Organic light-emitting element

Abstract

An organic light-emitting element using a compound represented by the following general formula has excellent performance. In the formula, one of X1 and X2 is N and the other is C-Y3, one of Y1 to Y3 is a cyano group and the remaining two are aryl groups or heteroaryl groups, L1 is a single bond or a linking group, two to four of R1 to R5 are donor groups, and one of R1 to R3 is a cyano group, a diaryl cyanophenyl group, or the like.

Description

Organic light-emitting devices

[0001] The present invention relates to an organic light-emitting device using a compound having a specific structure.

[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 to find more useful compounds and provide organic light-emitting devices with good performance. They have then conducted extensive research to derive a general formula for a more useful compound and to improve the performance of organic light-emitting devices by using the compound represented by that general formula.

[0008] As a result of intensive research to achieve the above object, the present inventors have found that an organic light-emitting device with excellent performance can be provided by using a compound having a structure that satisfies specific conditions. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] An organic light-emitting device containing 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 Y４ ~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 [3] The organic light-emitting element according to [1], wherein R is a cyano group or a group represented by general formula (A). ２ [4] The organic light-emitting element according to [1], wherein R is a cyano group or a group represented by general formula (A). 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 organic light-emitting device according to any one of [1] to [3], wherein R １ ~R ５ [6] The organic light-emitting device 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 organic light-emitting device 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 organic light-emitting device according to any one of [1] to [6], wherein Y is N. １ ~Y ３[9] The organic light-emitting device 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 a substituted or unsubstituted carbazol-9-yl group which may be fused. １ and L ２

[10] The organic light-emitting device according to any one of [1] to [8], wherein R is a single bond. １ ~R ５

[11] The organic light-emitting device 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 organic light-emitting element 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 organic light-emitting device according to any one of [1] to

[11] , wherein two of R １ ~R ５

[14] The organic light-emitting element according to any one of [1] to

[11] , wherein three of the donor groups and Y １ ~Y ６ The organic light-emitting device according to any one of [1] to

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

[15] The organic light-emitting device according to any one of [1] to

[14] , which is an organic electroluminescence device.

[16] The organic light-emitting device according to

[15] , wherein the organic electroluminescence device has a layer containing the compound, and the layer also contains a host material.

[17] The organic light-emitting device according to

[15] or

[16] , wherein the organic electroluminescence device has a layer containing the compound, and the layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

[18] The organic light-emitting device according to

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

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

[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) used in the organic light-emitting device of the present invention will be described. General Formula (1)

[0012] In general formula (1), X １ and X ２ represents N on one side and C-Y on the other side. ３ In one aspect of the present invention, X １ is N and X ２ is C-Y ３ In one aspect of the present invention, X １ is C-Y ３ and X ２ is N. In general formula (1), X １ and X ２ Both of them cannot be N. １ and X ２ In comparison with a compound in which both are N, the compound represented by the general formula (1) exhibits superior luminescence properties.

[0013] In the general formula (1), Y１ ~Y ３ One 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 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 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., 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, this 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. 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. In Table 4, in order to make the correspondence easier to understand, 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 it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. 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) may be formed into a film by a coating method regardless of its molecular weight. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0074] In the present invention, a compound containing multiple structures represented by general formula (1) in its molecule can be used as a light-emitting material, etc. For example, a polymerizable group can be pre-prepared in the structure represented by general formula (1), and the polymer obtained by polymerizing the polymerizable group can be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) can be prepared, and this can be polymerized alone or copolymerized with other monomers to obtain a polymer having repeating units, and this polymer can be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) can be coupled to obtain dimers or trimers, and these can be used as light-emitting materials.

[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 １１Preferably, 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 substituent. Preferably, it is 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] The compound represented by general formula (1) is a compound that can be used in various semiconductor devices. For example, it can be used in organic light-emitting devices that emit light, organic light-receiving devices that receive light, and devices that cause light-mediated energy transfer within the device. For example, an organic electroluminescence device can be fabricated using a compound represented by general formula (1). For example, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1). For example, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). Compounds represented by general formula (1) include compounds that can emit delayed fluorescence. Compounds represented by general formula (1) include compounds with a high proportion of delayed fluorescence components. For example, compounds in which 80% or more of the total emission is delayed fluorescence components, for example, compounds in which 90% or more of the total emission is delayed fluorescence components, are included. 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 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. 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 some embodiments of the present disclosure, compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, compounds represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means.In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (e.g., 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 (e.g., 780 nm-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 donor groups, and for example, by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole, a compound of general formula (1) in which a substituted or unsubstituted carbazol-9-yl group is the donor group can be synthesized. For details of the reaction conditions, please refer to the synthesis examples described below.

