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

Abstract

By using a compound represented by the indicated general formula, it is possible to provide an organic light-emitting element having favorable properties. D1 and D2 are each a carbazole structure. Ar is an aromatic ring. Ya to Ye are each N or C. One C among Ya to Yc is bonded to D2. One C among Ya to Ye is bonded to Acp. The symbol a is 1 to 3. Acp represents an a-valent acceptor group.

Description

Compounds, light-emitting materials, and organic light-emitting devices

[0001] This invention relates to compounds having good properties. The invention also relates to light-emitting materials using these compounds, and to organic light-emitting devices such as organic light-emitting devices using these compounds.

[0002] Research on organic light-emitting devices is actively being conducted. For example, there is a lot of research being done to improve the luminescence efficiency of light-emitting devices such as organic electroluminescent devices (organic EL devices). In particular, various methods are being used to improve luminescence efficiency by newly developing and combining electron transport materials, hole transport materials, and light-emitting materials that make up organic electroluminescent devices. Among these, there is also research on organic electroluminescent devices that utilize delayed fluorescence materials.

[0003] Delayed fluorescence materials are materials that, in their excited state, emit fluorescence when they return from the excited singlet state to the ground state after undergoing a reverse intersystem crossover from the excited triplet state to the excited singlet state. This fluorescence is called delayed fluorescence because it is observed later than fluorescence directly generated from the excited singlet state (normal fluorescence) from the ground state. For example, when a luminescent compound is excited by carrier injection, the probability of generating the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to improving the luminescence efficiency if only fluorescence from the directly generated excited singlet state is used. On the other hand, with delayed fluorescence materials, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission via the reverse intersystem crossover pathway described above, resulting in higher luminescence efficiency compared to normal fluorescence materials.

[0004] Since this principle was revealed, various studies have led to the discovery of various delayed fluorescence materials, and their application to organic light-emitting devices such as organic electroluminescent elements has been proposed. Among these are many compounds in which a benzene ring is substituted with a donor group and an acceptor group. For example, compounds have been proposed that have a skeleton in which a benzene ring is substituted with a carbazole-9-yl group, which is a donor group, and a substituted triazinyl group, which is an acceptor group (see Non-Patent Document 1).

[0005] Dyes and Pigments 151 (2018) 75-80

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

[0007] Under such circumstances, the present inventors have conducted extensive research aimed at providing more useful compounds for organic light-emitting devices. Then, they have earnestly proceeded with in-depth studies aimed at deriving and generalizing the general formula of more useful compounds for organic light-emitting devices.

[0008] As a result of earnest studies to achieve the above object, the present inventors have found that compounds having a structure satisfying specific conditions have excellent light-emitting characteristics, and that an organic light-emitting device with excellent performance can be provided by using such compounds. The present invention has been proposed based on such findings, and specifically, it has the following configuration.

[0009] [1] A compound represented by the following general formula (1). General formula (1) [In general formula (1), Y ａ ~Y ｅ each independently represents N or C, and a hydrogen atom, a deuterium atom or a substituent is bonded to the C. Y ａ ~Y ｃ One of them represents C bonded to D ２ . The other Y ａ ~Y ｅ One of them represents C bonded to Acp. The remaining Y ａ ~Y ｅ One of them may be C bonded to a linking group D ３ that is linked to Ar. Further, one of the remaining Y ａ ~Y ｅ may be C bonded to a linking group D ４ that is linked to Ar. Finally, one of the remaining Y ａ ~Yｅ One of them is a linking group D that connects to Ar. ５ It may also be a C that combines with D. １ ~D ５ Each of these independently represents a group represented by the following general formula (2). D in general formula (1) １ ~D ５ The minimum number of linked atoms in the cyclic structure formed by two of these, ring B, and Ar is 10 to 14, independently for each. The minimum number of linked atoms is the number of ring constituent atoms when the ring constituent atoms are selected in such a way that the number of atoms constituting the ring of the cyclic structure is minimized. Ar represents an aromatic ring which may contain nitrogen atoms as ring skeleton constituent atoms, and the aromatic ring may be substituted or fused with other rings. a represents an integer from 1 to 3. When a is 2 or more, multiple Y ａ ~Y ｅ , D １ ~D ５ And Ar may be the same or different. Acp represents an α-valent acceptor group. ] General formula (2) [In general formula (2), R １１ ~R １９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, or 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 １７ , R １７ and R １８ , R １８ and R １９ They bond to each other to form a ring structure. １４ and R １５ When they bond with each other, they are called single bonds, -O-, -S-, -N(R) ２０ )-,-C(R ２１ ) (Caution ２２ )-,-Si(R ２３ ) (Caution ２４ ) - forms one of the following. ２０ ~R ２４Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. * represents a bonding site, and either of the two *s may be bonded to ring B. ] [2] D １ ~D ５ The compound according to [1] wherein at least one of the atoms is bonded to ring B by a nitrogen atom. [3] D １ ~D ５ The compound according to [1] or [2], wherein the shortest number of linked atoms in the cyclic structure formed by two of the atoms, ring B, and Ar is all 12. [4] D １ ~D ５ A compound according to any one of [1] to [3], wherein the linking group has the same structure. [5] D ３ ~D ５ When D does not exist, １ and D ２ The number of constituent atoms of the ring skeleton of ring B that connects them in the shortest possible way, and D １ and D ２ A compound described in any one of [1] to [4], wherein the number of constituent atoms of the Ar ring skeleton that connects them in the shortest possible way is the same. ３ ~D ５ "When there is no Y" is what is meant by "the remaining Y" in [1]. ａ ~Y ｅ " is a linking group D that connects with Ar ３ Even C which bonds with Ar, and the linking group D which bonds with Ar ４ Even C which bonds with Ar, and the linking group D which bonds with Ar ５ This refers to the case where it is not a C that is bonded to it. [6] The compound according to any one of [1] to [5], wherein Acp is bonded to ring B in a six-membered heteroaromatic ring containing a nitrogen atom as a ring skeleton constituent atom. [7] The compound according to [6], wherein the six-membered heteroaromatic ring is substituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. [8] The compound according to any one of [1] to [7], wherein a is 1. [9] The compound according to any one of [1] to [7], wherein a is 2 or 3.

[10] The remaining Y ａ ~Y ｅ One of them is a linking group D that connects to Ar. ３ A compound according to any one of [1] to [9], wherein a is 1 and Y ａ ~Yｃ One of them is C to which Acp is bonded, and the other Y ａ ~Y ｅ A compound according to any one of [1] to

[10] , wherein at least one of the C groups is bonded to a group having the same structure as Acp.

[12] A light-emitting material comprising a compound according to any one of [1] to

[11] .

[13] A film comprising a compound according to any one of [1] to

[11] .

[14] An organic light-emitting element comprising a compound according to any one of [1] to

[11] .

[15] An organic light-emitting element according to

[14] , which is an organic electroluminescent element.

[16] An organic light-emitting element according to

[15] , wherein the organic electroluminescent element has a layer comprising the compound, and the layer also comprises a host material.

[17] An organic light-emitting element according to

[16] , wherein the layer comprises a light-emitting material in addition to the compound and the host material, and the lowest excitation singlet energy of the compound is lower than that of the host material and higher than that of the light-emitting material.

[18] An organic light-emitting element according to

[17] , wherein the layer further comprises a delayed fluorescence material.

[19] An organic light-emitting element according to any one of

[14] to

[18] , which emits fluorescence or delayed fluorescence.

[0010] The compounds of the present invention possess excellent properties and can be used as light-emitting materials. Furthermore, organic light-emitting devices such as organic light-emitting devices can be manufactured using the compounds of the present invention.

[0011] The contents of the present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention are deuterium atoms ( ２It can be replaced with H, deuterium D). In the chemical structural formulas in this specification, a hydrogen atom is represented as H or its representation is omitted. For example, when the representation of an atom bonded to a ring skeleton constituent carbon atom of a benzene ring is omitted, it is assumed that H is bonded to the ring skeleton constituent carbon atom at the position where the representation is omitted. In this specification, the term "substituent" means an atom or atomic group other than a hydrogen atom and a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0012] [Compound Represented by General Formula (1)] The compound represented by the following general formula (1) will be described. General formula (1)

[0013] In general formula (1), Y ａ ~Y ｅ each independently represents N or C, and a hydrogen atom, a deuterium atom or a substituent is bonded to the C. One of Y ａ ~Y ｃ represents C bonded to D ２ . One of the other Y ａ ~Y ｅ represents C bonded to Acp. One of the remaining Y ａ ~Y ｅ may be C bonded to a linking group D ３ that is linked to Ar. Further, one of the remaining Y ａ ~Y ｅ may be C bonded to a linking group D ４ that is linked to Ar. Finally, one of the remaining Y ａ ~Y ｅ may be C bonded to a linking group D ５ that is linked to Ar. In general formula (1), D １ ~D ５ each independently represents a group represented by the following general formula (2). General formula (2)

[0014] In general formula (2), R １１ ~R １９ each independently represents a hydrogen atom, a deuterium atom or a substituent, or R １１ and R１２ , R １２ and R １３ , 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 They bond to each other to form a ring structure. １１ ~R １９ The substituent represented by may be selected from substitution candidate group A described below, substitution candidate group B described below, substitution candidate group C described below, substitution candidate group D described below, or substitution candidate group E described below. In some embodiments of the present invention, R １１ ~R １９ The substituent represented by is selected from substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted heteroaryloxy groups. In some embodiments of the present invention, R １１ ~R １９ Each substituent represented by may independently be an alkyl group that is substituted with one or more atoms or groups selected from the group consisting of deuterium atoms, alkyl groups, aryl groups, and groups consisting of two or more of these, or an aryl group that is substituted with one or more atoms or groups selected from the group consisting of deuterium atoms, alkyl groups, aryl groups, and groups consisting of two or more of these.

[0015] The alkyl group in this invention may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched portions 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. Alternatively, 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 groups. The aryl group in this invention may be a monoring or a fused ring formed by the fusion of 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 benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, and pyrene rings. Specific examples of aryl groups include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, and 9-anthracenyl group. The number of constituent atoms of the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and can be selected within the range of 6 to 14 or within the range of 6 to 10. The heteroaryl group in this invention may be a monoring or a fused ring formed by the fusion of 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 pyridine rings, pyrimidine rings, and pyrrole rings, and these rings may have other rings fused to them. The fused ring is not limited to those containing heteroatoms as constituent atoms of the ring skeleton; for example, it may be a benzene ring.Specific examples of heteroaryl groups include 2-pyridyl, 3-pyridyl, 4-pyridyl, carbazole-9-yl, carbazole-1-yl, carbazole-2-yl, carbazole-3-yl, and carbazole-4-yl groups. The number of constituent atoms in the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within the range of 5 to 16 or 5 to 12. For the alkyl portion of the alkoxy group in this invention, refer to the description of alkyl groups above. For the aryl portion of the diarylamino group and the aryl portion of the aryloxy group in this invention, refer to the description of aryl groups above. For the heteroaryl portion of the heteroaryloxy group in this invention, refer to the description of heteroaryl groups above.

[0016] R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ The cyclic structure formed by the bonding of these elements may be an aromatic ring (including both aromatic rings whose ring skeleton consists only of carbon atoms and heteroaromatic rings that include heteroatoms as ring skeleton constituent atoms), an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or a ring formed by the fusion of these elements. Aromatic rings are preferred. Heteroaromatic rings containing heteroatoms as ring skeleton constituent atoms are preferably 5- to 7-membered rings; for example, 5-membered rings or 6-membered rings can be used. In some embodiments of the present invention, furan rings, thiophene rings, and pyrrole rings can be used as heteroaromatic rings. １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６, R １６ and R １７ , R １７ and R １８ , R １８ and R １９ The cyclic structure formed by the bonding of these elements may be substituted with deuterium atoms or substituents. The substituents may be selected from substitution candidate group A, substitution candidate group B, substitution candidate group C, substitution candidate group D, or substitution candidate group E described below. １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ The cyclic structure formed by the bonding of these elements may have further fused rings. The further fused rings may be aromatic rings (including both aromatic rings whose ring skeleton consists only of carbon atoms and heteroaromatic rings that include heteroatoms as ring skeleton constituent atoms), aliphatic hydrocarbon rings, or aliphatic heterocycles. In some preferred embodiments of the present invention, R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９The cyclic structure formed by the bonding of these elements 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. Preferably, the nitrogen atom constituting the pyrrole ring of indole is bonded to a substituted or unsubstituted aryl group, which may be substituted with a group selected from any of the substituent groups A to E. １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ Examples of aliphatic hydrocarbon rings formed by the bonding of these elements include substituted or unsubstituted cyclopentadiene rings. １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ Examples of aliphatic heterocycles formed by the bonding of these elements include substituted or unsubstituted silole rings. Preferably, the silicon atoms constituting the ring skeleton are bonded to alkyl groups which may be substituted with deuterium atoms or alkyl groups, or to aryl groups which may be substituted with deuterium atoms or alkyl groups. Furthermore, a spirosilafluorene structure may be formed. In some embodiments of the present invention, R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７, R １７ and R １８ , R １８ and R １９ None of the pairs are bonded to each other to form a ring structure. In some embodiments of the present invention, R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ One or two of these groups are linked together to form an aromatic ring.

[0017] R in general formula (2) １４ and R １５ When they bond with each other, they are called single bonds, -O-, -S-, -N(R) ２０ )-,-C(R ２１ ) (Caution ２２ )-,-Si(R ２３ ) (Caution ２４ ) - forms either of the following. If a single bond is formed, a carbazole ring is formed. R ２０ ~R ２４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. ２０ R is preferably a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. ２１ ~R ２４ Preferably, each of these is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. In some embodiments of the present invention, R ２０ ~R ２４R is an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and groups which are combinations of two or more thereof, or an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and groups which are combinations of two or more thereof. In some embodiments of the present invention, R １４ and R １５ They are bonded to each other to form a single bond. In some embodiments of the present invention, R １４ and R １５ These combine with each other to form -O- or -S-. In some embodiments of the present invention, R １４ and R １５ They combine with each other to form -N(R) ２０ ) - forms. In some embodiments of the present invention, R １４ and R １５ They combine with each other to form -C(R ２１ ) (Caution ２２ )- or -Si(R ２３ ) (Caution ２４ ) - forms.

[0018] In some embodiments of the present invention, R １４ and R １５ They bond to each other to form a single bond, R １１ ~R １３ and R １６ ~R １９ Each of these is independently a hydrogen atom; a deuterium atom; an alkyl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and groups formed by combinations of two or more of these; or an aryl group which may be substituted with one or more atoms or groups selected from the group consisting of a deuterium atom, an alkyl group, an aryl group, and groups formed by combinations of two or more of these.

[0019] In general formula (2), the two asterisks (*) represent bonding sites. One is a bonding site to ring B, and the other is a bonding site to Ar. Either of the two asterisks may be bonded to ring B. In some embodiments of the present invention, D present in the molecule １ ~D ５At least one of them is bonded to ring B by a nitrogen atom. In some embodiments of the present invention, D present in the molecule １ ~D ５ All of them are bonded to ring B by nitrogen atoms (for example, D ３ ~D ５ When D does not exist, １ and D ２ (It is bonded to ring B by a nitrogen atom). In some embodiments of the present invention, D present in the molecule １ ~D ５ At least one of them is a carbon atom and is bonded to ring B. In some embodiments of the present invention, D present in the molecule １ ~D ５ All of them are carbon atoms bonded to ring B (for example, D ３ ~D ５ When D does not exist, １ and D ２ (It is bonded to ring B by a carbon atom). In some embodiments of the present invention, D present in the molecule １ ~D ５ Some of the atoms are bonded to ring B by nitrogen atoms, and the rest are bonded to ring B by carbon atoms (for example, D ３ ~D ５ When D does not exist, １ and D ２ One of the atoms is bonded to ring B by a nitrogen atom, and the other is bonded to ring B by a carbon atom. (D present in the molecule) １ ~D ５ The structures may all be identical, only some may be identical, or all may be completely different from each other. For example, D １ and D ２ The structures may be the same or different.

[0020] In the following, D in general formula (1) １ ~D ５ Specific examples of linking groups that can be adopted are shown. However, D that can be adopted in the present invention １ ~D ５ The linking group is not interpreted restrictively by the following specific examples. In the following examples, * indicates the bonding site. The methyl group is CH ３ Because the notation is omitted, for example, D2 has two methyl groups.

[0021] In some embodiments of the present invention, D374 to D746 are disclosed in which all hydrogen atoms present in D1 to D373 are replaced with deuterium atoms. １ ~D ５ The donor groups that can be adopted are selected from the group consisting of D1 to D746. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D1 to D55 and groups obtained by substituting all hydrogen atoms present in these groups with deuterium atoms (hereinafter referred to as "total deuterated groups"). In some embodiments of the present invention, D １ ~D ５ The donor group that can be adopted is selected from D56 to D110 and its total deuterated group. In some embodiments of the present invention, D １ ~D ５ The donor group that can be adopted is selected from D111 to D163 and its total deuterated group. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D164 to D216 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D217 to D267 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor group that can be adopted is selected from D268 to D320 and its total deuterated group. In some embodiments of the present invention, D １ ~D ５The donor group that can be adopted is selected from D321 to D373 and its total deuterated group. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D1 to D9, D51 to D55, D111 to D119, D160 to D172, D213 to D225, D264 to D276, D317 to D329, D370 to D373 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D10 to D50, D120 to D159, D173 to D212, D226 to D263, D277 to D316, D330 to D369 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D18-D27, D48, D127-D136, D157, D180-D189, D210, D233-D242, D261, D284-D293, D314, D337-D346, D367 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D28-D37, D49, D137-D146, D158, D190-D199, D211, D243-D252, D262, D294-D303, D315, D347-D356, D368 and their total deuterated groups. In some embodiments of the present invention, D １ ~D ５ The donor groups that can be adopted are selected from D38-D47, D50, D147-D156, D159, D200-D209, D212, D253-D260, D263, D304-D313, D316, D357-D366, D369 and their total deuterated groups. In each structure of D1-D746, D １ ~D ５ In this specification, when the N atom is bonded to ring B, it is denoted as D1n to D746n (displayed by adding n to the end of D1 to D746). Also, in each structure of D1 to D746, D １ ~D ５In this specification, cases where a carbon atom is bonded to ring B are denoted as D1c to D746c (indicated by adding c to the end of D1 to D746).

[0022] In general formula (1), Ar represents an aromatic ring which may contain a nitrogen atom as a constituent atom of the ring skeleton. This aromatic ring may be substituted, and other rings may be fused to it. In some embodiments of the present invention, Ar is an aromatic ring. In some embodiments of the present invention, Ar is a pyridine ring. In some embodiments of the present invention, Ar is a pyrimidine ring. In some embodiments of the present invention, Ar is a triazine ring. D ３ ~D ５ When D does not exist, １ and D ２ The number of Ar ring skeleton constituent atoms that connect the two in the shortest possible way (hereinafter referred to as the "shortest number of connected atoms") is preferably 2 to 4. When Ar is a 1,3-phenylene group, D １ and D ２ The minimum number of linked atoms is 3, and for a 1,4-phenylene group, D １ and D ２ The minimum number of linked atoms is 4. In some embodiments of the present invention, D １ and D ２ The shortest number of linked atoms is 2. In some embodiments of the present invention, D １ and D ２ The minimum number of linked atoms is 3. In some embodiments of the present invention, D １ and D ２ The minimum number of atoms required to form a short-term bond is 4. The shortest bond consists of atoms that make up the ring skeleton of the aromatic ring represented by Ar. D ４ and D ５ When D does not exist, １ and D ２ The shortest number of connected atoms, D １ and D ３ The shortest number of connected atoms, D ２ and D ３The minimum number of atoms required to link the atoms is preferably 2 to 4, independently of each other. In some embodiments of the present invention, all three minimum number of atoms required to link the atoms are 3. In some embodiments of the present invention, two of the three minimum number of atoms required to link the atoms are 2 and one is 3. In some embodiments of the present invention, two of the three minimum number of atoms required to link the atoms are 2 and one is 4. The aromatic ring that Ar can take may be substituted with deuterium atoms or substituents. The substituent may be selected from substitution candidate group A described below, substitution candidate group B described below, substitution candidate group C described below, substitution candidate group D described below, or substitution candidate group E described below. In some embodiments of the present invention, the substituent is selected from substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted diarylamino groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted aryloxy groups, and substituted or unsubstituted heteroaryloxy groups. The aromatic ring that Ar can take may be a fused ring structure. D １ and D ２ The aromatic ring bonded to the compound may be further fused with one or more aromatic rings, or with one or more aliphatic hydrocarbon rings or one or more aliphatic heterocycles. For example, it may be a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, etc.

[0023] The following shows specific examples of linking groups that Ar of general formula (1) can adopt. However, the linking groups of Ar that can be adopted in the present invention are not limited to the following examples. In the following examples, * indicates the bonding site. The methyl group is CH ３ Because the notation is omitted, for example, Ar2 has one methyl group.

[0024] Ar114 to Ar226 are disclosed in which all hydrogen atoms present in Ar1 to Ar113 above are replaced with deuterium atoms. In some embodiments of the present invention, Ar in general formula (1) is selected from Ar1 to Ar226. In some embodiments of the present invention, Ar is selected from Ar1 to Ar6 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar7 to Ar18 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar19 to Ar25 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar26 to Ar32 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar33 to Ar35 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar36 to Ar53 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar54 to Ar95 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar96 to Ar113 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar1 to Ar18, Ar20, Ar21, Ar23 to Ar25, Ar27, Ar30 to Ar32, Ar72 to Ar95 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar19, Ar22, Ar26, Ar28, Ar29, Ar33 to Ar35, Ar54 to Ar71, Ar104 to Ar111 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar36 to Ar44, Ar96 to Ar99, Ar112 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar45 to Ar53, Ar100 to Ar103, Ar113 and their total deuterized groups. In some embodiments of the present invention, Ar is selected from Ar16 to Ar18, Ar42 to Ar44, Ar51 to Ar53, Ar60 to Ar62, Ar69 to Ar71 and their total deuterized groups.In some embodiments of the present invention, Ar is selected from Ar3, Ar6, Ar11-Ar15, Ar22-Ar25, Ar30, Ar31, Ar34, Ar35, Ar63-Ar71, Ar73-Ar77, Ar79-Ar83, Ar85-Ar89, Ar91-Ar95 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar7 to Ar15, Ar22 to Ar25, Ar29 to Ar32, Ar34, Ar35, Ar40, Ar41, Ar49, Ar50, Ar58, Ar59, Ar63 to Ar71, Ar76, Ar77, Ar82, Ar83, Ar88 to Ar95, Ar99, Ar103, Ar107, Ar111 and their total deuterated groups.

[0025] The following shows another specific example of a linking group that Ar in general formula (1) can adopt. However, the linking groups of Ar that can be adopted in the present invention are not limited to the following specific examples.

[0026] Ar292 to Ar356 are disclosed in which all hydrogen atoms present in Ar227 to Ar291 are replaced with deuterium atoms. In some embodiments of the present invention, Ar in general formula (1) is selected from Ar227 to Ar356. In some embodiments of the present invention, Ar is selected from Ar227 to Ar231 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar232 to Ar239 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar240 to Ar248 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar249 to Ar255 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar256 to Ar262 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar263 to Ar283 and their total deuterated groups. In some embodiments of the present invention, Ar is selected from Ar284 to Ar291 and their total deuterated groups.

