Compound, light emitting material, and delayed fluorescent material

Abstract

This compound represented by the general formula is useful as a compound for an organic optical semiconductor element. One of X1 or X2 represents N and the other represents C-Y3, one of Y1-Y3 represents a cyano group and the remaining two thereof and Y4 and Y5 each represent an aryl group or a heteroaryl group, R1 represents H or D, and one to three of R2-R4 are donor groups and the remainder represents H, D, an alkyl group, or an aryl group.

Description

Compound, luminescent material and delayed fluorescent material

[0001] The present invention relates to a compound, and a light-emitting material and a delayed fluorescent material using the compound.

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

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

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

[0005] WO2019 / 191665A1

[0006] To date, no compound has been provided that exhibits excellent performance when applied to organic light-emitting devices and has no practical problems. Therefore, it would be even more useful if a compound could be developed that could provide organic light-emitting devices with even better performance. However, improvements to these compounds are still in the trial-and-error stage, and it is not easy to generalize the chemical structures of useful compounds.

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

[0008] As a result of intensive research to achieve the above object, the present inventors have found that a compound having a structure that satisfies certain conditions is useful as a compound for an organic light-emitting device. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] A compound represented by the following general formula (1): General formula (1) [In the general formula (1), X １ and X ２ represents N on one side and C-Y on the other side. ３ Represents Y. １ ~Y ３ One of the groups represents a cyano group, and the other two and Y ４ and Y ５ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ represents a hydrogen atom or a deuterium atom, R ２ ~R ４ One to three of X each independently represent a donor group, and the rest represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.] [2] X １ is N and X ２ is C-Y ３ and Y ３ [3] The compound according to [1], wherein R is a cyano group. ２ ~R ４[4] The compound according to [1] or [2], wherein R ２ and R ４ [5] The compound according to any one of [1] to [3], wherein R ２ and R ４ are each independently a donor group, and R ３ [6] The compound according to [1] or [2], wherein R is a substituted or unsubstituted aryl group. ３ [7] The compound according to [5], wherein R is an aryl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group. ２ and R ４ [8] The compound according to [5] or [6], wherein Y １ ~Y ３ [9] The compound according to any one of [1] to [7], wherein one of R is a cyano group, and the remaining two are each independently a substituted or unsubstituted phenyl group, or an optionally fused substituted or unsubstituted carbazol-9-yl group. ２ ~R ４

[10] The compound according to any one of [1] to [8], wherein at least one of the one to three donor groups is a substituted or unsubstituted diarylamino group (two aryl groups may be bonded to each other). ２ ~R ４

[11] The compound according to [9], wherein at least one of the 1 to 3 donor groups is a substituted or unsubstituted carbazol-9-yl group which may be fused. １ ~Y ５

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

[10] , wherein at least one of the above groups contains a deuterium atom.

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

[10] .

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

[10] .

[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.

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

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

[0012] In general formula (1), X １ and X ２ represents N on one side and C-Y on the other side. 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 Both of them cannot be N. １ and X ２ In comparison with a compound in which both are N, the compound represented by the general formula (1) exhibits superior luminescence properties.

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

[0014] Y １ ~Y ３ The substituted or unsubstituted aryl group represented by Y may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. Specific examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected from the range of 6 to 14, or may be selected from the range of 6 to 10. Y １ ~Y ３ Specific examples of the substituted or unsubstituted aryl group that can be taken by R ２ ~R ４ Specific examples of the substituted or unsubstituted aryl group that can be taken by Y can be referred to. １ ~Y ３The substituted or unsubstituted heteroaryl group that can be taken by may be a group bonded via a carbon atom constituting an aromatic heterocycle or a group bonded via a nitrogen atom, but is preferably a group bonded via a nitrogen atom. Examples of aromatic heterocycles containing a bonded carbon atom include a pyridine ring, a pyrimidine ring, and a triazine ring. Examples of aromatic heterocycles containing a bonded nitrogen atom include a pyrrole ring. These aromatic heterocycles may be substituted, or may be fused with other rings. Examples of other rings include aromatic hydrocarbon rings and aromatic heterocycles, and rings formed by further condensing these rings may be fused with the aromatic heterocycle. In one aspect of the present invention, Y １ ~Y ３ Examples of the substituted or unsubstituted heteroaryl group that can be represented by the formula (a) include a donor group represented by the formula (b) described later, and further examples of the donor group represented by the formula (b) described later can be mentioned. ２ ~R ４ The explanations and specific examples of the donor groups that can be used can be referred to.

[0015] In a preferred embodiment of the present invention, Y １ ~Y ３ In a preferred embodiment of the present invention, one of Y 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 fused. ３ represents a cyano group, and Y １ and Y ２ each independently represents 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 fused). １ and Y ２ In a preferred embodiment of the present invention, Y １ ~Y ３ At least one of Y is a substituted or unsubstituted aryl group. １ is a substituted or unsubstituted aryl group. For example, Y ２is a substituted or unsubstituted aryl group. For example, Y １ and Y ２ are each independently a substituted or unsubstituted aryl group. In one embodiment of the present invention, the substituted or unsubstituted aryl group referred to here is an unsubstituted aryl group (e.g., an unsubstituted phenyl group) or a phenyl group substituted with a deuterium atom (e.g., a perdeuterated phenyl group). In one embodiment of the present invention, the substituted aryl group referred to here is 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 among these, an alkyl group which may be substituted with a deuterium atom is more preferred. The alkyl group referred to here preferably has 1 to 10 carbon atoms, for example 3 to 10 carbon atoms.

[0016] Y in general formula (1) ４ and Y ５ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ４ and Y ５ The substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group that can be taken by Y １ ~Y ３ In one embodiment of the present invention, reference can be made to the description of the substituted or unsubstituted aryl group and the substituted or unsubstituted heteroaryl group that Y may take. ４ and Y ５ are each independently a substituted or unsubstituted aryl group. ４ and Y ５ In one embodiment of the present invention, one of Y is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group. ４ and Y ５ are each independently a substituted or unsubstituted heteroaryl group. ４ and Y ５At least one of the groups is a substituted or unsubstituted aryl group. In one embodiment of the present invention, the substituted or unsubstituted aryl group referred to here is an unsubstituted aryl group (for example, an unsubstituted phenyl group) or a phenyl group substituted with a deuterium atom (for example, a perdeuterated phenyl group). In one embodiment of the present invention, the substituent of the substituted aryl group referred to here is 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 among these, an alkyl group which may be substituted with a deuterium atom is more preferred. The number of carbon atoms in the alkyl group referred to here is preferably 1 to 10, for example 3 to 10. In one preferred embodiment of the present invention, Y ４ and Y ５ One of the groups is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring.

[0017] In one aspect of the present invention, Y ３ represents a cyano group. ３ In one embodiment of the present invention, when Y is a cyano group, various embodiments will be described. １ , Y ２ , Y ４ , Y ５ One of the groups is a substituted or unsubstituted carbazol-9-yl group which may be fused, and the remaining three groups are substituted or unsubstituted aryl groups. １ and Y ２ is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. ４ and Y ５ In one embodiment of the present invention, one of Y is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. １ , Y ２ , Y ４ , Y ５ Two of the groups are substituted or unsubstituted carbazol-9-yl groups which may be fused together, and the remaining two are substituted or unsubstituted aryl groups. １ and Y ２ One of the two and Y ４ and Y ５In one embodiment of the present invention, one of Y is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. １ , Y ２ , Y ４ , Y ５ In one aspect of the present invention, Y １ and Y ４ are identical, and Y ２ and Y ５ are the same, but Y １ and Y ４ In one aspect of the present invention, Y １ and Y ４ are identical, but Y ２ Tomo Y ５ In one aspect of the present invention, Y １ and Y ４ and Y ５ are identical, but Y ２ In one aspect of the present invention, Y １ and Y ２ and Y ４ are identical, but Y ５ In one aspect of the present invention, Y １ and Y ２ are identical, and Y ４ and Y ５ In one aspect of the present invention, Y １ and Y ２ are identical, and Y ４ and Y ５ are the same, but Y １ and Y ２ In one aspect of the present invention, Y １ and Y ２ are different from each other, and Y ４ and Y ５ In one aspect of the present invention, Y １ and Y ２ are different from each other, and Y ４ and Y ５ In one aspect of the present invention, Y １ and Y ２ contains deuterium atoms but does not contain hydrogen atoms. ４ and Y ５ contains deuterium atoms but no hydrogen atoms. １ , Y２ , Y ４ , Y ５ contains deuterium atoms but no hydrogen atoms.

[0018] R in general formula (1) １ represents a hydrogen atom or a deuterium atom. １ is a hydrogen atom. In one aspect of the present invention, R １ is a deuterium atom.

[0019] R in general formula (1) ２ ~R ４ One to three of these are independently donor groups. The donor groups referred to here do not include alkyl groups optionally substituted with a deuterium atom or an aryl group, and aryl groups optionally substituted with a deuterium atom, an alkyl group, or an aryl group. The "donor group" can be selected from groups with a negative Hammett σp value. The "acceptor group" can be selected from groups with a positive Hammett σp value. The Hammett σp value was proposed by L. P. Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is the constant (σp) specific to the substituent in the para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above formula, k0 represents the rate constant of the benzene derivative having no substituent, k represents the rate constant of the benzene derivative substituted with a substituent, K0 represents the equilibrium constant of the benzene derivative having no substituent, K represents the equilibrium constant of the benzene derivative substituted with a substituent, and ρ represents a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett's σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0020] R ２ ~R ４The donor group preferably has a σp of −0.3 or less, more preferably −0.5 or less, and even more preferably −0.7 or less. For example, it may be selected from the range of −0.9 or less, or −1.1 or less.

[0021] 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 to which a substituted amino group is bonded via a linking group. For example, it may be an aryl group bonded to a substituted amino group, particularly a phenyl group bonded to a substituted amino group, or an alkenylene group bonded to a substituted amino group. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0022] R ２ ~R ４ The donor group that can be taken by the formula (a) is preferably a group represented by the following general formula (a) or a group to which a group represented by the following general formula (a) is bonded via a linking group. The linking group here is preferably a π-conjugated linking group, and examples thereof include an arylene group and an alkenylene group, and specific examples thereof include a 1,4-phenylene group, a 1,3-phenylene group, a perdeuterated 1,4-phenylene group, and a perdeuterated 1,3-phenylene group.

[0023] In the general formula (a), Z １ is C-R １４ or N, Z ２ is C-R１５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N. Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １４ and R １５ , R １５ and R １６ , R １６ and R １７ may be bonded to each other to form a cyclic structure.