[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] [Organic Light-Emitting Device] An organic light-emitting device containing a compound represented by general formula (1) will be described. An organic light-emitting device using a compound represented by general formula (1) has excellent performance. For example, organic light-emitting devices containing a compound represented by general formula (1) include those that can extend the device life by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those that can increase the luminous efficiency by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those that can reduce the driving voltage by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those that can increase the proportion of delayed fluorescent components in the emitted light by using a compound represented by general formula (1). In one embodiment of the present invention, a compound represented by general formula (1) is used as a light-emitting material for an organic light-emitting device. For example, a compound represented by general formula (1) is used as a light-emitting material in an emitting layer. Compounds represented by general formula (1) include compounds with a high delayed fluorescent component. For this reason, in one aspect of the present invention, a compound represented by general formula (1) is used as a delayed fluorescent material, for example, by generating delayed fluorescence from the compound represented by general formula (1), thereby achieving high light emission efficiency. In one aspect of the present invention, a compound represented by general formula (1) is used as a host material. In one aspect of the present invention, a compound represented by general formula (1) is used together with one or more light-emitting materials. The light-emitting material here may be a fluorescent material, a phosphorescent material, or a delayed fluorescent material. For example, a fluorescent material having a lower minimum excited singlet energy than the compound represented by general formula (1) is used together with the compound represented by general formula (1). In one aspect of the present invention, a compound represented by general formula (1) is used as a hole-transporting material. In one aspect of the present invention, a compound represented by general formula (1) is used as an electron-transporting material. In an embodiment, the light-emitting layer of an organic light-emitting device contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In an embodiment, the substrate is a film-forming surface.In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects 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 general formula (1) improves the light extraction efficiency from the light-emitting layer. The organic light-emitting device of the present invention is particularly preferably used as an organic light-emitting diode, etc. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device). In some embodiments, the organic light-emitting device is an organic electroluminescence device (organic EL device). In some embodiments, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In some embodiments, the lowest excited singlet energy level of the compound represented by general formula (1) contained in the light-emitting layer is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In some embodiments, the organic photoluminescence device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an emitting layer. In some embodiments, the organic layer includes only an emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0086] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. In other words, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a thermally activated delayed fluorescent material (TADF) and a host material are used. In some embodiments, the TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer. In some embodiments, the organic electroluminescent device has a layer containing a compound represented by general formula (1). In some embodiments, the layer also contains a host material.In one embodiment, the layer containing the compound represented by general formula (1) and a host material also contains a delayed fluorescent material having a structure outside the range of general formula (1), and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound represented by general formula (1). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent device has a layer containing the compound represented by general formula (1) and a light-emitting material having a structure outside the range of general formula (1) (this layer may further contain a host material). In one embodiment, the lowest excited singlet energy of the light-emitting material having a structure outside the range of general formula (1) is lower than that of the compound represented by general formula (1). In one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the light-emitting material having a structure outside the range of general formula (1) is maximized.

[0087] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[0088]

[0089] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0090] Further examples of the light-emitting material include compounds represented by the following general formula (2):

[0091] In general formula (2), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４At least one of the C-R groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0092] In one aspect of the present invention, X ２ When is O or NR, R ７ is an acceptor group, or R ６ and R ７ are bonded to each other to form an acceptor group, or R ７ and R ８ In one embodiment of the present invention, X ３ When is O or NR, R １０ is an acceptor group, or R ９ and R １０ are bonded to each other to form an acceptor group, or R １０ and R １１ In one embodiment of the present invention, X ４ When is O or NR, R １５ is an acceptor group, or R １４ and R １５ are bonded to each other to form an acceptor group, or R １５ and R １６ In one embodiment of the present invention, X ２ is NR, R is a substituted or unsubstituted phenyl group, and R ８In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ３ is NR, R is a substituted or unsubstituted phenyl group, and R ９ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ４ is NR, R is a substituted or unsubstituted phenyl group, and R １６ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. １ is NR, R is a substituted or unsubstituted phenyl group, and R １ When a carbazole ring is formed by directly bonding to the carbon atom to which is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is on the phenyl group). In one embodiment of the present invention, the compound is represented by the following general formula (2a):

