Compound, light-emitting material, and delayed fluorescence material

Abstract

The compound represented by the general formula shown herein is useful as a compound for an organic light-emitting element. One among X1 and X2 is N, and the other is C-Y3; one among Y1-Y3 is a cyano group, and each of the remaining two is an aryl group or a heteroaryl group; L1 is a single bond or a linking group; two to four among R1-R5 are donor groups; and one among R1-R3 is a cyano group, a diaryl cyanophenyl group, or the like.

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 L 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 represents a single bond or a divalent linking group. １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ ~R ５ Two to four of R are independently donor groups, １ ~R ３ One of the groups is a cyano group or a group represented by the following general formula (A): X ３ and X ４ represents N on one side and C-Y on the other side. ６ represents Y ４ ~Y ６one represents a cyano group, and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, or ３ and X ４ represents N, and Y ４ represents a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Y ５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ represents a single bond or a divalent linking group.] [2] R ３ is a cyano group or a group represented by general formula (A). ２ is a cyano group or a group represented by general formula (A). [4] The compound according to [1], １ ~R ３ one of which is a group represented by general formula (A), and X １ and X ３ are identical, and X ２ and X ４ are identical, and Y １ and Y ４ are identical, and Y ２ and Y ５ are identical, and L １ and L ２ [5] The compound according to any one of [1] to [3], wherein R １ ~R ５ [6] The compound according to any one of [1] to [4], wherein at least one of R is a deuterium atom, an alkyl group, or an aryl group optionally substituted with an aryl group. １ and R ５ [7] The compound according to any one of [1] to [5], wherein at least one of X is a hydrogen atom or a deuterium atom. １ and X ３ [8] The compound according to any one of [1] to [6], wherein Y is N. １ ~Y ３[9] The compound according to any one of [1] to [7], 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. １ and L ２

[10] The compound according to any one of [1] to [8], wherein R is a single bond. １ ~R ５

[11] The compound according to any one of [1] to [9], wherein at least one of the two to four donor groups is a substituted or unsubstituted diarylamino group (two aryl groups may be bonded to each other). １ ~R ５

[12] The compound according to

[10] , wherein at least one of the two to four donor groups is a substituted or unsubstituted carbazol-9-yl group which may be fused. １ ~R ５

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

[11] , wherein two of R １ ~R ５

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

[11] , wherein three of the donor groups and Y １ ~Y ６

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

[14] .

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

[14] .

[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 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 １ ~R ５ 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 also be mentioned. １ ~R ５ 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 aryl group. １ is a substituted aryl group. For example, Y ２ is a substituted aryl group. For example, Y １ and Y ２are each independently a substituted aryl group. The substituent of the substituted aryl group referred to here is preferably an alkyl group optionally substituted with a deuterium atom, or an aryl group optionally substituted with a deuterium atom or an alkyl group, more preferably an alkyl group optionally substituted with a deuterium atom. The alkyl group referred to here preferably has 1 to 10 carbon atoms, for example 3 to 10 carbon atoms.

[0015] L in general formula (1) １ represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L １ is a single bond. In one aspect of the present invention, L １ is a substituted or unsubstituted arylene group. １ is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group is １ ~R ５ The description of the aryl group and the preferred range thereof can be referred to in the section on the heteroarylene group. Examples of the heteroarylene group include a linking group in which a nitrogen atom is introduced in place of at least one of the ring skeleton carbon atoms constituting the arylene group. １ However, the L that can be used in the present invention is １ is not to be construed as being limited by these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0016]

[0017] All hydrogen atoms in L2 to L13 are replaced with deuterium atoms, and L14 to L25 are disclosed. １ is selected from the group consisting of L1 to L25. １ is selected from the group consisting of L1 to L7, L14 to L19. １is selected from the group consisting of L1, L8 to L13, and L20 to L25. １ is selected from the group consisting of L2 to L25. １ is L1.

[0018] R in general formula (1) １ ~R ５ are each independently a donor group. The donor group referred to here does not include an alkyl group optionally substituted with a deuterium atom or an aryl group, or an aryl group 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 a constant (σp) specific to a substituent in the following equation, which holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above formula, k0 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).

[0019] R １ ~R ５ The 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.

[0020] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group, or a group 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.

[0021] R １ ~R ５ The donor group represented by the formula (a) is preferably a group represented by the formula (a) below, or a group to which the group represented by the formula (a) below is bonded via a linking group. The linking group referred to here is preferably a π-conjugated linking group, for example, an arylene group or an alkenylene group, and specific examples thereof include the above-mentioned L1 to L25.

[0022] In the general formula (a), 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 ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １４and R １５ , R １５ and R １６ , R １６ and R １７ may be bonded to each other to form a cyclic structure.

[0023] Z １ ~Z ４ 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 , R１６ and R １７ may 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 , R１６ and R １７ are not bonded to each other to form a ring structure.

[0024] 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. ５is 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.

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

[0026] 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, Z １ ~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.

[0027] R １ ~R ５The 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 ５ The 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.

[0028] In one aspect of the present invention, R １ ~R ５ 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." １ ~R ５The 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.

[0029] 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).

[0030] 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.

[0031] 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.

[0032] 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.

[0033] In the following, R in general formula (1) １ ~R ５ 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.

[0034] The compounds D1 to D532 above in which all hydrogen atoms have been replaced with deuterium atoms are disclosed as D815 to D1346.

[0035] 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.

[0036] 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.

[0037] In one aspect of the present invention, R １ ~R ５ In one embodiment of the present invention, two of R １ ~R ５ In one embodiment of the present invention, three of R １ ~R ５ In one embodiment of the present invention, four of R １ ~R ５ In one embodiment of the present invention, two to four of R １ ~R ５ In one embodiment of the present invention, all of the donor groups taken by R １ ~R ５ In one embodiment of the present invention, two of R are the same donor group and one or two are different donor groups. １ ~R ５ In one embodiment of the present invention, three of the groups R are the same donor group and one of the groups R is a different donor group. ５ is a donor group. In one embodiment of the present invention, at least R ４ is a donor group. In one embodiment of the present invention, at least R ３ is a donor group. In one embodiment of the present invention, at least R ２ is a donor group. In one embodiment of the present invention, at least R １ is a donor group. In one embodiment of the present invention, R ５ and R ４ In one aspect of the invention, R５ and R ３ In one aspect of the invention, R ５ and R ２ In one aspect of the invention, R ５ and R １ In one aspect of the invention, R ４ and R ３ In one aspect of the invention, R ４ and R ２ In one aspect of the invention, R ４ and R １ In one aspect of the invention, R ３ and R ２ In one aspect of the invention, R ３ and R １ In one aspect of the invention, R ２ and R １ In one aspect of the invention, R ５ and R ４ and R ３ In one aspect of the invention, R ５ and R ４ and R ２ In one aspect of the invention, R ５ and R ４ and R １ In one aspect of the invention, R ５ and R ３ and R ２ In one aspect of the invention, R ５ and R ３ and R １ In one aspect of the invention, R ５ and R ２ and R １ In one aspect of the invention, R ４ and R ３ and R ２ In one aspect of the invention, R ４ and R ３ and R １ In one aspect of the invention, R ４ and R２ and R １ In one aspect of the invention, R ３ and R ２ and R １ In one aspect of the invention, R ５ and R ４ and R ３ and R ２ is a donor group. In one embodiment of the present invention, R ５ and R ４ and R ３ and R １ is a donor group. In one embodiment of the present invention, R ５ and R ４ and R ２ and R １ is a donor group. In one embodiment of the present invention, R ５ and R ３ and R ２ and R １ is a donor group. In one embodiment of the present invention, R ４ and R ３ and R ２ and R １ is a donor group. １ ~R ５ The donor group represented by R is preferably a group containing at least one (for example, only one) substituted or unsubstituted diarylamino group (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. １ ~R ５ 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.

