H-4-azadibenzo[g,ij]naphtho[2,1,8-cde]azulene (1.44 g, 4.96 mmol) in NMP (25 mL), and the mixture was stirred at 150 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The obtained solid was purified by column chromatography (toluene) to give compound P as a yellow solid (2.64 g, 1.69 mmol, yield 68%). 1 1H-NMR (400 MHz, CDCl3): δ 9.25-9.21 (m, 1H), 8.19-8.14 (m, 2H), 7.90-6.87 (m, 37H), 6.75-6.34 (m, 1H). ASAP MS spectrum analysis: C 110 H 41 D 20 N9O2: Theoretical value 1559.62, Observed value 1560.47. Using the neat thin film obtained by depositing compound P on a quartz substrate under a vacuum of less than 1 × 10 -3 Pa, the energy of the HOMO of compound P was 5.68 eV and the energy of the LUMO was 3.38 eV.

[0147] (Example 16) Synthesis of compound Q [Chemical formula]

[0148] Synthesis of Compound Q Under a nitrogen stream, potassium phosphate (0.54 g, 2.55 mmol) was added to a solution of Compound 1f (1.00 g, 1.02 mmol) and 2-phenyl-5H-benzo[f]chromeno[3,2-c]carbazole (0.51 g, 1.53 mmol) in NMP (20 mL), and the mixture was stirred at 130 °C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:dichloromethane = 8:2) to obtain yellow Compound Q (0.5 g, 0.38 mmol, 38% yield). 1 H-NMR (400 MHz, CDCl3): δ 9.06 (s, 1H), 8.08 (dd, J = 1.2 Hz, J = 0.4 Hz, 1H), 7.74 (dd, J = 7.6 Hz, J = 0.8 Hz, 1H), 7.55 - 7.50 (m, 3H), 7.42 - 7.37 (m, 2H), 7.35 - 7.21 (m, 5H), 7.16 (d, J = 8.4 Hz, 1H), 6.99 (dd, J = 7.6 Hz, J = 2 Hz, 1H). ASAP MS spectrum analysis: C 88 H 15 D 36 N9O: Theoretical value 1285.65, Observed value 1286.52.

[0149] (Test Example 1) Preparation and Evaluation of Thin Films Compound A and Compound H1 described below were vapor-deposited from different vapor-deposition sources on a quartz substrate under a vacuum of less than 1 × 10 -3 Pa to form a thin film with a thickness of 100 nm and a concentration of Compound A of 35 wt%. Using Compounds E - O, Comparative Compound 1, and Comparative Compound 2 instead of Compound A, thin films were formed in the same manner. However, the concentrations of Compounds E, F, H - O, and Comparative Compound 1 were 20 wt%. For each of the formed thin films, the photoluminescence when irradiated with excitation light of 300 nm was analyzed, and the emission peak wavelength (λmax) and the ratio of the delayed fluorescence component during emission were measured. The results are shown in the following table. Compounds A, E to O represented by the general formula (1) have a larger ratio of the delayed fluorescence component than Comparative Compound 1 (4CzTPN-d) known as an excellent delayed fluorescence material and Comparative Compound 2 having a structure similar to the general formula (1). It was confirmed. Compound A has a structure in which a cyanodiarylpyrimidyl group is introduced instead of the diaryltriazinyl group of Comparative Compound 2, and the other structures are common. From this, it was confirmed that by introducing a cyanodiarylpyrimidyl group instead of the diaryltriazinyl group to form a compound of the general formula (1), the ratio of the delayed fluorescence component increases.

Table 8

[0150] Using Compound B instead of Compound A, a thin film was formed in the same procedure as for Compound A. Also, using Compound C and Compound D instead of Compound A, thin films with a concentration of 20% by weight were formed respectively. When these thin films and the above thin film of Comparative Compound 1 were irradiated with excitation light of 300 nm to measure the photoluminescence quantum efficiency (PLQY), it was confirmed that when using Compound B, Compound C, or Compound D, the PLQY was 20 to 40% higher than when using Comparative Compound 1. Similarly, when comparing the PLQY of the thin film of Compound G and the thin film of Comparative Compound 2, when using Compound G, the PLQY was 10% or more higher than when using Comparative Example 2 and reached 93.4%.