[0093] In general formula (2a), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R１１ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of Ar is O or NR, and the remaining may be O or NR or may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ Each of C-R in general formula (2a) independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ , C-R ３ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0094] Further examples of the light-emitting material include compounds represented by the following general formula (3):

[0095] In general formula (3), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0096] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. ３ and R １０ are each independently a substituted amino group. １ and R ３ , and R ２ and R １０ In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0097] Further examples of the light-emitting material include compounds represented by the following general formula (4):

[0098] In general formula (4), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0099] In one aspect of the present invention, Z １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. １ ~R ９ are each independently a substituted or unsubstituted aryl group or an acceptor group, or R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. ８ is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, a benzothiophene ring, and an indole ring.

[0100] Further examples of the light-emitting material include compounds having a fused ring structure A (in which hydrogen atoms may be substituted with deuterium atoms or substituents) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring.

[0101] In the structure α, X １ and X ２ each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent; Z and X ２ In the fused ring structure A, the structure fused to b and X may be bonded to each other to form a cyclic structure. １ , b and Z, Z and X ２ may be bonded to each other to form a cyclic structure.

[0102] Further examples of the light-emitting material include compounds represented by the following general formula (5):

[0103] In the general formula (5), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0104] Further examples of the light-emitting material include compounds represented by the following general formula (6):

[0105] In general formula (6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ ~R ７ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３, Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0106] Further examples of the light-emitting material include compounds represented by the following general formula (7):

[0107] In the general formula (7), X ４ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ａ ~R ７ａ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ａ and R ５ａ , R ５ａ and R ６ａ , R ６ａ and R ７ａ , R ７ａ and R １ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0108] Further examples of the light-emitting material include compounds represented by the following general formula (8):

[0109] In the general formula (8), Z １represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ８ ~R １４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0110] Further examples of the light-emitting material include compounds represented by the following general formula (9):

[0111] In the general formula (9), Z １ and Z ４ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R １５ ~R １７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.１ and R １ , Z ４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0112] Further examples of the light-emitting material include compounds represented by the following general formula (10):

[0113] In the general formula (10), Z １ and Z ５ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0114] Further examples of the light-emitting material include compounds represented by the following general formula (11):

[0115] In the general formula (11), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２１ ~R ２７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ , R ２６ and R ２７ may be bonded to each other to form a cyclic structure.

[0116] Further examples of the light-emitting material include compounds represented by the following general formula (12):

[0117] In the general formula (12), Z １ and Z ６ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２８ ~R ３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ may be bonded to each other to form a cyclic structure.

[0118] Further examples of the light-emitting material include compounds represented by the following general formula (13):

[0119] In the general formula (13), Z １ and Z ７ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.)

[0120] Further examples of the light-emitting material include compounds represented by the following general formula (14):

[0121] In the general formula (14), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ３１ ~R ４４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R ３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ , R ３７ and R ３８ , R ３８ and R ３９ , R ３９ and R ４０ , R ４０ and R ４１ , R ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ may be bonded to each other to form a cyclic structure.

[0122] Further examples of the light-emitting material include compounds represented by the following general formula (15):

[0123] In the general formula (15), Z １ and Z ８ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R１ and R ５１ ~R ６０ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , R ５１ and R ５２ , R ５２ and R ５３ , R ５３ and R ５４ , R ５４ and R ５５ , R ５５ and R ５６ , R ５６ and R ５７ , R ５７ and R ５８ , R ５８ and R ５９ , R ５９ and R ６０ , R ６０ and Z ８ may be bonded to each other to form a cyclic structure.

[0124] Further examples of the light-emitting material include compounds represented by the following general formula (16):

[0125] In the general formula (16), Z １ , Z ８ and Z ９ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８may be bonded to each other to form a cyclic structure.

[0126] Further examples of the light-emitting material include compounds represented by the following general formula (17):

[0127] In the general formula (17), Z １ , Z ９ and Z １０ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６７ ~R ６９ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７０ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , Z ９ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ , R ６９ and Z １０ , Z １０ and R ７０ may be bonded to each other to form a cyclic structure.