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

[0039] L in general formula (A) ２ represents a single bond or a divalent linking group. ２ For details, see L in general formula (1). １ In a preferred embodiment of the present invention, the description, preferred ranges, and specific examples of L ２ Is L １ In one embodiment of the present invention, X in general formula (A) is the same as ３ and X ４ represents N on one side and C-Y on the other side. ６ represents Y ４ ~Y ６ One of X represents a cyano group, and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ３ , X ４ , Y ４ ~Y ６ For details and specific examples, see X in general formula (1). １ , X ２ , Y １ ~Y ３ In a preferred embodiment of the present invention, the L ２ , X ３ , X ４ , Y ４ ~Y ６ are, in order, L in general formula (1) １ , X １ , X ２ , Y １ ~Y ３ In this case, two identical substituents represented by general formula (A) are present in the molecule of the compound. In another embodiment of the present invention, X in general formula (A) ３ and X ４ represents N, and Y ４ represents a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Y ５represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ４ is a cyano group, and Y ５ is a substituted or unsubstituted aryl group, Y ４ is a cyano group, and Y ５ When Y is a substituted or unsubstituted heteroaryl group, ４ and Y ５ are each independently a substituted or unsubstituted aryl group (Y ４ and Y ５ may be the same or different), Y ４ and Y ５ are each independently a substituted or unsubstituted heteroaryl group (Y ４ and Y ５ may be the same or different), Y ４ is a substituted or unsubstituted aryl group, and Y ５ is a substituted or unsubstituted heteroaryl group.

[0040] In one aspect of the present invention, R １ is a cyano group. ２ is a cyano group. ３ is a cyano group. １ is a group represented by general formula (A), and in this case, for example, L ２ , X ３ , X ４ , Y ４ ~Y ６ In order, L １ , X １ , X ２ , Y １ ~Y ３ In one aspect of the invention, R ２ is a group represented by general formula (A), and in this case, for example, L ２ , X ３ , X ４ , Y ４ ~Y ６ In order, L １ , X １ , X ２ , Y １ ~Y３ In one aspect of the invention, R ３ is a group represented by general formula (A), and in this case, for example, L ２ , X ３ , X ４ , Y ４ ~Y ６ In order, L １ , X １ , X ２ , Y １ ~Y ３ is the same as

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

[0042] R in general formula (1) １ ~R ５ Among these, the group that is not a hydrogen atom, a deuterium atom, a cyano group, a group represented by general formula (A), or a donor group is preferably 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). Furthermore, it is more preferable that the group is an alkyl group which may be substituted with a deuterium atom, an aryl group, or a substituent having a structure in which two or more of these are bonded; or an aryl group which may be substituted with a deuterium atom, an alkyl group, an aryl group, a silyl group, or a substituent having a structure in which two or more of these are bonded. Furthermore, it is even more preferable that the group is an aryl group which may be substituted with a deuterium atom, an alkyl group, an aryl group, or a substituent having a structure in which two or more of these are bonded. In one aspect of the present invention, R １ ~R ５Among these, one to two (e.g., one, e.g., two) are each independently a deuterium atom, an alkyl group, an aryl group, or an aryl group optionally substituted with a substituent having a structure in which two or more of these are bonded, for example, a phenyl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group. The alkyl group may be linear, branched, or cyclic. In addition, two or more of the linear portion, cyclic portion, and 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 alkyl groups 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 alkyl group may be further substituted with an aryl group or the like. The aryl group may be a monocyclic 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 rings 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 １ ~R ５Specific 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.

[0043] 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. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar1 to Ar75. １ ~R ５ 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. １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar28 to Ar75. １ ~R ５ 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.

[0044] In general formula (1), R １ ~R ５ Two of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ do not bond to each other to form a cyclic structure.１ The benzene ring has a structure in which it can freely rotate around the single bond between the benzene ring and the R １ , R ２ The descriptions are R ５ , R ４ Therefore, for example, R ４ is a group represented by general formula (A), by rotating the benzene ring, R ２ is a group represented by general formula (A), and if the compound satisfies all other conditions of general formula (1), it can be said to be a compound encompassed by general formula (1).

[0045] As compound group 1 of the present invention, X １ is N and X ２ is C-CN, and L １ is a single bond, and R ３ Compound group 1 is a compound group of general formula (1) in which Y is a cyano group (CN). １ and Y ２ Compound group 1a, Y each independently represent a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group); １ and Y ２ Compound group 1b, Y １ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group), and Y ２Compound group 1c includes compounds in which R is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused). Compound groups 1a to 1c each further include compounds which satisfy at least one of the following additional conditions. In one embodiment of the present invention, R １ , R ２ , R ４ , R ５ is a donor group. In one embodiment of the present invention, R １ , R ２ , R ４ is a donor group, and R ５ is a hydrogen atom or a deuterium atom. １ , R ２ , R ４ is a donor group, and R ５ is a substituted or unsubstituted aryl group. １ , R ２ , R ５ is a donor group, and R ４ is a hydrogen atom or a deuterium atom. １ , R ２ , R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. １ , R ５ is a donor group, and R ２ , R ４ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ４ is a donor group, and R ２ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ２ is a donor group, and R ４ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ２ , R ４ is a donor group, and R １ , R５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ２ , R ４ , R ５ In one embodiment of the present invention, the donor groups adopted by R １ , R ２ , R ４ , R ５ The donor groups taken by R are not all the same, but are different donor groups, or only some of the donor groups are the same. １ , R ２ , R ４ , R ５ In one embodiment of the present invention, three of R １ , R ２ , R ４ , R ５ In one embodiment of the present invention, two of R １ , R ２ , R ４ , R ５ The donor group adopted by R contains a deuterium atom. １ , R ２ , R ４ , R ５ In one embodiment of the present invention, the donor group adopted by R １ , R ２ , R ４ , R ５ In one embodiment of the present invention, one or two of R １ , R ２ , R ４ , R ５ One or two of the atoms are hydrogen atoms or deuterium atoms. Compound group 1 is X １ is N and X ２ is C-CN, but this is X １ is C-CN, and X ２ is N, this is referred to as Compound Group 1'. Compound Group 1' also includes Compound Groups 1'a to 1'c corresponding to Compound Groups 1a to 1c, and includes compounds that satisfy at least one of the additional conditions described in Compound Group 1.

[0046] As compound group 2 of the present invention, X １ is N and X ２ is C-CN, and L １ is a single bond, and R ３ is a group represented by general formula (A), and X ３ is N and X ４ is C-CN, and L ２ Compound group 2 includes a compound group of general formula (1) in which Y １ , Y ２ , Y ４ , Y ５ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group). １ , Y ２ , Y ４ , Y ５ are the same), Y １ , Y ２ , Y ４ , Y ５ are each independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be fused). １ , Y ２ , Y ４ , Y ５ are the same), Y １ , Y ４ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group), and Y ２ , Y ５ is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused) (e.g., a compound group 2c in which Y １ and Y ４ are the same, Y ２ and Y ５Compound Groups 2a to 2c each further include compounds that satisfy at least one of the additional conditions described in Compound Group 1. Compound Group 2 includes X １ is N and X ２ is C-CN, but this is X １ is C-CN, and X ２ The compound group in which X is N is referred to as compound group 2'. Compound group 2' also includes compound groups 2'a to 2'c corresponding to compound groups 2a to 2c, and includes compounds in which at least one of the additional conditions described in compound group 1 is satisfied. Compound group 2' is X ３ is N and X ４ is C-CN, but this is X ３ is C-CN, and X ４ is N, this is referred to as Compound Group 2''. Compound Group 2'' also includes Compound Groups 2''a to 2''c corresponding to Compound Groups 2a to 2c, and includes compounds that satisfy at least one of the additional conditions described in Compound Group 1.