[0024] Z １ ~Z ４ In one embodiment of the present invention, the number of N's is preferably 0 to 3, and more preferably 0 to 2. １ ~Z ４ In one aspect of the present invention, the number of N is 1. １ ~Z ４ The number of N is 0. １４ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. The deuterium atom or substituent here may be selected from, for example, Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a plurality of groups A to E. １４ ~R １７ When two or more of R represent deuterium atoms or substituents, the two or more deuterium atoms or substituents may be the same or different. １４ ~R １７ The number of substituents is preferably 0 to 2, for example, R １４ ~R １７ The number of substituents among R may be one, １４ ~R １７ The number of substituents is 0 (R １４ ~R １７ may be a hydrogen atom or a deuterium atom).１４ ~R １７ When the number of substituents among １４ ~R １７ may be all hydrogen atoms, all deuterium atoms, or some hydrogen atoms and the rest deuterium atoms. １４ and R １５ , R １５ and R １６ , R １６ and R １７may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic ring or a heteroaromatic ring is preferred. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to herein may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to herein may be selected from Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a combination of groups A to E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the deuterium atom or substituent that may 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 embodiment of the present invention, a pair of R １４ and R １５ , R １５ and R １６ , R １６ and R １７are not bonded to each other to form a ring structure.

[0025] In the general formula (a), Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is C, and Ar ５ is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. ５ An example of the aromatic ring that can be used by Ar is a benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. ５ The heteroaromatic ring that can be adopted by Z is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the heteroaromatic ring. In one embodiment of the present invention, Z ５ is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. ５ is N, and the heteroaromatic ring is a pyrrole ring of a substituted or unsubstituted indole, or an imidazole ring of a substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to here may be selected from Group A described below, Group B described below, Group C described below, Group D described below, or Group E described below, or may be selected from a plurality of groups A to E.

[0026] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0027] In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ may be bonded to each other to form a cyclic structure. １ ~Z ４ , R １４ ~R １７ For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. ６ ~Z ９ , R １８ ~R ２１ is Z in general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order to Z in general formula (a). １ ~Z ４ , R １４ ~R １７ In one aspect of the present invention, Z１ ~Z ４ , Z ６ ~Z ９ In one embodiment of the present invention, the number of N's is preferably 0 to 2, and more preferably 0 or 1. １ ~Z ４ , Z ６ ~Z ９ In a preferred embodiment of the present invention, the number of N groups is 1. １ ~Z ４ , Z ６ ~Z ９ The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0028] R ２ ~R ４ The donor group that may be taken by is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted or may be substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to here may be selected from Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a combination 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 at least a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group. For example, it may be substituted with at least an alkyl group which may be substituted with a deuterium atom. Furthermore, one or more rings may be fused to the two benzene rings constituting the carbazol-9-yl group. In a preferred embodiment of the present invention, R １ ~R ５The donor group that can be taken by is a carbazol-9-yl group, which may be substituted with a deuterium atom or a substituent selected from Group E described below, and may have one or more fused rings. When a compound with a short emission wavelength is desired, it is preferable to use a carbazol-9-yl group substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group or an aryl group. When a carbazol-9-yl group not fused with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one position from the 2- to 7-positions, more preferably at least one position from the 3- or 6-positions, and even more preferably two positions from the 3- and 6-positions.

[0029] In one aspect of the present invention, R ２ ~R ４ The donor group R can take is a carbazol-9-yl group in which one or more rings are fused, and hereinafter this is referred to as a "ring-fused carbazol-9-yl group." ２ ~R ４ The ring-fused carbazol-9-yl group represented by the formula (I) may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent may be selected from Group A described below, Group B described below, Group C described below, Group D described below, or Group E described below, or may be selected from a plurality of groups A to E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a deuterium atom or a substituent selected from Group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted with an aryl group, and the aryl group may be further substituted with one or more groups 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 groups are bonded. For example, the ring-fused carbazol-9-yl group is substituted with a deuterium atom; an alkyl group optionally substituted with a deuterium atom or an aryl group; and an aryl group optionally substituted with one or more selected from the group consisting of a deuterium atom, an alkyl group, or an aryl group.

[0030] The total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0031] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring formed by further condensing these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In one embodiment of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a deuterium atom or a substituent (excluding cases where only a deuterium atom is present) selected from Group E described below, and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In one embodiment of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group to which a benzothieno structure is fused, for example, two or more carbazol-9-yl groups.

[0032] As the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group can be used. Furthermore, as the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used. Furthermore, examples of the ring-fused carbazol-9-yl group include a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, and a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group.

[0033] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted with a substituent at either the 3-position or the 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0034] In the following, R in general formula (1) ２ ~R ４ The specific examples given here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may have a further ring condensed thereto), but the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C ６ H ５ ) and * indicates the bond position. Methyl groups are omitted, so for example, D2 has one methyl group. However, deuterated methyl groups are ３ Also, C ６ D ５ represents a phenyl group in which all hydrogen atoms are deuterated (perdeuterated phenyl group). D represents a deuterium atom.

[0035] The compounds D1 to D532 above in which all hydrogen atoms have been replaced with deuterium atoms are disclosed as D815 to D1346.

[0036] R １ ~R ５ Among the donor groups that can be employed, specific examples that are not substituted or unsubstituted carbazol-9-yl groups are listed below. However, the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples.

[0037] All hydrogen atoms in D1347 to D1374 are replaced with deuterium atoms, and the resulting compounds are disclosed as D1399 to D1426. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1426. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1346. １~R ５ The donor group that R can take is 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, and D797 to D803. １ ~R ５ The donor group that R can take is 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, and D805 to D814. １ ~R ５ The donor group that R can take is selected from the group consisting of D533 to D1346 and D1375 to D1426. １ ~R ５ The donor group that R can take is selected from the group consisting of D533 to D1346. １ ~R ５ The donor groups that can be taken are 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 D8 In a more preferred embodiment of the present invention, R １ ~R ５The donor groups that can be taken are 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, D 815, D820, D821, D822, D823, D828, D829, D832, D834, D840, D841, D858, D870, D871, D888, D898, D900, D902, D904, D944, D959, D992, D997, D1004, D1007.

[0038] In general formula (1), R ２ ~R ４ In one embodiment of the present invention, one to three of R ２ ~R ４ In one aspect of the present invention, one of R ２ ~R ４ Among R ２ In one embodiment of the present invention, only R ２ ~R ４ Among R ３ In one embodiment of the present invention, only R ２ ~R ４ Among R ４ In one embodiment of the present invention, only R ２ ~R ４ In one embodiment of the present invention, two or three of R ２ is a donor group. In one embodiment of the present invention, at least R ３ is a donor group. In one embodiment of the present invention, at least R ４ is a donor group. In one embodiment of the present invention, R ２ ~R ４ In one embodiment of the present invention, two of R are donor groups. For example, two donor groups are the same, and for example, two donor groups are different from each other. ２ and R ４ In one aspect of the invention, R ２ and R ３In one aspect of the invention, R ３ and R ４ In one aspect of the invention, R ２ ~R ４ In one embodiment of the present invention, three of R ２ ~R ４ In one embodiment of the present invention, all of the donor groups taken by R ２ ~R ４ Two of the groups are the same donor group and one is a different donor group. For example, R ２ and R ４ are the same donor groups, and R ３ is a donor group different from the above. In one embodiment of the present invention, R ２ ~R ４ are different donor groups. ２ ~R ４ The donor group represented by R is preferably a group containing at least one (for example, only one, for example, only two, for example, three) 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 fused. ２ ~R ４ It is also preferable that all of the donor groups represented by the formula (I) are groups containing substituted or unsubstituted diarylamino groups (two aryl groups may be bonded to each other), for example, a substituted or unsubstituted diarylamino group (two aryl groups may be bonded to each other), for example, a substituted or unsubstituted carbazol-9-yl group which may be fused.

[0039] R ２ ~R ４When two of the groups independently represent a donor group, the remaining group represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group (e.g., having 1 to 20 carbon atoms), or a substituted or unsubstituted aryl group (e.g., having 6 to 22 carbon atoms). In one embodiment of the present invention, the remaining group is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, the remaining group is a substituted or unsubstituted alkyl group. The substituted alkyl group is preferably substituted with a deuterium atom, an aryl group, or a substituent having a structure in which two or more of these groups are bonded. In a preferred embodiment of the present invention, the remaining group is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R ３is a substituted or unsubstituted aryl group. The substituted aryl group is preferably 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. The alkyl group may be linear, branched, or cyclic. In addition, two or more of the linear portion, the cyclic portion, and the branched portion may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. In addition, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decanyl, isodecanyl, cyclopentyl, cyclohexyl, and cycloheptyl. The aryl group may be a single ring or a fused ring formed by condensing two or more rings. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. Specific examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected from the range of 6 to 14, or may be selected from the range of 6 to 10. In the following, R ２ ~R ４ Specific examples of optionally substituted aryl groups that can be used are listed below. However, the aryl groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[0040] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar27 are substituted with deuterium atoms are exemplified here as Ar49 to Ar75 in this order. ２ ~R ４ The aryl group that R can take is selected from the group consisting of Ar1 to Ar75. ２ ~R ４ The aryl group that R can take is 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, and Ar70. ２ ~R ４ The aryl group that R can take is selected from the group consisting of Ar28 to Ar75. ２ ~R ４ The aryl group which can be taken by Ar is selected from the group consisting of Ar49, Ar50, Ar53, Ar55, Ar58, Ar60, Ar62, Ar63, Ar68, Ar69, and Ar70.

[0041] In general formula (1), R ２ ~R ４ Two of R ２ and R ３ do not bond to each other to form a ring structure, and R ３ and R ４ do not bond to each other to form a ring structure.

[0042] As compound group 1 of the present invention, X １ is N and X ２ is C-CN, and Y １ , Y ２ , Y ４ , Y ５ and each independently represents a substituted or unsubstituted aryl group. １ and Y ２ Compound group 1a, Y １ and Y ２Compound group 1b, Y ４ and Y ５ Compound group 1c, Y ４ and Y ５ Compound group 1d, Y １ Y ４ and Y ５ Compound group 1e, Y １ Y ４ and Y ５ Compound group 1f, Y １ and Y ４ are the same, and Y ２ and Y ５ Compound group 1g, Y １ , Y ２ , Y ４ , Y ５ Compound group 1h, Y １ , Y ２ , Y ４ , Y ５ and a compound group 1i in which all of the compounds are different from each other.