[0128] Further examples of the light-emitting material include compounds represented by the following general formula (18):

[0129] In the general formula (18), Z １ , Z １１ and Z １２ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0130] Further examples of the light-emitting material include compounds represented by the following general formula (19):

[0131] In the general formula (19), Z １ and Z １１ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７６ ~R ８２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R ７５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R ７８ , R ７８ and R ７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0132] Further examples of the light-emitting material include compounds represented by the following general formula (20):

[0133] In the general formula (20), X ５ represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R １０１ ~R １３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １０１ and R １０２ , R １０２ and R １０３ , R １０３ and R １０４ , R １０４ and R １０５ , R １０５ and R １０６ , R １０６ and R １０７ , R １０７ and R １０８ , R １０８ and R １０９ , R １０９ and R １１０ , R １１０ and R １１１ , R １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , R １１４ and R １１５ , R １１５ and R １１６ , R １１６ and R １１７ , R １１７ and R １１８ , R １１８ and R １１９ , R １１９ and R １２０ , R １２０ and R １２１ , R １２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R １２５ , R １２５ and R １２６ , R １２６and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R １３０ and R １０１ may be bonded to each other to form a cyclic structure.

[0134] Further examples of the light-emitting material include compounds represented by the following general formula (21):

[0135] In general formula (21), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R ２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0136] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. １ and Z １ are bonded to each other to form a ring structure. １ and Z １ are bonded to each other to form a pyrrole ring.

[0137] Further examples of the light-emitting material include compounds represented by the following general formula (22):

[0138] In the general formula (22), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring. For a detailed description of the compound represented by general formula (22), as well as preferred ranges and specific examples thereof, reference can be made to paragraphs

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification. Examples of compounds encompassed by general formula (22) include the following compounds:

[0139] Further examples of the light-emitting material include compounds represented by the following general formula (23):

[0140] In the general formula (23), X is an oxygen atom or a sulfur atom (for example, an oxygen atom). １ ~R ２１ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９, R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ may be bonded to each other to form a cyclic structure. １ ~R ２１ , A １ , A ２ For a detailed description and preferred range of R in general formula (22), １ ~R １２ , R １８ ~R ２６ , A １ , A ２ The detailed description and preferred range of the compound of formula (23) can be referred to. Examples of the compound encompassed by formula (23) include the following compounds.

[0141] In some embodiments, when a host material is used, the amount of the compound used in the present invention as the emissive material in the emissive layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 10% by weight or less. In some embodiments, the host material in the emissive layer is an organic compound having hole transport and electron transport functions. In some embodiments, the host material in the emissive layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the emissive layer is an organic compound having a high glass transition temperature.

[0142] In some embodiments, the host material is selected from the group consisting of: In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of general formula (1) may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of general formula (1), the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0143] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0144] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0145] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0146] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0147] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0148]

[0149] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0150] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0151] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0152]

[0153] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0154]

[0155] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0156] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0157]

[0158] Electron Transport Layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0159]

[0160] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0161]

[0162] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0163] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0164] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0165] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0166] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0167] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0168] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0169] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0170] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0171] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0172] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0173] 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.).

[0174] (Synthesis Example 1) Synthesis of Compound A

[0175] 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.

[0176] 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.

[0177] (Synthesis Example 2) Synthesis of Compounds B and C

[0178] 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.

[0179] 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).

[0180] 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.

[0181] 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%).

[0182] 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. －３ When 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.

[0183] (Synthesis Example 3) Synthesis of Compound D

[0184] 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. 1H-NMR (400 MHz, CDCl3): δ 7.49 (dd, J = 7.1, 4.6 Hz, 1H). ASAP mass spectrometry: theoretical 245.24, observed 246.18.

[0185] 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.

[0186] 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 the mixture was stirred for 1 hour. After the reaction was complete, 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).

[0187] 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.

[0188] (Synthesis Example 4) Synthesis of Compound E

[0189] 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.

[0190] 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).

[0191] 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.

[0192] (Synthesis Example 5) Synthesis of Compound F

[0193] 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.

[0194] 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 －３When 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.

[0195] (Synthesis Example 6) Synthesis of Compound G

[0196] 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).