[0047] As compound group 3 of the present invention, X １ is N and X ２ is C-CN, and L １ is a single bond, and R ２ Compound group 3 includes compounds of general formula (1) in which Y is a cyano group (CN). １ and Y ２ Compound group 3a, Y each independently represent a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group); １ and Y ２ Compound group 3b, Y １ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group), and Y２ is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused). Compound groups 3a to 3c each further include compounds which satisfy at least one of the following additional conditions. In one embodiment of the present invention, R １ , R ３ , R ４ , R ５ is a donor group. In one embodiment of the present invention, R １ , R ３ , R ４ is a donor group, and R ５ is a hydrogen atom or a deuterium atom. １ , R ３ , R ４ is a donor group, and R ５ is a substituted or unsubstituted aryl group. １ , R ３ , R ５ is a donor group, and R ４ is a hydrogen atom or a deuterium atom. １ , R ３ , R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. １ , R ４ , R ５ is a donor group, and R ３ is a hydrogen atom or a deuterium atom. １ , R ４ , R ５ is a donor group, and R ３ is a substituted or unsubstituted aryl group. ３ , R ４ , R ５ is a donor group, and R １ is a hydrogen atom or a deuterium atom. ３ , R ４ , R ５ is a donor group, and R １ is a substituted or unsubstituted aryl group.１ , R ５ is a donor group, and R ３ , R ４ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ４ is a donor group, and R ３ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ３ is a donor group, and R ４ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ３ , R ５ is a donor group, and R １ , R ４ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ３ , R ４ is a donor group, and R １ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ４ , R ５ is a donor group, and R １ , R ３ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. １ , R ３ , R ４ , R ５ In one embodiment of the present invention, the donor groups adopted by R １ , R ３ , R ４ , R ５ The donor groups taken by R are not all the same, but are different donor groups, or only some of the donor groups are the same. １ , R ３ , R ４ , R ５ In one embodiment of the present invention, three of R １ , R３ , R ４ , R ５ In one embodiment of the present invention, two of R １ , R ３ , R ４ , R ５ The donor group adopted by R contains a deuterium atom. １ , R ３ , R ４ , R ５ In one embodiment of the present invention, the donor group adopted by R １ , R ３ , R ４ , R ５ In one embodiment of the present invention, one or two of R １ , R ３ , R ４ , R ５ One or two of the atoms are hydrogen atoms or deuterium atoms. Compound group 3 is X １ is N and X ２ is C-CN, but this is X １ is C-CN, and X ２ is N, which is referred to as compound group 3'. Compound group 3' also includes compound groups 3'a to 3'c corresponding to compound groups 3a to 3c, and includes compounds that satisfy at least one of the additional conditions described in compound group 3.

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

[0049] As compound group 5 of the present invention, X １ is N and X ２ is C-CN, and L １ is a single bond, and R １ is a cyano group (CN). １ and Y ２ Compound group 5a, Y each independently represent a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group); １ and Y ２ Compound group 5b, Y １ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group), and Y ２ is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused). Compound groups 5a to 5c each further include compounds which satisfy at least one of the following additional conditions. In one embodiment of the present invention, R ２ , R ３ , R ４ , R ５ is a donor group. In one embodiment of the present invention, R ２ , R ３ , R ４ is a donor group, and R ５ is a hydrogen atom or a deuterium atom. ２ , R３ , R ４ is a donor group, and R ５ is a substituted or unsubstituted aryl group. ２ , R ３ , R ５ is a donor group, and R ４ is a hydrogen atom or a deuterium atom. ２ , R ３ , R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. ２ , R ４ , R ５ is a donor group, and R ３ is a hydrogen atom or a deuterium atom. ２ , R ４ , R ５ is a donor group, and R ３ is a substituted or unsubstituted aryl group. ３ , R ４ , R ５ is a donor group, and R ２ is a hydrogen atom or a deuterium atom. ３ , R ４ , R ５ is a donor group, and R ２ is a substituted or unsubstituted aryl group. ２ , R ５ is a donor group, and R ３ , R ４ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ２ , R ４ is a donor group, and R ３ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ２ , R ３ is a donor group, and R ４ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ３, R ５ is a donor group, and R ２ , R ４ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ３ , R ４ is a donor group, and R ２ , R ５ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ４ , R ５ is a donor group, and R ２ , R ３ are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. ２ , R ３ , R ４ , R ５ In one embodiment of the present invention, the donor groups adopted by R ２ , R ３ , R ４ , R ５ The donor groups taken by R are not all the same, but are different donor groups, or only some of the donor groups are the same. ２ , R ３ , R ４ , R ５ In one embodiment of the present invention, three of R ２ , R ３ , R ４ , R ５ In one embodiment of the present invention, two of R ２ , R ３ , R ４ , R ５ The donor group adopted by R contains a deuterium atom. ２ , R ３ , R ４ , R ５ In one embodiment of the present invention, the donor group adopted by R ２ , R ３ , R ４ , R ５ In one embodiment of the present invention, one or two of R ２ , R ３ , R４ , R ５ One or two of the atoms are hydrogen atoms or deuterium atoms. Compound group 5 is X １ is N and X ２ is C-CN, but this is X １ is C-CN, and X ２ is N, which is referred to as compound group 5'. Compound group 5' also includes compound groups 5'a to 5'c corresponding to compound groups 5a to 5c, and includes compounds that satisfy at least one of the additional conditions described in compound group 5.

[0050] As the compound group 6 of the present invention, X １ is N and X ２ is C-CN, and L １ is a single bond, and R １ is a group represented by general formula (A), and X ３ is N and X ４ is C-CN, and L ２ Compound group 4 is a compound group of general formula (1) in which Y １ , Y ２ , Y ４ , Y ５ is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group). １ , Y ２ , Y ４ , Y ５ are the same), Y １ , Y ２ , Y ４ , Y ５ are each independently a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted diarylamino group, for example, a substituted or unsubstituted carbazol-9-yl group which may be fused). １ , Y ２ , Y ４ , Y ５ are the same), Y １ , Y ４is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted phenyl group, for example, a phenyl group which may be substituted with a deuterium atom or a substituent selected from Group E described below, for example, a phenyl group substituted with an alkyl group), and Y ２ , Y ５ is a substituted or unsubstituted heteroaryl group (e.g., a substituted or unsubstituted diarylamino group, e.g., a substituted or unsubstituted carbazol-9-yl group which may be fused) (e.g., a compound group 6c in which Y １ and Y ４ are the same, Y ２ and Y ５ Compound Groups 6a to 6c each further include compounds that satisfy at least one of the additional conditions described in Compound Group 5. Compound Group 6 includes X １ is N and X ２ is C-CN, but this is X １ is C-CN, and X ２ The compound group 6' is defined as compound group 6'. Compound group 6' also includes compound groups 6'a to 6'c corresponding to compound groups 6a to 6c, and includes compounds that satisfy at least one of the additional conditions described in compound group 5. Compound group 6' is defined as X ３ is N and X ４ is C-CN, but this is X ３ is C-CN, and X ４ is N, this is referred to as Compound Group 6''. Compound Group 6'' also includes Compound Groups 6''a to 6''c corresponding to Compound Groups 6a to 6c, and includes compounds that satisfy at least one of the additional conditions described in Compound Group 5.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 4 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, among the compounds represented by general formula (1), Y １ and Y ２ is a phenyl group (Ar1), and X １ is N and X ２ is C-CN, and L １ is a single bond, and R ３ is a cyano group (CN), and R １, R ２ , R ４ , R ５ are the same and are any of D1 to D1426. That is, R of the compound having the following structure １ , R ２ , R ４ , R ５ The structures of compounds 1 to 1426 are individually identified by listing them in order in Table 1.