[0043] As compound group 2 of the present invention, X １ is N and X ２ is C-CN, and Y １ , Y ２ , Y ４ are each independently a substituted or unsubstituted aryl group, and Y ５ Compound group 2 includes a compound group of general formula (1) in which Y is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. １ and Y ２ Compound group 2a, Y １ and Y ２ Compound group 2b, Y ４ Y １ and Y ２ Compound group 2c, Y ４ Y １ Ya Y ２ Compound group 2d, Y １ , Y ２ , Y ４ Compound group 2e, Y １ , Y ２ , Y ４ and a compound group 2f in which all of the compounds are different from each other.

[0044] As compound group 3 of the present invention, X １ is N and X ２ is C-CN, and Y １ , Y ４ , Y ５ are each independently a substituted or unsubstituted aryl group, and Y ２ is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. ４ and Y ５ Compound group 3a, Y ４ and Y ５ Compound group 3b, Y １ Y ４ and Y ５ Compound group 3c, Y １ Y ４ Ya Y ５ Compound group 3d, Y １ , Y ４ , Y ５ Compound group 3e, Y １ , Y ４ , Y ５ and compound group 3f, in which all of the above are different from each other.

[0045] As compound group 4 of the present invention, X １ is N and X ２ is C-CN, and Y １ and Y ４ are each independently a substituted or unsubstituted aryl group, and Y ２ and Y ５ Compound group 4 includes a compound group of general formula (1) in which Y is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. １ and Y ４ Compound group 4a, Y １ and Y ４ Compound group 4b, Y ２ and Y ５ Compound group 4c, Y ２ and Y ５ Compound group 4d, Y １ and Y ４ are the same, and Y ２and Y ５ Compound group 4e, Y １ and Y ４ are the same, and Y ２ and Y ５ Compound group 4f, Y １ and Y ４ is different, Y ２ and Y ５ Compound group 4g, Y １ and Y ４ is different, Y ２ and Y ５ The compound group 4h includes compounds in which

[0046] Compound groups 1a to 1i, compound groups 2a to 2f, compound groups 3a to 3f, and compound groups 4a to 4h each further include compounds that satisfy at least one of the following additional conditions. １ , Y ２ , Y ４ , Y ５ The substituted or unsubstituted aryl group which Y may take is an aryl group which may be substituted with a deuterium atom (for example, a phenyl group or a perdeuterated phenyl group). １ , Y ２ , Y ４ , Y ５ At least one of the substituted or unsubstituted aryl groups that Y may take is a substituted aryl group (e.g., a substituted phenyl group), and the substituent of the aryl group is an alkyl group optionally substituted with a deuterium atom, or an aryl group optionally substituted with a deuterium atom, an alkyl group, an aryl group, or a group in which two or more of these are bonded. １ , Y ２ , Y ４ , Y ５ The substituted or unsubstituted heteroaryl group represented by Y is a substituted or unsubstituted carbazol-9-yl group which may be fused to a ring. １ , Y ２ , Y ４ , Y ５ The substituted or unsubstituted heteroaryl group represented by Y may be a substituted or unsubstituted carbazol-9-yl group that is not fused to a ring. １ , Y２ , Y ４ , Y ５ The substituted or unsubstituted heteroaryl group represented by Y is a fused substituted or unsubstituted carbazol-9-yl group. １ , Y ２ , Y ４ , Y ５ The substituted or unsubstituted heteroaryl group that R may take is a substituted carbazol-9-yl group, and the substituent of the carbazol-9-yl group is an alkyl group that may be substituted with a deuterium atom, or an aryl group that may be substituted with a deuterium atom, an alkyl group, an aryl group, or a group in which two or more of these are bonded. ２ ~R ４ are each independently a donor group, for example, R ２ and R ４ are the same and R ３ are different, for example, R ２ ~R ４ are all the same, for example, R ２ ~R ４ In one aspect of the present invention, R ２ ~R ４ Two of them (for example, R ２ and R ４ ) are each independently a donor group, and the remaining one (e.g., R ３ ) is a substituted or unsubstituted aryl group. ２ ~R ４ In one embodiment of the present invention, the donor groups R ２ ~R ４ At least one of the donor groups that R can take is a fused substituted or unsubstituted carbazol-9-yl group. ２ ~R ４At least one of the donor groups that R may take is a substituted carbazol-9-yl group that may be fused (for example, the substituent is an alkyl group that may be substituted with a deuterium atom, or an aryl group that may be substituted with a deuterium atom, an alkyl group, an aryl group, or a group in which two or more of these are bonded). ２ ~R ４ The donor group that can be taken by contains a deuterium atom but does not contain a hydrogen atom.

[0047] In a preferred embodiment of the present invention, the compound represented by general formula (1) has a structure represented by the following general formula (1a):

[0048] In the general formula (1a), Y １ , Y ２ , Y ４ and Y ５ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ represents a hydrogen atom or a deuterium atom, R ２ ~R ４ Among these, one to three (preferably two or three) independently represent a donor group, and the remaining represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. １ , Y ２ , Y ４ , Y ５ , R １ ~R ４ For the description, preferred ranges, and specific examples of R, please refer to the corresponding descriptions in the description of general formula (1) above. ２ ~R ４ are each independently a donor group. ２ and R ４ are each independently a donor group, and R ３ is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0049] When a compound emitting light with a short wavelength is provided, it is preferable to employ a compound having, in the molecule, a deuterium atom or a carbazol-9-yl group substituted with an aryl group which may be substituted with an alkyl group or an aryl group.

[0050] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing no hydrogen atoms but containing deuterium atoms.

[0051] In the present specification, "Group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 atoms constituting the ring skeleton), a heteroaryloxy group (for example, The group consisting of alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. The alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups, alkenyl groups, alkynyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups may be substituted with a deuterium atom constituting group A and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. As used herein, "Group B" refers to a group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), heteroaryloxy groups (e.g., having 5 to 30 ring skeleton atoms), and diarylaminoamino groups (e.g., having 0 to 20 carbon atoms). The alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heteroaryl groups, heteroaryloxy groups, and diarylaminoamino groups referred to here may be substituted with the deuterium atoms constituting Group B and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded.As used herein, "Group C" refers to a group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). The alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups referred to here may be substituted with a deuterium atom constituting Group C and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group D" refers to a group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms). The alkyl groups, aryl groups, and heteroaryl groups referred to here may be substituted with a deuterium atom constituting Group D and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group E" refers to a group consisting of a deuterium atom, alkyl groups (e.g., having 1 to 20 carbon atoms), and aryl groups (e.g., having 6 to 22 carbon atoms). The alkyl group and aryl group referred to here may be substituted with a deuterium atom constituting Group E and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted," the substituted deuterium atom or substituent may be selected, for example, from Group A, Group B, Group C, Group D, or Group E.

[0052] Specific examples of the compound represented by general formula (1) are shown below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R in general formula (1) ２ and R ４ Specific examples of combinations of donor groups are shown as P1 to P2033476. ２ is D1 and R ４ The combinations where R is D1 to D1426 are shown as P1 to P1426 in order.２ is D1 and R ４ The combination where D1 is P1, and R ２ is D1 and R ４ Let P2 be the combination where D2 is ２ is D1 and R ４ The combinations are identified in the same way, with the combination where D3 is P3. The combinations from the second row onwards are identified in the same way.

[0053] Tables 2 and 3 show specific examples of compounds represented by the following general formula: １ is N and X ２ is C-CN, and Y １ ~Y ４ is a phenyl group (Ar1), and R １ Specific examples of compounds in which is a hydrogen atom are shown below.

[0054] In Tables 2 and 3, R ２ , R ３ , R ４ The structures of compounds 1 to 2899736776 are individually identified by indicating R ２ ~R ４ In Table 3, R ３ is a substituted or unsubstituted aryl group, and R ２ and R ４ The columns of Compounds 1 to 2033476 in Table 2 show examples of compounds in which R ３ is fixed to D1, and R ２ and R ４The combinations of P1 to P2033476 shown in Table 1 are identified as compounds 1 to 2033476 in that order. ３ is D1 and R ２ and R ４ The combination of P1 (R ２ and R ４ and both are D1) is specified as Compound 1. ３ is D1 and R ２ and R ４ The combination of P2 (R ２ is D1 and R ４ is D2) is identified as Compound 2. ３ is D1 and R ２ and R ４ The combination of P2033476 (R ２ and R ４ The column for compounds 2033477 to 4066952 in Table 2 identifies the compound 2033476. ３ is fixed at D2, and R ２ and R ４ The combinations of P1 to P2033476 shown in Table 1 are identified as compounds 2033477 to 4066952 in order. ３ is fixed to D3, and R ２ and R ４ The combinations of P1 to P2033476 shown in Table 1 are identified in order as compounds 4066953 to 6100428. The compounds in the subsequent rows of Table 2 and Table 3 are identified in the same manner.

[0055] Compounds 2899736777 to 3052247476 shown in Table 3 are R ３ is a substituted or unsubstituted aryl group, and R ２ and R ４ is a specific example of a donor group. ３ and R ４ The compounds in which R is replaced are exemplified here as Compounds 3052247477 to 3204758176. ４ is a substituted or unsubstituted aryl group, and R ２ and R ３ is a specific example of a donor group. ３ and R ２ The compounds in which R is replaced are exemplified here as Compounds 3204758177 to 3357268876. ２ is a substituted or unsubstituted aryl group, and R ３ and R ４ is a specific example of a donor group. １ Specific examples of compounds in which R is a hydrogen atom are given below. １ The compounds in which the above are substituted with deuterium atoms are shown here as compounds 3357268877 to 6714537752 in order.

[0056] So far, Y in general formula (1) １ , Y ２ , Y ４ , Y ５ is a phenyl group (Ar1), and X １ is N and X ２ Compounds 1 to 6714537752 were identified as compounds 1 to 6714537752. Table 4 shows the Y １ and Y ２ The compounds in which the phenyl group (Ar1) is changed as shown in Table 4 are listed in order in the form of a table. １ and Y ２In the second row of Table 4, for example, Compound 1(1) is a compound 1 in which Y is a phenyl group (Ar1). １ and Y ２ Compound 2(1) shows a compound having a structure in which Y in Compound 2 is Ar2. １ and Y ２ In the same manner, compound 6714537752 (1) is obtained by replacing Y of compound 6714537752 with Ar2. １ and Y ２ The structures of compounds 1(2) to 6714537752(2) onwards in the third row are specified in the same way as in the second row.