[0027] In general formula (1), ring B represents a six-membered aromatic ring. ａ ~Y ｅ Each of these independently represents N or C, and a hydrogen atom, deuterium atom, or substituent is bonded to the C. ａ ~Y ｃ One of them is D ２ This represents C which is combined with Y. ａ ~Y ｅ One of them represents C which combines with Acp. The remaining Y ａ ~Y ｅ One of them is a linking group D that connects to Ar. ３ It may also be a C that is combined with Y. ａ ~Y ｅ One of them is a linking group D that connects to Ar. ４ It may also be a C that combines with it. The last remaining Y ａ ~Y ｅ One of them is a linking group D that connects to Ar. ５ It may also be a C that combines with Y. ａ ~Y ｅ When the number of N elements is 0, ring B is a benzene ring. ａ ~Y ｅ When the number of Ns among them is 1, ring B is a pyridine ring. In some embodiments of the present invention, Y ａ N is Y ｂ Is C bonded to Acp, or Y ｃ This is C that bonds with Acp. In some embodiments of the present invention, Y ｂ N is Y ａ Is C bonded to Acp, or Y ｃ This is C that bonds with Acp. In some embodiments of the present invention, Y ｃ N is Y ａ Is C bonded to Acp, or Y ｂ This is C that bonds with Acp. ａ ~Y ｅ When the number of Ns among them is 2, ring B is a pyrimidine ring. In some embodiments of the present invention, Y ａ C is bonded to Acp, and Y ｂ and Y ｄ Is it N or Y?ｃ and Y ｅ In some embodiments of the present invention, Y ｂ C is bonded to Acp, and Y ａ and Y ｃ Is it N or Y? ｃ and Y ｅ In some embodiments of the present invention, Y ｃ C is bonded to Acp, and Y ａ and Y e Is it N or Y? ｂ and Y ｄ N is Y ａ ~Y ｅ When the number of Ns among them is 3, ring B is a triazine ring. In some embodiments of the present invention, Y ａ and Y ｃ and Y ｅ If N is Y ｂ Is C bonded to Acp, or Y ｄ This is C that bonds with Acp. ａ is D ２ When representing C which is combined with D, １ and D ２ The minimum number of connected atoms in ring B is 2. ｂ is D ２ When representing C which is combined with D, １ and D ２ The minimum number of connected atoms in ring B is 3. At this time, Y ａ It can be N or C. ｃ is D ２ When representing C which is combined with D, １ and D ２ The shortest number of connected atoms in ring B is 4. At this time, Y ａ and Y ｂ One of the elements is C to which Acp is bonded, and the other can be N or C. ａ ~Y ｃ One of them is D ２ This represents C that is bonded with Y, and all other Y ａ ~Y ｅ One of them represents C which is bonded with Acp, and the remaining Y ａ ~Y ｅ Each of these is an independent linking group D that connects to Ar. ３~D ５ It may be a carbon bonded to any of the above, or a carbon bonded to any other substituent, or a carbon bonded to a hydrogen atom or a deuterium atom, or it may be N. The remaining Y ａ ~Y ｅ One of them is a linking group D that connects to Ar. ３ C is bonded with D ４ and D ５ When none exists, a tri-ring structure is formed between Ar and ring B, where there are three rings. That is, Ar and ring B are D １ , D ２ , D ３ The remaining Y is bonded via a total of three linking groups. ａ ~Y ｅ Two of these are linking groups D that connect with Ar. ３ C that bonds with Ar and linking group D that bonds with Ar ４ C is bonded with D ５ When none exists, a four-ring structure is formed between Ar and ring B, where four rings are present. That is, Ar and ring B are D １ , D ２ , D ３ , D ４ The remaining Y ａ ~Y ｅ However, the linking group D connects to Ar. ３ C that bonds with Ar, and D that links with Ar. ４ C that bonds with Ar, and D that links with Ar. ５ When C is bonded to Ar, a five-ring structure is formed between Ar and ring B, with five rings between them. That is, Ar and ring B are D １ , D ２ , D ３ , D ４ , D ５The linkage is through a total of five linking groups. When there are 3 to 5 linking groups linking Ar and ring B, all of these linking groups may have the same structure, one may have a different structure, or all of them may have different structures. Furthermore, all of the linking groups may be bonded to ring B by nitrogen atoms, some may be bonded to ring B by nitrogen atoms and some by carbon atoms, or all may be bonded to ring B by carbon atoms. In some embodiments of the present invention, D ３ ~D ５ It does not exist (no 3-5 ring structure is formed). In some embodiments of the present invention, D ４ and D ５ It does not exist (a bi-ring or tri-ring structure is formed). The remaining Y ａ ~Y ｅ represents C, and C may be bonded to a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from substitution candidate group A, substitution candidate group B, substitution candidate group C, substitution candidate group D, or substitution candidate group E described below. Also, the substituent is Y ａ ~Y ｃ The substituent may have the same structure as Acp bonded to C. In some embodiments of the present invention, Y ｂ and Y ｄ This is Acp, which has the same structure. Also, the remaining Y ａ ~Y ｅ The carbon atom represented by may have an acceptor group attached as a substituent. It is preferable that such an acceptor group is attached to the meta position of Acp.

[0028] Acceptor groups can be selected from groups with a positive Hammett σp value. The Hammett σp value, proposed by L. P. Hammett, quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is a constant (σp) specific to the substituent in the following equations that hold between substituents and the reaction rate constant or equilibrium constant in para-substituted benzene derivatives: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant for unsubstituted benzene derivatives, k is the rate constant for substituted benzene derivatives, K0 is the equilibrium constant for unsubstituted benzene derivatives, K is the equilibrium constant for substituted benzene derivatives, and ρ is the reaction constant determined by the type and conditions of the reaction. For an explanation of "Hammett's σp value" and the numerical values ​​of each substituent in this invention, refer to the description of σp value in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991). The acceptor group that can be used in this invention may be selected from groups with a σp of 0.3 or higher, groups with a σp of 0.5 or higher, groups with a σp of 0.7 or higher, groups with a σp of 0.9 or higher, or groups with a σp of 1.1 or higher.

[0029] D in general formula (1) １ ~D ５ The minimum number of linked atoms in the cyclic structure formed by two of these atoms, Ar, and ring B is 10 to 14, independently for each. Here, "minimum number of linked atoms" refers to the number of ring constituent atoms when the ring constituent atoms are selected in such a way that the number of atoms constituting the ring of the cyclic structure is minimized. In some embodiments of the present invention, D １ ~D ５ A 10-membered ring is included as a ring containing two of the members. In some embodiments of the present invention, D １ ~D ５ An 11-membered ring is included as a ring containing two of the members. In some embodiments of the present invention, D １ ~D ５ A 12-membered ring is included as a ring containing two of the members. In some embodiments of the present invention, D１ ~D ５ A 13-membered ring is included as a ring containing two of the members. In some embodiments of the present invention, D １ ~D ５ A 14-membered ring is included as a ring containing two of the members. In some embodiments of the present invention, D １ ~D ５ The rings containing two of these are all 11-13 member rings. In some embodiments of the present invention, D １ ~D ５ The ring containing two of these is either an 11-membered ring or a 12-membered ring. In some embodiments of the present invention, D １ ~D ５ The rings containing two of these are all 12-membered or 13-membered rings. In some embodiments of the present invention, D １ ~D ５ The rings containing two of these are all 10-membered, 12-membered, or 14-membered rings. In some embodiments of the present invention, D １ ~D ５ The rings containing two of these are all 12-membered rings. In general formula (1), D １ and D ２ Only rings containing D exist, ３ ~D ５ When there is no ring containing D １ and D ２ The shortest number of connected atoms in ring B and D １ and D ２ It is preferable that the number of shortest linking atoms of Ar connecting them is the same. In some embodiments of the present invention, the number of shortest linking atoms is 2 in both cases. In some preferred embodiments of the present invention, the number of shortest linking atoms is 4 in both cases. In some even more preferred embodiments of the present invention, the number of shortest linking atoms is 3 in both cases. In some embodiments of the present invention, ring B and Ar have the same ring skeleton. Hereinafter, ring B and D １ ~D ５ We will illustrate with examples of cyclic structures composed of two of these and Ar, where the shortest number of linked atoms is 10 to 14. For convenience, we will select a benzene ring as ring B and D １ ~D ５Although a carbazole ring is selected as Ar and a benzene ring as Ar are shown, the structure is not limited to these selected structures and can be modified within the range of general formula (1). Furthermore, although a structure in which the nitrogen atom of the carbazole ring is bonded to ring B and the carbon atom is bonded to Ar is shown below, one or more carbazole rings may be replaced with a structure in which the carbon atom is bonded to ring B and the nitrogen atom is bonded to Ar. For this reason, the present invention is not interpreted as being limited by the types exemplified below.

[0030] 10-membered ring type

[0031] 11-membered ring type

[0032] 12-membered ring type

[0033] 13-membered ring type

[0034] 14-membered ring type

[0035] D in general formula (1) １ and D ２ These may be the same structure or different structures. In some preferred embodiments of the present invention, D １ and D ２ They have the same structure. If they have the same structure, D １ and D ２ Both may be bonded to ring B by N atoms, and D １ and D ２ One of them may be bonded to ring B with a C atom and the other to ring B with a N atom, or D １ and D ２ Both may be bonded to ring B by C atoms. Preferably, D １ and D ２ Both are bonded to ring B by N atoms, or D １ and D ２ This is the case where one of the atoms is bonded to ring B by a carbon atom and the other is bonded to ring B by an nitrogen atom, and even more preferably is D １ and D ２ This is the case when both are bonded to ring B by N atoms. In some embodiments of the present invention, D １ and D２ Both are bonded to ring B by N atoms, and Ar is a substituted or unsubstituted arylene group (the minimum number of linked atoms is, for example, 3 or 4). In some embodiments of the present invention, D １ and D ２ Both are bonded to ring B by an N atom, and Ar is a substituted or unsubstituted heteroarylene group (e.g., a pyridine ring, e.g., a pyrimidine ring, e.g., a triazine ring). In some embodiments of the present invention, D １ and D ２ One side is bonded to ring B by a C atom, and the other side is bonded to ring B by an N atom, and Ar is a substituted or unsubstituted arylene group (the minimum number of linked atoms is, for example, 3 or 4). In some embodiments of the present invention, D １ and D ２ One side is bonded to ring B by a carbon atom, and the other side is bonded to ring B by a nitrogen atom, and Ar is a substituted or unsubstituted heteroarylene group (e.g., a pyridine ring, a pyrimidine ring, a triazine ring, etc.). The above D １ and D ２ The relationship is D ３ If D exists, １ and D ３ Relationship, D ２ and D ３ This can also be applied to the relationship D. ３ and D ４ If such a relationship exists, it can also be applied to the relationship between one of them and another. Furthermore, D ３ and D ４ and D ５ Even if such relationships exist, the relationship between one of them and another can also be applied.

[0036] In Table 1 below, D １ and D ２ Here are some specific examples of combinations of the linking group represented by and the linking group represented by Ar. １ and D ２ Q1 to Q265576 are shown as specific examples of cases where the elements have the same structure and are both bonded to ring B by an N atom. Each row in Table 1 displays 746 combinations in one row. For example, the first row of Table 1 shows that Ar is Ar1, and D １and D ２ Let Q1 be a combination where both are D1n, and Ar is Ar1, and D １ and D ２ Let Q2 be the combination where both are D2n, and Ar is Ar1, and D １ and D ２ The 746 combinations (Q1 to Q746) are shown in one row, with Q3 being the combination where both are D3n. Similarly, the second row of Table 1 shows that Ar is Ar2, and D １ and D ２ Let Q747 be the combination where both are D1n, and Ar is Ar2, and D １ and D ２ Let Q748 be the combination where both are D2n, and Ar is Ar2, and D １ and D ２ The combinations where both elements are D3n are designated as Q749, and 746 combinations (Q747 to A1492) are shown together in one row. The combinations in the third row and beyond are shown in the same manner.

[0037]

[0038] In Table 2 below, D １ and D ２ Further specific examples of combinations of the linking group represented by and the linking group represented by Ar are shown. Here, D １ and D ２ Specific examples of cases where are the same are shown as Q1 to Q7170552. Each row in Table 2 displays 265,576 combinations in one row. For example, the first row of Table 2 is D １ and D ２ The combinations of having the same structure and both being D1n to D746n, and Ar being Ar1 to Ar356, are collectively shown as Q1 to Q265576. Here, first, Ar is fixed to Ar1, D １ and D ２ The combinations of D1n to D746n are designated as Q1 to Q746 in order, and then Ar is fixed to Ar2, D １ and D ２The combinations of D1n to D746n are designated as Q747 to Q1492 in order, and Ar is fixed to Ar3, D １ and D ２ The combinations of D1n to D746n are sequentially designated as Q1493 to Q2238, thereby identifying Q1 to Q265576. In other words, the rows for Q1 to Q265576 in Table 2 are a single row display of Q1 to Q265576 in Table 1. In the rows for Q265577 to Q531152 in Table 2, D １ It is fixed to D1c, D ２ The combinations where D1n to D746n and Ar is Ar1 to Ar356 are shown together as Q265577 to Q531152. Similarly in this section, first Ar is fixed to Ar1, D ２ The combinations of D1n to D746n are designated as Q265577 to Q266322 in order, and then Ar is fixed to Ar2, D ２ The combinations of D1n to D746n are sequentially designated as Q266323 to Q267068, thereby identifying Q265577 to Q531152. The combinations in subsequent stages are shown in the same manner.

[0039]

[0040] In general formula (1), a represents an integer from 1 to 3. In some embodiments of the present invention, a is 1. In some embodiments of the present invention, a is 2 or 3, for example 2, for example 3. When a is 2 or 3, a number of Y ａ ~Y ｅ , D １ ~D ５ Ar may be the same or different. In some embodiments of the present invention, a number of Y ａ ~Y ｅ , D １ ~D ５Ar and A are identical in each case. In this case, Acp has a groups with the same structure bonded to it. Below, examples of structures when a is 1 to 3 are shown as general formulas. General formula (1A) shows an example of the structure when a is 1. General formulas (1B) and (1B') show examples of the structure when a is 2. General formulas (1C) and (1C') show examples of the structure when a is 3.

[0041] D in the five general formulas above １ , D ２ Ar, Y ａ ~Y ｅ For the definition and explanation of Y in general formula (1A), refer to the corresponding description in general formula (1). ａ , Y ｃ , Y ｄ , Y ｅ One of them represents C-Acp. The five general formulas above are Y ｂ is D ２ This shows variations in the structure of C that is bonded with Y. ａ is D ２ A general formula showing variations in the structure of C that is bonded with Y ｃ is D ２ A general formula showing variations in the structure of C that combines with can be shown in the same way as the five general formulas above.

[0042] In general formula (1), Acp represents an α-valent acceptor group. The acceptor group is selected from groups in which σp is positive. σp is measured using a monovalent group in which (a-1) substituents attached to Acp are replaced with hydrogen atoms. σp is preferably 0.3 or higher, may be 0.5 or higher, or 0.7 or higher. For example, it may be selected from a range of 0.9 or higher, or from a range of 1.1 or higher.

[0043] When a is 1, Acp represents a monovalent acceptor group. The monovalent acceptor group can be selected from commonly used electron-withdrawing groups. In some embodiments of the present invention, the monovalent acceptor group is a group containing a cyano group, such as a cyano group, a cyano-substituted aryl group, or a cyano-substituted heteroaryl group. In some embodiments of the present invention, the monovalent acceptor group is a group containing a fluorinated alkyl group, such as a perfluoroalkyl group. Specific examples include a trifluoromethyl group, a trifluoromethyl-substituted aryl group, or a trifluoromethyl-substituted heteroaryl group. In some embodiments of the present invention, the monovalent acceptor group is a heteroaryl group containing a nitrogen atom as an atom constituting the ring skeleton, such as a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted pyridyl group.

[0044] In the following, I-1 to I-1743 are given as specific examples where Acp is a monovalent acceptor group. However, the monovalent acceptor group Acp that can be used in the present invention is not limited by the following specific examples. In the following specific examples, * indicates a bonding site.

[0045]

[0046] I-15 to I-1743 are shown in the following general formula and table. In the following general formula, the methyl group is CH ３ The labeling is omitted. Therefore, for example, V-5 and V-9 have a methyl group.

[0047] R in general formulas V-1 to V-19 ｘ and R ｙ The groups identified in Table 3-1 below are designated as specific examples of Acp from I-15 to I-11965. The specific examples listed in Table 3-1 are R ｘ and R ｙ Same structure (R ｘ = R ｙ ) Specific examples (I-1 to I-5999) and Rｘ and R ｙ These are specific examples (I-6000 to I-11965) that differ. In each row of Table 3-1, multiple specific examples are displayed together in one row. For example, in the first row, R of general formula V-1 ｘ and R ｙ Let's consider a specific example I-15 where both are Z1, and R ｘ and R ｙ Let's consider a specific example I-16 where both are Z2, and R ｘ and R ｙ Using the example I-17 where both are Z3, R ｘ and R ｙ The elements Z1 to Z315 are identified in order as specific examples I-15 to I-329, grouped together in one row. The structures of the specific examples are identified in the same manner in subsequent rows.

[0048] Furthermore, R in general formulas V-1 to V-19 ｘ and R ｙ The groups identified in Table 3-2 below are shown as specific examples of Acp from I-15 to I-93494. In Table 3-2, V is changed sequentially from V-1 to V-19, and R ｙ The results of changing Z1 to Z315 in order are shown together in one row. Here, V is first fixed to V-1, and R ｙ The elements that are sequentially set from Z1 to Z315 are designated as I-15 to I-329, and then V is fixed to V-2, R ｙ The elements are identified sequentially from Z1 to Z315, and then from I-330 to I-644. The structure is identified sequentially in the same manner for the second row and beyond. In other words, the first and second rows of Table 3-2 are a two-row display of the structures identified in Table 3-1. Note that only the first row of Table 3-2 is R ｘ and R ｙ They are identical, and from the second row onwards, R ｘ and R ｙ They are different from each other.

[0049] Groups obtained by substituting all hydrogen atoms in Z4 to Z95 with deuterium atoms are defined as Z96 to Z187. For example, Z103 is a hyperdeuterated phenyl group (C ６ D ５ ) and Z139 is a perdeuterated carbazole-9-yl group. In addition, there are further paraphenylene groups (-pC) at the positions indicated by * in Z4 to Z10. ６ H ４ The groups to which the -) is attached are designated as Z188 to Z194, and further metaphenylene groups (-mC) are added at the positions indicated by * in Z4 to Z10. ６ H ４ The groups to which the -) is attached are designated as Z195 to Z201. Furthermore, a paraphenylene group (-pC) is added to the * positions of Z39 to Z95. ６ H ４ The groups to which the -) is attached are designated as Z202 to Z258, and further metaphenylene groups (-mC) are added at the positions indicated by * in Z39 to Z95. ６ H ４Groups to which a -) is bonded are designated as Z259 to Z315. In some embodiments of the present invention, the monovalent acceptor group is selected from I-1 to I-93494. In some embodiments of the present invention, the monovalent acceptor group is selected from I-1 to I-14. In some embodiments of the present invention, the monovalent acceptor group is selected from I-15 to I-5999. In some embodiments of the present invention, the monovalent acceptor group is selected from I-6000 to I-11965. In some embodiments of the present invention, the monovalent acceptor group is selected from I-11966 to I-17912. In some embodiments of the present invention, the monovalent acceptor group is selected from I-17913 to I-23840. In some embodiments of the present invention, the monovalent acceptor group is selected from I-23841 to I-29749. In some embodiments of the present invention, the monovalent acceptor group is selected from I-29750 to I-35639. In some embodiments of the present invention, the monovalent acceptor group is selected from I-35640 to I-41510. In some embodiments of the present invention, the monovalent acceptor group is selected from I-41511 to I-47362. In some embodiments of the present invention, the monovalent acceptor group is selected from I-47363 to I-53195. In some embodiments of the present invention, the monovalent acceptor group is selected from I-53196 to I-59009. In some embodiments of the present invention, the monovalent acceptor group is selected from I-59010 to I-64804. In some embodiments of the present invention, the monovalent acceptor group is selected from I-64805 to I-70580. In some embodiments of the present invention, the monovalent acceptor group is selected from I-70581 to I-76337. In some embodiments of the present invention, the monovalent acceptor group is selected from I-76338 to I-82075. In some embodiments of the present invention, the monovalent acceptor group is selected from I-82076 to I-87794. In some embodiments of the present invention, the monovalent acceptor group is selected from I-87795 to I-93494.

[0050] The following are specific examples of cases where Acp is a divalent acceptor group. However, the divalent acceptor group Acp that can be used in the present invention is not limited by the following examples. In the following examples, * indicates a bonding site, and D represents a deuterium atom.

[0051]

[0052] The following are specific examples of cases where Acp is a trivalent acceptor group. However, the trivalent acceptor group Acp that can be used in the present invention is not limited by the following examples. In the following examples, * indicates a bonding site, and D represents a deuterium atom.

[0053]

[0054] Compound group 1 of the present invention includes a group of compounds in which a of general formula (1) is 1 and Acp is a monovalent acceptor group. Compound group 1 is Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ at least one of (preferably Y) ｄ Compound group 1a, where C is bonded to an acceptor group having the same structure as Acp; Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ at least one of (preferably Y) ｄ ) is a group of compounds 1b to which an acceptor group having a different structure from Acp is bonded; Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ These are all compounds 1c, which are not C to which an acceptor group is bonded; and Y ｃ C is bonded to Acp, and Y ａ, Y ｂ , Y ｄ , Y ｅ at least one of (preferably Y) ａ and Y ｅ Compound group 1d, where at least one of the C atoms is a carbon atom to which an acceptor group having the same structure as Acp is bonded; Y ｃ C is bonded to Acp, and Y ａ , Y ｂ , Y ｄ , Y ｅ at least one of (preferably Y) ａ and Y ｅ Compound group 1e, where at least one of the C atoms is a carbon atom to which an acceptor group having a structure different from Acp is bonded; Y ｃ C is bonded to Acp, and Y ａ , Y ｂ , Y ｄ , Y ｅ These all include compound group 1f, which is not C to which an acceptor group is bonded. For each of these compound groups 1a to 1f, examples of embodiments that also satisfy the following additional conditions can be given. One of the additional conditions is the presence of D in the molecule of general formula (1). １ ~D ５ All of them are bonded to ring B by nitrogen atoms and to Ar by carbon atoms (for example, D ３ ~D ５ When D does not exist, １ and D ２ (It is bonded to ring B by a nitrogen atom and to Ar by a carbon atom). One of the additional conditions is the presence of D in the molecule of general formula (1). １ ~D ５ All of them are linking groups with the same structure (for example, D ３ ~D ５ When D does not exist, １ and D ２ (These are linking groups with the same structure.) One of the additional conditions is that the Ar in general formula (1) is a carbon atom and D is present in the molecule. １ ~D ５ It is a linking group that attaches to (for example, D ３ ~D ５ When it does not exist, Ar is a carbon atom D １ and D ２(A linking group that bonds to the ring.) One of the addition conditions is that Ar in general formula (1) contains a benzene ring. Another addition condition is that Ar in general formula (1) contains a pyridine ring, a pyrimidine ring, or a triazine ring. Another addition condition is that Acp in general formula (1) is bonded to ring B as a six-membered heteroaromatic ring containing a nitrogen atom as a ring skeleton component, and that six-membered heteroaromatic ring is substituted with a substituted or unsubstituted aryl group. Another addition condition is that Acp in general formula (1) is bonded to ring B as a six-membered heteroaromatic ring containing a nitrogen atom as a ring skeleton component, and that six-membered heteroaromatic ring is substituted with a substituted or unsubstituted heteroaryl group (for example, a substituted or unsubstituted carbazole-9-yl group). Another addition condition is that Acp in general formula (1) is bonded to ring B as a six-membered heteroaromatic ring containing three nitrogen atoms as ring skeleton components. The group consisting of the addition conditions described so far is called the addition condition group. One of the additional conditions is that it simultaneously satisfies any two additional conditions selected from the above set of additional conditions. Another of the additional conditions is that it simultaneously satisfies any three additional conditions selected from the above set of additional conditions. Another of the additional conditions is that it simultaneously satisfies any four additional conditions selected from the above set of additional conditions.

[0055] Compound group 2 of the present invention includes a group of compounds in which a of general formula (1) is 2 and Acp is a divalent acceptor group. Compound group 2 is Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ at least one of (preferably Y) ｄ ) is a group of compounds 2a to which an acceptor group is bonded; Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ The two compounds 2b and Y are not all C to which an acceptor group is bonded. ｃ C is bonded to Acp, and Y ａ , Y ｂ , Y ｄ , Y ｅ at least one of (preferably Y) ａ and Yｅ Compound group 2c and Y, where at least one of the C groups is to which an acceptor group is bonded; ｃ C is bonded to Acp, and Y ａ , Y ｂ , Y ｄ , Y ｅ The two compounds 2d and Y are not all C to which an acceptor group is bonded. ａ ~Y ｅ , D １ , D ２ , compound group 2e and Y, in which two groups composed of Ar have the same structure. ａ ~Y ｅ , D １ , D ２ This includes a group of compounds 2f in which two groups composed of Ar have different structures. For each of these groups of compounds 2a to 2f, examples can be given in which the additional conditions described in groups 1a to 1f are also satisfied.