[0151] (Test Example 2) Fabrication and evaluation of green organic electroluminescence device On a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed, each thin film was vacuum-deposited by a vacuum deposition method with a vacuum degree of 5.0×10 -5It was laminated in Pa. First, the compound HAT-CN described below was formed on ITO to a thickness of 10 nm, the compound NPD described below was formed thereon to a thickness of 30 nm, the compound TrisPCz described below was further formed thereon to a thickness of 10 nm, and H2 was formed thereon to a thickness of 5 nm. Next, the compound H2 and the compound A were co-evaporated from different evaporation sources to form a layer with a thickness of 40 nm as the light-emitting layer. The concentration of the compound A in the light-emitting layer was 35% by mass. Next, the compound SF3-TRZ described below was formed to a thickness of 10 nm, and then the compound Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer were 30% by mass and 70% by mass, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic electroluminescence device. Using the compound B, the compound H, the compound I, the comparative compound 2, and the comparative compound 3 instead of the compound A, respectively, each organic electroluminescence device was fabricated by the same procedure. However, the concentration in the light-emitting layer of the comparative compound 2 was 45% by weight or 65% by weight. Each organic electroluminescence device was continuously caused to emit light at 12.6 mA / cm 2 and the time (LT95) until the light-emitting intensity decreased to 95% of that at the start of driving was measured. The results are shown in the following table. The results are shown as relative values when the LT95 of the comparative compound 3 is taken as 1. When the compound A and the compound B were used, it was confirmed that the device lifetime was 1000 times or more longer than when the comparative compound 3 was used, and 2 times or more longer than when the comparative compound 2 was used. The compound A has a structure in which a cyanodiarylpyrimidyl group is introduced instead of the diaryltriazinyl group of the comparative compound 2, and the other structures are common. From this, it was confirmed that by introducing a cyanodiarylpyrimidyl group instead of the diaryltriazinyl group to form a compound of the general formula (1), the device lifetime becomes longer.

Table 9

[0152] In the manufacturing process of the organic electroluminescence device in Test Example 2, each organic electroluminescence device was fabricated in the same procedure using Compound Q instead of Compound A. The external quantum efficiency (EQE) of the organic electroluminescence devices using Compound H, Compound I, Compound Q, and Comparative Compound 2 was measured at 6.3 mA / cm 2 The results are shown in the following table. It was confirmed that an element with high external quantum efficiency can be realized by using the compound of General Formula (1). [Table 10]

[0153] (Test Example 3) Fabrication and Evaluation of Red Organic Electroluminescence Device On a 2-mm-thick glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm, each thin film was laminated by vacuum evaporation at a vacuum degree of 1 × 10 -6 Pa. First, HAT-CN was formed on the ITO to a thickness of 5 nm, NPD was formed thereon to a thickness of 60 nm, and then Compound EB1 described below was formed thereon to a thickness of 10 m. Next, Compound H3 described below, Compound H4 described below, and Compound E were co-evaporated from different evaporation sources to form a light-emitting layer with a thickness of 40 nm. At this time, the concentrations in the light-emitting layer were 45% by weight of H3 as the first host material, 20% by weight of H4 as the second host material, and 35% by weight of Compound E. Next, HB1 was formed to a thickness of 10 nm, and then SF3-TRZ was formed to a thickness of 30 nm. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was formed to a thickness of 100 nm to form a cathode, thereby obtaining an organic electroluminescence device. Each organic electroluminescence device was fabricated in the same procedure using Comparative Compound 1 instead of Compound E. Each organic electroluminescence device was measured at 50 mA / cm 2Emission was continuously carried out, and the time (LT95) until the emission intensity decreased to 95% of that at the start of driving was measured. The results are shown in the following table. The results are shown as relative values when the LT95 of Comparative Compound 1 is taken as 1. When Compound E was used, it was confirmed that the device lifetime was about 4.6 times or more longer than when Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used. [Table 11]

[0154] Using Compound F instead of Compound E, each organic electroluminescence device was fabricated by the same procedure. For each organic electroluminescence device using Compound E, Compound F, and Comparative Compound 1, the driving voltage when emitting light at 15.4 mA / cm 2 was measured. The results are shown in the following table. When Compound E and Compound F were used, it was confirmed that the driving voltage was lower than when Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used. [Table 12]

[0155] (Test Example 4) Fabrication and Evaluation of Organic Electroluminescence Device Using Assist Dopant The light-emitting layer was co-evaporated from different evaporation sources of H3, H4, Compound E, and Compound ET1 described later. The only change was that a layer with a thickness of 40 nm containing 44.7% by weight of H3 as the first host material, 20% by weight of H4 as the second host material, 35% by weight of Compound E as the assist dopant, and 0.3% by weight of ET1 as the dopant (light-emitting material) was formed. Otherwise, an organic electroluminescence device was fabricated by the same manufacturing method as in Test Example 3. Using Comparative Compound 1 instead of Compound E, each organic electroluminescence device was fabricated by the same procedure. Each organic electroluminescence device was driven at 50 mA / cm 2Emission was continuously carried out, and the time (LT95) until the emission intensity decreased to 95% of that at the start of driving was measured. The results are shown in the following table. The results are shown as relative values when the LT95 of Comparative Compound 1 is set to 1. When Compound E was used, it was confirmed that the device lifetime was 3.1 times longer than that of Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material. [Table 13]

[0156] An organic electroluminescence device was fabricated in the same procedure using Compound F instead of Compound E. For each of the organic electroluminescence devices using Compound E, Compound F, and Comparative Compound 1, the driving voltage when emitting light at 15.4 mA / cm 2 was measured. The results are shown in the following table. When Compound E and Compound F were used, it was confirmed that the driving voltage was lower than when Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used. [Table 14]