[0055] In Table 2, the structures of compounds 1 to 18848500 are shown as variations of the structure represented by general formula (1). １ and Y ２ is a phenyl group (Ar1), and X １ is N and X ２ is C-CN, and L １ is a single bond, and R １ ~R ５ is a group specified in Table 2. That is, R of a compound having the following structure １ ~R ５ The structures of compounds 1 to 18848500 are individually identified by showing them in order in Table 2. The columns of compounds 1 to 1426 in Table 2 are １ and Y ２ is fixed to the phenyl group (Ar1), and X １ is fixed to N, and X ２ is fixed to C-CN, and L １ is fixed to a single bond, and R ３ is fixed to a cyano group (CN), and R １ , R ２ , R ４ , R ５ In other words, the column of Compounds 1 to 1426 in Table 2 shows the structures of Compounds 1 to 1426 in Table 1 all together in one column. The column of Compounds 1427 to 2852 in Table 2 shows the structures of Compounds 1 to 1426 in Table 1 all together in one column. １ and Y ２is fixed to the phenyl group (Ar1), and X １ is fixed to N, and X ２ is fixed to C-CN, and L １ is fixed to a single bond, and R １ is fixed to a hydrogen atom, and R ３ is fixed to a cyano group (CN), and R ２ , R ４ , R ５ The compounds D1 to D1426 having the same structure are identified as compounds 1427 to 2852 in order. １ and Y ２ is fixed to the phenyl group (Ar1), and X １ is fixed to N, and X ２ is fixed to C-CN, and L １ is fixed to a single bond, and R ２ is fixed to a hydrogen atom, and R ３ is fixed to a cyano group (CN), and R １ , R ４ , R ５ The compounds D1 to D1426, which have the same structure, are identified as compounds 2853 to 4278 in this order. The structures of the compounds are identified in the same manner in the subsequent columns. １ and Y ２ is fixed to the phenyl group (Ar1), and X １ is fixed to N, and X ２ is fixed to C-CN, and L １ is fixed to a single bond, and R ２ and R ５ is fixed to D57, and R ３ is fixed to CN, and R １ varies from Ar1 to Ar75, and R ４ In this case, when there are two types of variables, Ar1 to Ar75 are fixed first, and D1 to D56 and D58 to D1426 are varied to assign compound numbers in order. １ is fixed to Ar1, and R ４ These are designated D1 to D56, D58 to D1426 in order, and are identified as compounds 9979 to 11403 in order. １ is fixed to Ar2, and R４ These are designated D1 to D56, D58 to D1426 in order, and are identified as compounds 11404 to 12828 in order. １ is fixed to Ar3, and R ４ These are identified in the order of D1 to D56, D58 to D1426, and then identified as compounds 12829 to 14253. １ is fixed to Ar75, and R ４ In the rightmost column of Table 2, R １ ~R ５ For example, for compounds 1 to 1426 in the top row, R １ and R ２ and R ４ and R ５ In Table 2, "(A)" denotes a group represented by general formula (A), and Y ４ and Y ５ is a phenyl group (Ar1), and X ３ is N and X ４ is C-CN, and L ２ represents a group in which "D" is a single bond. In Table 2, "D" represents a deuterium atom.

[0056] In Table 2, Y in general formula (1) １ and Y ２ is a phenyl group (Ar1), and X １ is N and X ２ is C-CN, and L １ is fixed to a group where R is a single bond １ ~R ５ Compounds in which the group represented by general formula (A) is not present were identified as compounds 1 to 10554355. Table 3 shows the Y １ and Y ２ The compounds in which the phenyl group (Ar1) is changed as shown in Table 3 are listed in order in the form of a table. In Table 3, in order to make the correspondence easier to understand, １ and Y ２ In the second row of Table 3, 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 10554355 (1) is obtained by replacing Y of compound 10554355 with Ar2. １ and Y ２The structures of compounds 1(2) to 10554355(2) onwards in the third row are specified in the same way as in the second row.

[0057] In Table 2, Y in general formula (1) １ and Y ２ is a phenyl group (Ar1), and X １ is N and X ２ is C-CN, and L １ is fixed to a group where R is a single bond １ ~R ３ is a group represented by general formula (A), and Y ３ and Y ４ Compounds in which Y is a phenyl group (Ar1) were identified as compounds 10554356 to 18848500. Table 4 shows the Y ４ and Y ５ 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. ４ and Y ５ In the second row of Table 4, for example, compound 10554356(1) is the compound 10554356, and the compound 10554356 is the compound 10554356. ４ and Y ５ In addition, compound 10554357(1) shows a compound having a structure in which Y of compound 10554357 is ４ and Y ５ In the same manner, compound 18848500 (1) is obtained by replacing Y of compound 18848500 with Ar2. ４ and Y ５ The structures of the compounds 10554356(2) to 18848500(2) onwards in the third row are also specified in the same way as in the second row.

[0058]

[0059] In Table 4, Y in general formula (1) １ and Y ２ Specific examples of compounds in which Ar1 is a phenyl group are shown as compounds 10554356 to 18848500 and compounds 10554356(n) to 18848500(n) [wherein n is 1 to 898]. In Table 5 below, the Y of these compounds １ and Y ２ The compounds in which n and Y are changed to the groups shown in Table 5 are shown. In Table 5, n and Y of compounds 1(n) to 6714537752(n) are １ and Y ２ For ease of understanding, the first row of Table 5 lists the Y of compounds 10554356(n) to 18848500(n) [where n is 1 to 898]. １ and Y ２ The second row of Table 5 shows the Y of compounds 10554356 to 18848500 and compounds 10554356(n) to 18848500(n) [where n is 1 to 898]. １ and Y ２ The compounds in which both are changed to Ar2 are shown in order as Compounds 10554356(n) to 18848500(n) [where n is 899 to 1797]. The third row of Table 5 shows the Y values ​​of Compounds 10554356 to 18848500 and Compounds 10554356(n) to 18848500(n) [where n is 1 to 898]. １ and Y ２ The compounds in which both are changed to Ar3 are shown in order as compounds 10554356(n) to 18848500(n) [where n is 1798 to 2696]. The structures of the subsequent compounds are identified in the same manner.

[0060]

[0061] As shown in Table 2, compounds 1 to 10554355 are R １ ~R ３ In place of the cyano group, X ３ and X ４ is N and L ２ Table 6 shows variations of compounds to which a group of general formula (A) in which is a single bond is bonded. That is, Table 6 shows variations of compounds having a structure represented by any of the following general formulas. In Table 6, for each of compounds 1 to 10554355, a cyano group is bonded to Y ４ and Y ５ The group [X ３ and X ４ is N and L ２ In the first row of Table 6, for example, Compound 1 (808201) has a cyano group of Compound 1 that is changed to Y ４ and Y ５ is Ar1, and X ３ and X ４ is N and L ２ represents a compound having a structure based on general formula (A) in which Y is a single bond. Compound 2 (808201) is a compound having a structure based on general formula (A) in which the cyano group of Compound 2 is replaced by Y ４ and Y ５ is Ar1, and X ３ and X ４ is N and L ２ represents a compound having a structure based on general formula (A) in which Y is a single bond. Similarly, compound 10554355 (808201) has a cyano group in compound 10554355 substituted with Y ４ and Y ５ is Ar1, and X ３ and X ４ is N and L ２ indicates a compound having a structure based on general formula (A), which is a single bond. The structures thereafter are specified in the same way as in the first row.