[0057]

[0058] In Table 4, Y in general formula (1) ４ and Y ５ Specific examples of compounds in which Ar1 is a phenyl group are shown as Compounds 1 to 6714537752 and Compounds 1(n) to 6714537752(n) [where n is 1 to 898]. In Table 5 below, the Y of these compounds ４ and Y ５ The compounds obtained by sequentially changing the groups shown in Table 5 are shown in a format specifying n in Compounds 1(n) to 6714537752(n). For ease of understanding, the first row of Table 5 lists the Y groups of Compounds 1(n) to 6714537752(n) [where n is 1 to 898]. ４ and Y ５ The second row of Table 5 shows the Y of compounds 1 to 6714537752 and compounds 1(n) to 6714537752(n) [where n is 1 to 898]. ４ and Y ５The compounds in which both are changed to Ar2 are shown in order as Compound 1(n) to Compound 6714537752(n) [where n is 899 to 1797]. The third row of Table 5 shows the Y of Compounds 1 to 6714537752 and Compounds 1(n) to 6714537752(n) [where n is 1 to 898]. ４ and Y ５ The compounds in which both are changed to Ar3 are shown in order as compounds 1(n) to 6714537752(n) [where n is 1798 to 2696]. The structures of the subsequent compounds are identified in the same manner.

[0059]

[0060] All compounds identified by the above numbers are considered to be individually disclosed. It should be noted that, among the specific examples of compounds listed above, when rotamers exist, the mixture of rotamers and each separated rotamer are also considered to be disclosed herein. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 6714537752 and compounds 1(n) to 6714537752(n) [where n is 1 to 808200]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 1 to 2899736776 and compounds 1(n) to 2899736776(n) [where n is 1 to 808200]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of compounds 2899736777 to 3052247476 and compounds 2899736777(n) to 3052247476(n) [where n is 1 to 808200]. In one embodiment of the present invention, the compound is selected from the group of compounds consisting of compounds 3052247477 to 3204758176, and compounds 3052247477(n) to 3204758176(n) [wherein n is from 1 to 808200]. In one embodiment of the present invention, the compound is selected from the group of compounds consisting of compounds 3204758177 to 3357268876, and compounds 3204758177(n) to 3357268876(n) [wherein n is from 1 to 808200]. In one embodiment of the present invention, the compound is selected from the group of compounds consisting of compounds 3357268877 to 6714537752, and compounds 3357268877(n) to 6714537752(n) [wherein n is from 1 to 808200].

[0061] Examples of the compounds represented by general formula (1) are listed below.

[0062] Examples of other compounds represented by general formula (1) are given below.

[0063] Examples of other compounds represented by general formula (1) are given below.

[0064] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and even more preferably 1000 or less, when, for example, an organic layer containing the compound represented by general formula (1) is intended to be formed into a film by vapor deposition and used. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) is useful as a light-emitting material and can be used as a delayed fluorescent material. For example, the compounds represented by general formula (1) include compounds with a high delayed fluorescent component content. Organic light-emitting devices using the compound represented by general formula (1) have good light-emitting properties. For example, the compounds represented by general formula (1) include compounds that can extend the device life when used in organic light-emitting devices. For example, the compounds represented by general formula (1) include compounds that can increase the luminous efficiency when used in organic light-emitting devices. For example, the compounds represented by general formula (1) include compounds that can reduce the driving voltage when used in organic light-emitting devices. The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. Using a coating method, even compounds with relatively large molecular weights can be formed into a film. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents, which makes it easy to apply a coating method to the compound represented by general formula (1) and also easy to purify to increase the purity.

[0065] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0066] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0067] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４ each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent here 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 the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0068] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0069] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group.

[0070] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0071] In some embodiments, the compound represented by general formula (1) is a light-emitting material. Compounds represented by general formula (1) include compounds with long luminescence lifetimes. Compounds represented by general formula (1) can improve luminescence characteristics when used in organic light-emitting devices. For example, compounds represented by general formula (1) include compounds that can extend device lifetimes when used in organic light-emitting devices. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. Compounds represented by general formula (1) include compounds with a high proportion of delayed fluorescent components. For example, compounds in which 80% or more of the total emission is the delayed fluorescent component, for example, compounds in which 90% or more of the total emission is the delayed fluorescent component, are included. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm). In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (eg, 280-400 nm) when excited by thermal or electronic means.In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means.

[0072] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴThe quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0073] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. The compound represented by general formula (1) can be synthesized by combining R ２ ~R ４ One to three of these are each independently a donor group, and for example, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is a donor group can be synthesized by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole. For details of the reaction conditions, please refer to the examples described later.

[0074] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0075] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing a compound represented by general formula (1) is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing a compound represented by general formula (1) is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing a compound represented by general formula (1) can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited thereto. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or a mixture of the compounds may be co-deposited from a single deposition source. When a single vapor deposition source is used, a mixed powder of compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In some embodiments, co-deposition is performed under conditions where the deposition rates (weight loss rates) of the multiple compounds contained in a single vapor deposition source are identical or nearly identical, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the vapor deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed as a vapor deposition source, a film having a desired composition ratio can be easily formed. In some embodiments, the temperature at which each compound to be co-deposited has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0076] [Examples of Use of Compounds Represented by General Formula (1)] By using a compound represented by general formula (1), an organic light-emitting device with excellent performance can be fabricated. In some embodiments of the present invention, an organic electroluminescence device can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present invention, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). The compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferred for use in organic light-emitting diodes, etc. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of a compound represented by general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In some embodiments, the compounds represented by 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 some embodiments, the compound represented by general formula (1) includes a delayed fluorescence (delayed fluorescence material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescence material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescence material. In some embodiments, the present invention relates to a compound represented by general formula (1) that can be used as a host material and can be used together with one or more light-emitting materials, which can be fluorescent materials, phosphorescent materials, or TADF (delayed fluorescent materials). In some embodiments, the compound represented by general formula (1) can also be used as a hole-transporting material. In some embodiments, the compound represented by general formula (1) can be used as an electron-transporting material. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In some embodiments, the substrate is a film-forming surface.In some embodiments, the orientation of the compound represented by formula (1) relative to the film-forming surface influences or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by formula (1) improves light extraction efficiency from the light-emitting layer. For details of use in organic light-emitting devices, see paragraphs

[0063] to

[0099] of WO 2022 / 168956 A1, which is incorporated herein by reference. For example, the compound represented by formula (1) can be used in combination with a host material described in paragraphs

[0123] to

[0145] of WO 2022 / 270602 A1, which is incorporated herein by reference, or in combination with a dopant described in paragraphs

[0006] to

[0129] of WO 2022 / 270354 A1, which is incorporated herein by reference.

[0077] The features of the present invention will be explained in more detail below with reference to examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.).

[0078] (Example 1) Synthesis of Compound A

[0079] Synthesis of Compound 1a Under a nitrogen stream, tetrahydrofuran (THF, 472 mL) and 1-bromo-2,3,4-trifluorobenzene (10.0 g, 47.3 mmol) were placed in a reaction vessel and cooled to -78°C. A 1.0 mol / L lithium diisopropylamide, n-hexane-tetrahydrofuran solution (52.0 mL, 52.0 mmol) was added dropwise, and the mixture was stirred at -78°C for 1 hour. Tributyltin chloride (17.2 g, 52.0 mmol) was added at -78°C, and the mixture was then warmed to room temperature and stirred overnight. After adding water, the organic layer was extracted with methylene chloride, washed with saturated saline, and dried over magnesium sulfate. After filtration and concentration using an evaporator, liquid 1a was obtained.

[0080] Synthesis of Compound 3a: A solution of the obtained compound 1a in toluene (470 mL) was bubbled with nitrogen. Under a nitrogen stream, compound 2a (17.4 g, 47.3 mmol) and bis(triphenylphosphine)palladium(II) dichloride (2.25 g, 3.78 mmol) were added to this solution, and the mixture was heated and stirred at 110°C overnight. The reaction vessel was cooled to room temperature and passed through a funnel (Kiriyama Funnel) packed with Celite / silica gel / Celite. The solution was concentrated using an evaporator and then reprecipitated with toluene / hexane to obtain a white solid 3a (9.64 g, 17.7 mmol, yield 38%). ASAP MS spectrum analysis: C 27 HD 13 BrF3N4: Theoretical value 543.12, Observed value 544.34.

[0081] Synthesis of Compound 6a: A reaction mixture of compound 3a (1.75 g, 3.22 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.117 g, 0.161 mmol), potassium acetate (1.57 g, 16.0 mmol), bis(pinacolato)diboron (2.45 g, 9.66 mmol), and 1,4-dioxane (32 mL) was stirred overnight at 110°C. After cooling to room temperature, the resulting crude product of compound 4a was used directly in the next reaction. THF (32 mL) and water (16 mL) were added to the crude product of compound 4a, and compound 5a (2.00 g, 6.62 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.068 g, 0.097 mmol), and sodium carbonate (0.683 g, 6.45 mmol) were added, followed by heating and stirring at 75°C overnight. The reaction vessel was cooled to room temperature, filtered, and washed with water, methanol, methylene chloride, and ethyl acetate. The resulting solid was dried to give compound 6a (1.40 g, 1.91 mmol, 60% yield) as a light gray solid. ASAP MS spectrum analysis: 44 HD 23 F3N7: Theoretical value 730.35, Observed value 731.61.

[0082] Synthesis of Compound A: Under a nitrogen stream, tripotassium phosphate (6.58 g, 31.0 mmol) was added to a solution of compound 6a (3.5 g, 4.78 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (5.43 g, 31.0 mmol) in N-methyl-2-pyrrolidone (NMP, 48 mL), and the mixture was stirred at 110°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 resulting solid was purified by column chromatography (toluene:hexane = 1:1) to obtain yellow compound A (3.0 g, 2.50 mmol, yield 53%). 1 H-NMR (400 MHz, CDCl): δ 9.16 (s, 1H). ASAP MS spectral analysis: C 80 HD 47 N 10 : Theoretical value 1195.70, observed value 1196.97.