[0056] Compound group 3 of the present invention includes a group of compounds in which a of general formula (1) is 3 and Acp is a trivalent acceptor group. Compound group 3 is Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ at least one of (preferably Y) ｄ ) is a group of compounds 3a to which an acceptor group is bonded; Y ｂ C is bonded to Acp, and Y ａ , Y ｃ , Y ｄ , Y ｅ The group of compounds 3b and Y are all not C to which an acceptor group is bonded. ｃ C is bonded to Acp, and Y ａ , Y ｂ , Y ｄ , Y ｅ at least one of (preferably Y) ａ and Y ｅ Compound group 3c and Y, where at least one of the C groups is to which the acceptor group is bonded; ｃ C is bonded to Acp, and Y ａ , Yｂ , Y ｄ , Y ｅ The group of compounds 3d and Y are all not C to which an acceptor group is bonded. ａ ~Y ｅ , D １ , D ２ , compound group 3e and Y, in which two groups composed of Ar have the same structure. ａ ~Y ｅ , D １ , D ２ This includes a group of compounds 3f in which two groups composed of Ar have different structures. For each of these groups of compounds 3a to 3f, examples can be given in which the additional conditions described in groups 1a to 1f are also satisfied.

[0057] It is preferable that the compound represented by general formula (1) does not contain metal atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, 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 atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound that does not contain hydrogen atoms but contains deuterium atoms.

[0058] In this specification, "substitution candidate group" refers to a set (group) of elements used for the substitution of a hydrogen atom, and may include not only substituents but also deuterium atoms. In this specification, "substitution candidate group A" refers to deuterium atoms, hydroxyl groups, halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), alkyl groups (e.g., 1 to 40 carbon atoms), alkoxy groups (e.g., 1 to 40 carbon atoms), alkylthio groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), aryloxy groups (e.g., 6 to 30 carbon atoms), arylthio groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 atoms in the ring skeleton), heteroaryloxy groups (e.g., 5 to 30 atoms in the ring skeleton), heteroaryl This refers to a group consisting of a group comprising lucio groups (e.g., 5 to 30 atoms in the ring skeleton), acyl groups (e.g., 1 to 40 carbon atoms), alkenyl groups (e.g., 1 to 40 carbon atoms), alkynyl groups (e.g., 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups with 1 to 40 carbon atoms), and nitro groups, and a group consisting of a combination of two or more atoms or substituents selected from this group. In this specification, "Substitution Candidate Group B" means the group consisting of a group consisting of deuterium atoms, alkyl groups (e.g., 1 to 40 carbon atoms), alkoxy groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), aryloxy groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 atoms in the ring skeleton), heteroaryloxy groups (e.g., 5 to 30 atoms in the ring skeleton), and diarylamino groups (e.g., 0 to 20 carbon atoms), and a group consisting of a combination of two or more elements (atoms or groups) selected from this group. In this specification, "Substitution Candidate Group C" means the group consisting of a group consisting of deuterium atoms, alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and diarylamino groups (e.g., 12 to 20 carbon atoms), and a group consisting of a combination of two or more elements (atoms or groups) selected from this group.In this specification, "Substitution Candidate Group D" means the group consisting of a group consisting of deuterium atoms, alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), and heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and a group consisting of a combination of two or more elements (atoms or groups) selected from this group. In this specification, "Substitution Candidate Group E" means the group consisting of a group consisting of deuterium atoms, alkyl groups (e.g., 1 to 20 carbon atoms), and aryl groups (e.g., 6 to 22 carbon atoms), and a group consisting of a combination of two or more elements (atoms or groups) selected from this group. In this specification, when it is stated that a substitution is "substituted or unsubstituted" or "may be substituted," the elements used for substitution may be selected from, for example, Substitution Candidate Group A, Substitution Candidate Group B, Substitution Candidate Group C, Substitution Candidate Group D, or Substitution Candidate Group E.

[0059] The following shows specific examples of compounds represented by general formula (1). First, Table 4 below shows specific examples of compounds represented by general formula (1A) where a is 1 and Acp is a monovalent acceptor group. In the first row of Table 4, the structures of compound 1 (Acp) to compound 7170552 (Acp) are shown together in one row. In this row, the Y of general formula (1) ａ and Y ｄ It is fixed to C-H, Y ｃ and Y ｅ C-Acp has the same structure, D １ , D ２ The combinations of Ar from Q1 to Q7170552 are designated as Compound 1 (Acp) to Compound 7170552 (Acp) in order. That is, Y ａ and Y ｄ C-H and Y ｃ and Y ｅ This is C-Acp, and D １ , D ２ Compound 1 (Acp) is defined as the one in which the Ar combination is Q1, and Y ａ and Y ｄ C-H and Y ｃ and Y ｅThis is C-Acp, and D １ , D ２ The compound in which the Ar combination is Q2 is defined as compound 2 (Acp), and Y ａ and Y ｄ C-H and Y ｃ and Y ｅ This is C-Acp, and D １ , D ２ Compound 3 (Acp) is defined as the compound in which the Ar combination is Q3, and subsequent compounds are identified in the same manner. Compounds are identified in the same manner from the second row onward. The "Acp" in parentheses is replaced with a monovalent acceptor group from I-1 to I-93494. For example, a compound in which Compound 1 (Acp) has a structure in which Acp is I-1 is indicated as Compound 1 (I-1). Similarly, a compound in which Compound 1 (Acp) has a structure in which Acp is I-2 is indicated as Compound 1 (I-2), and a compound in which Compound 1 (Acp) has a structure in which Acp is I-93494 is indicated as Compound 1 (I-93494). In the same manner, compounds in each of Compounds 2 (Acp) through 7170552 (Acp) can be identified as having Acp from I-1 to I-93494. In this manner, Table 4 discloses compounds 1 (I-1) to 372868704 (I-93494) as specific examples. These compounds are disclosed individually in this specification. General formula (1A)

[0060] Table 5 below shows specific examples of compounds represented by general formula (1), where a is 2 and Acp is a divalent acceptor group, as an example of a compound represented by general formula (1B). The first row of Table 5 shows the structures of compounds 372868705 to 380039256 together in one row. In this row, Acp of general formula (1B) is fixed to II-1, and Y ａ and Y ｄ and Y ｅ It is fixed to C-H, D １ , D ２ The combinations of Ar, Q1 to Q7170552, are designated as compounds 372868705 to 380039256 in order. That is, Acp is II-1, and Y ａand Y ｄ and Y ｅ C-H and D １ , D ２ The compound 372868705 is one in which the Ar combination is Q1, and Acp is II-1, Y ａ and Y ｄ and Y ｅ C-H and D １ , D ２ Compounds are identified in the same manner as compound 372868706 when the Ar combination is Q2. Compounds are identified in the same manner from the second row onward. In Table 5, "C-Acp" indicates a structure in which a perdeuterated diphenyltriazinyl group is bonded to a carbon atom. One of the perdeuterated phenyl groups of this perdeuterated diphenyltriazinyl group can be substituted with various substituents, such as a perdeuterated carbazole-9-yl group. General formula (1B)

[0061] Table 6 below shows specific examples of compounds represented by general formula (1), where a is 2 and Acp is a divalent acceptor group, as an example of a compound represented by general formula (1B'). Each compound in Table 6 is identified in the same manner as in Table 5. General formula (1B')

[0062] Table 7 below shows specific examples of compounds represented by general formula (1), where a is 3 and Acp is a trivalent acceptor group, as an example of a compound represented by general formula (1C). Each compound in Table 7 is identified in the same manner as in Table 5. General formula (1C)

[0063] Table 8 below shows specific examples of compounds represented by general formula (1), where a is 3 and Acp is a trivalent acceptor group, as an example of a compound represented by general formula (1C'). Each compound in Table 8 is identified in the same manner as in Table 5. General formula (1C')

[0064] Compounds obtained by substituting all hydrogen atoms in each of the compounds specified in Tables 4 to 8 with deuterium atoms are disclosed here as Compound 1(I-1)(D) to Compound 6912412128(D), in that order.

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

[0066] The compounds identified in Tables 3-8 all have the general formula (1) Ar and ring B as D １ and D ２ It has a structure that is bonded only through D in general formula (1). ３ ~D ５ It has a structure in which there is no D. In the following, Ar and ring B of general formula (1) are D １ and D ２ In addition to being connected via D ３ Let's explain the structure in which they are bonded via D. Ar and ring B are further bonded via D ３ When Ar and D are connected via １ ~D ３ This forms a triple-bridged structure. At this time, D ２ and D ３ Y constitutes ring B. ａ ~Y ｅ It may be bonded to any of the carbon atoms (C) represented by. In some embodiments of the present invention, D ２ is Y ａ It combines with C, which represents D ３ is Y ｂ It is bonded to C, which is represented by D. In some embodiments of the present invention, D ２ is Y ａIt combines with C, which represents D ３ is Y ｃ It is bonded to C, which is represented by D. In some embodiments of the present invention, D ２ is Y ａ It combines with C, which represents D ３ is Y ｄ It is bonded to C, which is represented by D. In some embodiments of the present invention, D ２ is Y ｂ It combines with C, which represents D ３ is Y ｃ It is bonded to C, which is represented by D. In some embodiments of the present invention, D ２ is Y ｂ It combines with C, which represents D ３ is Y ｄ It is bonded with C, which is represented by the general formula (1) Y ａ ~Y ｅ One of them represents the carbon that bonds with Acp. D is the carbon atom at position 1 when the carbon to which Acp is bonded is considered to be the carbon atom at position 1. １ ~D ３ The bonding positions may be positions 2, 3, and 4, positions 2, 3, and 5, positions 2, 3, and 6, positions 2, 4, and 6, positions 3, 4, and 5, or positions 3, 4, and 6. Preferred positions are positions 2, 3, and 4, positions 2, 4, and 6, and positions 3, 4, and 5, with the most preferred being positions 2, 4, and 6. In some embodiments of the present invention, Y ｃ Acp is. In some preferred embodiments of the present invention, Y ｃ Acp is D ２ Y ｂ It combines with C, which represents D ３ is Y ｄ It bonds with C represented by . Between Ar and ring B, D １ ~D ３ When a triple cross-linked structure is formed by D １ ~D ３ All of them may have the same structure, two may be identical and one different, or all three may be different from each other. Also, ring B has D １ ~D ３D may be bonded by nitrogen atoms or by carbon atoms. In some preferred embodiments of the present invention, １ ~D ３ In all of these, they are bonded by nitrogen atoms. In some embodiments of the present invention, D １ ~D ３ Of these, only two are bonded by nitrogen atoms, and the rest are bonded by carbon atoms. In some embodiments of the present invention, D １ ~D ３ Only one of them is bonded by a nitrogen atom, while the rest are bonded by carbon atoms.

[0067] In the following, D is between Ar and ring B. １ ~D ３ Specific examples of compounds in which a triple crosslinking structure is formed are shown below.

[0068] Next, between Ar and ring B, D １ ~D ３ The table below shows specific examples of compounds in which a triple crosslinked structure is formed. Here, we show specific examples of compounds having a structure represented by the following general formula (1D). General formula (1D)

[0069] In compounds where a triple crosslinking structure is formed, Ar is a trivalent aromatic ring. Ar is D １ ~D ３ It bonds with. Specific examples of structures that can be used as Ar in compounds where a triple crosslink structure is formed are shown below. These Ars are not limited to the structure represented by general formula (1D), but also include D between Ar and ring B. １ ~D ３ This can be widely used in structures in which a triple crosslinked structure is formed. Furthermore, the trivalent aromatic ring Ar that can be used in this invention is not interpreted restrictively by the following specific examples. In the following specific examples, * indicates a bonding site. The methyl group is CH ３ The display has been omitted.

[0070] Ar244 to Ar259 are disclosed as Ar244 to Ar259, in which all hydrogen atoms present in Ar227 to Ar242 are replaced with deuterium atoms.

[0071] In Table 9 below, D １ ~D ３ Here are some specific examples of combinations of the linking group represented by and the linking group represented by Ar. １ and D ２ and D ３ Specific examples of cases where are the same are shown as P1 to P24618. Each row in Table 9 displays 24618 combinations in one row. For example, the first row of Table 9 is D １ ~D ３ The combinations of which have the same structure and are all D1n to D746n, and Ar being Ar227 to Ar259, are grouped together as P1 to P24618. Here, first Ar is fixed to Ar227, D １ ~D ３ The combinations of D1n to D746n are designated as P1 to P746 in order, and then Ar is fixed to Ar228, D １ ~D ３ The combinations of D1n to D746n are designated as P747 to P1492 in order, and Ar is fixed to Ar229, D １ ~D ３ P1 to P24618 are identified by assigning combinations of D1n to D746n in order to P1493 to P2238. In the section of Table 9 from P24619 to P49236, D １ It is fixed to D1c, D ２ and D ３ The combinations where D1n to D746n and Ar is Ar227 to Ar259 are shown together as P24619 to P49236. Similarly in this section, first Ar is fixed to Ar227, D ２ and D ３ The combinations of D1n to D746n are designated as P24619 to P25364 in order, and then Ar is fixed to Ar228, D ２ P24619 to P49236 are identified by assigning combinations of D1n to D746n sequentially to P25365 to P26110. The combinations in subsequent rows are shown in the same manner.

[0072] Table 10 below shows specific examples of compounds represented by general formula (1D). The first row of Table 10 shows the structures of compounds 6159504168 (Acp) to 6160808921 (Acp) together in one row. In this row, the Y of general formula (1D) ａ It is fixed to C-H, Y ｃ and Y ｅ C-Acp has the same structure, D １ , D ２ , D ３ The combinations of Ar from P1 to P1304754 are designated as compounds 6159504168 (Acp) to 6160808921 (Acp), respectively. That is, Y ａ C-H and Y ｃ and Y ｅ This is C-Acp, and D １ , D ２ , D ３ The compound in which the Ar combination is P1 is designated as compound 6159504168 (Acp), and Y ａ C-H and Y ｃ and Y ｅｄ This is C-Acp, and D １ , D ２ , D ３ The compound in which the Ar combination is P2 is designated as compound 6159504169 (Acp), and Y ａ C-H and Y ｃ and Y ｅ This is C-Acp, and D １ , D ２ , D ３Compound 6159504170 (Acp) is defined as compound 6159504170 (Acp) when the Ar combination is Q3, and subsequent compounds are identified in the same manner. Compounds are identified in the same manner from the second row onward. The "Acp" in parentheses is replaced with a monovalent acceptor group from I-1 to I-93494. For example, a compound 6159504168 (Acp) having a structure in which Acp is I-1 is denoted as compound 6159504168 (I-1). Similarly, a compound 6159504168 (Acp) having a structure in which Acp is I-2 is denoted as compound 6159504168 (I-2), and a compound 6159504168 (Acp) having a structure in which Acp is I-93494 is denoted as compound 6159504168 (I-93494). In the same manner, compounds with Acp values ​​from I-1 to I-93494 can be identified for each of compounds 6159504169 (Acp) to 6177770723 (Acp). In this way, Table 10 discloses each of the compounds from 6159504168 (I-1) to 6177770723 (I-93494) as specific examples. These compounds are disclosed individually in this specification.

[0073] The structure represented by general formula (1) also includes embodiments in which a quadruple crosslink structure or a quintuple crosslink structure is formed between Ar and ring B. When a quadruple crosslink structure is formed between Ar and ring B, Y ａ ~Y ｅ A bridge structure may be formed between any three of these carbon atoms (C). ａ ~Y ｅ One of these represents the carbon atom bonded to Acp. When the carbon atom to which Acp is bonded is considered to be the carbon atom at position 1, the carbon atoms at positions 2, 3, 4, and 6 may be used to form the cross-linking structure, or the carbon atoms at positions 2, 3, 5, and 6 may be used to form the cross-linking structure. In some embodiments of the present invention, Y ｂ This represents C that is bonded with Acp, and Y ａ and Y ｃ and Y ｄ Y is used to form a cross-linked structure. In some embodiments of the present invention, Y ｃrepresents C that binds to Acp, and Y ｂ and Y ｄ and Y ｅ is used for the formation of a crosslinked structure. When a quadruple crosslinked structure is formed by a donor group (D １ to D ４ ), all of the donor groups may have the same structure, or only one may be different, or all four may be different from each other. Also, the donor group may be bonded to the ring B by a nitrogen atom or a carbon atom. In some preferred embodiments of the present invention, all four donor groups are bonded by nitrogen atoms. In some embodiments of the present invention, some of the donor groups are bonded by nitrogen atoms and some are bonded by carbon atoms. In some embodiments of the present invention, all four donor groups are bonded by carbon atoms. Hereinafter, specific examples of compounds in which a quadruple crosslinked structure is formed are shown.

[0074] When a quintuple crosslinked structure is formed between the Ar ring B, the donor group (D １ to D ５ ) may all have the same structure, or only one may be different, or all five may be different from each other. Also, the donor group may be bonded to the ring B by a nitrogen atom or a carbon atom. In some preferred embodiments of the present invention, all five donor groups are bonded by nitrogen atoms. In some embodiments of the present invention, some of the donor groups are bonded by nitrogen atoms and some are bonded by carbon atoms. In some embodiments of the present invention, all five donor groups are bonded by carbon atoms. Hereinafter, specific examples of compounds in which a quintuple crosslinked structure is formed are shown.

[0075] The compound represented by the general formula (1) also includes those having a structure in which two sets of double crosslinked structures are formed using the carbon atoms (C) represented by three of Y ａ to Y ｅ . In some embodiments of the present invention, D ２ is Y ａA double crosslink structure is formed by bonding to the carbon atom (C) represented by Y, and furthermore, ｃ C and Y represented by ｄ Another double crosslink structure may be formed by the C represented by . Specific examples of compounds having such a structure are shown below.

[0076] Another example of a structure in which two sets of double-bridged structures are formed is D ２ Y ｂ A double crosslink structure is formed by bonding to the carbon atom (C) represented by Y, and furthermore, ｃ C and Y represented by ｅ In some embodiments, C represents a different double bridge structure, or D ２ Y ａ A double crosslink structure is formed by bonding to the carbon atom (C) represented by Y, and furthermore, ｃ C and Y represented by ｅ Another embodiment is also described in which a different double-bridged structure is formed by C represented by .

[0077] Compounds represented by general formula (1) include Y ａ ~Y ｅ This also includes structures in which a double-bridged structure and a triple-bridged structure are formed using four of the carbon atoms (C) represented by D ２ Y ａ A double crosslink structure is formed by bonding to the carbon atom (C) represented by Y, and furthermore, ｃ C and Y represented by ｄ C and Y represented by ｅA triple crosslinked structure is formed by the C represented by . In structures where two sets of double crosslinked structures are formed, or in structures where a double crosslinked structure and a triple crosslinked structure are formed, all donor groups constituting the crosslinked structure may have the same structure, one may be different, or all may be different from each other. Furthermore, the donor groups may be bonded to ring B by nitrogen atoms or by carbon atoms. In some preferred embodiments of the present invention, all donor groups are bonded by nitrogen atoms. In some embodiments of the present invention, some of the donor groups are bonded by nitrogen atoms and some are bonded by carbon atoms. In some embodiments of the present invention, all donor groups are bonded by carbon atoms.

[0078] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when intended to be used as a film formed by vapor deposition on an organic layer containing the compound represented by general formula (1). The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). The compound represented by general formula (1) may be formed as a film by coating regardless of its molecular weight. Using the coating method makes it possible to form films even of compounds with relatively large molecular weights. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. For this reason, the compound represented by general formula (1) is easy to apply the coating method to and is easy to purify to increase its purity.

[0079] Compounds represented by general formula (1) are useful as light-emitting materials. Therefore, organic light-emitting devices can be manufactured using compounds represented by general formula (1). Organic light-emitting devices using compounds represented by general formula (1) have high luminous efficiency and excellent device durability. Furthermore, compounds represented by general formula (1) can be effectively used in organic light-emitting devices.

[0080] Applying the present invention, it is conceivable to use compounds containing multiple structures represented by general formula (1) within the molecule as luminescent materials. For example, polymerizable groups may be pre-existing in the structure represented by general formula (1), and polymerized to obtain polymers obtained by polymerizing these polymerizable groups may be used as luminescent materials. For example, a monomer containing a polymerizable functional group at any part of general formula (1) may be prepared, and this may be polymerized alone or copolymerized with other monomers to obtain polymers having repeating units, which may then be used as luminescent materials. Alternatively, dimers or trimers may be obtained by coupling compounds having the structure represented by general formula (1), and these may be used as luminescent materials.

[0081] Examples of polymers having repeating units that include a structure represented by general formula (1) include polymers that include a structure represented by either of the following two general formulas.

[0082] In the general formula above, Q represents a group containing the structure represented by general formula (1), and L １ and L ２ The symbol represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ It is preferable that the structure is represented by -. Here, X １１ L represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ R represents a linking group, which is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms. In the above general formula, R １０１ , R １０２ , R １０３ and R １０４Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. Preferably, these are a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom; more preferably, these are an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, these are an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms. １ and L ２ The linking group represented by can bond to any part of the general formula (1) that constitutes Q. Two or more linking groups may be linked to a single Q to form a cross-linked structure or a network structure.

[0083] As a concrete example of a repeating unit structure, we can cite the structure represented by the following formula.

[0084] Polymers having repeating units including these formulas can be synthesized by introducing a hydroxyl group to any of the sites in general formula (1), reacting it with the following compounds as a linker to introduce polymerizable groups, and then polymerizing those polymerizable groups.

[0085] A polymer containing a structure represented by general formula (1) within its molecule may consist only of repeating units having the structure represented by general formula (1), or it may contain 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 two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers commonly used in copolymerization. For example, repeating units derived from monomers having ethylenically unsaturated bonds, such as ethylene and styrene, can be cited.

[0086] In one embodiment, the compound represented by general formula (1) is a light-emitting material. Among the compounds represented by general formula (1), there are compounds with a long luminescence lifetime. Among the compounds represented by general formula (1), there are compounds with high orientation. When used in organic light-emitting devices, the compounds represented by general formula (1) can improve the luminescence characteristics. For example, among the compounds represented by general formula (1), there are compounds that can extend the device lifetime when used in organic light-emitting devices. In one embodiment, the compound represented by general formula (1) is a compound that can emit delayed fluorescence. Among the compounds represented by general formula (1), there are compounds with a large proportion of delayed fluorescence components. For example, there are compounds in which 80% or more of the total emission is the delayed fluorescence component, and for example, 90% or more of the total emission is the delayed fluorescence component. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the UV region, the blue, green, yellow, orange, or red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the red or orange regions of the visible spectrum (e.g., about 620 nm to about 780 nm, or about 650 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the orange or yellow regions of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, or about 570 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may 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 this disclosure, a compound represented by general formula (1) may 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 some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the ultraviolet spectral region (e.g., 280 to 400 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means.

[0087] The electronic properties of a small molecule chemical library can be calculated using known ab initio quantum chemical calculations. For example, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be analyzed using time-dependent density functional theory with 6-31G*, Becke's three parameters, and a set of functions known as the Lee-Yang-Parr hybrid functional as a basis, to screen molecular fragments (parts) having HOMO above a certain threshold and LUMO below a certain threshold. This allows for the selection of donor parts ("D") when the HOMO energy (e.g., ionization potential) is above -6.5 eV, for example. Alternatively, when the LUMO energy (e.g., electron affinity) is below -0.5 eV, for example, acceptor parts ("A") can be selected. The bridge portion ("B") is a strongly conjugated system that can strictly restrict the receptor and donor portions to specific stereochemistrys, for example, thereby preventing duplication between the π-conjugated systems of the donor and receptor portions. In one embodiment, the compound library is selected using one or more of the following characteristics: 1. Emission near a specific wavelength; 2. A calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ Value 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In one embodiment, the difference (ΔE) between the lowest singlet excited state and the lowest triplet excited state at 77K 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 one embodiment, ΔE ＳＴThe values ​​are 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 some embodiments, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example, 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 higher.

[0088] [Synthesis Method of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) include novel compounds. Compounds represented by general formula (1) can be synthesized by combining known reactions. For example, compounds represented by general formula (1) can be synthesized using known coupling reactions. Compounds represented by general formula (1) can also be synthesized using known ring-closing reactions. Furthermore, compounds represented by general formula (1) can be synthesized using known substitution reactions. For details of reaction conditions, please refer to the synthesis examples described later.