[0062] In Table 6, Y in general formula (1) １ and Y ２ Specific examples of compounds in which Ar1 is represented by Compound 1(n) to Compound 10554355(n) [where n is 808201 to 809099]. In Table 7 below, Y of these compounds １ and Y ２ The compounds in which the Y groups are respectively changed to the groups shown in Table 7 are shown. For ease of understanding, the first row of Table 7 shows the Y groups of Compounds 1(n) to 10554355(n) [where n is 809100 to 809998]. １ and Y ２ The second row of Table 7 shows that both of the Y １ and Y ２ The compounds in which both are changed to Ar2 are shown in order as Compound 1(n) to Compound 10554355(n) [where n is 809999 to 810897]. The third row of Table 5 shows the Y １ and Y ２ The compounds in which both are changed to Ar3 are shown in order as Compound 1(n) to Compound 10554355(n) [where n is 810898 to 811796]. The structures of the subsequent compounds are identified in the same manner.

[0063]

[0064] 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 consisting of compounds 1 to 18848500, compounds 1(n) to 18848500(n) [where n is 1 to 898], compounds 10554356(n) to 18848500(n) [where n is 899 to 808200], and compounds 1(n) to 10554355(n) [where n is 808201 to 1617300]. In one aspect of the present invention, a compound is selected from the group consisting of compounds 1 to 18848500 and compounds 1(n) to 18848500(n) [where n is 1 to 74]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 18,848,500(n) [wherein n is 75 to 746]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 18,848,500(n) [wherein n is 747 to 870]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 18,848,500(n) [wherein n is 871 to 898]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10,554,355(n) [wherein n is 758,641 to 758,715]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10,554,355(n) [wherein n is 808,201 to 808,275]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 808276 to 809071]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 809072 to 809099]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 809100 to 876524]. In one embodiment of the present invention, a compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 876525 to 1480652].In one aspect of the present invention, the compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 1480653 to 1592128]. In one aspect of the present invention, the compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 1592129 to 1617300]. In one aspect of the present invention, the compound is selected from the group of compounds consisting of compounds 1(n) to 10554355(n) [where n is 1 to 808200].

[0065] Examples of the compounds represented by general formula (1) are listed below.

[0066] Examples of other compounds represented by general formula (1) are given below.

[0067] Examples of other compounds represented by general formula (1) are given below.

[0068] Examples of other compounds represented by general formula (1) are given below.

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

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

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

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

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] [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 １ ~R ５ Two to four of these groups 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.

[0083] 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).

[0084] [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.

[0085] [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.

[0086] 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.).

[0087] (Example 1) Synthesis of Compound A

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

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

[0090] Example 2: Synthesis of Compounds B and C

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

[0092] Synthesis of Intermediate c: Under a nitrogen atmosphere, anhydrous tetrahydrofuran (80 mL) was added to intermediate b (12.0 g, 25.3 mmol) and cooled to 0°C. Lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 30 mL, 39 mmol) was then added, the mixture was warmed to room temperature, and stirred overnight. The reaction solution was then cooled to 0°C again, and hydrogen chloride (approximately 6 M ethanol diluted solution, 100 mL) was added. The mixture was warmed to room temperature and stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitate was filtered. The resulting precipitate was washed with water to obtain intermediate c (10.2 g, 20.8 mmol, 79.5% yield). ASAP mass spectrometry analysis: theoretical value 528.11, observed value 491.65 (-HCl).

[0093] Synthesis of Compound B Under a nitrogen atmosphere, dimethylformamide (120 mL) was added to a mixture of intermediate c (6.20 g, 12.6 mmol), benzoylacetonitrile (3.66 g, 25.2 mmol), benzaldehyde (2.68 g, 25.2 mmol), and sodium carbonate (4.01 g, 37.8 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and recrystallized to obtain Compound B (2.75 g, 3.90 mmol, yield 30.9%).1 H-NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 8.33 (s, 1H), 7.46-7.40 (m, 6H), 7.33-7.29 (m, 4H). ASAP mass spectrometry: Calculated 704.89, Observed 705.69. －３ When a neat thin film obtained by vapor-depositing Compound B at less than 100 Pa was measured, the HOMO energy of Compound B was 6.02 eV and the LUMO energy was 3.64 eV.

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

[0095] Synthesis of Compound C Under a nitrogen atmosphere, dimethylformamide (30 mL) was added to a mixture of intermediate d (3.00 g, 5.16 mmol), benzoylacetonitrile (2.25 g, 15.5 mmol), benzaldehyde (1.64 g, 15.5 mmol), and sodium carbonate (3.28 g, 31.0 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and recrystallized to obtain Compound C (0.789 g, 3.90 mmol, yield 21.7%). 1 H-NMR (400 MHz, CDCl3): δ 9.05 (s, 1H), 7.43-7.29 (m, 6H), 7.22-7.10 (m, 4H). ASAP mass spectrometry: Calculated 935.16, Observed 935.63. －３When a neat thin film obtained by vapor-depositing Compound C at less than 100 Pa was measured, the HOMO energy of Compound C was 6.19 eV and the LUMO energy was 3.36 eV.

[0096] (Example 3) Synthesis of Compound D

[0097] Synthesis of Intermediate e Under a nitrogen atmosphere, anhydrous xylene (60 mL) was added to a mixture of 2,5-difluoro-1,4-benzenedicarbonitrile (4.70 g, 28.6 mmol), bromobenzene-d5 (2.32 g, 14.3 mmol), palladium(II) acetate (0.321 g, 1.43 mmol), tricyclohexylphosphine (1.21 g, 4.30 mmol), 2-ethylhexanoic acid (0.23 mL, 1.4 mmol), and potassium carbonate (2.97 g, 21.5 mmol), and the mixture was heated to 110°C and stirred overnight. After completion of the reaction, the precipitate was filtered off, and the solution was recovered and concentrated under reduced pressure. The resulting mixture was purified by silica gel column chromatography to obtain Intermediate e (4.55 g, 1.03 mmol, crude yield 130%). This mixture was used directly in the next reaction without further purification. 1 H-NMR (400 MHz, CDCl3): δ 7.49 (dd, J = 7.1, 4.6 Hz, 1H). ASAP mass spectrometry: theoretical 245.24, observed 246.18.

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

[0099] Synthesis of Intermediate g: Under a nitrogen atmosphere, anhydrous tetrahydrofuran (40 mL) was added to intermediate f (1.92 g, 3.45 mmol) and the mixture was cooled to 0°C. Lithium bis(trimethylsilyl)amide (1.3 M tetrahydrofuran solution, 3.9 mL, 5.1 mmol) was then added, the mixture was warmed to room temperature, and stirred overnight. The reaction solution was then cooled to 0°C again, and hydrogen chloride (approximately 6 M ethanol diluted solution, 14 mL) was added. The mixture was warmed to room temperature and stirred for 1 hour. After completion of the reaction, the solution was concentrated, and the precipitate was filtered. The resulting precipitate was washed with water and methanol to obtain intermediate g (2.15 g, 3.75 mmol, crude yield 109%). This product was used directly in the next reaction without further purification. ASAP mass spectrometry analysis: theoretical value 609.24, observed value 573.66 (-HCl).

[0100] Synthesis of Compound D Under a nitrogen atmosphere, dimethylformamide (40 mL) was added to a mixture of intermediate g (2.15 g, 3.75 mmol), benzoylacetonitrile (0.590 g, 4.12 mmol), benzaldehyde (0.430 g, 4.12 mmol), and sodium carbonate (1.19 g, 11.3 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain Compound D (0.900 g, 1.14 mmol, yield 31%). 1 H-NMR (400 MHz, CDCl3): δ 8.38 (s, 1H), 7.46-7.43 (m, 2H), 7.34-7.32 (m, 8H). ASAP mass spectrometry: theoretical 786.02, observed 786.84. －３ When a neat thin film obtained by vapor-depositing Compound D at less than 100 Pa was measured, the HOMO energy of Compound D was 6.15 eV and the LUMO energy was 3.82 eV.