[0083] (Example 2) Synthesis of Compound B

[0084] Synthesis of Compound 2b: A solution of compound 1a (23.6 g, 47.3 mmol) in toluene (470 mL) was bubbled with nitrogen. Under a nitrogen stream, compound 1b (13.1 g, 47.3 mmol) and bis(triphenylphosphine)palladium(II) dichloride (2.65 g, 3.78 mmol) were added to this solution, and the mixture was heated and stirred at 110°C overnight. The reaction vessel was cooled to room temperature, and methylene chloride was added and passed through a celite / silica gel / celite funnel (Kiriyama Funnel). The solution was concentrated using an evaporator and then reprecipitated with toluene / methanol to obtain a white solid 2b (6.81 g, 15.0 mmol, yield 32%). ASAP MS spectrum analysis: C 21 HD 10 BrF3N3: Theoretical value 451.07, Observed value 452.25.

[0085] Synthesis of Compound 3b A reaction mixture of compound 2b (6.81 g, 15.0 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.09 g, 1.50 mmol), potassium acetate (7.36 g, 75.0 mmol), bis(pinacolato)diboron (11.4 g, 45.0 mmol), and 1,4-dioxane (150 mL) was stirred at 110°C overnight. The mixture was cooled to room temperature, dissolved in methylene chloride, and passed through a celite / silica gel / celite funnel (Kiriyama Funnel). The solution was concentrated using an evaporator to obtain a white solid 3b (3.0 g, 15 mmol, 40% yield).

[0086] Synthesis of Compound 4b: Under a nitrogen stream, compound 5a (1.99 g, 6.60 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.21 g, 0.30 mmol), and sodium carbonate (1.27 g, 12.0 mmol) were added to a solution of compound 3b (3.0 g, 6.0 mmol) in THF (60 mL) and water (30 mL), and the mixture was heated and stirred at 75°C overnight. The reaction vessel was cooled to room temperature, filtered, and then washed with water, methanol, methylene chloride, and ethyl acetate. The resulting solid was dried to give compound 4b (3.56 g, 5.57 mmol, 93% yield) as a light gray solid. ASAP MS spectral analysis: C 38 HD 20 F3N6: Theoretical value 638.30, observed value 639.46.

[0087] Synthesis of Compound 5b Under a nitrogen stream, potassium carbonate (1.29 g, 9.38 mmol) was added to a solution of compound 4b (2.0 g, 3.13 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.37 g, 7.82 mmol) in NMP (100 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 resulting solid was purified by column chromatography (toluene:hexane = 1:1) to give compound 5b (1.80 g, 1.89 mmol, yield 61%) as a yellow solid. ASAP MS spectrum analysis: C 62 HD 36 FN8: Theoretical value 948.54, Observed value 949.95.

[0088] Synthesis of Compound B Under a nitrogen stream, potassium carbonate (0.78 g, 5.67 mmol) was added to a solution of compound 5b (1.80 g, 1.89 mmol) and 9H-carbazole-1,2,4,5,6,7,8-d7-3-carbonitrile (0.75 g, 3.78 mmol) in NMP (20 mL), and the mixture was stirred at 140°C for 16 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 obtained solid was purified by column chromatography (toluene) to obtain compound B (1.37 g, 1.21 mmol, yield 64%) as a yellow solid.1 H-NMR (400 MHz, CDCl): δ 9.29 (s, 1H). ASAP MS spectral analysis: 75 HD 43 N 10 : Theoretical value 1127.64, observed value 1129.09.

[0089] (Example 3) Synthesis of Compound C

[0090] Synthesis of Compound C: Under a nitrogen stream, potassium carbonate (1.72 g, 12.5 mmol) was added to a solution of compound 4b (1.6 g, 2.5 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.75 g, 10.0 mmol) in NMP (25 mL), and the mixture was stirred at 150°C for 2 days. 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 resulting solid was purified by column chromatography (toluene) to give compound C (0.58 g, 0.52 mmol, yield 21%) as a yellow solid. 1 H-NMR (400 MHz, CDCl): δ 9.18 (s, 1H). ASAP MS spectral analysis: C 74 HD 44 N 9　 : Theoretical value 1103.66, observed value 1105.38.

[0091] (Example 4) Synthesis of Compound D

[0092] Synthesis of Compound 1d Under a nitrogen stream, THF (210 mL) and 1-bromo-2,4-difluorobenzene (16.3 g, 84.8 mmol) were placed in a reaction vessel and cooled to -78°C. A 1.0 mol / L lithium diisopropylamide, n-hexane-tetrahydrofuran solution (100.0 mL, 100 mmol) was added dropwise, followed by stirring at -78°C for 1 hour. A THF (170 mL) solution of iodine (27.9 g, 110 mmol) was added at -78°C, followed by stirring for an additional 1 hour. The temperature was raised to room temperature and stirred overnight. Water was added, followed by quenching with 10% hydrochloric acid. THF was removed using an evaporator, methylene chloride was added, and the organic layer was extracted, washed with saturated brine, and dried over magnesium sulfate. After filtration, the mixture was concentrated using an evaporator and then purified by silica gel column chromatography (hexane) to obtain a transparent liquid 1d (26.0 g, 81.5 mmol, yield 96%). 1 H-NMR (400 MHz, CDCl): δ 7.59-7.48 (m, 1H), 6.87-6.77 (m, 1H). ASAP MS spectral analysis: C6H2BrF2I: calcd 317.84, found 317.94.

[0093] Synthesis of Compound 2d: Under a nitrogen stream, phenyl-d5-boronic acid (1.98 g, 15.6 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.55 g, 0.78 mmol), and potassium carbonate (4.31 g, 31.2 mmol) were added to a solution of compound 1d (5.0 g, 15.6 mmol) in 1,4-dioxane (78 mL) and water (26 mL), and the mixture was stirred at 70°C for 18 hours. The reaction vessel was cooled to room temperature, and ethyl acetate and water were added to extract the organic layer. The organic layer was washed with saturated brine and then dried over magnesium sulfate. After filtration and concentration using an evaporator, the mixture was purified by silica gel column chromatography (hexane) to obtain a transparent liquid 2d (3.48 g, 12.6 mmol, 81% yield). 1 H-NMR (400 MHz, CDCl): δ 7.54-7.47 (m, 1H), 6.96-6.90 (m, 1H). ASAP MS spectral analysis: 12 H2D5BrF2: Calculated 273.00, Observed 273.07.

[0094] Synthesis of Compound 4d Under a nitrogen stream, THF (24 mL) and compound 2d (1.94 g, 7.07 mmol) were placed in a reaction vessel and cooled to -78°C. A 1.0 mol / L lithium diisopropylamide, n-hexane-tetrahydrofuran solution (7.8 mL, 7.8 mmol) was added dropwise, followed by stirring at -78°C for 30 minutes. Tributyltin chloride (2.55 g, 7.8 mmol) was added at -78°C, followed by stirring for 30 minutes, warming to room temperature, and stirring overnight. After adding water, the organic layer was extracted with methylene chloride, washed with saturated saline, and dried over magnesium sulfate. After filtration and concentration using an evaporator, compound 3d was obtained as a brown, transparent liquid. The crude product of compound 3d was dissolved in toluene (470 mL) and nitrogen was bubbled through the solution. Compound 1b (2.35 g, 8.47 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.247 g, 0.353 mmol) were added to the solution under a nitrogen stream, and the mixture was heated and stirred at 100 °C overnight. The reaction vessel was cooled to room temperature, and the mixture was dissolved in methylene chloride and passed through a Celite / silica gel / Celite funnel (Kiriyama Funnel). The solution was concentrated using an evaporator and then reprecipitated with dichloromethane / hexane to give white solid 4d (1.60 g, 3.10 mmol, yield 44%). 1 H-NMR (400 MHz, CDCl3): δ 8.73 (t, J = 7.8 Hz, 1H). ASAP MS spectrum analysis: C 27 HD 15 BrF2N3: Theoretical value 514.14, Observed value 515.41.

[0095] Synthesis of Compound 6d: Under a nitrogen atmosphere, a reaction mixture of compound 4d (1.6 g, 3.10 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.11 g, 0.15 mmol), potassium acetate (0.897 g, 9.14 mmol), bis(pinacolato)diboron (1.54 g, 6.10 mmol), and 1,4-dioxane (10 mL) was stirred overnight at 110°C. After cooling to room temperature and concentrating using an evaporator, THF (15 mL) and water (5 mL) were added, and compound 5a (1.10 g, 3.65 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.106 g, 0.152 mmol), and sodium carbonate (0.968 g, 9.14 mmol) were added, followed by heating and stirring at 80°C overnight. The reaction vessel was cooled to room temperature, filtered, and washed with water and methanol. Toluene was added, and the mixture was heated at 120°C for washing. The resulting solid was dried to give compound 6d (1.53 g, 2.17 mmol, 71% yield) as a pale yellow solid. ASAP MS spectrum analysis: C 44 HD 25 F2N6: Theoretical value 701.38, Observed value 702.76.

[0096] Synthesis of Compound D: Under a nitrogen stream, a reaction vessel was charged with a solution of compound 6d (1.0 g, 1.42 mmol), 5H-benzofuro[3,2-c]carbazole (0.802 g, 3.12 mmol) in NMP (28 mL), and potassium carbonate (6.58 g, 31.0 mmol). The mixture was stirred at 120°C overnight and at 130°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 resulting solid was purified by column chromatography (toluene:hexane = 7:3) to obtain compound D (0.61 g, 0.52 mmol, yield 36%) as a yellow solid. 1 H-NMR(400 MHz, CDCl3): δ 9.30 (s, 1H), 8.24 (d, J = 7.6 Hz, 2H), 7.95-7.82 (m, 4H), 7.67-7.60 (m, 2H), 7.44-7.24 (m, 12H). ASAP MS spectrum analysis: C 80 H21 D 25 N8O2: Theoretical value 1175.53, Observed value 1177.21.

[0097] (Example 5) Synthesis of Compound E

[0098] Synthesis of Compound 2e Compound 1d (5.62 g, 17.6 mmol), compound 1e (5.99 g, 21.1 mmol), tetrakis(triphenylphosphine)palladium(0) (1.01 g, 0.88 mmol), potassium carbonate (4.86 g, 35.2 mmol), 1,4-dioxane (29 mL), and water (10 mL) were added to a reaction vessel under a nitrogen atmosphere and stirred at 80°C overnight. The reaction vessel was cooled to room temperature, and toluene and water were added to extract the organic layer. The organic layer was washed with saturated brine and then dried over magnesium sulfate. After filtration and concentration using an evaporator, the mixture was purified by silica gel column chromatography (hexane) to obtain a transparent liquid, 2e (4.84 g, 11.2 mmol, yield 64%). ASAP MS spectrum analysis: C 24 H5D 10 BrF2: Theoretical value 430.10, Observed value 431.31.