[0197] 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%).

[0198] 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.

[0199] 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.

[0200] 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.

[0201] (Synthesis Example 7) Synthesis of Compound H

[0202] 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.

[0203] 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.

[0204] (Synthesis Example 8) Synthesis of Compound I

[0205] 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.

[0206] 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.

[0207] 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

[0208] 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

[0209] (Synthesis Example 9) Synthesis of Compound J

[0210] 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).

[0211] 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.

[0212] (Synthesis Example 10) Synthesis of Compound K

[0213] 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.

[0214] 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.

[0215] (Synthesis Example 11) Synthesis of Compound L

[0216] 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.

[0217] 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.

[0218] (Synthesis Example 12) Synthesis of Compound M

[0219] 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.

[0220] 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).

[0221] (Synthesis Example 13) Synthesis of Compound N

[0222] 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.

[0223] 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.

[0224] 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.

[0225] 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.

[0226] (Synthesis Example 14) Synthesis of Compound O

[0227] 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.

[0228] 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.

[0229] 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.

[0230] 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.

[0231] (Synthesis Example 15) Synthesis of Compound P

[0232] 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.

[0233] 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.

[0234] (Synthesis Example 16) Synthesis of Compound Q

[0235] 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.

[0236] (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).

[0237] 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.

[0238] (Example 2) Fabrication and Evaluation of Green Organic Electroluminescence Devices Each thin film was deposited by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed, 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).

[0239] In the manufacturing process of the organic electroluminescence device in 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).

[0240] (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.

[0241] 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.

[0242] Example 4 Preparation and Evaluation of Organic Electroluminescence Device Using Assist Dopant

[0047] Organic electroluminescence devices were prepared by the same method as in Example 3, except that the light-emitting layer was formed by co-depositing H3, H4, compound E, and compound ET1 (described below) from different evaporation 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.

[0243] 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.

[0244] 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 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 %. The external quantum efficiency (EQE) of each prepared device was measured in the same manner as in Example 2, and the device lifetime (LT95) was measured in the same manner as in 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.

[0245]

[0246] Example 6: Preparation and Evaluation of Yet Another Organic Electroluminescence Device Using an Assist Dopant Organic electroluminescence devices were prepared using the same method as in 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 using 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 using the same method as in 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.

[0247]

[0248]

[0249]

[0250] By using the compound represented by general formula (1), an organic light-emitting device having good light-emitting properties can be provided, and therefore the present invention has high industrial applicability.

Claims

1. An organic light-emitting device comprising a compound represented by the following 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 organic light-emitting element according to claim 1 , wherein is a cyano group or a group represented by general formula (A):

3. R ２ The organic light-emitting element 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 organic light-emitting device according to claim 1 , wherein 5. R １ ~R ５ The organic light-emitting device according to claim 1 , wherein at least one of the groups is a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group.

6. R １ and R ５ The organic light-emitting element according to claim 1 , wherein at least one of is a hydrogen atom or a deuterium atom.

7. X １ and X ３ The organic light-emitting device according to claim 1 , wherein 8. Y １ ~Y ３ The organic light-emitting element 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 a substituted or unsubstituted carbazol-9-yl group which may be condensed.

9. L １ and L ２ The organic light-emitting device according to claim 1 , wherein is a single bond.

10. R １ ~R ５ 2. The organic light-emitting device 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 11. The organic light-emitting device according to claim 10, wherein at least one of the two to four donor groups is a substituted or unsubstituted carbazol-9-yl group which may be condensed.

12. R １ ~R ５ The organic light-emitting element according to claim 1 , wherein two of the groups are the donor groups.

13. R １ ~R ５ The organic light-emitting element according to claim 1 , wherein three of the groups are the donor groups.

14. The donor group and Y １ ~Y ６ The organic light-emitting device according to claim 1 , wherein at least one of the groups comprises a deuterium atom.

15. The organic light-emitting device according to any one of claims 1 to 14, which is an organic electroluminescence device.

16. The organic light-emitting device of claim 15, wherein the organic electroluminescent device has a layer comprising the compound, the layer also comprising a host material.

17. The organic light-emitting device according to claim 15, wherein the organic electroluminescent device has a layer containing the compound, and the layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

18. The organic light-emitting device according to claim 17, wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

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