[0101] (Example 4) Synthesis of Compound E

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

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

[0104] Synthesis of Compound E Under a nitrogen atmosphere, dimethylformamide (30 mL) was added to a mixture of intermediate i (2.38 g, 3.29 mmol), benzoylacetonitrile (0.888 g, 6.12 mmol), benzaldehyde (0.649 g, 6.12 mmol), and sodium carbonate (3.89 g, 36.7 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain Compound E (1.70 g, 1.89 mmol, yield 61.7%). 1 H-NMR (400 MHz, CDCl3): δ 8.88 (s, 1H), 8.45 (s, 1H), 8.35-8.21 (m, 5H), 8.19-8.07 (m, 4H), 7.88-7.75 (m, 2H), 7.69-7.23 (m, 15H), 7.22-7.14 (m, 4H). ASAP mass spectrometry: Calculated 901.08, observed 901.65. A 1×10 vacuum was applied to a quartz substrate. －３ When a neat thin film obtained by vapor-depositing Compound E at less than 100 Pa was measured, the HOMO energy of Compound E was 6.03 eV and the LUMO energy was 3.69 eV.

[0105] (Example 5) Synthesis of Compound F

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

[0107] Synthesis of Compound F Under a nitrogen atmosphere, dimethylformamide (500 mL) was added to a mixture of intermediate j (3.40 g, 5.44 mmol), 12H-[1]benzothieno[2,3-a]carbazole (4.46 g, 16.3 mmol), and cesium carbonate (5.32 g, 16.3 mmol), and the mixture was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain Compound F (1.16 g, 1.03 mmol, yield 18.8%). 1 H-NMR (400 MHz, CDCl3): δ 9.07 (s, 1H), 8.26 (d, J = 7.3 Hz, 1H), 8.16-8.07 (m, 3H), 7.75 (d, J = 7.8 Hz, 1H), 7.53-7.30 (m, 11H), 7.24-7.18 (m, 4H). ASAP mass spectrometry: Calculated 1131.75, observed 1131.90. The sample was stored on a quartz substrate in a vacuum of 1 × 10 －３ When a neat thin film obtained by vapor-depositing Compound F at less than 100 Pa was measured, the HOMO energy of Compound F was 6.01 eV and the LUMO energy was 3.80 eV.

[0108] (Example 6) Synthesis of Compound G

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

[0110] Synthesis of Intermediate m Intermediate k (4.33 g, 20.3 mmol) was placed in a 1 L three-neck flask and purged with nitrogen. 500 mL of THF was added and cooled to -80°C. A 1.0 mol / L solution of lithium diisopropylamide in n-hexane-tetrahydrofuran (22.3 mL, 22.3 mmol) was added dropwise, followed by stirring for 15 minutes. Iodine (5.67 g, 22.3 mmol) was added and stirred for 30 minutes. A 1.0 mol / L solution of lithium diisopropylamide in n-hexane-tetrahydrofuran (22.3 mL, 22.3 mmol) was then added dropwise, followed by stirring for 20 minutes. Iodine (6.19 g, 24.4 mmol) was then added. After warming to room temperature, saturated aqueous ammonium chloride and ethyl acetate were added, and the organic layer was extracted. The organic layer was then washed with saturated brine. The mixture was dried over magnesium sulfate, filtered, and concentrated to give a crude product, which was recrystallized from methanol to give intermediate m (6.98 g, 15.0 mmol, yield 74%).

[0111] Synthesis of Intermediate n Intermediate m (7.1 g, 15.3 mmol) and copper(I) cyanide (2.05 g, 22.9 mmol) were placed in a 100 mL three-neck flask, and after replacing the atmosphere with nitrogen, 35 mL of N,N-dimethylformamide (DMF) was added, and the mixture was heated to 100°C and stirred for 19 hours. Toluene was added, and the mixture was filtered through Celite. After that, aqueous ammonia was added, and the organic layer was extracted and washed with saturated brine. The mixture was dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to obtain intermediate n (3.6 g, 9.89 mmol, yield 65%) as a white solid. ASAP mass spectrometry analysis: C 13 D5F3IN: Theoretical value 364.0, Observed value 365.1.

[0112] Synthesis of Intermediate p Intermediate n (2.66 g, 7.3 mmol) was placed in a 500 mL three-neck flask and purged with nitrogen. 65 mL of THF was then added and cooled to -78°C. 2 M isopropyl magnesium chloride THF solution (10 mL, 20 mmol) was added dropwise and stirred for 30 minutes. 1 M zinc chloride THF solution (50 mL, 50 mmol) was added and stirred for 1 hour. The mixture was warmed to room temperature, and tetrakis(triphenylphosphine)palladium(0) (0.95 g, 0.82 mmol), 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (4.79 g, 16.42 mmol), and 65 mL of THF were added. The mixture was heated to 70°C and stirred for 15 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was extracted. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and then purified by silica gel column chromatography to obtain intermediate p (2.52 g, 5.10 mmol, yield 70%) as a white solid. 1 H-NMR (400 MHz, CDCl3): δ7.73-7.77 (m, 4H), 7.56-7.62 (m, 2H), 7.48-7.55 (m, 4H). ASAP MS spectrum analysis: C 30 H 10 D5F3N4: Theoretical value 493.2, Observed value 494.4.

[0113] Synthesis of Compound G: In a 100 mL three-neck flask, intermediate p (2.2 g, 4.46 mmol), carbazole-1,2,3,4,5,6,7,8-d ８ (3.13 g, 17.8 mmol), potassium carbonate (3.08 g, 22.3 mmol), and nitrogen substitution were carried out, followed by the addition of 15 mL of DMF. The mixture was heated to 120°C and stirred for 13 hours, then cooled to room temperature, water was added, and the precipitated solid was filtered and washed with methanol. The resulting solid was purified by silica gel chromatography to give compound G (3.47 g, 3.61 mmol, 81% yield) as a yellow solid. 1 H-NMR (400 MHz, CDCl3): δ7.41-7.46 (m, 2H), 7.24-7.30 (m, 4H), 6.94-6.98 (m, 4H) ASAP mass spectrum analysis: C 66 H 10 D 29 N7 Theoretical value 958.51 Observed value 960.0.

[0114] (Example 7) Synthesis of Compound H

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

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

[0117] (Example 8) Synthesis of Compound I

[0118] Synthesis of Intermediate 1b Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (20.0 g, 90.8 mmol), phenyl-d5-boronic acid (24.1 g, 190 mmol), sodium carbonate (28.8 g, 272 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.18 g, 4.54 mmol), THF (180 mL), and degassed water (90 mL) were added to a reaction vessel and stirred at 80°C overnight. The reaction solution was cooled to room temperature, filtered, 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. Purification by column chromatography (methylene chloride:hexane = 1:1) afforded Intermediate 1b (27.7 g, 88.3 mmol, 80% yield) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 2.70 (s, 3H). ASAP MS spectrum analysis: C 18 H3D 10 N3S: theoretical value 313.44, observed value 314.38.

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

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

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

[0122] (Example 9) Synthesis of Compound J

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

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

[0125] (Example 10) Synthesis of Compound K

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

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

[0128] (Example 11) Synthesis of Compound L

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

[0130] Synthesis of Compound L: Under a nitrogen stream, tripotassium phosphate (0.99 g, 4.68 mmol) was added to a solution of intermediate 1e (2.40 g, 2.34 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.61 g, 3.51 mmol) in NMP (23 mL), and the mixture was stirred at 140°C for 3 hours. The reaction solution was cooled to room temperature, and water was added to quench the reaction. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in dichloromethane, coated on silica gel, and purified by column chromatography (dichloromethane:hexane = 9:1) to obtain Compound L as a yellow solid (2.02 g, 1.71 mmol, yield 73.4%). 1 H-NMR (400 MHz, CDCl): δ 9.23 (s, 1H, rotamer 1), 9.21 (s, 1H, rotamer 2). ASAP MS spectral analysis: 78 HD 42 N 11 : Theoretical value 1175.63, observed value 1176.91.