[0099] Synthesis of Compound 3e Under a nitrogen stream, THF (19 mL) and compound 2e (2.5 g, 5.79 mmol) were placed in a reaction vessel and cooled to -80°C. A 1.0 mol / L lithium diisopropylamide, n-hexane-tetrahydrofuran solution (6.9 mL, 6.9 mmol) was added dropwise, followed by stirring at -80°C for 30 minutes. Tributyltin chloride (2.27 g, 6.94 mmol) was added at -80°C, followed by stirring for 30 minutes, warming to room temperature, and stirring for 2 hours. Water was added, and the organic layer was extracted with methylene chloride, washed with saturated saline, and dried over magnesium sulfate. After filtration and concentration using an evaporator, compound 3e was obtained as a brown, transparent liquid. A toluene (38 mL) solution of the obtained crude product of compound 3e was bubbled with nitrogen, and then compound 1b (1.92 g, 6.94 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.202 g, 0.289 mmol) were added to the solution under a nitrogen stream and heated and stirred at 100°C overnight. The reaction vessel was cooled to room temperature, and the compound was dissolved in methylene chloride and passed through a Celite / silica gel / Celite funnel (Kiriyama Funnel). The solution was concentrated using an evaporator and then reprecipitated with toluene / hexane to obtain a white solid 4e (1.95 g, 2.89 mmol, 50% yield). ASAP MS spectrum analysis: C 39 H4D 20 BrF2N3: Theoretical value 671.24, Observed value 672.60.

[0100] Synthesis of Compound 6e: Under a nitrogen atmosphere, a reaction mixture of compound 4e (4.18 g, 6.21 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.226 g, 0.310 mmol), potassium acetate (1.82 g, 18.6 mmol), bis(pinacolato)diboron (3.14 g, 12.4 mmol), and 1,4-dioxane (20 mL) was stirred at 110°C for 5 hours. After cooling to room temperature and concentrating using an evaporator, THF (40 mL) and water (14 mL) were added, and compound 5a (2.06 g, 6.83 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.217 g, 0.310 mmol), and sodium carbonate (1.64 g, 15.5 mmol) were added, followed by heating and stirring at 75°C overnight. The reaction vessel was cooled to room temperature, filtered, and washed with water and toluene. Toluene was added, and the mixture was heated and washed at 100° C. The resulting solid was dried to give Compound 6e (1.20 g, 1.39 mmol, yield 23%) as a pale yellow solid.

[0101] Synthesis of Compound E: Under a nitrogen stream, tripotassium phosphate (0.73 g, 3.46 mmol) was added to a solution of compound 6e (0.85 g, 0.99 mmol) and 12H-[1]benzothieno[2,3-a]carbazole (0.675 g, 2.47 mmol) in NMP (13 mL), and the mixture was stirred at 130°C overnight. 2H-[1]benzothieno[2,3-a]carbazole (0.300 g, 1.1 mmol), tripotassium phosphate (0.35 g, 1.64 mmol), and NMP (10 mL) were added, and the mixture was further stirred at 150°C for 8 hours. The reaction solution was cooled to room temperature and quenched by adding water. The precipitated solid was filtered and washed with water and methanol. The obtained solid was purified by column chromatography (toluene:hexane=9:1) and reprecipitated with ethyl acetate / dichloromethane to obtain a yellow compound E (0.41 g, 0.30 mmol, yield 30.5%). 1H-NMR (400 MHz, CDCl3): δ 10.0 (s, 1H), 8.29-8.22 (m, 2H), 8.11-7.85(m, 9H), 7.54-7.32 (m, 7H), 7.25-7.04 (m, 2H), 7.00-6.95(m, 2H), 6.81-6.77(m, 1H). ASAP MS spectrum analysis: C 92 H 24 D 30 N2S2: Theoretical value 1364.58, Observed value 1366.34.

[0102] (Example 6) Synthesis of Compound F

[0103] Synthesis of Compound F: Under a nitrogen stream, a solution of compound 5e (1.2 g, 1.39 mmol), 5H-benzofuro[3,2-c]carbazole (0.892 g, 3.47 mmol) in NMP (28 mL) was charged with potassium carbonate (0.576 g, 4.17 mmol) in a reaction vessel, and the mixture was stirred at 130°C overnight. The reaction solution was cooled to room temperature, and water was added to quench the reaction. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by column chromatography (toluene:hexane = 8:2) and reprecipitated with ethyl acetate / dichloromethane to give yellow compound F (0.81 g, 0.606 mmol, yield 44%). 1 H-NMR (400 MHz, CDCl3): δ 9.45 (s, 1H, rotamer 1),9.44 (s, 1H, rotamer 2), 8.38-8.31 (m, 2H), 7.96-7.81 (m, 4H) 7.69-7.61 (m, 2H), 7.46-7.27 (m, 12H), 7.02-6.92 (m,2H), 6.87-6.84 (m, 1H). ASAP MS spectrum analysis: C 92 H 24 D 30 N8O2: Calculated 1332.63, Observed 1334.36.

[0104] (Example 7) Synthesis of Compound G

[0105] Synthesis of Compound 1g Under a nitrogen stream, 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (14.7 g, 64.0 mmol), (3,5-tert-butylphenyl)boronic acid (10.0 g, 42.7 mmol), potassium carbonate (17.6 g, 128 mmol), tetrakis(triphenylphosphine)palladium (1.47 g, 1.28 mmol), THF (142 mL), and degassed water (47 mL) were placed in a reaction vessel and stirred overnight at 70° C. The reaction solution was cooled to room temperature, filtered, and then 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. It was then purified by column chromatography (methylene chloride:hexane=2:8) to obtain Compound 1g as a white solid (10.59 g, 27.5 mmol, yield 64%). 1 H-NMR (400 MHz, CDCl3): δ 8.47 (d, J=2.4 Hz, 2H), 7.71 (t, J = 2.0 Hz, 1H), 1.43 (s, 18H). ASAP MS spectrum analysis: C 23 H 21 D5ClN3: Calculated 384.21, Observed 385.86.

[0106] Synthesis of Compound 2g: After bubbling nitrogen into a solution of compound 2e (4.40 g, 10.2 mmol) in toluene (68 mL), compound 5a (3.68 g, 12.2 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.357 g, 0.509 mmol) were added to the solution under a nitrogen stream, and the mixture was heated and stirred at 100 °C for 3 days. The mixture was cooled to room temperature, dissolved in methylene chloride, and passed through a Celite / silica gel / Celite funnel (Kiriyama Funnel). The solution was concentrated using an evaporator and then reprecipitated with toluene / hexane to obtain compound 2g (2.36 g, 3.38 mmol, yield 33%) as a white solid.

[0107] Synthesis of Compound 4g: Under a nitrogen atmosphere, a reaction mixture of compound 2g (1.39 g, 1.99 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.073 g, 0.10 mmol), potassium acetate (0.585 g, 5.97 mmol), bis(pinacolato)diboron (1.01 g, 3.98 mmol), and 1,4-dioxane (20 mL) was stirred at 110°C for 5 hours. After cooling to room temperature and concentrating using an evaporator, THF (10 mL) and water (3 mL) were added, and compound 1g (0.84 g, 2.18 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.139 g, 0.20 mmol), and sodium carbonate (0.526 g, 4.97 mmol) were added, followed by heating and stirring at 75°C overnight. The reaction vessel was cooled to room temperature, filtered, and washed with water and toluene. Toluene was added, and the mixture was heated and washed at 100°C. The resulting solid was dried, yielding 4 g of a pale yellow solid compound (0.79 g, 0.817 mmol, yield 41%). 1 H-NMR(400 MHz, CDCl3): δ 9.64 (t, J = 8.8 Hz, 1H), 8.60 (d, J = 2 Hz, 2H), 7.95 (t, J = 2.0 Hz, 1H), 7.84 (s, 2H), 7.69 (t, J = 2.0 Hz 1H), 1.391 (s, 18H). ASAP MS spectrum analysis: C 64 H 25 D 25 F2N6: Theoretical value 965.56, Observed value 967.11.

[0108] Synthesis of Compound G: Under a nitrogen stream, potassium carbonate (0.277 g, 2.01 mmol) was added to a solution of Compound 4g (0.78 g, 0.807 mmol) and 5H-benzofuro[3,2-c]carbazole (0.455 g, 1.77 mmol) in NMP (13 mL), and the mixture was stirred at 100°C overnight. The reaction solution was cooled to room temperature, and water was added to quench the reaction. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by column chromatography (toluene:hexane = 8:2) and reprecipitated with ethyl acetate / methanol to obtain yellow Compound G (0.475 g, 0.329 mmol, yield 41%). 1 H-NMR (400 MHz, CDCl3): δ 9.32 (s, 1H), 8.38-8.29 (m, 4H), 7.96-7.81(m, 4H), 7.69-7.59 (m, 3H), 7.46-7.26 (m, 12H), 6.96-6.82 (m, 3H), 1.31 (s, 9H), 1.30 (s, 9H). ASAP MS spectrum analysis: C 100 H 45 D 25 N8O2: Theoretical value 1439.72, Observed value 1441.51.

[0109] (Example 8) Synthesis of Compound H

[0110] Synthesis of Compound 1h: Under a nitrogen stream, magnesium (2.37 g, 97.8 mmol), 1,2-dibromoethane (0.18 g, 0.9 mmol), and THF (310 mL) were added to a reaction vessel and stirred at room temperature for 30 minutes. To this solution, a solution of 1-bromo-3,5-di-tert-butylbenzene (25.0 g, 93.2 mmol) in THF (93 mL) was added dropwise. After the addition was complete, the mixture was heated at 60°C for 2 hours. After cooling to room temperature, a solution of trichloro-1,3,5-triazine (17.20 g, 93.2 mmol) in THF (310 mL) was added dropwise. After the addition, the reaction solution was stirred at room temperature for 2 hours. After adding hydrochloric acid, the organic layer was extracted with methylene chloride, washed with saturated brine, and dried over magnesium sulfate. The resulting solution was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane=2:8) to obtain Compound 1h as a white solid (17.28 g, 51.0 mmol, yield 55%). 1 H-NMR (400 MHz, CDCl3): δ 8.34 (d, J = 2 Hz, 2H), 7.73 (t, J = 1.6 Hz, 1H), 1.395 (s, 18H). ASAP MS spectrum analysis: C 17 H 21 Cl2N3: Theoretical value 337.11, Observed value 338.23.