[0089] [Constructions using compounds represented by general formula (1)] In one embodiment, a compound represented by general formula (1) is used together with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) to form a solid film or layer. These one or more materials are materials that combine with the compound represented by general formula (1), disperse the compound, covalently bond with the compound, coat the compound, support the compound, or associate with the compound. For example, a film can be formed by combining the compound represented by general formula (1) with an electroactive material. In some cases, the compound represented by general formula (1) may be combined with a hole transport polymer. In some cases, the compound represented by general formula (1) may be combined with an electron transport polymer. In some cases, the compound represented by general formula (1) may be combined with both a hole transport polymer and an electron transport polymer. In some cases, the compound represented by general formula (1) may be combined with a copolymer having both a hole transport portion and an electron transport portion. Through these embodiments, electrons and / or holes formed in the solid film or layer can be made to interact with the compound represented by general formula (1).

[0090] [Film Formation] In one embodiment, a film containing the compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing the composition with the compound represented by general formula (1) is applied to a surface, and the film is formed after the solvent is removed. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition with the compound represented by general formula (1) is selected and used. In one embodiment, substituents (e.g., alkyl groups) that increase the solubility in organic solvents can be introduced into the compound contained in the composition. In one embodiment, a film containing the compound represented by general formula (1) can be formed by a dry process. In one embodiment, but is not limited to, vacuum deposition can be used as the dry process. When vacuum deposition is used, the compounds constituting the film may be co-deposited from individual deposition sources, or they may be co-deposited from a single deposition source containing a mixture of compounds. When using a single deposition source, a mixed powder of compound powders may be used, a compressed molded body made by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In one embodiment, by performing co-deposition under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, a film with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. By mixing multiple compounds in the same composition ratio as the composition ratio of the formed film to create a deposition source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound has the same weight loss rate can be identified, and that temperature can be adopted as the temperature during co-deposition.

[0091] [Organic Light-Emitting Devices] By using a compound represented by general formula (1), high-performance organic light-emitting devices can be fabricated. In one embodiment of the present invention, an organic electroluminescent device can be fabricated using a compound represented by general formula (1). In one embodiment of the present invention, a CMOS (complementary metal-oxide-semiconductor) can be fabricated using a compound represented by general formula (1). In one embodiment of the present invention, a solid-state image sensor (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). The compound represented by general formula (1) is useful as a material for organic light-emitting devices. It is particularly preferably used in organic light-emitting diodes. Organic Light-Emitting Diodes: Several embodiments of the present invention relate to the use of a compound represented by general formula (1) as a light-emitting material for organic light-emitting devices. In one embodiment, the compound represented by general formula (1) can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In one embodiment, the compound represented by general formula (1) includes a delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the compound represented by general formula (1) is applied to phosphorescence-sensitized fluorescence. In one embodiment, the present invention provides a delayed phosphor having a structure represented by general formula (1). In another embodiment, the present invention relates to the use of a compound represented by general formula (1) as a delayed phosphor. In another embodiment, the present invention can use a compound represented by general formula (1) as a host material and can be used together with one or more light-emitting materials, the light-emitting materials may be fluorescent materials, phosphorescent materials or TADF materials (delayed fluorescence materials). In another embodiment, the compound represented by general formula (1) can also be used as a hole transport material. In another embodiment, the compound represented by general formula (1) can be used as an electron transport material. In yet another embodiment, the present invention relates to a method for generating delayed fluorescence from a compound represented by general formula (1). In yet another embodiment, an organic light-emitting element containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In yet another embodiment, the light-emitting layer contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate.In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the direction of light propagation emitted by the aligned compound. In some embodiments, the light extraction efficiency from the light-emitting layer is improved by aligning the direction of light propagation emitted by the compound represented by general formula (1). Some embodiments of the present invention relate to organic light-emitting devices. In some embodiments, the organic light-emitting device includes a light-emitting layer. In some embodiments, the light-emitting layer includes a compound represented by general formula (1) as a light-emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescent device (organic PL device). In some embodiments, the organic light-emitting device is an organic electroluminescent 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). The other light-emitting materials may be fluorescent materials or phosphorescent materials. In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level and is located 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 other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least a light-emitting layer. In one embodiment, the organic layer includes only a light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include hole transport layers, hole injection layers, electron barrier layers, hole barrier layers, electron injection layers, electron transport layers, and exciton barrier layers. In one embodiment, 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.

[0092] Emitting layer: In some embodiments, the emissive 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 emissive material is used as the emissive layer. In some embodiments, the emissive layer includes an emissive material and a host material. In some embodiments, the emissive material is one or more compounds represented by general formula (1). In some embodiments, singlet and triplet excitons generated in the emissive material are confined within the emissive material to improve the light emission efficiency of organic electroluminescent elements and organic photoluminescent elements. In some embodiments, a host material is used in addition to the emissive material in the emissive layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excitation singlet energy and excitation triplet energy, at least one of which is higher than those of the emissive material of the present invention. In some embodiments, singlet and triplet excitons generated in the emissive material of the present invention are confined within the molecules of the emissive 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, even though high photoluminescence efficiency can still be obtained; that is, any host material capable of achieving high photoluminescence efficiency can be used in the present invention without particular limitation. In some embodiments, photoluminescence occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the synchrotron radiation includes both fluorescence and delayed fluorescence. In some embodiments, the synchrotron radiation includes synchrotron radiation from the host material. In some embodiments, the synchrotron radiation consists of synchrotron radiation from the host material. In some embodiments, the synchrotron radiation includes synchrotron radiation from a compound represented by general formula (1) and synchrotron radiation from the host material. In some embodiments, a TADF material and a host material are used. In some embodiments, the TADF material is an assist dopant with a lower excitation singlet energy than the host material in the light-emitting layer and a higher excitation 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 includes the host material.In one embodiment, a layer containing a compound represented by general formula (1) and a host material also contains a light-emitting material, where the lowest singlet excitation energy of the compound represented by general formula (1) is lower than that of the host material and higher than that of the light-emitting material. In this embodiment, when the organic electroluminescent element is energized, the amount of light emitted from the light-emitting material is maximized. In this embodiment, the layer may further contain a delayed fluorescence material. The lowest singlet excitation energy of this delayed fluorescence material may be lower than that of the compound represented by general formula (1) and higher than that of the light-emitting material, or lower than that of the light-emitting material. In another embodiment, the organic electroluminescent element has a layer containing a 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 this embodiment, when the organic electroluminescent element is energized, the amount of light emitted from the light-emitting material having a structure outside the range of general formula (1) is maximized. Also in this embodiment, the amount of light emitted from the light-emitting material having a structure outside the range of general formula (1) is greater than the amount of light emitted from the compound of general formula (1).

[0093] 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). 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, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluorantene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, duroridine derivatives, thiazole derivatives, and derivatives having metals (Al, Zn). These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons may be combined with each other. Below, examples of luminescent materials that can be used in combination with an assist dopant having the structure represented by general formula (1) are given.

[0094]

[0095] Also, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be adopted as a luminescent material used together with an assist dopant having a structure represented by the general formula (1).

[0096] Further, as the luminescent material, a compound represented by the following general formula (F1) can also be mentioned. General formula (F1)

[0097] In the general formula (F1), R １ , R ３ to R １６ each independently represent a hydrogen atom, a deuterium atom or a substituent. R 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. R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. X １ represents O or NR, and R represents a substituent. Among X ２ to X ４ , X ３ and X ４At least one of the atoms is O or NR, and the other may be O or NR, but may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. C-R in general formula (F1) 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 It may be replaced with N.

[0098] In some embodiments of the present invention, X ２ When R is O or NR, ７ Is R an acceptor group? ６ and R ７ Either they are bonded to each other to form an acceptor group, or R ７ and R ８ These are bonded to each other to form an acceptor group. In some embodiments of the present invention, X ３ When R is O or NR, １０ Is R an acceptor group? ９ and R １０ Either they are bonded to each other to form an acceptor group, or R １０ and R １１ These are bonded to each other to form an acceptor group. In some embodiments of the present invention, X ４ When R is O or NR, １５ Is R an acceptor group? １４ and R １５ Either they are bonded to each other to form an acceptor group, or R １５ and R １６ These are bonded to each other to form an acceptor group. In some embodiments of the present invention, X ２ NR is NR, and R is a substituted or unsubstituted phenyl group.８ When a carbazole ring is formed by direct bonding with a carbon atom to which it is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In some embodiments of the present invention, X ３ NR is NR, and R is a substituted or unsubstituted phenyl group. ９ When a carbazole ring is formed by direct bonding with a carbon atom to which it is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In some embodiments of the present invention, X ４ NR is NR, and R is a substituted or unsubstituted phenyl group. １６ When a carbazole ring is formed by direct bonding with a carbon atom to which it is bonded, at least one of the 3-position and 6-position of the carbazole ring is substituted with an acceptor group. In some embodiments of the present invention, X １ NR is NR, and R is a substituted or unsubstituted phenyl group. １ When a carbazole ring is formed by direct bonding with a carbon atom to which the phenyl group is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is located on the phenyl group). In some embodiments of the present invention, the compound is represented by the following general formula (F2). General formula (F2)

[0099] In the general formula (F2), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ Either they are bonded to each other to form an acceptor group, or R ２ and R ３ These groups are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R１０ , R １０ and R １１ , R １４ and R １５ , R １５ and R １６ They may be joined to each other to form a ring structure. １ X represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of the atoms is O or NR, and the other may be O or NR but not linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. Ar １ and Ar ２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. C-R in general formula (F2) 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 It may be replaced with N.

[0100] Furthermore, compounds represented by the following general formula (F3) can also be cited as luminescent materials. General formula (F3)

[0101] In the general formula (F3), 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 Each of these 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 , R６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ They may be bonded to each other to form a ring structure. C-R in general formula (F3) 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 This may be replaced with N.

[0102] In some embodiments of the present invention, R １ and R ２ R is a substituted or unsubstituted phenyl group, each independently of which other rings may be fused to it. In some embodiments of the present invention, R ３ and R １０ Each of these is independently a substituted amino group. In some embodiments of the present invention, R １ and R ３ , and, R ２ and R １０ At least one combination of these elements is bonded to each other to form a cyclic structure. In some embodiments of the present invention, the cyclic structure includes a benzoazavorin ring.

[0103] Furthermore, compounds represented by the following general formula (F4) can also be cited as luminescent materials. General formula (F4)

[0104] In the general formula (F4), Z １ and Z ２ Each of these independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R １ ~R ９ Each of these 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 They may be bonded to each other to form a ring structure. However, Z １ Z ２ , R １ and R ２ A ring formed by the bonding of these elements, R ２ and R ３ A ring formed by the bonding of these elements, R ４ and R ５ A ring formed by the bonding of these elements, and R ５ and R ６ At least one of the rings formed by the bonding of these elements 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, and R １ ~R ９ At least one of them is a substituted or unsubstituted aryl group, or an acceptor group, or Z １ and Z ２ At least one of the rings has an aryl group or an acceptor group as a substituent. Substitutable carbon atoms among the benzene ring skeleton constituent carbon atoms of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with nitrogen atoms. C-R in general formula (F4)１ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ It may be replaced with N.

[0105] In some embodiments of the present invention, Z １ and Z ２ However, each is independently a substituted or unsubstituted uncondensed benzene ring, a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. In some embodiments of the present invention, R １ ~R ９ However, each is independently a substituted or unsubstituted aryl group, or an acceptor group, or R １ and R ２ A ring formed by the bonding of these elements, R ２ and R ３ A ring formed by the bonding of these elements, R ４ and R ５ A ring formed by the bonding of these elements, and R ５ and R ６ One or more rings selected from the group consisting of rings formed by the bonding of to each other are a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or a pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings. In some embodiments of the present invention, R ８ The group is a substituted or unsubstituted aryl group, or an acceptor group. In some embodiments of the present invention, the group comprises two or more rings selected from the group consisting of a benzofuran ring, the benzothiophene ring, and the indole ring.

[0106] Furthermore, as a luminescent material, we can list compounds having a fused ring structure A (where hydrogen atoms in the structure may be substituted with deuterium atoms or substituents) in which 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 is fused to the carbon-carbon bond a of structure α below, or 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 is fused to the carbon-carbon bond b. Structure α

[0107] In structure α, X １ and X ２ Each independently represents a substituted or unsubstituted aryl group, or a nitrogen atom or oxygen atom to which a substituted or unsubstituted aryl group is bonded, Z represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R １ represents a hydrogen atom, a deuterium atom, or a substituent, and Z and X ２ They may be bonded to each other to form a ring structure. In the fused ring structure A, the structure condensed with b and X １ , a condensed structure with b and Z, Z and X ２ They may be joined together to form a ring structure.

[0108] Furthermore, compounds represented by the following general formula (F5) can also be cited as luminescent materials. General formula (F5)

[0109] In the general formula (F5), Z １ Z represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings. ２ and Z ３ Each of these independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R １R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ３ Z ３ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0110] Furthermore, compounds represented by the following general formula (F6) can also be cited as luminescent materials. General formula (F6)

[0111] In the general formula (F6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ Each of these independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R １ and R ４ ~R ７ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z３ Z ３ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0112] Furthermore, compounds represented by the following general formula (F7) can also be cited as luminescent materials. General formula (F7)

[0113] In the general formula (F7), X ４ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ Each of these independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R １ and R ４ａ ~R ７ａ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ３ Z ３ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0114] Furthermore, compounds represented by the following general formula (F8) can also be cited as luminescent materials. General formula (F8)

[0115] In the general formula (F8), Z １represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z ３ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １ and R ８ ~R １４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ３ Z 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 They may be joined together to form a ring structure.

[0116] Furthermore, compounds represented by the following general formula (F9) can also be cited as luminescent materials. General formula (F9)

[0117] In the general formula (F9), Z １ and Z ４ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ３ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １ and R １５ ~R １７ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ３Z 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 They may be joined together to form a ring structure.

[0118] Furthermore, compounds represented by the following general formula (F10) can also be cited as luminescent materials. General formula (F10)

[0119] In the general formula (F10), Z １ and Z ５ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ３ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ３ Z ３ and R ３ At least one pair of these elements are joined together to form a ring structure.

[0120] Furthermore, compounds represented by the following general formula (F11) can also be cited as luminescent materials. General formula (F11)

[0121] In the general formula (F11), Z １ represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z ２ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １ and R ２１ ~R ２７ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ２ R 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 They may be joined together to form a ring structure.

[0122] Furthermore, compounds represented by the following general formula (F12) can also be cited as luminescent materials. General formula (F12)

[0123] In the general formula (F12), Z １ and Z ６ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ２ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring.１ and R ２８ ~R ３０ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ２ R 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 ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ They may be joined together to form a ring structure.

[0124] Furthermore, compounds represented by the following general formula (F13) can also be cited as luminescent materials. General formula (F13)

[0125] In the general formula (F13), Z １ and Z ７ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, Z ２ R represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring. １ R represents a hydrogen atom, a deuterium atom, or a substituent. ２ and R ３ Each of these 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 They may be bonded to each other to form a ring structure. However, R ２ and Z ２ Z ２ and Z ７ Z ７ and R ３At least one pair of these elements are joined together to form a ring structure.

[0126] Furthermore, compounds represented by the following general formula (F14) can also be cited as luminescent materials. General formula (F14)

[0127] In the general formula (F14), Z １ R represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring. １ and R ３１ ~R ４４ Each of these 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 They may be joined together to form a ring structure.

[0128] Furthermore, compounds represented by the following general formula (F15) can also be cited as luminescent materials. General formula (F15)

[0129] In the general formula (F15), Z １ and Z ８Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ５１ ~R ６０ Each of these 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 They may be joined together to form a ring structure.

[0130] Furthermore, compounds represented by the following general formula (F16) can also be cited as luminescent materials. General formula (F16)

[0131] In the general formula (F16), Z １ Z ８ and Z ９ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ６１ ~R ６６ Each of these 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 R６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８ They may be joined together to form a ring structure.

[0132] Furthermore, compounds represented by the following general formula (F17) can also be cited as luminescent materials. General formula (F17)

[0133] In the general formula (F17), Z １ Z ９ and Z １０ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ６７ ~R ６９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ７０ R 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 They may be joined together to form a ring structure.

[0134] Furthermore, compounds represented by the following general formula (F18) can also be cited as luminescent materials. General formula (F18)

[0135] (In the general formula (F18), Z １ Z １１ and Z １２ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R１ and R ７２ ~R ７４ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, R ７１ R represents 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 They may be joined together to form a ring structure.

[0136] Furthermore, compounds represented by the following general formula (F19) can also be cited as luminescent materials. General formula (F19)

[0137] In the general formula (F19), Z １ and Z １１ Each of these independently represents a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, R １ and R ７６ ~R ８２ Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R ７５ R 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 ８２They may be joined together to form a ring structure.

[0138] Furthermore, compounds represented by the following general formula (F20) can also be cited as luminescent materials. General formula (F20)

[0139] In the general formula (F20), X ５ R 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. １０１ ~R １３０ Each of these 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 R１２５ , R １２５ and R １２６ , R １２６ and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R １３０ and R １０１ They may be joined together to form a ring structure.

[0140] Furthermore, compounds represented by the following general formula (F21) can also be cited as luminescent materials. General formula (F21)

[0141] In the general formula (F21), 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 of these independently represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted heteroaromatic ring, R ３ ~R ９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. However, R １ , R ２ Z １ and Z ２ At least one of these includes 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 R９ , R ９ and R １ These may be bonded to each other to form a cyclic structure. Among the benzene ring skeleton constituent carbon atoms that make up the benzofuran ring, the benzothiophene ring, and the indole ring, the replaceable carbon atoms may be substituted with nitrogen atoms. C-R in general formula (F21) ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ It may be replaced with N.

[0142] In some embodiments of the present invention, R １ and R ２ However, each independently comprises a ring structure selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. In some embodiments of the present invention, Z １ and Z ２ However, each is independently a substituted or unsubstituted uncondensed benzene ring, a furan ring formed by the condensation of a substituted or unsubstituted benzene ring, a thiophene ring formed by the condensation of a substituted or unsubstituted benzene ring, a pyrrole ring formed by the condensation of a substituted or unsubstituted benzene ring, a benzene ring formed by the condensation of a substituted or unsubstituted benzofuran ring, a benzene ring formed by the condensation of a substituted or unsubstituted benzothiophene ring, or a benzene ring formed by the condensation of a substituted or unsubstituted indole ring. In some embodiments of the present invention, R １ and Z １ These are bonded together to form a ring structure. In some embodiments of the present invention, R １ and Z １ These elements are bonded to each other, forming a pyrrole ring.

[0143] Furthermore, compounds represented by the following general formula (F22) can also be cited as luminescent materials. General formula (F22)

[0144] In the general formula (F22), X１ and X ２ In this case, one atom is a nitrogen atom, and the other is a boron atom. １ ~R ２６ A １ A ２ Each of these 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 They may be joined to each other to form a ring structure. However, X １ When R is a nitrogen atom, １７ and R １８ They bond to each other to form a single bond and create a pyrrole ring, X ２ When R is a nitrogen atom, ２１and R ２２ They bond to each other to form a single bond and create a pyrrole ring. However, X １ is a nitrogen atom, R ７ and R ８ and R ２１ and R ２２ The nitrogen atoms bond to form a six-membered ring, R １７ and R １８ When R is bonded to each other to form a single bond, １ ~R ６ At least one of them is a substituted or unsubstituted aryl group, or R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ One of these is bonded to another to form an aromatic hydrocarbon ring or a heteroaromatic ring. For a detailed description, preferred range and specific examples of the compound represented by general formula (F22), refer to

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification.

[0145] Furthermore, compounds represented by the following general formula (F23) can also be cited as luminescent materials. General formula (F23)

[0146] In the general formula (F23), R １ ~R ２２ Each of these 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, R and R ８ , R ８ and R ９ , R ９ and R１０ , R １０ and R １１ , R １２ and R １３ , 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, R and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ These may be joined together to form a ring structure. １ and X ２ Each of these independently represents O, S, or NR. R represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Compounds included in this general formula include the compounds represented by the general formula described in

[0022] of WO2022 / 085714A1, which is incorporated herein by reference, the compounds described in

[0040] to

[0043] and

[0221] , and BBCz-R(5) and BBCz-Y-II(6) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which is incorporated herein by reference.

[0147] Furthermore, compounds represented by the following general formula (F24) can also be cited as luminescent materials. General formula (F24)

[0148] In the general formula (F24), R １ ~R １７ Each of these 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 ５ and R ６ , R ６ and R７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , 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 １７ , R １７ and R １ These may be bonded to each other to form a cyclic structure. Examples of compounds included in this general formula are BBCz-SB(2), BBCz-G(3), and BBCz-Y(4) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which are cited herein as part of this specification.

[0149] Furthermore, compounds represented by the following general formula (F25) can also be cited as luminescent materials. General formula (F25)

[0150] In the general formula (F25), R １ ~R ２０ Each of these 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 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 １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R１５ and R １６ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ These may be bonded to each other to form a cyclic structure. Examples of compounds included in this general formula include BBCz-DB(1) of J. Am. Chem. Soc. 2020, 142, 46, 19468-19472, which are cited herein as part of this specification.

[0151] Furthermore, compounds represented by the following general formula (F26) can also be cited as luminescent materials. General formula (F26)

[0152] In the general formula (F26), X １ and X ２ Each of these independently represents either O or S. １ and Y ２ Each is independently a single bond, O, S or C(R) ａ ) (Caution ｂ ) represents R １ ~R ２２ , R ａ , R ｂ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, but R １ ~R ２２ At least one of them is a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R ７ and Y １ , Y １ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ , R １４and R １５ , R １６ and R １７ , R １７ and R １８ , R １８ and Y ２ , Y ２ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ They may be bonded to each other to form a ring structure. ２１ and R １ , R ４ and R ５ , R １０ and R １２ , R １５ and R １６ They are not bonded to each other to form a ring structure. C-R in general formula (F26) １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ , C-R １７ , C-R １８ , C-R １９ , C-R ２０ , C-R ２１ , C-R ２２ It may be replaced with N.

[0153] The following compounds are specific examples of compounds represented by the general formula (F26).

[0154] Furthermore, compounds containing the BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) structure can also be used as luminescent materials. For example, a compound represented by the following general formula (F27) can be used. General formula (F27)

[0155] In the general formula (F27), R １ ~R ９ Each of these is independently a hydrogen atom, a deuterium atom, or a substituent. １ ~R ７ At least one of these is preferably a group represented by the following general formula (F28), R ８ and R ９ It is preferably a halogen atom. General formula (F28)

[0156] In the general formula (F28), R １１ ~R １５ Each of the symbols represents an independent hydrogen atom, a deuterium atom, or a substituent, and the asterisk (*) represents a bond site.

[0157] The following are specific examples of luminescent materials. In the following structural formulas, t-Bu represents a tert-butyl group. As derivatives of the example compounds below, compounds in which at least one hydrogen atom is substituted with a deuterium atom, alkyl group, aryl group, heteroaryl group, or diarylamino group can also be listed.

[0158] In one embodiment, when a host material is used, the amount of the compound used in the present invention as a light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 1% by weight or more. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 20% by weight or less. In one embodiment, when a host material is used, the amount of the compound of general formula (1) as a light-emitting material contained in the light-emitting layer is 10% by weight or less. In one embodiment, the host material of the light-emitting layer is an organic compound having hole transport function and electron transport function. In one embodiment, the host material of the light-emitting layer is an organic compound that prevents an increase in the wavelength of synchrotron radiation. In one embodiment, the host material of the light-emitting layer is an organic compound having a high glass transition temperature.