[0157] (Test Example 5) Fabrication and evaluation of another organic electroluminescence device using an assist dopant The light-emitting layer was co-evaporated from different evaporation sources with H2, Compound H, and Compound ET2 described below. The only change was that a layer with a thickness of 40 nm containing 64.2 wt% of H2 as the host material, 35 wt% of Compound H as the assist dopant, and 0.8 wt% of ET2 as the dopant (light-emitting material) was formed. Otherwise, an organic electroluminescence device was fabricated by the same manufacturing method as in Test Example 3. Using Compound I, Compound M, and Comparative Compound 2 instead of Compound H, each organic electroluminescence device was fabricated in the same procedure. However, the concentration of Comparative Compound 2 in the light-emitting layer was 65 wt%, and the concentration of ET2 as the dopant (light-emitting material) was 0.8 wt%. For each of the fabricated elements, the external quantum efficiency (EQE) was measured in the same manner as in Test Example 2, and the element lifetime (LT95) was measured in the same manner as in Test Example 3. The results are shown in the following table. The element lifetime is shown as a relative value when the LT95 of Comparative Compound 2 is taken as 1. It was confirmed that the element using the compound represented by General Formula (1) had higher luminous efficiency and longer element lifetime than the element using Comparative Compound 2.

[0158]

Table 15

[0159] (Test Example 6) Fabrication and Evaluation of Another Organic Electroluminescence Element Using an Assist Dopant The light-emitting layer was co-evaporated from different evaporation sources of H2, Compound I, and Compound ET3 described below. The only difference was that a layer with a thickness of 40 nm containing 64.2 wt% of H2 as the host material, 35 wt% of Compound I as the assist dopant, and 0.8 wt% of ET3 as the dopant (light-emitting material) was formed. Otherwise, an organic electroluminescence element was fabricated by the same manufacturing method as in Test Example 3. Using Compound M, Compound N, Compound O, and Comparative Compound 2 instead of Compound I, each organic electroluminescence element was fabricated by the same procedure. However, the concentration of Comparative Compound 2 in the light-emitting layer was 65 wt%, and the concentration of ET2 as the dopant (light-emitting material) was 0.8 wt%. For each of the fabricated elements, the external quantum efficiency (EQE) was measured in the same manner as in Test Example 2. The results are shown in the following table. It was confirmed that the element using the compound represented by General Formula (1) had higher luminous efficiency than the element using Comparative Compound 2.

[0160]

Table 16

[0161]

Chemical Formula

[0162] [Chem.] [Chem.] [Industrial Applicability]

[0163] The compound of the present invention represented by the general formula (1) exhibits excellent performance as a compound for an organic light-emitting device. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1). General formula (1) 【Chemical 1】 In general formula (1), X １ and X ２ are such that one represents N and the other represents C-Y ３ . Y １ to Y ３ are such that one represents a cyano group and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L １ represents a single bond or a divalent linking group. R １ to R ５ each independently represent a hydrogen atom, a deuterium atom or a substituent. However, 2 to 4 of R １ to R ５ are each independently donor groups, and one of R １ to R ３ is a cyano group or a group represented by the following general formula (A). General formula (A) [Chemical 2] X ３ and X ４ wherein one represents N and the other represents C-Y ６ and Y ４ to Y ６ wherein one represents a cyano group and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, or X ３ and X ４ represent N, Y ４ represents a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Y ５ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. L ２ represents a single bond or a divalent linking group.]

2. R ３ The compound according to claim 1, wherein R is a cyano group or a group represented by the general formula (A).

3. R ２ The compound according to claim 1, wherein R is a cyano group or a group represented by the general formula (A).

4. R １ ~R ３ One of them is a group represented by the general formula (A), and X １ and X ３ are the same, X ２ and X ４ are the same, Y １ and Y ４ are the same, Y ２ and Y ５ are the same, L １ and L ２ are the same, the compound according to claim 1.

5. R １ to R ５ The compound according to claim 1, wherein at least one of them is an aryl group which may be substituted with a deuterium atom, an alkyl group or an aryl group.

6. R １ and R ５ The compound according to claim 1, wherein at least one of them is a hydrogen atom or a deuterium atom.

7. X １ and X ３ The compound according to claim 1, wherein N is N.

8. Y １ ~Y ３ Of these, one is a cyano group, and the remaining two are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazol-9-yl group which may be condensed, the compound according to claim 1.

9. L １ and L ２ The compound according to claim 1, wherein is a single bond.

10. R １ to R ５ The compound according to claim 1, wherein at least one of two to four of the donor groups is a substituted or unsubstituted diarylamino group (the two aryl groups may be bonded to each other).

11. R １ to R ５ The compound according to claim 10, wherein at least one of two to four of the donor groups is a substituted or unsubstituted carbazol-9-yl group which may be condensed.

12. R １ to R ５ The compound according to claim 1, wherein two of them are the donor groups.

13. R １ to R ５ The compound according to claim 1, wherein three of them are the donor groups.

14. The donor group and Y １ ~Y ６ The compound according to claim 1, wherein at least one of ~Y contains a deuterium atom.

15. A luminescent material comprising the compound according to any one of Claims 1 to 14.

16. A delayed fluorescence material comprising the compound according to any one of Claims 1 to 14.

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