[0111] Synthesis of Compound 2h: Under a nitrogen stream, THF (147 mL) was added to compound 1h (5.00 g, 14.7 mmol) and the mixture was cooled to -5°C. To the resulting solution, a solution of carbazole-1,2,3,4,5,6,7,8-d8 (2.57 g, 14.7 mmol) and sodium hydride (0.64 g, 16.1 mmol) in THF (74 mL) was added dropwise. After the dropwise addition, the reaction solution was warmed to 0°C and stirred for 1 hour. After the temperature was raised to room temperature and an aqueous ammonium chloride solution was added, the organic layer was extracted with methylene chloride, washed with saturated brine, and dried over magnesium sulfate. The resulting solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (methylene chloride:hexane = 3:7) to obtain compound 2h (1.32 g, 8.81 mmmmol, yield 60%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 8.50 (d, J=1.6 Hz, 2H), 7.75 (t, J= 2.0Hz, 1H), 1.46 (s, 18H). ASAP MS spectrum analysis: C 29 H 21 D8ClN4: Calculated 476.26, Observed 477.43.

[0112] Synthesis of Compound 3h THF (157 mL) and 1-bromo-2,3,4-trifluorobenzene (10.0 g, 47.3 mmol) were placed in a reaction vessel under a nitrogen stream and cooled to -78°C. A 1.0 mol / L lithium diisopropylamide, n-hexane-tetrahydrofuran solution (57 mL, 56.7 mmol) was added dropwise, followed by stirring at -78°C for 1 hour. Tributyltin chloride (10.6 g, 56.7 mmol) was added at -78°C, followed by heating to room temperature and stirring for 2 hours. Water was added, and the organic layer was extracted with methylene chloride, washed with saturated saline, and dried over magnesium sulfate. After filtration, the mixture was concentrated using an evaporator to obtain a brown liquid. A toluene (236 mL) solution of the obtained compound was subjected to nitrogen bubbling. Compound 5a (17.4 g, 52.0 mmol) and bis(triphenylphosphine)palladium(II) dichloride (1.65 g, 2.36 mmol) were added to this solution under a nitrogen stream, and the mixture was heated and stirred at 90 °C overnight. The reaction vessel was cooled to room temperature and passed through a funnel (Kiriyama Funnel) packed with Celite / silica gel / Celite. The solution was concentrated using an evaporator and then reprecipitated with toluene / hexane to give white solid 3h (8.33 g, 17.4 mmol, 37% yield). 1 H-NMR (400 MHz, CDCl3): δ 8.41 (dt, J = 7.2 Hz, J = 2.8 Hz, 1H). ASAP MS spectrum analysis: C 23 HD 10 F3N3: Theoretical value 475.07, Observed value 476.27.

[0113] Synthesis of Compound 4h: Under a nitrogen atmosphere, a reaction mixture of compound 3h (2.80 g, 5.87 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.21 g, 0.29 mmol), potassium acetate (1.43 g, 14.6 mmol), bis(pinacolato)diboron (2.97 g, 11.7 mmol), and 1,4-dioxane (59 mL) was stirred overnight at 110°C. After cooling to room temperature and concentrating using an evaporator, THF (59 mL) and water (19 mL) were added, and compound 2h (3.35 g, 7.04 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.41 g, 0.59 mmol), and sodium carbonate (1.24 g, 11.7 mmol) were added, followed by heating and stirring at 75°C for 6 hours. The reaction vessel was cooled to room temperature, filtered, and washed with water and toluene. Toluene was added, and the mixture was heated at 100° C. for washing. The resulting solid was dried to give compound 4h (2.25 g, 2.68 mmol, yield 41%) as a light gray solid. 1 H-NMR (400 MHz, CDCl3): δ 9.44 (t, J = 6.8 Hz, 1H), 8.65-8.59 (m, 2H), 7.76-7.72 (m, 1H), 1.43 (s, 18H). ASAP MS spectrum analysis: C 52 H 22 D 18 F3N7: Theoretical value 837.44, Observed value 838.87.

[0114] Synthesis of Compound H: Under a nitrogen stream, tripotassium phosphate (3.12 g, 14.7 mmol) was added to a solution of compound 4h (2.25 g, 2.68 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (2.10 g, 12.0 mmol) in NMP (27 mL), and the mixture was stirred at 150°C for 6 hours. The reaction solution was cooled to room temperature, and water was added to quench the reaction. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by column chromatography (toluene:hexane = 8:2) and reprecipitated with ethyl acetate / methanol to obtain compound H (0.34 g, 0.26 mmol, yield 10%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ 9.03 (s, 1H), 8.06 (d, J = 2.0 Hz, 2H), 7.55 (t, J = 2.0 Hz, 1H), 1.25 (s, 18H). MALDI-TOF MS spectrum analysis: C 88 H 22 D 42 N 10 : Theoretical value 1302.80, observed value 1304.2450.

[0115] (Example 9) Synthesis of Compound I

[0116] Synthesis of Compound 1i: Under a nitrogen stream, magnesium (1.79 g, 73.9 mmol), 1,2-dibromoethane (0.12 g, 0.7 mmol), and THF (225 mL) were added to a reaction vessel and stirred at room temperature for 30 minutes. To this solution, a solution of 1-bromo-4-tert-butylbenzene (15.0 g, 70.5 mmol) in THF (48 mL) was added dropwise. After the addition was complete, the mixture was heated at 60°C for 1 hour. After cooling to room temperature, a solution of trichloro-1,3,5-triazine (12.40 g, 67.2 mmol) in THF (225 mL) was added dropwise. After the addition, the reaction solution was stirred at room temperature for 2 hours. After adding hydrochloric acid, the organic layer was extracted with methylene chloride, washed with saturated brine, and dried over magnesium sulfate. The resulting solution was concentrated under reduced pressure using an evaporator and then purified by column chromatography (methylene chloride:hexane=2:8) to obtain Compound 1i as a white solid (7.35 g, 26.0 mmol, yield 39%). 1 H-NMR (400 MHz, CDCl3): δ 8.42 (dt, J = 9.2 Hz, J = 2.0 Hz,2H), 7.54 (dt, J = 9.2 Hz, J = 2.0 Hz,2H), 1.37 (s, 9H). ASAP MS spectrum analysis: C 13 H 13 Cl2N3: Theoretical 281.05, Observed 282.26.

[0117] Synthesis of Compound 2i: Under a nitrogen stream, THF (89 mL) was added to compound 1i (5.00 g, 17.7 mmol) and the mixture was cooled to -5°C. To the resulting solution, a solution of carbazole-1,2,3,4,5,6,7,8-d8 (3.10 g, 17.7 mmol) and 60% sodium hydride (0.78 g, 19.4 mmol) in THF (44 mL) was added dropwise. After the dropwise addition, the reaction solution was warmed to 0°C and stirred for 1 hour. After the temperature was raised to room temperature and an aqueous ammonium chloride solution was added, the organic layer was extracted with methylene chloride, washed with saturated saline, and dried over magnesium sulfate. The resulting solution was concentrated under reduced pressure using an evaporator and purified by column chromatography (methylene chloride:hexane = 3:7) to obtain compound 2i (5.97 g, 14.1 mmmmol, yield 80%) as a white solid. 1 H-NMR (400 MHz, CDCl3): δ 8.53 (dt, J = 8.8 Hz, J = 2.0 Hz, 2H), 8.63 (dt, J = 8.4 Hz, J = 2 Hz, 2H), 1.41 (s, 9H). ASAP MS spectrum analysis: C 25 H 13 D8ClN4: Calculated 420.20, Observed 421.48.

[0118] Synthesis of Compound 3i: Under a nitrogen atmosphere, a reaction mixture of compound 3h (6.15 g, 12.90 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.47 g, 0.65 mmol), potassium acetate (3.16 g, 32.2 mmol), bis(pinacolato)diboron (6.55 g, 25.8 mmol), and 1,4-dioxane (130 mL) was stirred overnight at 110°C. After cooling to room temperature and concentrating using an evaporator, THF (130 mL) and water (43 mL) were added, and compound 2i (6.48 g, 15.4 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.91 g, 1.29 mmol), and sodium carbonate (2.73 g, 25.8 mmol) were added, followed by heating and stirring at 75°C for 6 hours. The reaction vessel was cooled to room temperature, filtered, and washed with water and toluene. Toluene was added, and the mixture was heated at 100° C. for washing. The resulting solid was dried to give Compound 3i (7.10 g, 9.08 mmol, yield 71%) as a light gray solid. 1 H-NMR(400 MHz, CDCl3): δ 9.57 (td, J = 8.4 Hz, J = 2 Hz, 1H), 8.65 (d, J = 8.8 Hz, J = 2 Hz, 2H), 7.64 (d, J = 8.8 Hz, J = 2Hz, 2H), 1.44 (s, 9H). ASAP MS spectrum analysis: C 48 H 14 D 18 F3N7: Theoretical value 781.38, Observed value 782.84.

[0119] Synthesis of Compound I: Under a nitrogen stream, tripotassium phosphate (5.03 g, 23.7 mmol) was added to a solution of compound 3i (3.10 g, 3.96 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (3.45 g, 19.7 mmol) in NMP (80 mL), and the mixture was stirred at 120°C for 3 hours. After stirring at 130°C for 4 hours, carbazole-1,2,3,4,5,6,7,8-d8 (0.70 g, 3.98 mmol), tripotassium phosphate (1.00 g, 4.71 mmol), and NMP (3 mL) were added, and the mixture was stirred at 130°C for 6 hours. The reaction solution was cooled to room temperature and quenched by adding water. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by column chromatography (toluene:hexane=8:2) and reprecipitated with ethyl acetate / methanol to give yellow Compound I (1.50 g, 1.20 mmol, yield 30%). 1 H-NMR (400 MHz, CDCl3): δ 9.14 (s, 1H), 7.47 (d, J = 8.8 Hz, 2H), 7.20(d, J = 8.8 Hz, 2H), 1.30 (s, 9H). ASAP MS spectrum analysis: C 84 H 14 D 42 N 10 : Theoretical value 1246.73, Observed value 1247.61.