[0159] In some embodiments, the host material is selected from the group consisting of: In one embodiment, the light-emitting layer contains two or more structurally different TADF molecules. For example, the light-emitting layer can contain three materials in which the excited singlet energy levels are highest in the host material, followed by the first TADF molecule and then the second TADF molecule. In this case, both the first TADF molecule and the second TADF molecule have a difference ΔE between their lowest excited singlet energy level and their lowest excited triplet energy level of 77K. ＳＴThe luminescence voltage is 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 luminescent layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the luminescent layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the luminescent layer may be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the luminescent layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecules, and 0.1 to 30% by weight of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20-45% by weight of the host material, 50-75% by weight of the first TADF molecule, and 5-20% by weight of the second TADF molecule. In one embodiment, the photo-excited emission quantum yield φPL1(A) of a co-evaporated film of the first TADF molecule and the host material (concentration of the first TADF molecule in this co-evaporated film = A by weight) and the photo-excited emission quantum yield φPL2(A) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = A by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photo-excited emission quantum yield φPL2(B) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = B by weight) and the photo-excited emission quantum yield φPL2(100) of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In one embodiment, the light-emitting layer can contain three different structural TADF molecules. The compound of general formula (1) may be any of the multiple TADF compounds contained in the light-emitting layer. In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain any metal elements.In one embodiment, the light-emitting layer may be made of a material composed 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 may be made of a material composed 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 may be made of a material composed 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 may be a known delayed fluorescence material. Preferred delayed fluorescence materials include paragraphs 0008-0048 and 0095-0133 of WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of Japanese Patent Publication No. 2013-256490, paragraphs 0008~0020 and 0038~0040 of Japanese Patent Publication No. 2013-116975, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359, paragraph 0 of WO2013 / 161437 Paragraphs 008-0054 and 0101-0121 of Japanese Patent Publication No. 2014-9352, paragraphs 0007-0041 and 0060-0069 of Japanese Patent Publication No. 2014-9224, paragraphs 0008-0048 and 0067-0076 of Japanese Patent Publication No. 2017-119663, paragraphs 0013-0025 of Japanese Patent Publication No. 2017-119664, Japanese Patent Publication No. 2 This includes compounds included in the general formulas described in paragraphs 0012 to 0025 of Japanese Patent Publication No. 017-222623, paragraphs 0010 to 0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016 to 0044 of Japanese Patent Application Publication No. WO2018 / 047853, particularly exemplary compounds that can emit delayed fluorescence.Furthermore, here we have Japanese Patent Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO20 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, JP 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 A light-emitting material that can emit delayed fluorescence, as described in Publication No. 1, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, can preferably be used. The above publications described in this paragraph are incorporated herein by reference as part of this specification.

[0160] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0161] Substrate: In some embodiments, the organic electroluminescent element of the present invention is held by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent elements, such as glass, transparent plastic, quartz, and silicon.

[0162] Anode: In some embodiments, the anode of an organic electroluminescent apparatus is made from a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and selected from 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 produced by vapor deposition 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., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto 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 synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms or less per unit area. 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.

[0163] 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-injection 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 ) mixtures, indium, lithium-aluminum mixtures and rare earth elements are selected. In some embodiments, a mixture of an electron-injection metal and a second metal which is a stable metal having a higher work function than the electron-injection metal is used. In some embodiments, the mixture is a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) are selected from a mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or cathode of the organic electroluminescent element is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, a transparent or translucent electroluminescent element improves light radiance. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with respect to the anode from the conductive transparent material described above. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[0164] 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 includes a hole injection layer and an electron injection layer. The injection layer can be located between the anode and the light-emitting layer or hole transport layer, and between the cathode and the light-emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0165]

[0166] Next, we will list some examples of preferred compounds that can be used as electron injection materials.

[0167] 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 to the outside of the light-emitting layer. In some embodiments, an electron barrier layer exists between the light-emitting layer and the hole transport layer, preventing electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole barrier layer exists between the light-emitting layer and the electron transport layer, preventing holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing to the outside of the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. As used herein, the terms “electron barrier layer” or “exciton barrier layer” include layers that have both the functions of an electron barrier layer and an exciton barrier layer.

[0168] Hole barrier layer: The hole barrier layer functions as an electron transport layer. In some embodiments, the hole barrier layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material used for the hole barrier layer may be the same material described above for the electron transport layer. The following are examples of preferred compounds that can be used for the hole barrier layer.

[0169]

[0170] Electron barrier layer: The electron barrier layer transports holes. In some embodiments, during hole transport, the electron barrier layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material used for the electron barrier layer may be the same material described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron barrier materials are listed below.

[0171]

[0172] Exciton Barrier Layer: The exciton barrier layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the optical emission efficiency of the device is improved. In some embodiments, the exciton barrier layer may be adjacent to only one side of the light-emitting layer, either the anode side or the cathode side, or one exciton barrier layer may be adjacent to the anode side of the light-emitting layer and another exciton barrier layer may be adjacent to the cathode side of the light-emitting layer. In some embodiments, when the exciton barrier layer is on the anode side, it may be located between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton barrier layer is on the cathode side, it may be located between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, electron barrier layer, or similar layer is located between the anode and the exciton barrier layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron barrier layer, hole barrier layer, or similar layer is located between the cathode and an exciton barrier layer adjacent to the cathode-side light-emitting layer. In some embodiments, the exciton barrier layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the light-emitting material, respectively.

[0173] 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 properties of hole injection or transport properties and electron barrier properties. 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, indrocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, aminosubstituted 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 porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. 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.

[0174]

[0175] 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 have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier 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, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethane, 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.

[0176]

[0177] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0178]

[0179] While specific examples of preferred materials that can be used in organic electroluminescent elements have been provided, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials with specific functions can be repurposed as materials with other functions.

[0180] 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 includes an OLED having at least one organic layer comprising an anode, a cathode, and a light-emitting layer between the anode and the cathode. In some embodiments, the components described herein may be incorporated into a variety of photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the components may be useful for facilitating charge transfer or energy transfer within the device and / or as hole transport materials. Examples of such devices include 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-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0181] Bulb or Lamp: In some embodiments, the electronic device includes an OLED comprising an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is an OLED light comprising: a circuit board having a first surface with a mounting surface and a second surface opposite thereto, defining at least one opening; at least one OLED on the mounting surface having a light-emitting configuration comprising an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture. In some embodiments, the OLED light has a plurality of OLEDs mounted on the circuit board such that light is emitted in a plurality of directions. In some embodiments, some of the light emitted in the 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.

[0182] Displays or Screens: In some embodiments, the light-emitting layer of the present invention can be used in screens or displays. In some embodiments, the compounds according to the present invention are deposited onto a substrate using processes such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD), but are not limited. In some embodiments, the substrate is a photoplate structure useful in two-sided etching, providing pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern allows for the arrangement of very steep, narrow tie bars between pixels in the vertical direction, and large, wide oblique apertures in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays while optimizing chemical vapor deposition onto the TFT backplane. Internal patterning of the pixels allows for the configuration of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within a pixel area protects etching in a particular area until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at a similar etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone pattern, etching with varying degrees of protection within the pixels becomes possible, enabling localized, deep etching necessary to form steep vertical bevels. A preferred material for the deposition mask is Invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at a steel mill. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming aperture regions within the 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 processed using wet chemical etching. In further embodiments, the screen or display pattern is processed using plasma etching.

[0183] 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, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel.

[0184] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising the steps of: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units in cell panel units on the barrier layer; forming an encapsulation layer on each of the display units of the cell panel; and coating an organic film on the interface portions between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edges of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in the soft cutting of the mother panel in cell panel units. In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may have a thin-film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, wherein the organic film coated on the interface portions is formed 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 unit is connected to the TFT layer by a passivation layer, a planarization film between them, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to the display unit or the encapsulation layer.

[0185] Each of the organic film and the planarization film may contain either polyimide or 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 the steps of attaching a carrier substrate made of glass material to another surface of the base substrate before forming a barrier layer on one surface of the base substrate made of polyimide, 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 placed on the TFT layer for coating the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, as well as the organic film formed at the edges of the barrier layer, is made 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 at the edge of the barrier layer, so that a portion of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film surrounds the edge of the barrier layer while being in contact with the barrier layer.

[0186] 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 the source / drain electrodes 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 having a TFT layer and a light-emitting unit will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display unit and preventing the penetration of external moisture may be formed as a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the edge of the barrier layer while in contact with the barrier layer.

[0187] 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 glass material, which is then 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, the base substrate is formed on all surfaces of the mother panel, while the barrier layer is formed according to the size of each cell panel, thereby creating grooves in the interface portions between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0188] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, where a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, a TFT layer is formed for each cell panel, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on the TFT layer and cover the TFT layer. For example, while a planarization film made of polyimide or acrylic is formed, the groove in the interface portion is covered with an organic film made of polyimide or acrylic, for example. This prevents cracking by allowing the organic film to absorb the impact generated when each cell panel is cut along the groove at the interface portion. That is, if all barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the impact generated is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between barrier layers may be covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel is cut softly and cracking in the barrier layer is prevented. In one embodiment, the organic film and the planarizing film covering the grooves of the interface portion are arranged with a gap between them. For example, if the organic film and the planarizing film are connected to each other as a single layer, there is a risk that external moisture may penetrate the display unit through the remaining parts of the planarizing film and organic film. Therefore, the organic film and the planarizing film are arranged with a gap between them so that the organic film is spaced away from the display unit.

[0189] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is placed on the display unit to cover it. This separates the carrier substrate supporting the base substrate from the base substrate after the mother panel is completely manufactured. In some embodiments, when a laser beam is radiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficients between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut in cell panel units. In some embodiments, the mother panel is cut along the interface portions between the cell panels using a cutter. In some embodiments, the grooves of the interface portions along which the mother panel is cut are covered with an organic film so that the organic film absorbs shock during cutting. In some embodiments, cracking of the barrier layer can be prevented during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film coated on the edges of the barrier layer.

[0190] The features of the present invention will be further described in detail below with reference to synthesis examples and embodiments. The materials, processing content, 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 interpreted as being limited by the specific examples shown below. The luminescence characteristics were evaluated using a source meter (Keithley Corporation: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In the following synthesis examples, THF represents tetrahydrofuran, DMF represents N,N-dimethylformamide, NMP represents N-methyl-2-pyrrolidone, and LDA represents lithium diisopropylamide.

[0191] (Synthesis Example 1) Synthesis of intermediate b of compound A

[0192] Intermediate a (15.3 g, 18 mmol), 2-chloro-4,6-di(phenyl-d ５ A mixture of 12.5 g, 45 mmol of 1,3,5-triazine, tetrakis(triphenylphosphine)palladium (0) (1.04 g, 0.90 mmol), potassium carbonate (7.45 g, 53.9 mmol), THF (68 mL), and deionized water (22 mL) was stirred at 75°C for 15 hours. After the mixture cooled to room temperature, the precipitated solid was washed with deionized water, methanol, and hexane in that order. The obtained solid was washed with hot toluene, cooled to room temperature, filtered off, and washed with toluene and hexane in that order. 9.21 g (15.4 mmol, yield 85%) of white solid intermediate b was obtained. APCI-MS: Calculated value 596.31 (C 36 H2D 20 F2N6), Observed value 597.43 ([M+H) + ).

[0193] Synthesis of intermediate c

[0194] A mixture of 1,4-benzenediboronic acid bis(pinacol) ester (10 g, 30 mmol), 1-bromocarbazole (16 g, 65 mmol), potassium carbonate (15 g, 109 mmol), and tetrakis(triphenylphosphine)palladium (0) (1.7 g, 1.5 mmol) was mixed with THF (150 mL) and water (50 mL), and heated and stirred at 75°C under a nitrogen atmosphere for 24 hours. After cooling to room temperature, aqueous ammonium chloride solution was added, and the organic phase was separated. The aqueous phase was extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (dichloromethane / hexane = 4 / 6) to obtain 11 g (27 mmol, 89% yield) of intermediate c. 1H NMR (400 MHz, CDCl3): d 8.38 (s, 2H), 8.12 (d, J = 7.6 Hz, 4H), 8.06 (s, 1H), 7.81-7.33 (m, 3H), 7.54 (dd, J = 7.6, 1.2 Hz, 2H), 7.41 (d, J = 4.4 Hz, 4H), 7.36 (t, J = 7.6 Hz, 2H), 7.28-7.23 (m, 2H). APCI-MS: Calculated value 408.16 (C 30 H 20 N2), Observed value 408.23 (M + ).

[0195] Synthesis of compound A

[0196] A mixture of intermediate b (1.19 g, 2.00 mmol), intermediate c (0.984 g, 2.41 mmol), potassium carbonate (1.13 g, 8.18 mmol), and DMF (40 mL) was stirred at 150°C for 14 hours. After cooling to room temperature, deionized water was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 1.27 g (1.32 mmol, yield 66%) of compound A as a yellow-green solid. 1 H NMR (400 MHz, DMSO-d6): d 9.14 (s, 1H), 8.18 (s, 1H), 8.13-8.08 (m, 4H), 7.40-7.27 (m, 9H), 7.24-7.20 (m, 2H), 7.12 (t, J = 7.6 Hz, 1H), 7.02-7.00 (m, 2H). APCI-MS: Calculated value 964.46 (C 66 H 20 D 20 N8), Observed value 965.75 ([M+H] + ).

[0197] (Synthesis Example 2) Synthesis of Compound B

[0198] A mixture of intermediate d (3.0 g, 4.4 mmol), intermediate c (2.3 g, 5.6 mmol), potassium carbonate (1.85 g, 13.4 mmol), and DMF (90 mL) was refluxed at a bath temperature of 160°C for 117 hours. After cooling to room temperature, aqueous ammonium chloride and methanol were added to precipitate the product. The obtained solid was washed with methanol and purified by silica gel column chromatography (dichloromethane / hexane = 3 / 7) to obtain 0.79 g (0.76 mmol, yield 17%) of compound A. 1 H NMR (400 MHz, DMSO-d6): d 8.82 (s, 1H), 7.96-7.92 (m, 4H), 7.53 (t, J= 1.6 Hz, 1H), 7.49 (d, J = 7.8 Hz, 2H), 7.41-7.36 (m, 3H), 7.19 (td, J = 8.0, 1.2 Hz, 2H), 7.15-7.12 (m, 4H), 7.02 (dd, J = 7.8, 1.8 Hz, 2H). APCI-MS: Calculated value 1045.53 (C 72 H 19 D 25 N8), Observed value 1046.88 ([M+H] + ).

[0199] (Synthesis Example 3) Synthesis of intermediate f of compound C

[0200] Under a nitrogen atmosphere, intermediate a (2.30 g, 6.28 mmol), intermediate e (5.79 g, 15.7 mmol), potassium carbonate (2.60 g, 18.8 mmol), water (10 mL), and tetrahydrofuran solution (35 mL) were mixed with tetrakis(triphenylphosphine)palladium (0) (0) and heated and stirred at 75°C for 16 hours. The reaction solution was allowed to cool to room temperature, and water was added to stop the reaction, resulting in the precipitation of a white powder. This powder was filtered and washed with methanol, hexane, and hot toluene to obtain a white solid intermediate f (3.08 g, 3.94 mmol, yield 62%). APCI-MS: Calculated value 780 (C 48 H2D 26 F2N8), Observed value 780 (M + ).

[0201] Synthesis of compound C

[0202] Under a nitrogen atmosphere, a dimethylformamide solution (64 mL) of intermediate f (2.50 g, 3.20 mmol), potassium carbonate (1.76 g, 12.8 mmol), and intermediate c (1.56 g, 3.84 mmol) was heated and stirred at 150°C for 24 hours. The reaction mixture was allowed to return to room temperature, and water was added to stop the reaction, resulting in the precipitation of a white powder. After filtering this powder, it was washed with methanol, and the resulting residue was purified by silica gel column chromatography using a hexane:dichloromethane = 1:1 mixed solvent as the eluent to obtain a white solid compound c (0.13 g, 0.11 mmol, yield 3.5%). 1 1H NMR (400 MH) Z , CDCl3): d 9.00 (s, 1H), 8.11 (dd, J = 7.6 H Z , 1.2 H Z , 2H), 8.01 (d, J = 7.6 H Z , 2H), 7.82 (s, 1H), 7.52-7.42 (m, 6H), 7.35-7.25 (m, 5H), 7.20-7.17 (m, 2H), 7.05 (t, J = 7.6 H Z , 1H). APCI-MS: Calculated value 1149 (C 78 H 20 D 26 N 10 ), Observed value 1149 (M + ).

[0203] (Synthesis Example 4) Synthesis of intermediate i of compound D

[0204] Under a nitrogen atmosphere, a THF solution (21 mL) of intermediate i (1.0 g, 5.1 mmol) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 5.4 mL, 5.4 mmol) was added over 15 minutes. After stirring for 1 hour, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.2 mL, 5.9 mmol) was added, and the mixture was stirred for a further 2 hours. The reaction solution was heated to room temperature, and water (7 mL), intermediate h (2.0 g, 5.5 mmol), potassium carbonate (1.5 g, 11 mmol), and tetrakis(triphenylphosphine)palladium (0) (300 mg, 0.26 mmol) were added, and the mixture was heated and stirred at 70°C for 18 hours. After cooling to room temperature, methanol and water were added, and the resulting solid was collected and washed with methanol to obtain 2.7 g (5.1 mmol) of intermediate i. APCI-MS: Calculated value 522.21 (C 32 H8D 10 F2N4O), Observed value 523.28 ([M+H] + ).

[0205] Synthesis of compound D

[0206] Intermediate i (2.0 g, 3.8 mmol), intermediate c (1.9 g, 4.7 mmol), and potassium carbonate (1.6 g, 12 mmol) were mixed with DMF (80 mL) and heated and stirred at 150 °C under a nitrogen atmosphere for 67 hours. The reaction solution was cooled to room temperature and water and methanol were added. The precipitate was collected and washed with water and methanol. This was purified by silica gel column chromatography (dichloromethane / hexane = 4 / 6) to obtain 2.1 g (2.4 mmol, 62% yield) of compound D. 1H NMR (400 MHz, CDCl3): d 9.02 (s, 1H), 8.96 (d, J = 1.6 Hz, 1H), 8.10-8.06 (m, 3H), 7.95-7.89 (m, 3H), 7.62-7.58 (m, 2H), 7.53-7.48 (m, 2H), 7.44-7.18 (m, 12H), 7.13 (d, J = 8.0 Hz, 1H), 7.05 (dt, J = 7.6, 1.6 Hz, 1H). APCI-MS: Calculated value 890.36 (C 62 H 26 D 10 N6O), observed value 890.49 (M + ).

[0207] (Synthesis Example 5) Synthesis of intermediate j of compound E

[0208] A mixture of 3,5-dibromopyridine (3.7 g, 16 mmol), 9H-carbazole-1-boronic acid pinacol ester (10.0 g, 34 mmol), potassium carbonate (8.6 g, 62 mmol), and tetrakis(triphenylphosphine)palladium (0) (900 mg, 0.78 mmol) was mixed with 1,4-dioxane (75 mL) and water (25 mL), and the mixture was heated and stirred at 100°C under a nitrogen atmosphere for 17 hours. After cooling to room temperature, aqueous ammonium chloride solution was added, and the organic phase was separated and concentrated. The crude product was washed with methanol, purified by silica gel column chromatography (dichloromethane / methanol = 100 / 4), and further reprecipitation with dichloromethane / methanol yielded 5.5 g (13 mmol, 86% yield) of intermediate j. 1 H NMR (400 MHz, CDCl3): d 9.00 (d, J = 9.2 Hz, 4H), 8.29 (t, J = 1.8 Hz, 1H), 8.09 (dd, J= 7,4, 3.0 Hz, 4H), 7.45-7.36 (m, 6H), 7.33-7.23 (m, 4H). APCI-MS: Calculated value 409.16 (C 29 H 19 N3), Observed value 410.12 ([M+H] + ).

[0209] Synthesis of compound E

[0210] Intermediate j (2.5 g, 6.1 mmol), intermediate k (2.2 g, 5.0 mmol), and potassium carbonate (2.1 g, 15 mmol) were mixed with DMF (100 mL) and heated and stirred at 150 °C under a nitrogen atmosphere for 48 hours. The reaction solution was cooled to room temperature and water and methanol were added. The precipitate was collected and washed with water, methanol, and hexane. This was purified twice by silica gel column chromatography (dichloromethane / methanol = 100 / 4 and toluene / ethyl acetate = 9 / 1) to obtain 1.8 g (2.3 mmol, 45% yield) of compound E. 1 H NMR (400 MHz, CDCl3): d 8.95 (s, 1H), 8.55 (d, J = 2.0 Hz, 1H), 8.34 (d, J = 2.0 Hz, 1H), 8.15 (dd, J = 7.2, 2.0 Hz, 1H), 8.09 (dt, J = 8.0, 1.0 Hz,1H), 7.97 (dd, J = 6.4, 2.8 Hz, 1H), 7.91 (dt, J = 8.0, 1.0 Hz,1H), 7.89 (t, J = 2.0 Hz, 1H), 7.40 (ddd, J = 8.6, 6.8, 1.2 Hz, 1H), 7.37-7.15 (m, 8H), 7.13 (d, J = 8.0 Hz, 1H). APCI-MS: Calculated value 806.37 (C 55 H 18 D 15 N7), Observed value 807.50 ([M+H] + ).

[0211] (Synthesis Example 6) Synthesis of intermediate l of compound F

[0212] 2,4-chloro-6-(phenyl-d ５A mixture of 1,3,5-triazine (3.44 g, 15 mmol), 2,4-difluorophenylboronic acid (5.67 g, 35.9 mmol), tetrakis(triphenylphosphine)palladium (0) (0.875 g, 0.757 mmol), potassium carbonate (12.5 g, 90.4 mmol), THF (60 mL), and deionized water (20 mL) was stirred at 75°C for 16 hours. After the mixture cooled to room temperature, the precipitated solid was washed with deionized water, methanol, and hexane in that order to obtain 2.25 g (5.82 mmol, yield 39%) of a white solid intermediate l. 1 H NMR (400 MHz, CDCl3): d 8.53 (td, J = 8.7, 6.6 Hz, 1H), 7.10-7.05 (m, 1H), 7.01 (ddd, J= 12.5, 7.3, 2.6 Hz, 1H). APCI-MS: Calculated value 386.12 (C 21 H6D5F4N3), Observed value 387.41 ([M+H] + ).

[0213] Synthesis of compound F

[0214] A mixture of intermediate l (1.23 g, 3.18 mmol), intermediate c (3.13 g, 7.66 mmol), tripotassium phosphate (4.77 g, 22.4 mmol), and NMP (64 mL) was stirred at 180°C for 61 hours. After cooling to room temperature, reprecipitation was performed by adding ethyl acetate, deionized water, and methanol. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.91 g (1.70 mmol, yield 53%) of compound F as a pale yellow solid. APCI-MS: Calculated value 1122.42 (C 81 H 42 D5N7), Observed value 1123.71 ([M+H] + ).

[0215] (Synthesis Example 7) Synthesis of intermediate m of compound G

[0216] 2,4-Difluorophenylboronic acid (4.2 g, 27 mmol), 2-chloro-4,6-di(phenyl-d ５ A mixture of )-1,3,5-triazine (7.0 g, 25 mmol), tetrakis(triphenylphosphine)palladium (0) (0.90 g, 0.78 mmol), and potassium carbonate (7.0 g, 51 mmol) was mixed with THF (90 mL) and water (30 mL), and the mixture was heated and stirred at 75°C under a nitrogen atmosphere for 19 hours. After cooling to room temperature, aqueous ammonium chloride solution and methanol were added. The precipitate was collected and washed with water and methanol to obtain 7.2 g (20 mmol, 80% yield) of intermediate m. 1 H NMR (400 MHz, CDCl3): d 8.58-8.48 (m, 1H), 7.10-6.97 (m, 2H). APCI-MS: Calculated value 355.17 (C 21 H3D 10 F2N3), Observed value 355.41 (M + ).

[0217] Synthesis of compound G

[0218] Intermediate m (1.6 g, 4.5 mmol), intermediate c (1.2 g, 2.9 mmol), and potassium carbonate (1.2 g, 8.7 mmol) were mixed with DMF (50 mL) and heated and stirred at 150°C under a nitrogen atmosphere for 40 hours. The reaction solution was cooled to room temperature, and aqueous ammonium chloride solution and methanol were added. The precipitate was collected and washed with water and methanol. This was dissolved in dichloromethane, filtered through a short silica gel column, and further purified by silica gel column chromatography (dichloromethane / hexane = 3 / 7). This was reprecipitated with dichloromethane / methanol and washed with methanol to obtain 0.94 g (1.3 mmol, 41% yield) of compound G. 1H NMR (400 MHz, CDCl3): d 8.21 (dd, J = 7.0, 1.0 Hz, 2H), 8.16 (d, J = 8.0 Hz, 1H), 8.09 (dd, J = 7.0, 1.0 Hz, 1H), 7.99 (d, J = 7.6 Hz, 1H), 7.64 (d, J = 2.4 Hz, 1H), 7.50-7.46 (m, 1H), 7.42-7.31 (m, 8H), 7.28-7.24 (m, 1H), 7.15 (dt, J = 7.2, 0.8 Hz, 1H), 7.11-7.02 (m, 4H). APCI-MS: Calculated value 723.32 (C 51 H 21 D 10 N5), Observed value 723.56 (M + ).