[0131] (Example 12) Synthesis of Compound M

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

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

[0134] (Example 13) Synthesis of Compound N

[0135] Synthesis of Intermediate 1g Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (10.0 g, 45.4 mol), (3,5-di-tert-butylphenyl)boronic acid (22.3 g, 95.3 mmol), potassium carbonate (18.7 g, 136 mmol), tetrakis(triphenylphosphine)palladium (2.62 g, 2.27 mmol), THF (151 mL), and degassed water (50 mL) were added to a reaction vessel and stirred at 70°C overnight. The reaction solution was cooled to room temperature, filtered, 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 = 1:1) to obtain Intermediate 1g (12.84 g, 24.3 mmol, yield 53%) as a transparent liquid. 1 H-NMR (400 MHz, CDCl3): δ 7.86 (d, J=1.6 Hz, 4H), 7.63 (t, J = 1.6 Hz, 2H), 2.70 (s, 3H), 1.40 (s, 36H). ASAP MS spectrum analysis: C 34 H 45 N3S: theoretical value 527.33, observed value 528.64.

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

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

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

[0139] (Example 14) Synthesis of Compound O

[0140] Synthesis of Intermediate 1h Under a nitrogen stream, 4,6-dichloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile (10.0 g, 45.5 mmol), (4-tert-butylphenyl)boronic acid (16.9 g, 95.3 mmol), potassium carbonate (18.7 g, 136 mmol), tetrakis(triphenylphosphine)palladium (2.62 g, 2.27 mmol), THF (151 mL), and degassed water (50 mL) were added to a reaction vessel and stirred at 70°C overnight. The reaction solution was cooled to room temperature, filtered, 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 = 1:1) to give Intermediate 1h (11.96 g, 28.5 mmol, yield 63%) as a white solid. 1 H-NMR(400 MHz, CDCl3): δ 8.01 (dt, J= 8.4 Hz, J= 2.0 Hz, 4H), 7.57 (d, J = 8.0 Hz, J = 1.6 Hz, 4H), 2.69 (s, 3H), 1.38 (s, 18H). ASAP MS spectrum analysis: C 26 H 29 N3S: theoretical value 415.21, observed value 416.44.

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

[0142] Synthesis of Intermediate 3h: Compound 1a (2.5 g, 6.51 mmol) in a THF (81 mL) and water (27 mL) mixed solvent was bubbled with nitrogen. Under a nitrogen stream, intermediate 2h (5.77 g, 14.3 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.46 g, 0.65 mmol), and sodium carbonate (2.06 g, 19.2 mmol) were added to this solution and heated and stirred at 75 °C for 18 hours. 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. Purification by column chromatography (toluene:hexane = 2:8) afforded intermediate 3h (3.82 g, 4.40 mmol, yield 68%) as a white solid. 1H-NMR(400 MHz, CDCl3): δ 9.20 (td, J = 8 Hz, J = 2 Hz, 1H), 8.17 (dt, J= 8.8 Hz, 2.0 Hz, 8H), 7.62 (dt, J = 8.8, 2.0 Hz, 8H), 1.40 (s, 36H). ASAP MS spectrum analysis: C 56 H 53 F3N6: Theoretical value 866.43, Observed value 867.86.

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

[0144] (Example 15) Synthesis of Compound P

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

[0146] Synthesis of Compound P Under a nitrogen stream, potassium carbonate (1.02 g, 7.44 mmol) was added to a solution of compound 1k (3.20 g, 2.48 mmol) and 4H-4-azadibenzo[g,ij]naphtho[2,1,8-cde]azulene (1.44 g, 4.96 mmol) in NMP (25 mL), and the mixture was stirred at 150°C overnight. The reaction solution was cooled to room temperature, and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The resulting solid was purified by column chromatography (toluene) to give compound P (2.64 g, 1.69 mmol, yield 68%) as a yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 9.25-9.21 (m, 1H), 8.19-8.14 (m, 2H), 7.90-6.87 (m, 37H), 6.75-6.34 (m, 1H). ASAP MS spectrum analysis: C 110 H 41 D 20N9O2: Theoretical value 1559.62, Observed value 1560.47. Vacuum degree 1×10 on a quartz substrate －３ When a neat thin film obtained by vapor deposition of Compound P at less than 100 Pa was measured, the HOMO energy of Compound P was 5.68 eV and the LUMO energy was 3.38 eV.

[0147] (Example 16) Synthesis of Compound Q

[0148] Synthesis of Compound Q: Under a nitrogen stream, tripotassium phosphate (0.54 g, 2.55 mmol) was added to a solution of Compound 1f (1.00 g, 1.02 mmol) and 2-phenyl-5H-benzofuro[3,2-c]carbazole (0.51 g, 1.53 mmol) in NMP (20 mL), and the mixture was stirred at 130°C overnight. The reaction solution was cooled to room temperature and quenched by adding water. The solution was filtered, and the solid remaining in the funnel was washed with water and methanol. The solid was dissolved in toluene and purified by column chromatography (toluene:dichloromethane = 8:2) to obtain a yellow Compound Q (0.5 g, 0.38 mmol, yield 38%). 1 H-NMR (400 MHz, CDCl3): δ 9.06 (s, 1H), 8.08 (dd, J =1.2 Hz, J = 0.4 Hz, 1H), 7.74 (dd, J =7.6 Hz, J = 0.8 Hz, 1H), 7.55-7.50 (m, 3H), 7.42-7.37 (m, 2H) 7.35-7.21 (m, 5H), 7.16 (d, J = 8.4 Hz, 1H), 6.99 (dd, J = 7.6 Hz, J = 2 Hz, 1H). ASAP MS spectrum analysis: C 88 H 15 D 36 NO: Calculated 1285.65, Observed 1286.52.

[0149] (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 －３The thin films were evaporated at less than 100 Pa to form thin films with a compound A concentration of 35 wt % to a thickness of 100 nm. Thin films were formed in the same manner using compounds E to O, comparative compound 1, and comparative compound 2 instead of compound A. However, the concentrations of compounds E, F, H to O, and comparative compound 1 were 20 wt %. Photoluminescence was analyzed when each formed thin film 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. Compounds A and E to O represented by general formula (1) were confirmed to have a higher proportion of delayed fluorescent components than comparative compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescent material, and comparative compound 2, which has a structure similar to general formula (1). Compound A has a structure in which a cyanodiarylpyrimidyl group has been introduced instead of the diaryltriazinyl group of comparative compound 2, but the other structures are the same. This confirms that the proportion of delayed fluorescent components increases when a cyanodiarylpyrimidyl group is introduced instead of a diaryltriazinyl group to form the compound of general formula (1).

[0150] A thin film was formed using Compound B instead of Compound A in the same manner as Compound A. Furthermore, Compounds C and D were used instead of Compound A to form thin films at a concentration of 20 wt %. Each of these thin films and the thin film of Comparative Compound 1 was irradiated with 300 nm excitation light to measure the photoluminescence quantum efficiency (PLQY). It was confirmed that the PLQY was 20 to 40% higher when Compounds B, C, and D were used than when Comparative Compound 1 was used. Similarly, the PLQY of a thin film of Compound G was compared with that of a thin film of Comparative Compound 2, and the PLQY was 93.4%, which was 10% or more higher when Compound G was used than when Comparative Example 2 was used.