[0120] (Test Example 1) Preparation and Evaluation of Thin Films Compound A and Compound H1 (described later) were evaporated onto a quartz substrate from different evaporation sources at a vacuum of 1×10 －３ The thin films were vapor-deposited at less than 100 Pa to form thin films with a concentration of Compound A of 20 wt % to a thickness of 100 nm. Thin films were formed in the same manner using Compounds B, C, E, F, G, H, Comparative Compound 1 (described below), and Comparative Compound 2 (described below) instead of Compound A. Photoluminescence was analyzed when each of the formed thin films was irradiated with 300 nm excitation light, and the emission peak wavelength (λmax) and the proportion of delayed fluorescent components in the emission were measured. The results are shown in the table below. It was confirmed that the compound represented by general formula (1) had a higher proportion of delayed fluorescent components than Comparative Compounds 1 and 2, which have structures similar to General Formula (1).

[0121] (Test Example 2) Fabrication and Evaluation of Green Organic Electroluminescence Devices Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed by vacuum deposition at a vacuum degree of 5.0×10 －５ The layers were laminated at 10 Pa. First, a compound HAT-CN described below was formed on ITO to a thickness of 10 nm, a compound NPD described below was formed thereon to a thickness of 30 nm, a compound TrisPCz described below was formed thereon to a thickness of 10 nm, and a compound H2 was formed thereon to a thickness of 5 nm. Next, a compound H2 described below and a compound A were co-deposited from different evaporation sources to form a layer with a thickness of 40 nm, which served as an emitting layer. The concentration of compound A in the emitting layer was 35% by mass. Next, a compound SF3-TRZ described below was formed to a thickness of 10 nm, and then compounds Liq and SF3-TRZ described below were co-deposited 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 vapor-deposited to a thickness of 100 nm to form a cathode, thereby preparing an organic electroluminescence device. Instead of Compound A, Compound B, Compound C, and Comparative Compounds 1 to 4 described below were used, respectively, to prepare organic electroluminescence devices by the same procedure. However, the concentration of Comparative Compound 1 in the light-emitting layer was 65 wt %, and the concentration of Comparative Compound 2 in the light-emitting layer was 55 wt %. The external quantum efficiency (EQE) of each organic electroluminescence device was 6.3 mA / cm ２ The results are shown in the table below. It was confirmed that the compound represented by general formula (1) had a higher external quantum efficiency than comparative compounds 1 and 2, which have structures similar to general formula (1).

[0122] Next, for the organic electroluminescence device using compound A and the organic electroluminescence device using comparative compound 3, 12.6 mA / cm ２The device was allowed to emit light at 400 rpm, and the time (LT95) until the emission intensity decreased to 95% of that at the start of operation was measured. The results are shown in the table below. The results are shown as relative values ​​when the LT95 of the device using comparative compound 3 was set to 1. It was confirmed that compound A represented by general formula (1) had a longer device life than comparative compound 3, which is similar in that it contains a triazinyl group substituted with a perdeuterated phenyl group and a perdeuterated carbazol-9-yl group, and three perdeuterated carbazol-9-yl groups.

[0123] Furthermore, the LT95 was measured in the same manner for each of the organic electroluminescence devices using Compound B, Compound C, and Comparative Compound 4. The results are shown in the table below. The results are shown as relative values ​​when the LT95 of the device using Comparative Compound 4 was set to 1. It was confirmed that Compounds B and C represented by general formula (1) had longer device lifetimes than Comparative Compound 4, which has in common the fact that it contains a triazinyl group substituted with two perdeuterated phenyl groups and three substituted or unsubstituted perdeuterated carbazol-9-yl groups.

[0124] (Test Example 3) Preparation and Evaluation of Organic Electroluminescence Device Using Assist Dopant

[0047] Organic electroluminescence devices were prepared by the same method as in Test Example 2, except that the emitting layer was formed by co-evaporating the below-described H2, Compound A, and below-described Compound ET2 from different evaporation sources to form a 40 nm-thick layer containing 64.2 wt% of the host material H2, 35 wt% of the assist dopant Compound A, and 0.8 wt% of the dopant (light-emitting material) ET2. Instead of Compound A, Compounds B, C, D, H, I, below-described Comparative Compound 1, and below-described Comparative Compound 2 were used to prepare organic electroluminescence devices by the same procedure. However, the concentration of Comparative Compound 1 in the emitting layer was 65 wt%, the concentration of Comparative Compound 2 in the emitting layer was 55 wt%, and the concentration of ET2, the dopant (light-emitting material) of these devices, was 0.8 wt%. Furthermore, in the device using comparative compound 2, H3 was used instead of H2 as the host material. The external quantum efficiency (EQE) of each of the fabricated devices was measured using the same method as in Test Example 2. The results are shown in the table below. It was confirmed that the compound represented by general formula (1) had a higher external quantum efficiency than comparative compounds 1 and 2, which have structures similar to general formula (1).

[0125] Organic electroluminescence devices were prepared in the same manner as in Test Example 3, except that Compound E, Compound F, and Comparative Compound 4 described below were used instead of Compound A. The LT95 of each of the organic electroluminescence devices using Compound D, Compound E, Compound F, Comparative Compound 1, and Comparative Compound 4 was measured in the same manner as in Test Example 2. The results are shown in the table below. The results are shown as relative values, with the LT95 of the device using Comparative Compound 4 being set at 1. It was confirmed that Compounds D, E, and F represented by general formula (1) had longer device lifetimes than Comparative Compounds 1 and 4, which have in common the fact that they contain a triazinyl group substituted with two perdeuterated phenyl groups.

[0126] Organic electroluminescence devices were prepared in the same manner as in Test Example 3, except that Comparative Compound 2 described below was used instead of Compound A. The LT95 of each of the organic electroluminescence devices using Compound A, Comparative Compound 2, and Comparative Compound 3 was measured in the same manner as in Test Example 2. The results are shown in the table below. The results are shown as relative values, with the LT95 of the device using Comparative Compound 3 set at 1. It was confirmed that Compound A represented by general formula (1) had a longer device life than Comparative Compound 2 and Comparative Compound 3, which are common in that they contain a triazinyl group substituted with a perdeuterated phenyl group and a perdeuterated carbazol-9-yl group, and three perdeuterated carbazol-9-yl groups.

[0127] (Test Example 4) Preparation and Evaluation of Another Organic Electroluminescence Device Using an Assist Dopant

[0049] Organic electroluminescence devices were prepared by the same method as in Test Example 2, except that the emitting layer was formed by co-evaporating the below-described H2, Compound A, and below-described Compound ET1 from different evaporation sources to form a 40 nm-thick layer containing 64.2 wt% of the host material H2, 35 wt% of the assist dopant Compound A, and 0.8 wt% of the dopant (light-emitting material) ET1. Instead of Compound A, Compounds B, C, F, Comparative Compound 1 and Comparative Compound 2 were used to prepare organic electroluminescence devices by the same procedure. However, the concentration of Comparative Compound 1 in the emitting layer was 65 wt%, the concentration of Comparative Compound 2 in the emitting layer was 55 wt%, and the concentration of ET2, the dopant (light-emitting material) in these devices, was 0.8 wt%. The external quantum efficiency (EQE) of each of the fabricated devices was measured in the same manner as in Test Example 2. The results are shown in the table below. It was confirmed that the compound represented by general formula (1) had a higher external quantum efficiency than comparative compounds 1 and 2, which have structures similar to general formula (1).

[0128] Organic electroluminescence devices were prepared using comparative compound 4 instead of compound A in the same manner as in Test Example 4. The LT95 of each of the organic electroluminescence devices using compounds B, C, D, F, and comparative compound 4 described below was measured in the same manner as in Test Example 2. The results are shown in the table below. The results are shown as relative values, with the LT95 of the device using comparative compound 4 set at 1. It was confirmed that the compound represented by general formula (1) had a longer device life than comparative compound 4, which is similar in that it has a triazinyl group substituted with two perdeuterated phenyl groups.

[0129] Organic electroluminescence devices were prepared in the same manner as in Test Example 4, except that Comparative Compound 3 described below was used instead of Compound A. The LT95 of each of the organic electroluminescence devices using Compound A, Comparative Compound 2, and Comparative Compound 3 was measured in the same manner as in Test Example 2. The results are shown in the table below. The results are shown as relative values, with the LT95 of the device using Comparative Compound 3 set at 1. It was confirmed that Compound A represented by general formula (1) had a longer device life than Comparative Compound 2 and Comparative Compound 3, which are common in that they contain a triazinyl group substituted with a perdeuterated phenyl group and a perdeuterated carbazol-9-yl group, and three perdeuterated carbazol-9-yl groups.

[0130] Each organic electroluminescence device using Compound A and Comparative Compounds 1 to 4 was continuously driven to emit light at 20,000 nits, and the time (LT95) until the luminous intensity decreased to 95% of that at the start of driving was measured. The results are shown in the table below. The results are shown as relative values, with the LT95 of the device using Comparative Compound 31 set to 1. It was confirmed that the compound represented by general formula (1) had a longer device life than Comparative Compounds 1 to 4, which have similar structures.

[0131]

[0132]

[0133] The compound of the present invention represented by the general formula (1) exhibits excellent performance as a compound for an organic light-emitting device, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) [In the general formula (1), X １ and X ２ One represents N and the other represents C-Y ３ Represents Y. １ ~Y ３ One of them represents a cyano group, and the other two and Y ４ and Y ５ Each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ represents a hydrogen atom or a deuterium atom, R ２ ~R ４ one to three of these each independently represent a donor group, and the rest represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

2. X １ is N and X ２ is C-Y ３ And Y ３ The compound according to claim 1 , wherein is a cyano group.

3. R ２ ~R ４ The compound of claim 1 , wherein each is independently a donor group.

4. R ２ and R ４ The compound according to claim 3, wherein are identical.

5. R ２ and R ４ are each independently a donor group, R ３ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group.

6. R ３ The compound according to claim 5 , wherein is an aryl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group.

7. R ２ and R ４ The compound of claim 5 , wherein are identical.

8. Y １ ~Y ３ The compound according to claim 1, wherein one of the groups is a cyano group, and the remaining two groups are each independently a substituted or unsubstituted phenyl group, or an optionally fused substituted or unsubstituted carbazol-9-yl group.

9. R ２ ~R ４ The compound according to claim 1, wherein at least one of the 1 to 3 donor groups is a substituted or unsubstituted diarylamino group (two aryl groups may be bonded to each other).

10. R ２ ~R ４ The compound according to claim 9, wherein at least one of the one to three donor groups is an optionally fused substituted or unsubstituted carbazol-9-yl group.

11. The donor group and Y １ ~Y ５ The compound of claim 1 , wherein at least one of the following groups contains a deuterium atom:

12. A light-emitting material comprising the compound according to any one of claims 1 to 11.

13. A delayed fluorescent material comprising the compound according to any one of claims 1 to 11.

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