[0219] (Synthesis Example 8) Synthesis of intermediate n of compound H

[0220] A mixture of 2,4-difluoro-5-iodopyridine (5.86 g, 24.3 mmol) and THF (120 mL) was cooled to -50°C, and the mixture was stirred for 1 hour with the addition of the Turbogrignard reagent (approximately 1.3 MTHF solution, 19 mL, 25.0 mmol). Zinc chloride (approximately 1 MTHF solution, 29 mL, 29.0 mmol) was added to the mixture and stirred at -50°C for 30 minutes, then stirred at room temperature for 2 hours. The solvent was removed by distillation, and tetrakis(triphenylphosphine)palladium (0) (0.577 g, 0.499 mmol), 2,4-chloro-6-(phenyl-d ５ )-1,3,5-triazine (2.32 g, 10.0 mmol) and 1,4-dioxane (100 mL) were added and the mixture was stirred at 110°C for 14 hours. After the mixture was cooled to room temperature, deionized water was added and the precipitated solid was removed by Celite filtration. The obtained filtrate was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane) to obtain 2.49 g (6.41 mmol, yield 64%) of the pale orange solid intermediate n. 1H NMR (400 MHz, CDCl3): d 9.37 (d, J = 10.1 Hz, 1H), 6.88 (dd, J = 10.0, 2.2 Hz, 1H). APCI-MS: Calculated value 388.11 (C 19 H4D5F4N5), Observed value 389.16 ([M+H] + ).

[0221] Synthesis of compound H

[0222] A mixture of intermediate n (1.54 g, 3.96 mmol), intermediate c (3.93 g, 9.62 mmol), potassium carbonate (3.90 g, 28.2 mmol), and DMF (80 mL) was stirred at 150°C for 12 hours. After cooling to room temperature, methanol was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene) to obtain 0.708 g (0.629 mmol, yield 16%) of compound H as a yellow solid. APCI-MS: Calculated value 1124.42 (C 79 H 40 D5N9), Observed value 1125.73 ([M+H] + ).

[0223] (Synthesis Example 9) Synthesis of intermediate o of compound I

[0224] A mixture of 2-phenylpyridine (3.1 g, 20 mmol), 1-bromocarbazole (11 g, 44 mmol), dichloro(p-cymene)ruthenium(II) dimer (0.31 g, 0.50 mmol), triphenylphosphine (0.50 g, 2.0 mmol), potassium carbonate (11 g, 80 mmol), and NMP (40 mL) was stirred at 110°C for 85 hours. After cooling the mixture to room temperature, 400 mL of water was added and the mixture was stirred at room temperature for 20 minutes to precipitate a solid. After removing the water by decantation, ethyl acetate and water were added, and the separated organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain 12 g of crude product (black viscous solid). This was purified by silica gel column chromatography (hexane / ethyl acetate = 8 / 1) to obtain 3.6 g (7.4 mmol, yield 37%) of intermediate o. APCI-MS: Calculated value 485.19 (C 35 H 23 N3), observed value 486.35 ([M+H] + ).

[0225] Synthesis of Compound I

[0226] A mixture of intermediate b (1.7 g, 2.9 mmol), intermediate o (1.7 g, 3.5 mmol), potassium carbonate (1.6 g, 12 mmol), and DMF (60 mL) was stirred at 150°C for 112 hours. After the mixture cooled to room temperature, 150 mL of 5% ammonium chloride aqueous solution and 200 mL of methanol were added, and the precipitated solid was filtered off. The obtained solid was washed with methanol and then hexane, and dried to obtain 2.70 g of a yellow solid as the crude product. This was purified by silica gel column chromatography to obtain 0.4 g (0.38 mmol, yield 13%) of compound I. APCI-MS: Calculated value 1041.49 (C 71 H 23 D 20 N9), observed value 1042.87 ([M+H] + ).

[0227] (Synthesis Example 10) Synthesis of Compound J

[0228] Under a nitrogen atmosphere, a dimethylformamide solution (37 mL) containing intermediate d (1.25 g, 1.84 mmol), potassium carbonate (1.02 g, 7.37 mmol), and intermediate p (1.09 g, 2.21 mmol) was heated and stirred at 150°C for 48 hours. The reaction mixture was allowed to return to room temperature, and water was added to stop the reaction, resulting in the precipitation of a white powder. This powder was washed with dichloromethane to obtain compound J. APCI-MS: Calculated value 1130 (C 75 H 15 D 30 N 11 ), observed value 1130 (M + ).

[0229] (Synthesis Example 11) Synthesis of intermediate q of compound K

[0230] Under a nitrogen atmosphere, 3,5-dibromobenzonitrile (3.50 g, 13.4 mmol), 1-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-9H-carbazole (8.61 g, 29.4 mmol), potassium carbonate (9.25 g, 67.0 mmol), water (22 mL), and tetrahydrofuran solution (67 mL) were mixed with tetrakis(triphenylphosphine)palladium (0) (0) (0.77 g, 0.67 mmol). The mixture was heated and stirred at 75°C for 40 hours. The reaction solution was allowed to cool to room temperature, water was added to stop the reaction, and the mixture was extracted with ethyl acetate. The solvent was removed by evaporation. The resulting residue was purified by silica gel column chromatography using toluene as the eluent to obtain a white solid intermediate q (3.30 g, 7.61 mmol, yield 56%). 1 1H NMR (400 MH) Z , CDCl3): d 8.31-8.27 (m, 3H), 8.17 (d, J = 7.6 H Z , 2H), 8.12 (d, J = 7.6 H Z , 2H), 8.07 (d, J = 1.2 H Z , 2H), 7.51 (d, J = 1.2 H Z, 2H), 7.46-7.43 (m, 4H), 7.41-7.36 (m, 2H), 7.18-7.16 (m, 2H). APCI-MS: Calculated value 433 (C 31 H 19 N3), Observed value 433 (M + ).

[0231] Synthesis of compound K

[0232] Under a nitrogen atmosphere, a dimethylformamide solution (77 mL) of intermediate b (2.30 g, 3.85 mmol), potassium carbonate (2.12 g, 15.4 mmol), and intermediate q (2.00 g, 4.62 mmol) was heated and stirred at 150°C for 19 hours. The reaction mixture was allowed to return to room temperature, and water was added to stop the reaction, resulting in the precipitation of a white powder. After filtering this powder, it was washed with methanol, and the resulting residue was purified by silica gel column chromatography using a hexane:toluene = 1:1 mixed solvent as the eluent to obtain compound K (0.90 g, 0.90 mmol, yield 23%) as a white solid. 1 1H NMR (400 MH) Z , CDCl3): d 8.97 (s, 1H), 8.16-8.13 (m, 3H), 8.02 (d, J = 7.6 H Z , 2H), 7.69-7.64 (m, 4H), 7.49-7.41 (m, 4H), 7.20-7.09 (m, 5H). APCI-MS: Calculated value 989 (C 67 H 19 D 20 N9), observed value 989 (M + ).

[0233] (Synthesis Example 12) Synthesis of intermediate r of compound L

[0234] A mixture of 1,3,5-phenyltriboronic acid tris(pinacol) ester (5.36 g, 11.7 mmol), 1-bromocarbazole (9.56 g, 38.8 mmol), tetrakis(triphenylphosphine)palladium (0) (1.26 g, 1.09 mmol), potassium carbonate (15.4 g, 111 mmol), 1,4-dioxane (90 mL), and deionized water (30 mL) was stirred at 110°C for 15 hours. After the mixture cooled to room temperature, the organic phase and aqueous phase were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 5.51 g (9.60 mmol, yield 82%) of the pale yellow solid intermediate r. 1 H NMR (400 MHz, CDCl3): d 8.45 (s, 3H), 8.18-8.13 (m, 9H), 7.63 (dd, J = 7.4, 1.0 Hz, 3H), 7.43-7.40 (m, 9H), 7.28-7.24 (m, 3H). APCI-MS: Calculated value 573.22 (C 42 H 27 N3), Observed value 574.38 ([M+H] + ).

[0235] Synthesis of intermediate s

[0236] A mixture of 1,3,5-trifluorobenzene (4.02 g, 30.4 mmol) and THF (150 mL) was cooled to -85°C, and LDA (1.07 MTHF / hexane solution, 30 mL, 32.5 mmol) was added and the mixture was stirred for 1 hour. Zinc chloride (approximately 1 MTHF solution, 38 mL, 38.0 mmol) was added to the mixture and stirred at -85°C for 30 minutes, then stirred at room temperature for 1 hour. Palladium acetate (0.282 g, 1.25 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.731 g, 2.51 mmol), 2-chloro-4,6-di(phenyl-d ５6.96 g, 25.0 mmol of )-1,3,5-triazine was added and the mixture was stirred at 75°C for 15 hours. After the mixture cooled to room temperature, deionized water was added, and the precipitated solid was removed by Celite filtration. The obtained filtrate was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:5) to obtain 8.67 g (23.2 mmol, yield 93%) of the white solid intermediate s. 1 H NMR (400 MHz, CDCl3): d 6.89-6.82 (m, 2H). APCI-MS: Calculated value 373.16 (C 21 H2D 10 F3N3), Observed value 374.27 ([M+H] + ).

[0237] Synthesis of compound L

[0238] A mixture of intermediate r (2.05 g, 3.57 mmol), intermediate s (1.12 g, 3.00 mmol), potassium carbonate (2.07 g, 15.0 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 60 mL) was stirred at 230°C for 1 hour. After cooling to room temperature, saturated ammonium chloride aqueous solution was added to reprecipitation. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.07 g (1.20 mmol, yield 40%) of compound L as a pale yellow solid. 1 H NMR (400 MHz, DMSO-d6): d 8.26 (t, J = 6.8 Hz, 2H), 8.05 (d, J = 8.0 Hz, 2H), 7.94-7.92 (m, 3H), 7.72 (s, 2H), 7.52-7.27 (m, 13H), 7.15 (d, J = 1.4 Hz, 2H), 7.09 (ddd, J = 8.0, 5.6, 2.4 Hz, 2H). APCI-MS: Calculated value 886.36 (C 63 H 27 D10 N6), Observed value 887.63 ([M+H] + ).

[0239] (Synthesis Example 13) Synthesis of intermediate u of compound M

[0240] Intermediate t (12.6 g, 48.9 mmol), 2-chloro-4,6-di(phenyl-d ５ A mixture of 16.3 g, 58.6 mmol of 1,3,5-triazine, 2.82 g, 2.44 mmol of tetrakis(triphenylphosphine)palladium, 20.4 g, 147 mmol of potassium carbonate, 180 mL of THF, and 60 mL of deionized water was stirred at 75°C for 22 hours. After the mixture was cooled to room temperature, the precipitated solid was washed with ethyl acetate and then hexane to obtain 6.73 g (18.0 mmol, 37% yield) of a white solid intermediate u. 1 H NMR (400 MHz, CDCl3): d 9.49 (d, J = 9.8 Hz, 1H), 7.30 (d, J = 9.6 Hz, 1H). APCI-M: Theoretical value 372.13 (C 20 H2D 10 ClFN4), Observed value 373.42 ([M+H] + ).

[0241] Synthesis of intermediate v

[0242] A mixture of intermediate u (3.74 g, 10.0 mmol), 9H-carbazole-1-boronic acid pinacol ester (3.51 g, 11.9 mmol), tetrakis(triphenylphosphine)palladium (0) (0.581 g, 0.502 mmol), potassium carbonate (5.54 g, 40.0 mmol), toluene (70 mL), 1-butanol (20 mL), and deionized water (10 mL) was stirred at 100°C for 15 hours. After the mixture cooled to room temperature, deionized water was added, and the precipitated solid was washed with deionized water, methanol, and hexane in that order. The obtained solid was purified using a short column (toluene) to obtain 3.97 g (7.88 mmol, yield 79%) of the yellow solid intermediate v. 1H NMR (400 MHz, CDCl3): d 11.47 (s, 1H), 9.90 (d, J = 10.3 Hz, 1H), 8.23 ​​(d, J = 7.6 Hz, 1H), 8.13 (d, J = 7.6 Hz, 1H), 8.00 (d, J = 7.3 Hz, 1H), 7.88 (d, J = 12.6 Hz, 1H), 7.61 (d, J = 8.2 Hz, 1H), 7.49 (td,J = 7.2, 0.8 Hz, 1H), 7.35 (t, J = 7.7 Hz, 1H), 7.28 (td, J = 6.8, 0.8 Hz, 1H). APCI-MS: Calculated value 503.23 (C 32 H 10 D 10 FN5), Observed value 504.95 ([M+H] + ).

[0243] Synthesis of compound M

[0244] A mixture of intermediate v (3.82 g, 7.58 mmol), potassium carbonate (1.58 g, 11.4 mmol), and DMF (76 mL) was stirred at 150°C for 22 hours. After cooling to room temperature, methanol was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene) to obtain 1.97 g (2.03 mmol, yield 54%) of compound M as a yellow solid. 1 H NMR (400 MHz, DMSO-d6) :δ 9.40 (s, 1H), 8.24 (dd, J = 7.9, 1.3 Hz, 1H), 8.16 (d, J = 7.6 Hz, 1H), 8.05 (s, 1H), 7.66 (dd, J = 7.3, 1.1 Hz, APCI-MS: Calculated value 966.45 (C 64 H 18 D20 N 10 ), Observed value 967.62 ([M+H] + ).

[0245] (Synthesis Example 14) Synthesis of intermediate w of compound N

[0246] A mixture of intermediate u (2.94 g, 7.88 mmol), intermediate v (3.83 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.468 g, 0.404 mmol), potassium carbonate (4.52 g, 32.7 mmol), toluene (56 mL), 1-butanol (16 mL), and deionized water (8 mL) was stirred at 100°C for 14 hours. After the mixture cooled to room temperature, the precipitated solid was washed with deionized water, methanol, and hexane in that order. The obtained solid was washed with hot toluene and purified using a short column (toluene) to obtain 3.09 g (5.20 mmol, yield 66%) of intermediate w, a reddish-yellow solid. 1 H NMR (400 MHz, DMSO-d6): d 12.25 (s, 1H), 9.95 (d, J = 10.8 Hz, 1H), 9.04 (s, 1H), 8.47-8.40 (m, 2H), 8.27 (d, J = 7.6 Hz, 1H), 7.91 (d, J = 8.2 Hz, 1H), 7.83 (d, J = 7.8 Hz, 1H), 7.57-7.46 (m, 3H), 7.38 (t, J = 7.4 Hz, 1H). APCI-MS: Calculated value 593.24 (C 38 H 13 D 10 FN5O), Observed value 594.29 ([M+H] + ).

[0247] Synthesis of compound N

[0248] A mixture of intermediate w (3.09 g, 5.20 mmol), potassium carbonate (1.08 g, 7.81 mmol), and DMF (100 mL) was stirred at 150°C for 62 hours. After cooling to room temperature, deionized water was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene) to obtain 1.96 g (1.70 mmol, yield 65%) of compound N as a yellow solid. 1 H NMR (400 MHz, DMSO-d6): d 9.51 (s, 2H), 8.44 (s, 2H), 8.40 (dd, J = 6.8, 1.6 Hz, 2H), 8.25 (s, 2H), 8.22 (dd, J = 7.7, 0.8 Hz, 2H), 7.84 (d, J = 8.2 Hz, 2H), 7.54 (td, J = 7.7, 1.3 Hz, 2H), 7.49-7.39 (m, 6H), 7.21 (d,J = 7.3 Hz, 2H). APCI-MS: Calculated value 1146.47 (C 76 H 23 D 20 N 10 O2), Observed value 1147.54 ([M+H] + ).

[0249] (Synthesis Example 15) Synthesis of intermediate x of compound O

[0250] A mixture of 1-bromo-3,5-difluoro-2-iodobenzene (11.4 g, 36.0 mmol) and THF (180 mL) was cooled to -50°C, and the mixture was stirred for 1 hour with the addition of the Turbogrignard reagent (approximately 1.3 MTHF solution, 30 mL, 39.0 mmol). Zinc chloride (approximately 1 MTHF solution, 45 mL, 45.0 mmol) was added to the mixture and stirred at -50°C for 30 minutes, then stirred at room temperature for 2 hours. Tetrakis(triphenylphosphine)palladium (0) (1.79 g, 1.55 mmol) and 2-chloro-4,6-bis(phenyl-d) were added to the reaction mixture. ５)-1,3,5-triazine (8.35 g, 30.0 mmol) was added and the mixture was stirred at 80°C for 15 hours. After the mixture cooled to room temperature, water was added and the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:4) to obtain 10.9 g (25.1 mmol, yield 70%) of the white solid intermediate x. 1 H NMR (400 MHz, CDCl3): d 7.34 (dt, J = 7.6, 2.1 Hz, 1H), 7.00 (td, J = 8.9, 2.3 Hz, 1H). APCI-MS: Calculated value 434.09 (C 21 H3D 10 BrF2N3), Observed value 434.24 ([M+H] + ).

[0251] Synthesis of intermediate y

[0252] A mixture of intermediate x (9.13 g, 21.0 mmol), 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (6.80 g, 23.1 mmol), tetrakis(triphenylphosphine)palladium (0) (1.22 g, 1.05 mmol), potassium carbonate (8.71 g, 63.0 mmol), 1,4-dioxane (75 mL), and water (20 mL) was stirred at 110°C for 15 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 9.89 g (19.0 mmol, 90% yield) of the white solid intermediate y. 1H NMR (400 MHz, CDCl3): d 8.25 (s, 1H), 8.00 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 7.6 Hz, 1H), 7.40-7.31 (m, 2H), 7.25-7.06 (m, 5H). APCI-MS: Calculated value 521.24 (C 33 H 11 D 10 F2N4), Observed value 521.73 ([M+H] + ).

[0253] Synthesis of intermediate z

[0254] A mixture of intermediate y (26.6 g, 51.0 mmol), 1,3-dibromo-5-iodobenzene (27.0 g, 74.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (9.32 g, 10.1 mmol), 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene(xantphos, 11.8 g, 20.4 mmol), sodium tert-butoxide (9.82 g, 102 mmol), and xylene (250 mL) was stirred at 150°C for 5 hours. After the mixture cooled to room temperature, the reaction mixture was filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated, and the crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 4.59 g (6.08 mmol, yield 12%) of intermediate z as a pale orange solid. 1H NMR (400 MHz, CDCl3): d 8.13-8.11 (m, 1H), 7.98 (s, 1H), 7.94 (dt, J = 7.7, 1.5 Hz, 1H), 7.75 (t, J = 1.6 Hz, 0H), 7.56 (t, J = 1.7 Hz, 1H), 7.49 (ddd, J = 8.8, 7.6, 1.2 Hz, 1H), 7.39-7.35 (m, 1H), 7.28-7.26 (m, 1H), 7.02 (t, J = 7.6 Hz, 1H), 6.96 (dd, J = 7.3, 1.4 Hz, 1H), 6.87 (ddd, J = 10.5, 8.1, 1.9 Hz, 1H), 6.54 (ddd, J = 8.6, 2.5, 1.3 Hz, 1H). APCI-MS: Calculated value 753.09 (C 39 H 13 D 10 Br2F2N4), Observed value 753.10 ([M+H] + ).

[0255] Synthesis of intermediate aa

[0256] A mixture of intermediate z (4.59 g, 6.08 mmol), 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.96 g, 13.5 mmol), tetrakis(triphenylphosphine)palladium (0) (0.350 g, 0.302 mmol), potassium carbonate (5.16 g, 37.3 mmol), 1,4-dioxane (24 mL), and water (8 mL) was stirred at 110°C for 16 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 2:3) to obtain 3.32 g (3.58 mmol, yield 59%) of the white solid intermediate aa. 1H NMR (400 MHz, CDCl3): d 8.36 (s, 1H), 8.27 (d, J = 7.8 Hz, 2H), 8.17-8.12 (m, 3H), 7.99-7.97 (m, 2H), 7.93 (d, J = 7.8 Hz, 2H), 7.77 (s, 1H), 7.55-7.49 (m, 3H), 7.43-7.36 (m, 4H), 7.29-7.26 (m, 2H), 7.19-7.09 (m, 3H), 7.02 (t, J= 7.4 Hz, 1H), 6.96 (dd, J = 7.4, 1.3 Hz, 1H), 6.79-6.75 (m, 2H), 6.61 (td, J = 9.3, 2.1 Hz, 1H). APCI-MS: Calculated value 927.39 (C 63 H 29 D 10 F2N6), Observed value 927.09 ([M+H] + ).

[0257] Synthesis of compound O

[0258] A mixture of intermediate aa (3.29 g, 3.55 mmol), tripotassium phosphate (11.3 g, 53.3 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 72 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, saturated ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.89 g (2.13 mmol, yield 60%) of compound O as a white solid. 1H NMR (400 MHz, DMSO-d6): d 8.29 (t, J = 8.2 Hz, 2H), 8.21 (d, J = 7.8 Hz, 1H), 8.04 (dd, J = 7.8, 1.1 Hz, 2H), 8.00 (t, J = 1.8 Hz, 1H), 7.95 (d, J= 7.8 Hz, 1H), 7.61 (d, J = 2.1 Hz, 1H), 7.55 (d, J = 2.1 Hz, 1H), 7.53-7.48 (m, 4H), 7.45 (t, J = 7.1 Hz, 1H), 7.40-7.31 (m, 7H), 7.27-7.22 (m, 3H), 7.16-7.13 (m, 1H), 7.03 (t, J = 7.6 Hz, 1H). MALDI-TOF-MS: Calculated value 886.36 (C 63 H 26 D 10 N6), observed value 886.36 (M + ).

[0259] (Synthesis Example 16) Synthesis of the synthetic intermediate ab of compound P A mixture of 1-bromo-2,4,6-trifluorobenzene (6.26 g, 29.7 mmol) and THF (150 mL) was cooled to -20°C, and the mixture was stirred for 1 hour with the addition of the turbogrignard reagent (approximately 1.3 MTHF solution, 25.5 mL, 33.1 mmol). To the reaction mixture, 2,4-dichloro-6-(phenyl-d ５ )-1,3,5-triazine (10.7 g, 46.3 mmol) was dissolved in THF (30 mL) and added, and the mixture was stirred at 10°C for 19 hours. After the mixture cooled to room temperature, aqueous ammonium chloride solution was added, and the organic phase and aqueous phase were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:4) to obtain 2.80 g (8.57 mmol, yield 29%) of the white solid intermediate ab. APCI-MS: Calculated value 327.07 (C 15 H3D5ClF3N3), Observed value 326.70 ([M+H] + ).

[0260] Synthesis of intermediate ac

[0261] A mixture of intermediate ab (2.76 g, 8.44 mmol), dibenzofuran-4-boronic acid (2.01 g, 9.48 mmol), tetrakis(triphenylphosphine)palladium (0) (0.494 g, 0.427 mmol), potassium carbonate (3.58 g, 25.9 mmol), 1,4-dioxane (30 mL), and deionized water (10 mL) was stirred at 110°C for 19 hours. After the mixture cooled to room temperature, the solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was dissolved in dichloromethane and filtered through silica gel. The silica gel was washed with dichloromethane, and the filtrate was concentrated to obtain 2.72 g (5.93 mmol, 70% yield) of the white solid intermediate ac. 1 H NMR (400 MHz, CDCl3): d 8.68 (dd, J = 7.8, 1.4 Hz, 1H), 8.21 (dd, J = 7.7, 1.3 Hz, 1H), 8.03 (dt, J = 7.6, 0.6 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.55 (m, 2H), 7.42 (t, J = 7.4 Hz, 1H), 6.89 (dd, J = 8.7, 7.8 Hz, 2H). APCI-MS: Calculated value 459.15 (C 27 H 10 D5F3N3O), Observed value 459.24 ([M+H] + ).

[0262] Synthesis of compound P

[0263] A mixture of intermediate ac (2.45 g, 5.34 mmol), intermediate r (3.40 g, 5.92 mmol), tripotassium phosphate (17.3 g, 81.5 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 110 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, saturated ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.70 g (1.74 mmol, yield 33%) of compound P as a pale yellowish-green solid. 1 H NMR (400 MHz, CDCl3): d 8.16 (dd, J = 7.8, 1.1 Hz, 2H), 8.13 (t, J = 1.7 Hz, 1H), 7.97 (dd, J = 7.9, 1.3 Hz, 2H), 7.94 (dd, J = 7.6, 1.4 Hz, 1H), 7.90-7.86 (m, 3H), 7.53-7.46 (m, 3H), 7.43-7.41 (m, 7H), 7.39-7.24 (m, 8H), 7.15-7.11 (m, 4H), 7.04 (t, J = 7.7 Hz, 1H), 6.87 (dd, J = 7.8, 1.1 Hz, 1H). MALDI-TOF-MS: Calculated value 972.35 (C 69 H 34 D5N6O), Observed value 972.35 ([M+H] + ).