[0151] (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 －５The 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 H, Compound I, Comparative Compound 2, and Comparative Compound 3 were used to prepare organic electroluminescence devices in the same manner. However, the concentration of Comparative Compound 2 in the light-emitting layer was 45 wt % or 65 wt %. Each organic electroluminescence device was operated at a current of 12.6 mA / cm . ２ The 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 comparative compound 3 is set to 1. It was confirmed that when compound A and compound B were used, the device lifetime was more than 1,000 times longer than when comparative compound 3 was used, and more than twice as long as when comparative compound 2 was used. Compound A has a structure in which a cyanodiarylpyrimidyl group is introduced instead of the diaryltriazinyl group of comparative compound 2, but the other structures are the same. This confirms that the device lifetime is extended by introducing a cyanodiarylpyrimidyl group instead of the diaryltriazinyl group to form a compound of general formula (1).

[0152] In the manufacturing process of the organic electroluminescence device in Test Example 2, each organic electroluminescence device was manufactured by the same procedure except that Compound Q was used instead of Compound A. The external quantum efficiency (EQE) of the organic electroluminescence devices using Compound H, Compound I, Compound Q, and Comparative Compound 2 was 6.3 mA / cm ２ The results are shown in the table below. It was confirmed that a device with high external quantum efficiency can be realized by using the compound of general formula (1).

[0153] (Test Example 3) Fabrication and Evaluation of Red Organic Electroluminescence Device Each thin film was deposited by vacuum deposition on a 2 mm thick glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, at a vacuum degree of 1×10. －６ The layers were laminated at 100 Pa. First, HAT-CN was formed to a thickness of 5 nm on ITO, NPD was formed thereon to a thickness of 60 nm, and then compound EB1 (described below) was formed thereon to a thickness of 10 nm. Next, compound H3 (described below), compound H4 (described below), and compound E were co-deposited from different evaporation sources to form an emitting layer with a thickness of 40 nm. At this time, the concentrations in the emitting layer were 45 wt % of the first host material H3, 20 wt % of the second host material H4, and 35 wt % of compound E. Next, HB1 was formed to a thickness of 10 nm, followed by SF3-TRZ to a thickness of 30 nm. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was formed to a thickness of 100 nm to form a cathode, thereby forming an organic electroluminescence device. Each organic electroluminescence device was fabricated using comparative compound 1 instead of compound E, following the same procedure. Each organic electroluminescence element was subjected to a current of 50 mA / cm ２ The 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, with the LT95 of comparative compound 1 set to 1. It was confirmed that when compound E was used, the device lifetime was approximately 4.6 times longer than when comparative compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used.

[0154] Each organic electroluminescence device was produced in the same manner using Compound F instead of Compound E. For each organic electroluminescence device using Compound E, Compound F, or Comparative Compound 1, a luminance of 15.4 mA / cm ２ The driving voltage was measured when light was emitted at 1000 kJ / cm2. The results are shown in the table below. It was confirmed that when Compound E and Compound F were used, the driving voltage was lower than when Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used.

[0155] (Test Example 4) Preparation and Evaluation of Organic Electroluminescence Device Using Assist Dopant

[0047] Organic electroluminescence devices were prepared by the same method as in Test Example 3, except that the light-emitting layer was formed by co-depositing H3, H4, compound E, and compound ET1 (described later) from different deposition sources to form a 40 nm-thick layer containing 44.7 wt% of H3 as the first host material, 20 wt% of H4 as the second host material, 35 wt% of compound E as the assist dopant, and 0.3 wt% of ET1 as the dopant (light-emitting material). Using comparative compound 1 instead of compound E, each organic electroluminescence device was prepared by the same procedure. Each organic electroluminescence device was operated at 50 mA / cm ２ The 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, with the LT95 of comparative compound 1 set to 1. It was confirmed that when compound E was used, the device lifetime was 3.1 times longer than that of comparative compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material.

[0156] Organic electroluminescence devices were prepared in the same manner using Compound F instead of Compound E. For each of the organic electroluminescence devices using Compound E, Compound F, and Comparative Compound 1, a luminescence of 15.4 mA / cm ２The driving voltage was measured when light was emitted at 1000 kJ / cm2. The results are shown in the table below. It was confirmed that when Compound E and Compound F were used, the driving voltage was lower than when Comparative Compound 1 (4CzTPN-d), which is known as an excellent delayed fluorescence material, was used.

[0157] (Test Example 5) Preparation and Evaluation of Another Organic Electroluminescence Device Using an Assist Dopant Organic electroluminescence devices were prepared by the same method as in Test Example 3, except that the emitting layer was formed by co-evaporating H2, Compound H, and Compound ET2 (described below) 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 H, and 0.8 wt % of the dopant (emitting material) ET2. Instead of Compound H, Compound I, Compound M, and Comparative Compound 2 were used to prepare organic electroluminescence devices by the same procedure. However, the concentration of Comparative Compound 2 in the emitting layer was 65 wt %, and the concentration of the dopant (emitting material) ET2 was 0.8 wt %. For each of the prepared devices, the external quantum efficiency (EQE) was measured in the same manner as in Test Example 2, and the device lifetime (LT95) was measured in the same manner as in Test Example 3. The results are shown in the table below. The device lifetime is shown as a relative value when the LT95 of Comparative Compound 2 is set to 1. It was confirmed that the device using the compound represented by general formula (1) had higher luminous efficiency and longer device lifetime than the device using Comparative Compound 2.

[0158]

[0159] (Test Example 6) Preparation and Evaluation of Yet Another Organic Electroluminescence Device Using an Assist Dopant

[0044] Organic electroluminescence devices were prepared by the same method as in Test Example 3, except that the emitting layer was formed by co-evaporating H2, Compound I, and Compound ET3 (described below) 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 I, and 0.8 wt% of the dopant (emitting material) ET3. Instead of Compound I, Compound M, Compound N, Compound O, and Comparative Compound 2 were used to prepare organic electroluminescence devices by the same procedure. However, the concentration of Comparative Compound 2 in the emitting layer was 65 wt%, and the concentration of the dopant (emitting material) ET2 was 0.8 wt%. The external quantum efficiency (EQE) of each of the prepared devices was measured by the same method as in Test Example 2. The results are shown in the table below. It was confirmed that the device using the compound represented by general formula (1) had higher luminous efficiency than the device using comparative compound 2.

[0160]

[0161]

[0162]

[0163] The compound of the present invention represented by the general formula (1) exhibits excellent performance as a compound for an organic light-emitting device, 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 L 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 R represents a single bond or a divalent linking group. １ ~R ５ Each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ ~R ５ Two to four of R are independently a donor group; １ ~R ３ One of the groups is a cyano group or a group represented by the following general formula (A): X ３ and X ４ One represents N and the other represents C-Y ６ represents Y ４ ~Y ６ one represents a cyano group and the remaining two each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; or ３ and X ４ represents N, and Y ４ represents a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Y ５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ represents a single bond or a divalent linking group.

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

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

4. R １ ~R ３ one of the groups represented by formula (A) is a group represented by formula (A); １ and X ３ are identical, and X ２ and X ４ are identical, and Y １ and Y ４ are identical, and Y ２ and Y ５ are identical, and L １ and L ２ The compound of claim 1 , wherein 5. R １ ~R ５ 2. The compound of claim 1, wherein at least one of is an aryl group optionally substituted with a deuterium atom, an alkyl group, or an aryl group.

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

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

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. L １ and L ２ The compound of claim 1 , wherein is a single bond.

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

11. R １ ~R ５ The compound according to claim 10, wherein at least one of the two to four donor groups is an optionally fused substituted or unsubstituted carbazol-9-yl group.

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

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

14. The donor group and Y １ ~Y ６ The compound of claim 1 , wherein at least one of the following groups contains a deuterium atom:

15. A light-emitting material comprising the compound according to any one of claims 1 to 14.

16. A delayed fluorescent material comprising the compound according to any one of claims 1 to 14.

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