[0264] (Synthesis Example 17) Synthesis of the synthetic intermediate ad of compound Q

[0265] A mixture of 1-bromo-2,4,6-trifluorobenzene (6.38 g, 30.2 mmol) and THF (150 mL) was cooled to -20°C, and a turbogrignard reagent (approximately 1.3 MTHF solution, 25.5 mL, 33.1 mmol) was added and the mixture was stirred for 1 hour. Cyanuric acid chloride (8.33 g, 45.1 mmol) dissolved in THF (30 mL) was added to the reaction mixture and the mixture was stirred at 0°C for 18 hours. After the mixture was cooled to room temperature, an aqueous solution of ammonium chloride was added to separate the organic phase from the aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 3.22 g (11.5 mmol, yield 38%) of the white solid intermediate ad. 1 ¹H NMR (400 MHz, CDCl3): d 6.88-6.81 (m, 2H). APCI-MS: Calculated value 279.97 (C9H3Cl2F3N3), Observed value 279.99 ([M+H] + ).

[0266] Synthesis of intermediate ae

[0267] A mixture of intermediate ad (3.00 g, 10.7 mmol), dibenzofuran-2-ylboronic acid (5.03 g, 23.7 mmol), tetrakis(triphenylphosphine)palladium (0) (0.628 g, 0.543 mmol), potassium carbonate (8.96 g, 64.8 mmol), 1,4-dioxane (39 mL), and water (13 mL) was stirred at 110°C for 19 hours. After cooling the mixture to room temperature, the solid was filtered off and washed with water, methanol, ethyl acetate, and hexane in that order to obtain 3.93 g (7.23 mmol, yield 67%) of the white solid intermediate ae. APCI-MS: Calculated value 543.12 (C 33 H 16 F3N3O2), Observed value 543.50 ([M+H] + ).

[0268] Synthesis of compound Q

[0269] A mixture of intermediate ae (3.93 g, 7.23 mmol), intermediate r (4.55 g, 7.93 mmol), tripotassium phosphate (22.9 g, 107 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 150 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, reprecipitation was performed by adding aqueous ammonium chloride. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 0.849 g (0.803 mmol, yield 11%) of compound Q as a white solid. MALDI-TOF-MS: Calculated value 1057.33 (C 75 H 41 N6O2), Observed value 1057.33 ([M+H] + ).

[0270] (Synthesis Example 18) Synthesis of the synthetic intermediate af of compound R

[0271] Intermediate a (3.3 g, 4.00 mmol), 2-chloro-4-(2-dibenzofuranyl)-6-(phenyl-d ５ A mixture of )-1,3,5-triazine (3.6 g, 10.00 mmol), tetrakis(triphenylphosphine)palladium (0) (0.23 g, 0.20 mmol), potassium carbonate (1.66 g, 12.00 mmol), THF (15 mL), and water (5 mL) was stirred at 75°C for 15 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water, methanol, and hexane in that order. The obtained solid was washed with hot toluene, cooled to room temperature, and the solid was filtered off and washed with toluene and hexane in that order. 2.50 g (3.28 mmol, yield 81%) of the white solid intermediate af was obtained. APCI-MS: Calculated value 767.28 (C 48 H 17 D 10 F2N6O2), Observed value 767.53 ([M+H] + ).

[0272] Synthesis of compound R

[0273] A mixture of intermediate af (2.50 g, 3.26 mmol), intermediate c (1.60 g, 3.91 mmol), potassium carbonate (1.80 g, 13.0 mmol), and DMF (65 mL) was stirred at 150°C for 18 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 9:1) to obtain 0.72 g (0.63 mmol, yield 19%) of compound R as a yellow solid. 1 H NMR (400 MHz, CDCl3): d 9.17 (s, 1H), 9.01 (d, J = 1.6 Hz, 2H), 8.10 (d, J = 6.4 Hz, 4H), 8.03 (t, J = 8.4 Hz, 4H), 7.89 (s, 1H), 7.62-7.58. (m, 2H), 7.52-7.46 (m, 4H), 7.44-7.30 (m, 11H), 7.24-7.08 (m, 5H). APCI-MS: Calculated value 1135.43 (C 78 H 35 D 10 N8O2), Observed value 1135.84 ([M+H] + ).

[0274] (Synthesis Example 19) Synthesis of ag, a synthetic intermediate for compound S

[0275] A mixture of 2,4-difluoro-5-iodopyridine (5.72 g, 23.7 mmol) and THF (120 mL) was cooled to -50°C, isopropyl magnesium chloride (approximately 1 MTHF solution, 20 mL, 20.0 mmol) was added and the mixture was stirred for 1 hour, then zinc chloride (approximately 1 MTHF solution, 30 mL, 30.0 mmol) was added and the mixture was stirred for 30 minutes. After raising the reaction mixture to room temperature, 2-chloro-4,6-bis(phenyl-d) ５)-1,3,5-triazine (5.58 g, 20.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.19 g, 1.03 mmol) were added and the mixture was stirred at 80°C for 63 hours. After the mixture cooled to room temperature, water was added and the organic phase and aqueous phase were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:1) to obtain 5.07 g (14.2 mmol, yield 71%) of the white solid intermediate ag. 1 H NMR (400 MHz, CDCl3): d 9.39 (d, J = 10.1 Hz, 1H), 6.88 (dd, J = 9.8, 2.1 Hz, 1H). APCI-MS: Calculated value 357.18 (C 20 H3D 10 F2N4), Observed value 357.29 ([M+H] + ).

[0276] Synthesis of compound S

[0277] A mixture of intermediate ag (1.77 g, 4.96 mmol), intermediate c (2.45 g, 6.00 mmol), potassium carbonate (2.07 g, 15.0 mmol), and DMF (100 mL) was stirred at 150°C for 16 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 3:2) to obtain 2.57 g (3.54 mmol, yield 71%) of compound S as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): d 9.29 (s, 1H), 8.30 (d, J = 7.6 Hz, 2H), 8.20 (d, J = 6.9 Hz, 1H), 8.09 (d, J = 7.3 Hz, 1H), 7.96 (s, 1H), 7.63-7.03 (m, 14H). APCI-MS: Calculated value 725.33 (C 50 H 21 D 10N6), Observed value 725.49 ([M+H] + ).

[0278] (Synthesis Example 20) Synthesis of the synthetic intermediate ah of compound T

[0279] A mixture of 1,3-phenyldiboronic acid bis(pinacol) ester (4.3 g, 13.00 mmol), 1-bromo-3,6-di-tert-butylcarbazole (9.8 g, 27.30 mmol), tetrakis(triphenylphosphine)palladium (0) (0.75 g, 0.65 mmol), and potassium carbonate (7.19 g, 52.00 mmol) was mixed with toluene (39 mL), 1-butanol (13 mL), and deionized water (13 mL). The mixture was heated and stirred at 80°C under a nitrogen atmosphere for 12 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to separate the organic phase, and the aqueous phase was extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 6.8 g (10.7 mmol, yield 89%) of intermediate ah. APCI-MS: Calculated value 633.42 (C 46 H 53 N2), Observed value 633.80 ([M+H] + ).

[0280] Synthesis of compound T

[0281] A mixture of intermediate ag (1.42 g, 4.00 mmol), intermediate ah (3.04 g, 4.80 mmol), potassium carbonate (2.21 g, 16.00 mmol), and DMF (80 mL) was stirred at 150°C for 17 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (dichloromethane:hexane = 7:3) to obtain 1.31 g (1.37 mmol, yield 34%) of compound T as a yellow solid. 1H NMR (400 MHz, CDCl3): d 9.34 (s, 1H), 8.158 (t, J = 2.0 Hz, 2H), 8.10 (d, J = 2.0 Hz, 1H), 7.91 (d, J = 1.6 Hz, 1H), 7.64-7.50 (m, 5H), 7.18-7.13 (m, 2H), 7.06-6.97 (m, 3H), 6.708 (d, J = 8.0 Hz, 1H), 1.57-1.48 (m, 36H). APCI-MS: Calculated value 949.58 (C 66 H 53 D 10 N6), Observed value 950.00 ([M+H] + ).

[0282] (Synthesis Example 21) Synthesis of synthetic intermediate ai of compound U

[0283] In a 200 mL three-necked flask, 1-bromo-3,6-dimethylcarbazole (6.14 g, 22.4 mmol), 1,3,5-phenyltriboronic acid tris(pinacol) ester (3.19 g, 7.00 mmol), potassium carbonate (5.80 g, 42.0 mmol), tetrakis(triphenylphosphine)palladium (0) (404 mg, 350 mmol), dimethylacetamide (DMAc, 28.0 mL), and water (2.80 mL) were added and stirred at 120 °C. After the reaction was complete, the mixture was poured into water (84 mL) and the precipitate was filtered off. The resulting crude material was washed with THF / acetonitrile solvent to obtain 3.60 g of intermediate ai (pale orange solid) (yield 78.2%). APCI-MS: Calculated value 657.31 (C 48 H 39 N3), observed value 657.50 ([M+H] + ).

[0284] Synthesis of compound U

[0285] In a 200 mL three-necked flask, intermediate ai (4.93 g, 7.50 mmol), intermediate s (2.80 g, 7.50 mmol), potassium carbonate (5.18 g, 37.5 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 75.0 mL) were added and heated under reflux. After the reaction was complete, the mixture was poured into water (225 mL) and the precipitate was filtered off. The resulting crude product was washed with THF / acetonitrile solvent and then purified by column chromatography to obtain 0.732 g of compound U (yellow solid) (yield 10.0%). MALDI-MS: Calculated value 970.46(C) 69 H 38 D 10 N6), observed value 970.46 ([M+H] + ).

[0286] (Synthesis Example 22) Synthesis of Compound V

[0287] In a 200 mL three-necked flask, intermediate c (5.14 g, 12.6 mmol), intermediate s (4.48 g, 12.0 mmol), potassium carbonate (9.95 g, 72.0 mmol), and DMAc (60.0 mL) were added and stirred at 150°C. After the reaction was complete, carbazole-d ８ (3.15 g, 18.0 mmol) was added and the mixture was further stirred at 150°C. The reaction mixture was poured into water (240 mL) and the precipitate was filtered off. The resulting crude material was washed with acetonitrile and then purified by column chromatography to obtain 1.52 g of compound VT (white solid) (yield 14.2%). 1 H NMR (400MHz, CDCl3): d 8.24-8.19(d, 2H), 7.96-7.90 (m, 2H), 7.86-7.81 (d, 1H), 7.69-7.65 (m, 2H), 7.57-7.51 (m, 1H), 7.48-7.31 (m, 8H), 7.26-7.17 (m, 2H), 7.14-7.04 (m, 2H). APCI-MS: Calculated value 896.43 (C 63 H 20 D 18 N6), Observed value 896.50 ([M] + ).

[0288] (Synthesis Example 23) Synthesis of the synthetic intermediate aj of compound W

[0289] 1-Bromo-3-fluoro-4-iodobenzene (7.22 g, 24.0 mmol) was mixed with THF (100 mL), cooled to 0°C, and then Turbogrignard reagent (1.3 MTHF solution, 20.0 mL, 26.0 mmol) was added and the mixture was stirred for 2 hours. Then, zinc chloride (1 MTHF solution, 28.0 mL, 28.0 mmol) was added and the mixture was stirred at 0°C for 30 minutes, after which the mixture was heated to room temperature over 1 hour. To this mixture, tetrakis(triphenylphosphine)palladium (0) (1.15 g, 1.00 mmol) and 2-chloro-4,6-bis(phenyl-d) were added. ５ )-1,3,5-triazine (5.50 g, 20.0 mmol) was added and the mixture was heated and stirred at 75°C for 17 hours. After the mixture cooled to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene) to obtain 7.30 g (17.6 mmol, yield 88%) of the yellow solid intermediate aj. APCI-MS: Calculated value 416.10 (C 21 H4D 10 FN3), Observed value 416.42 ([M+H] + ).

[0290] Synthesis of intermediate ak

[0291] Intermediate aj (3.40 g, 8.16 mmol), 3,6-bis(phenyl-d ５A mixture of )-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (4.83 g, 10.6 mmol), tetrakis(triphenylphosphine)palladium (0) (0.47 g, 0.41 mmol), and potassium carbonate (2.25 g, 16.3 mmol) was mixed with toluene (24 mL), 1-butanol (8 mL), and water (8 mL). The mixture was heated and stirred at 80°C under a nitrogen atmosphere for 13 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to separate the organic phase, and the aqueous phase was extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (toluene / hexane = 7 / 3) to obtain 3.60 g (5.41 mmol, yield 66%) of intermediate ak. APCI-MS: Calculated value 665.37 (C 45 H 10 D 20 FN4), Observed value 665.72 ([M+H] + ).

[0292] Synthesis of compound W

[0293] A mixture of intermediate ak (1.40 g, 2.10 mmol), rubidium carbonate (1.96 g, 8.42 mmol), and 1-cyclohexyl-2-pyrrolidone (7 mL) was heated and stirred at 270°C for 8 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 0.49 g (0.37 mmol, yield 36%) of compound W as a yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.43 (d, J = 1.6 Hz, 2H), 8.29 (d, J = 1.6 Hz, 2H), 8.07 (d, J = 7.6 Hz, 2H), 7.83 (d, J = 1.6 Hz, 2H), 7.71 (d, J= 2.0 Hz, 2H), 7.59-7.51 (m, 4H), 7.19 (d, J = 8.4 Hz, 2H). APCI-MS: Calculated value 1289.72 (C90 H 17 D 40 N8), Observed value 1289.56 ([M+H] + ).

[0294] (Synthesis Example 24) Synthesis of al, an intermediate for the synthesis of compound X

[0295] A mixture of intermediate ak (3.98 g, 6.00 mmol), 1-bromo-3-iodobenzene (6.78 g, 24.0 mmol), potassium carbonate (4.14 g, 30.0 mmol), Cu powder (1.90 g, 30.0 mmol), 18-crown-6 (0.31 g, 1.2 mmol), and 1,2-dichlorobenzene (ODCB, 24 mL) was heated and stirred at 200°C for 20 hours. After the mixture cooled to room temperature, water was added and reprecipitation was performed. The resulting solid was filtered off, and the solid was washed with water, methanol, and hexane in that order to obtain the crude product. This was purified by silica gel column chromatography (toluene:hexane = 4:6) to obtain 2.20 g (2.75 mmol, yield 45%) of intermediate al. APCI-MS: Calculated value 819.31 (C 51 H 13 D 20 BrFN4), Observed value 819.70 ([M+H] + ).

[0296] Synthesis of intermediate am

[0297] Intermediate al (2.21 g, 2.70 mmol), 3,6-bis(phenyl-d ５A mixture of )-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (1.96 g, 4.32 mmol), tetrakis(triphenylphosphine)palladium (0) (0.15 g, 0.13 mmol), and potassium carbonate (0.74 g, 5.40 mmol) was mixed with toluene (9 mL), 1-butanol (3 mL), and water (3 mL), and heated and stirred at 80°C under a nitrogen atmosphere for 17 hours. After the mixture cooled to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off, and the solid was washed with water, methanol, and hexane in that order to obtain the crude product. This was purified by silica gel column chromatography (toluene:hexane = 4:6) to obtain 1.20 g (1.17 mmol, yield 43%) of intermediate am. APCI-MS: Calculated value 1068.59 (C 75 H 19 D 30 FN5), Observed value 1069.18 ([M+H] + ).

[0298] Synthesis of compound X

[0299] A mixture of intermediate am (1.06 g, 1.00 mmol), rubidium carbonate (0.92 g, 4.00 mmol), and N-methyl-2-pyrrolidone (NMP, 20 mL) was heated and stirred at 180°C for 17 hours. After cooling to room temperature, water was added and reprecipitation was performed. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 0.93 g (0.88 mmol, yield 88%) of compound X as a yellow solid. 1H NMR (400 MHz, CDCl3): d 8.47 (d, J = 1.6 Hz, 1H), 8.40 (d, J = 1.6 Hz, 1H), 8.36 (d, J = 1.6 Hz, 1H), 8.24 (s, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.72 (d, J = 1.6 Hz, 1H), 7.64 (d, J = 1.6 Hz, 1H), 7.58-7.45 (m, 3H), 7.38-7.30 (m, 2H), 7.22-7.00 (m, 5H). APCI-MS: Calculated value 1048.58 (C 75 H 18 D 30 N5), Observed value 1049.12 ([M+H] + ).

[0300] (Synthesis Example 25) Synthesis of the synthetic intermediate an of compound Y

[0301] 1,4-Benzene diboronic acid bis(pinacol) ester (4.60 g, 13.9 mmol), 1-bromo-2,6-di(phenyl-d ５ Carbazole (12.5 g, 30.6 mmol), potassium carbonate (11.6 g, 83.9 mmol), tetrakis(triphenylphosphine)palladium (0) (0.405 g, 0.350 mmol), 1,4-dioxane (50 mL), and water (20 mL) were added, and the mixture was heated and stirred at 110°C for 16 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane = 2:1) to obtain 6.64 g (9.05 mmol, yield 65%) of the pale yellowish-green intermediate an. 1H NMR (400 MHz, CDCl3): d 8.41 (s, 2H), 8.39-8.38 (m, 4H), 8.17 (t, J = 1.6 Hz, 1H), 7.88-7.78 (m, 5H), 7.68 (dd, J = 8.7, 1.8 Hz, 2H), 7.47 (d, J = 8.7 Hz, 2H). APCI-MS: Calculated value 733.42 (C 54 H 17 D 20 N2), Observed value 733.20 ([M+H] + ).

[0302] Synthesis of compound Y

[0303] A mixture of intermediate m (1.43 g, 4.02 mmol), intermediate an (3.25 g, 4.43 mmol), tripotassium phosphate (4.27 g, 20.1 mmol), and NMP (80 mL) was stirred at 170°C for 13 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 2.10 g (2.00 mmol, 50% yield) of compound Y as a pale yellowish-green solid. 1 H NMR (400 MHz, DMSO-d6): d 8.86 (dd, J = 3.8, 1.7 Hz, 2H), 8.75 (d, J = 1.8 Hz, 1H), 8.66 (d, J = 1.8 Hz, 1H), 8.36 (s, 1H), 8.23 ​​(d, J = 8.2 Hz, 1H), 7.88 (dd, J = 8.4, 1.6 Hz, 1H), 7.72-7.68 (m, 4H), 7.56 (dd, J= 8.2, 1.6 Hz, 1H), 7.49 (d, J = 8.5 Hz, 1H), 7.26-7.17 (m, 3H), 7.12 (d, J = 7.3 Hz, 1H). MALDI-TOF-MS: Calculated value 1047.57 (C 75 H 17 D 30 N5), Observed value 1047.55 (M + ).

[0304] (Synthesis Example 26) Synthesis of the synthetic intermediate ao of compound Z

[0305] A mixture of 1-bromo-3,5-difluorobenzene (2.39 g, 12.4 mmol) and THF (120 mL) was cooled to -85°C, and LDA (1.01 MTHF solution, 13 mL, 13.1 mmol) was added and the mixture was stirred for 1 hour. Zinc chloride (approximately 1 MTHF solution, 15 mL, 15.0 mmol) was added to the mixture and the mixture was stirred at -85°C for 30 minutes, then stirred at room temperature for 1 hour. Tetrakis(triphenylphosphine)palladium (0) (0.574 g, 0.497 mmol) and 2-chloro-4,6-di(phenyl-d) were added to the reaction mixture. ５ )-1,3,5-triazine (2.77 g, 9.97 mmol) was added and the mixture was stirred at 80°C for 16 hours. After the mixture cooled to room temperature, water was added and the mixture was filtered by Celite. The filtrate was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:5) to obtain 1.70 g (3.91 mmol, yield 39%) of the white solid intermediate ao. 1 H NMR (400 MHz, CDCl3): d 7.31-7.27 (m, 2H). APCI-MS: Calculated value 433.08 (C 21 H2D 10 BrF2N3), Observed value 433.60 (M + ).

[0306] Synthesis of intermediate ap

[0307] A mixture of intermediate ao (1.70 g, 3.91 mmol), 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (1.31 g, 4.47 mmol), tetrakis(triphenylphosphine)palladium (0) (0.236 g, 0.204 mmol), potassium carbonate (1.65 g, 11.9 mmol), 1,4-dioxane (15 mL), and water (5 mL) was stirred at 110°C for 15 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water, methanol, and hexane in that order to obtain 1.74 g (3.34 mmol, yield 86%) of the pale orange solid intermediate ap. 1 H NMR (400 MHz, CDCl3): d 8.37 (s, 1H), 8.16-8.12 (m, 2H), 7.50-7.28 (m, 7H). APCI-MS: calculated value 520.23 (C 33 H 10 D 10 F2N4), Observed value 520.6 (M + ).

[0308] Synthesis of intermediate aq

[0309] A mixture of intermediate ap (1.62 g, 3.11 mmol), 1,3-dibromo-5-iodobenzene (1.69 g, 4.67 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.412 g, 0.450 mmol), 4,5-bis(diphenylphosphin)-9,9-dimethylxanthene (xantphos, 0.180 g, 0.311 mmol), sodium tert-butoxide (0.602 g, 6.26 mmol), and xylene (30 mL) was stirred at 150°C for 1 hour. After the mixture cooled to room temperature, the reaction mixture was filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated, and the crude product was purified by flash column chromatography (dichloromethane:hexane = 1:3) to obtain 1.82 g (2.41 mmol, yield 78%) of the pale orange solid intermediate aq. 1H NMR (400 MHz, CDCl3): d 8.24 (dd, J = 6.2, 3.0 Hz, 1H), 8.19 (dt, J = 7.6, 1.0 Hz, 1H), 7.64 (t, J = 1.7 Hz, 1H), 7.49-7.43 (m, 3H), 7.39-7.35 (m, 2H), 7.29 (d, J = 1.6 Hz, 2H), 6.82 (d, J = 8.2 Hz, 2H). APCI-MS: Calculated value 752.08 (C 39 H 12 D 10 Br2F2N4), Observed value 752.2 (M + ).

[0310] Synthesis of intermediate ar

[0311] A mixture of intermediate aq (1.80 g, 2.38 mmol), 3,6-dimethyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (2.38 g, 7.40 mmol), tetrakis(triphenylphosphine)palladium (0) (0.141 g, 0.122 mmol), tripotassium phosphate (2.56 g, 12.1 mmol), 1,4-dioxane (18 mL), and water (6 mL) was stirred at 110°C for 16 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 1.30 g (1.32 mmol, yield 56%) of the pale yellowish-green solid intermediate ar. 1H NMR (400 MHz, CDCl3): d 8.30-8.25 (m, 2H), 8.20 (s, 2H), 8.12 (t, J = 1.5 Hz, 1H), 7.80 (s, 2H), 7.76 (s, 2H), 7.62 (d, J = 8.2 Hz, 1H), 7.54-7.52 (m, 3H), 7.44-7.41 (m, 3H), 7.30 (d, J = 1.1 Hz, 2H), 7.00 (dd, J = 8.4, 1.3 Hz, 2H), 6.92 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 8.2 Hz, 2H), 2.43 (s, 6H), 2.39 (s, 6H). APCI-MS: Calculated value 983.45 (C 67 H 37 D 10 F2N6), Observed value 984.02 ([M+H] + ).

[0312] Synthesis of compound Z

[0313] A mixture of intermediate ar (1.24 g, 1.26 mmol), tripotassium phosphate (1.36 g, 6.41 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 25 mL) was stirred at 230°C for 1 hour. After cooling to room temperature, saturated ammonium chloride aqueous solution was added and reprecipitation was performed. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 1:2) to obtain 0.90 g (0.954 mmol, yield 75%) of compound Z as a white solid. 1H NMR (400 MHz, CDCl3): 8.20 (dd, J = 7.9, 1.3 Hz, 1H), 8.16 (d, J = 7.8 Hz, 1H), 8.07 (t, J = 1.6 Hz, 1H), 7.75-7.75 (m, 2H), 7.65-7.65 (m, APCI-MS: Calculated value 943.43 (C 67 H 35 D 10 N6), Observed value 943.36 ([M+H] + ).

[0314] (Synthesis Example 27) Synthesis of as, an intermediate for the synthesis of compound AA

[0315] A mixture of intermediate ad (2.81 g, 10.0 mmol), 4-tert-butylphenylboronic acid (3.92 g, 22.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.582 g, 0.503 mmol), potassium carbonate (8.35 g, 60.4 mmol), 1,4-dioxane (36 mL), and water (12 mL) was stirred at 110°C for 38 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:2) to obtain 2.75 g (5.78 mmol, yield 58%) of the white solid intermediate as. 1 H NMR (400 MHz, CDCl3): d 8.59 (d, J = 8.7 Hz, 4H), 7.57 (d, J = 8.8 Hz, 4H), 6.87-6.80 (m, 2H), 1.39 (s, 18H). APCI-MS: Calculated value 475.22 (C 29 H 28 F3N3), Observed value 475.70 (M + ).

[0316] Synthesis of compound AA

[0317] A mixture of intermediate as (1.66 g, 3.49 mmol), intermediate r (2.20 g, 3.83 mmol), tripotassium phosphate (3.81 g, 17.9 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 70 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 1:2) to obtain 0.73 g (0.737 mmol, yield 21%) of compound AA as a white solid. 1 H NMR (400 MHz, CDCl3): d 8.17 (dd, J = 7.8, 1.1 Hz, 2H), 8.07 (t, J = 1.7 Hz, 1H), 7.99 (dd, J = 7.8, 1.4 Hz, 2H), 7.91 (d, J = 7.6 Hz, 2H), 7.50-7.24 (m, 19H), 7.18-7.12 (m, 8H), 1.30 (s, 18H). APCI-MS: Calculated value 989.44 (C 71 H 53 N6), Observed value 990.02 ([M+H] + ).

[0318] (Synthesis Example 28) Synthesis of as, a synthetic intermediate of compound AB

[0319] A mixture of 2,6-difluorobenzonitrile (1.69 g, 12.1 mmol) and THF (60 mL) was cooled to -85°C, and LDA (1.01 MTHF solution, 13 mL, 13.1 mmol) was added and the mixture was stirred for 2 hours. Isopropoxyboronic acid pinacol ester (3.0 mL, 15.0 mmol) was added to the mixture and the mixture was stirred at -85°C for 30 minutes, then stirred at room temperature for 1.5 hours. After distillation of the solution, tetrakis(triphenylphosphine)palladium (0) (0.582 g, 0.504 mmol), 4-bromobenzonitrile (1.82 g, 10.0 mmol), potassium carbonate (4.13 g, 29.9 mmol), 1,4-dioxane (36 mL), and water (12 mL) were added and the mixture was stirred at 110°C for 13 hours. After the mixture was cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:1) to obtain 1.49 g (6.20 mmol, yield 62%) of the white solid intermediate as. 1 H NMR (400 MHz, CDCl3): d 7.79 (d, J = 8.5 Hz, 2H), 7.70 (td, J = 8.6, 6.1 Hz, 1H), 7.61 (dd, J = 8.8, 1.6 Hz, 2H), 7.20 (ddd, J = 8.6, 6.1, 1.2Hz, 1H).

[0320] Synthesis of compound AB

[0321] A mixture of intermediate as (0.725 g, 3.02 mmol), intermediate an (2.41 g, 3.29 mmol), tripotassium phosphate (3.19 g, 15.0 mmol), and DMF (60 mL) was stirred at 150°C for 1 hour. After cooling to room temperature, ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 4:1) to obtain 1.45 g (1.55 mmol, yield 51%) of compound AB as a yellow solid. 1H NMR (400 MHz, DMSO-d6): d 8.84 (d, J = 10.8 Hz, 2H), 8.76 (d, J = 1.6 Hz, 2H), 7.89 (d, J = 8.5 Hz, 1H), 7.85 (d, J = 8.7 Hz, 1H), 7.74 (d, J= 8.2 Hz, 1H), 7.65-7.54 (m, 7H), 7.45 (t, J = 7.4 Hz, 1H), 7.36 (d,J = 6.9 Hz, 1H), 7.32 (d, J = 7.3 Hz, 1H), 7.26 (s, 1H), 7.21 (d, J= 7.6 Hz, 2H). APCI-MS: Calculated value 933.46 (C 68 H 21 D 20 N4), Observed value 934.11 ([M+H] + ).

[0322] (Synthesis Example 29) Synthesis of the synthetic intermediate au of compound AC

[0323] Under a nitrogen atmosphere, a mixture of 2,6-difluorobenzonitrile (2.7 g, 19.80 mmol) and THF (36 mL) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 21.6 mL, 21.60 mmol) was added over 15 minutes. After stirring for 1 hour, zinc chloride solution (1 M hexane / THF solution, 23.4 mL, 23.40 mmol) was added, and the mixture was stirred for another hour. The reaction solution was heated to room temperature, and 2-chloro-4,6-di(phenyl-d)nitrile was added. ５ )-Pyrimidine (4.9 g, 18.00 mmol), palladium acetate (0.20 g, 0.90 mmol), and Sphos (0.74 g, 1.80 mmol) were added and the mixture was heated and stirred at 80°C for 16 hours. After cooling to room temperature, aqueous ammonium chloride solution was added, and the organic phase was separated. The aqueous phase was then extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 3.0 g (7.92 mmol, yield 44%) of the intermediate au. APCI-MS: Calculated value 381.18 (C 22H3D 10 F2N4), Observed value 381.16 ([M+H] + ).

[0324] Synthesis of compound AC

[0325] A mixture of intermediate au (2.0 g, 5.3 mmol), intermediate an (4.2 g, 5.8 mmol), potassium carbonate (3.6 g, 26 mmol), and NMP (105 mL) was heated and stirred at 140°C for 3 hours under a nitrogen atmosphere. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 6:4) to obtain 0.88 g (0.82 mmol, yield 15%) of compound AC as a yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.47 (d, J = 1.6 Hz, 1H), 8.40 (d, J = 1.6 Hz, 1H), 8.36 (d, J = 2.0 Hz, 1H), 8.24 (d, J = 1.6 Hz, 1H), 8.09 (d, J= 8.0 Hz, 1H), 7.72 (d, J = 2.0 Hz, 1H), 7.64 (d, J = 1.6 Hz, 1H), 7.58-7.45 (m, 3H), 7.38-7.30 (m, 2H), 7.23-7.18 (m, 1H), 7.15-7.00 (m, 4H). APCI-MS: Calculated value 1072.58 (C 77 H 18 D 30 N5), Observed value 1072.87 ([M+H] + ).

[0326] (Synthesis Example 30) Synthesis of the synthetic intermediate av of compound AD

[0327] A mixture of intermediate aq (3.48 g, 4.61 mmol), bis(pinacolato)diborone (4.67 mmol, 18.4 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.170 g, 0.232 mmol), potassium acetate (2.76 g, 28.1 mmol), and 1,4-dioxane (23 mL) was stirred at 110°C for 13 hours. After the mixture cooled to room temperature, it was filtered through silica gel, and the silica gel was washed with dichloromethane. The filtrate was concentrated and washed with methanol and then hexane to obtain 3.77 g (4.44 mmol, 96% yield) of the pale orange solid intermediate av. 1 H NMR (400 MHz, CDCl3): d 8.38 (s, 1H), 8.24 (dd, J = 6.4, 2.5 Hz, 1H), 8.19 (d, J= 7.6 Hz, 1H), 7.68 (s, 2H), 7.44-7.30 (m, 5H), 6.76-6.72 (m, 2H), 1.22 (s, 12H), 1.15 (s, 12H).

[0328] Synthesis of intermediate aw

[0329] A mixture of intermediate av (3.76 g, 4.43 mmol), 6-bromo-5H-benzofl[3,2-c]carbazole (2.38 g, 7.40 mmol), tetrakis(triphenylphosphine)palladium (0) (0.265 g, 0.229 mmol), potassium carbonate (2.49 g, 18.0 mmol), 1,4-dioxane (34 mL), and water (11 mL) was stirred at 110°C for 15 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane = 3:2) to obtain 4.07 g (3.67 mmol, yield 83%) of the pale yellow solid intermediate aw. 1H NMR (400 MHz, CDCl3): d 8.66 (s, 2H), 8.44 (dd, J = 6.3, 2.6 Hz, 2H), 8.32-8.27 (m, 2H), 8.25 (t, J = 1.6 Hz, 1H), 8.02 (d, J = 4.6 Hz, 2H), 7.75 (dd, J = 7.7, 0.6 Hz, 2H), 7.71-7.67 (m, 5H), 7.56 (ddd, J = 8.4, 7.6, 1.2 Hz, 1H), 7.48-7.41 (m, 3H), 7.37 (ddd, J = 8.0, 7.2, 1.2Hz, 2H), 7.29-7.14 (m, 6H), 7.09-7.03 (m, 4H). APCI-MS: Calculated value 1107.41 (C 75 H 33 D 10 F2N6O2), Observed value 1107.98 ([M+H] + ).

[0330] Synthesis of compound AD

[0331] A mixture of intermediate aw (4.07 g, 3.68 mmol), tripotassium phosphate (3.94 g, 18.6 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 74 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, saturated ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 2.18 g (2.04 mmol, yield 56%) of compound AD as a yellow solid. 1H NMR (400 MHz, CDCl3): d 8.36 (dt, J = 7.6, 0.8 Hz, 2H), 8.28 (t, J = 1.6 Hz, 1H), 8.22 (dd, J = 7.8, 1.1 Hz, 1H), 8.19-8.17 (m, 1H), 8.00 (s, 2H), 7.95-7.93 (m, 2H), 7.68-7.66 (m, 2H), 7.52-7.29 (m, 17H), 7.25 (d, J = 1.6 Hz, 2H). APCI-MS: Calculated value 1067.39 (C 75 H 31 D 10 N6O2), Observed value 1067.97 ([M+H] + ).

[0332] (Synthesis Example 31) Synthesis of the synthetic intermediate ax of compound AE

[0333] A mixture of 2,3,5,6-tetrafluoro-1,1'-biphenyl-4,4'-dicarbonitric acid (3.0 g, 10.9 mmol), intermediate c (4.8 g, 12.0 mmol), potassium carbonate (7.5 g, 54.3 mmol), and NMP (108 mL) was stirred at 130°C for 3 hours. After cooling to room temperature, water was added and reprecipitation was performed. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 8:2) to obtain 1.15 g (0.63 mmol, yield 16%) of the white solid intermediate ax. APCI-MS: Calculated value 645.19 (C 44 H 23 F2N4), Observed value 645.54 ([M+H] + ).

[0334] Synthesis of compound AE

[0335] Intermediate ax (0.90 g, 1.40 mmol), carbazole-d ８A mixture of (2.45 g, 14.00 mmol), potassium carbonate (0.96 g, 7.00 mmol), and NMP (28 mL) was heated and stirred at 150°C for 3 hours under a nitrogen atmosphere. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 7:3) to obtain 0.94 g (0.98 mmol, yield 70%) of compound AE as a yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.21-8.18 (m, 1H), 7.83-7.78 (m, 3H), 7.77-7.72 (m, 2H), 7.64-7.59 (m, 2H), 7.29-7.06 (m, 14H). APCI-MS: Calculated value 955.43 (C 68 H 23 D 16 N6), Observed value 955.71 ([M+H] + ).

[0336] (Synthesis Example 32) Synthesis of the synthetic intermediate ay of compound AF

[0337] Under a nitrogen atmosphere, a THF solution (300 mL) of intermediate s (10 g, 26.7 mmol) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 26.7 mL, 26.7 mmol) was added over 15 minutes. After stirring for 1 hour, zinc chloride solution (1 M hexane / THF solution, 26.7 mL, 26.7 mmol) was added, and the mixture was stirred for a further 2 hours. The reaction solution was heated to room temperature, and 2-chloro-4,6-bis(phenyl-d) was added. ５ )-1,3,5-triazine (6.16 g, 22.2 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.28 mg, 0.05 mmol) were added and the mixture was heated and stirred at 75°C for 18 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water, methanol, and hexane in that order. The obtained solid was washed with hot toluene, cooled to room temperature, and the solid was filtered off and washed with toluene and hexane in that order. 12.6 g (20.4 mmol, yield 92.6%) of the white solid intermediate ay was obtained. APCI-MS: Calculated value 624.30 (C 36HD 20 F3N6), Observed value 624.73 ([M+H] + ).

[0338] Synthesis of compound AZ

[0339] A mixture of intermediate ay (2 g, 3.25 mmol), intermediate c (1.45 g, 3.57 mmol), potassium carbonate (2.23 g, 16.2 mmol), and N-methylpyrrolidone (81.2 mL) was stirred at 170°C for 18 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 2.4 g (2.44 mmol, yield 75%) of the yellow solid intermediate az. APCI-MS: Calculated value 993.46 (C 66 H 20 D 20 FN8), Observed value 993.19 ([M+H] + ).

[0340] Synthesis of compound AF

[0341] Intermediate az (1 g, 1.01 mmol), carbazole-d ８ A mixture of (0.354 g, 2.02 mmol), potassium carbonate (0.558 g, 4.04 mmol), and N-methylpyrrolidone (25 mL) was stirred at 170°C for 18 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 0.6 g (0.53 mmol, yield 52.6%) of compound AF as a yellow solid. APCI-MS: Calculated value 1138.58 (C 78 H 20 D 28 FN9), Observed value 1138.19 ([M+H] + ).

[0342] (Synthesis Example 33) Synthesis of Intermediate 2 of Compound AG

[0343] A mixture of 1-(4-bromophenyl)adamantane (1.74 g, 5.97 mmol) and THF (60 mL) was cooled to -75°C, and n-BuLi (1.51 M hexane solution, 4.5 mL, 6.80 mmol) was added and the mixture was stirred for 2 hours. Pinacol isopropoxyboronic acid (1.5 mL, 7.42 mmol) was added to the reaction mixture and the mixture was stirred for 0.5 hours, then stirred at room temperature for 3 hours. Intermediate ab (1.62 g, 5.00 mmol), tetrakis(triphenylphosphine)palladium (0) (0.296 g, 0.256 mmol), potassium carbonate (2.09 g, 15.1 mmol), and water (20 mL) were added to the reaction mixture and the mixture was stirred at 80°C for 19 hours. After the mixture was cooled to room temperature, it was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:4) to obtain 1.33 g (2.64 mmol, yield 53%) of the white solid intermediate ba. 1 H NMR (400 MHz, CDCl3): d 8.61 (d, J = 8.5 Hz, 2H), 7.55 (d, J = 8.4 Hz, 2H), 6.86-6.82 (m, 2H), 2.14 (s, 3H), 1.98 (d, J = 2.5 Hz, 6H), 1.84-1.77 (m, 6H). APCI-MS: Calculated value 503.25 (C 31 H 22 D5F3N3), Observed value 503.41 ([M+H] + ).

[0344] Synthesis of compound AG A mixture of intermediate ba (2.15 g, 4.28 mmol), intermediate r (2.07 g, 3.61 mmol), tripotassium phosphate (3.82 g, 18.0 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 72 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, saturated ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.87 g (1.84 mmol, yield 51%) of compound AG as a yellow-green solid. 1 H NMR (400 MHz, CDCl3): d 8.17 (d, J = 7.8 Hz, 2H), 8.05 (t, J = 1.6 Hz, 1H), 8.00 (dd, J = 7.8, 1.1 Hz, 2H), 7.91 (d, J = 7.8 Hz, 2H), 7.50-7.24 (m, 17H), 7.18-7.12 (m, 6H), 2.12 (s, 3H), 1.88 (d, J = 2.5 Hz, 6H), 1.83-1.75 (m, 6H). APCI-MS: Calculated value 1016.45 (C 73 H 46 D5N6), Observed value 1016.90 ([M+H] + ).

[0345] (Synthesis Example 34) Synthesis of intermediate bb of compound AH

[0346] A mixture of intermediate ab (2.09 g, 6.40 mmol), 4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-2-carbonitrile (1.95 g, 6.40 mmol), tetrakis(triphenylphosphine)palladium (0) (0.374 g, 0.324 mmol), potassium carbonate (2.62 g, 19.0 mmol), 1,4-dioxane (48 mL), and water (16 mL) was stirred at 110 °C for 12 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water. The crude product was dissolved in dichloromethane, filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 1.56 g (3.32 mmol, 52% yield) of the white solid intermediate bb. 1 H NMR (400 MHz, CDCl3): d 8.82 (d, J = 8.5 Hz, 2H), 7.82 (ddd, J = 8.0, 4.0, 0.8 Hz, 1H), 7.76 (d, J = 8.5 Hz, 2H), 7.71 (td, J = 7.8, 1.4 Hz, 1H), 7.60 (ddd, J = 7.6, 4.8, 0.8 Hz, 1H), 7.51 (td, J = 7.7, 1.3 Hz, 1H), 6.89-6.84 (m, 2H) APCI-MS: Calculated value 470.17 (C 28 H 11 D5F3N4), Observed value 470.49 ([M+H] + ).

[0347] Synthesis of compound AH

[0348] A mixture of intermediate bb (1.32 g, 2.81 mmol), intermediate r (1.33 g, 2.32 mmol), tripotassium phosphate (2.49 g, 11.7 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 12 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:1) to obtain 1.15 g (1.17 mmol, 50% yield) of compound AH as a yellow-green solid. 1 H NMR (400 MHz, CDCl3): d 8.18 (d, J = 7.8 Hz, 2H), 8.04-8.02 (m, 3H), 7.93 (d, J= 7.8 Hz, 2H), 7.80 (dd, J = 8.1, 1.3 Hz, 1H), 7.67 (td, J = APCI-MS: Calculated value 983.37 (C 70 H 35 D5N7), Observed value 983.59 ([M+H] + ).

[0349] (Synthesis Example 35) Synthesis of the synthetic intermediate bc of compound AI

[0350] A mixture of intermediate ab (2.03 g, 6.21 mmol), 2,6-dimethyl-4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-4-carbonitrile (1.74 g, 5.38 mmol), tetrakis(triphenylphosphine)palladium (0) (0.303 g, 0.262 mmol), potassium carbonate (2.15 g, 15.5 mmol), THF (40 mL), and water (12 mL) was stirred at 80°C for 16 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was filtered through silica gel, and the silica gel was washed with dichloromethane. The obtained filtrate was concentrated to obtain 2.12 g (4.26 mmol, 79% yield) of the pale orange solid intermediate bc. 1 H NMR (400 MHz, CDCl3): d 8.78 (dt, J = 8.3, 1.7 Hz, 2H), 7.44 (s, 2H), 7.33-7.30 (m, 2H), 6.89-6.84 (m, 2H), 2.09 (s, 6H). APCI-MS: Calculated value 498.20 (C 30 H 15 D5F3N4), Observed value 498.62 ([M+H] + ).

[0351] Synthesis of compound AI

[0352] A mixture of intermediate bc (2.09 g, 4.20 mmol), intermediate r (2.00 g, 3.49 mmol), tripotassium phosphate (3.78 g, 17.8 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 18 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:1) to obtain 1.70 g (1.68 mmol, yield 48%) of compound AI as a white solid. 1H NMR (400 MHz, CDCl3): d 8.17 (dd, J = 7.8, 1.1 Hz, 2H), 8.03 (t, J = 1.6 Hz, 1H), 8.00 (dd, J = 7.8, 1.1 Hz, 2H), 7.91 (d, J = 7.8 Hz, 2H), 7.51-7.28 (m, 18H), 7.23 (d, J = 8.0 Hz, 1H), 7.17-7.13 (m, 4H), 6.90 (d, J = 8.5 Hz, 2H), 2.01 (s, 6H). APCI-MS: Calculated value 1011.40 (C 72 H 39 D5N7), Observed value 1011.67 ([M+H] + ).

[0353] (Synthesis Example 36) Synthesis of intermediate bd of compound AJ

[0354] In a 100 mL three-necked flask, add 2-chloro-4,6-bis(phenyl-d ５ Pyrimidine (2.76 g, 10.0 mmol), 2,4,6-trifluorobenzonitrile (4.71 g, 30.0 mmol), palladium acetate (44.9 mg, 200 μmol), tricyclohexylphosphine (168 mg, 600 μmol), 2-ethylhexanoic acid (57.6 mg, 400 μmol), potassium carbonate (2.07 g, 15.0 mmol), and toluene (20.0 mL) were added, and the mixture was heated under reflux. After the reaction was complete, the precipitate was removed by filtration, and the resulting crude product was purified by silica gel chromatography to obtain 2.55 g of intermediate bd (pale yellow solid) (yield 64.2%). 1 ¹H NMR (400MHz, CDCl3): d 8.14 (s, 1H). APCI-MS: Calculated value 398.17 (C 23 H3D 10 F3N3), Observed value 398.30 ([M+H] + ).

[0355] Synthesis of compound AJ

[0356] In a 50 mL round-bottom flask, intermediate bd (1.19 g, 3.00 mmol), intermediate r (1.72 g, 3.00 mmol), potassium carbonate (4.14 g, 30.0 mmol), and NMP (15.0 mL) were added and heated under reflux. After the reaction was complete, the mixture was poured into water (30 mL) and the precipitate was filtered off. The resulting crude product was washed with THF / acetonitrile solvent and then purified by column chromatography to obtain 0.272 g of compound AJ (pale yellow solid) (yield 9.96%). 1 H NMR (400MHz, CDCl3): d 8.20-8.14 (m,3H), 8.04-7.97 (m,2H), 7.92 (d, 2H), 7.53(t, 1H), 7.51-7.45 (m, 3H), 7.43-7.27 (m, 10H), 7.18-7.12 (m, 4H). APCI-MS: Calculated value 911.37(C 65 H 27 D 10 N6), Observed value 911.60 ([M+H] + ).

[0357] (Synthesis Example 37) Synthesis of Compound AK

[0358] In a 50 mL round-bottom flask, intermediate bd (1.19 g, 3.00 mmol), intermediate c (1.22 g, 3.00 mmol), potassium carbonate (2.48 g, 18.0 mmol), and NMP (15.0 mL) were added and stirred at 150°C. After the reaction was complete, carbazole-d ８ (3.15 g, 18.0 mmol) was added and the mixture was further stirred at 150°C. The reaction mixture was poured into water (30 mL) and the precipitate was filtered off. The resulting crude product was washed with acetonitrile solvent and then purified by column chromatography to obtain 0.250 g of compound AK (white solid) (yield 12.3%). 1H NMR (400MHz, CDCl3): d 8.25-8.21 (m,2H), 8.01-7.97 (m,1H), 7.93 (s, 1H), 7.81-7.77 (m, 1H), 7.71-7.69 (m, 1H), 7.64-7.51 (m, 3H), 7.49-7.35 (m,7H), 7.03-6.90 (m, 4H). APCI-MS: Calculated value 921.44(C 65 H 21 D 18 N6), observed value 921.86 ([M+H] + ).

[0359] (Synthesis Example 38) Synthesis of be, an intermediate for the synthesis of compound AL

[0360] 1,3,5-Phenyltriboronic acid tris(pinacol) ester (2.96 g, 6.49 mmol), 1-bromo-9H-carbazole-d ７ A mixture of (5.43 g, 21.4 mmol), palladium(II) acetate (0.147 g, 0.655 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.378 g, 1.30 mmol), potassium carbonate (8.97 g, 64.9 mmol), 1,4-dioxane (48 mL), and water (16 mL) was stirred at 110°C for 14 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (toluene:hexane = 2:1) to obtain 1.57 g (2.64 mmol, yield 41%) of the white solid intermediate be. 1 H NMR (400 MHz, CDCl3): d 8.43 (s, 3H), 8.15 (s, 3H). APCI-MS: calculated value 594.35 (C 42 H6D 21 N3), Observed value 594.45 (M + ).

[0361] Synthesis of compound AL

[0362] A mixture of intermediate s (0.986 g, 2.64 mmol), intermediate be (1.30 g, 2.19 mmol), tripotassium phosphate (2.33 g, 11.0 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 11 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 0.69 g (0.760 mmol, yield 35%) of compound AL as a pale yellowish-green solid. 1 H NMR (400 MHz, CDCl3): d 8.03 (t, J = 1.6 Hz, 1H), 7.43 (s, 2H), 7.13 (d, J = 1.6 Hz, 2H). APCI-MS: Calculated value 907.49 (C 63 H5D 31 N6), Observed value 907.53 (M + ).

[0363] (Synthesis Example 39) Synthesis of intermediate bf of compound AM

[0364] Under a nitrogen atmosphere, a mixture of 2,6-difluorobenzonitrile (5.5 g, 39.6 mmol) and THF (80 mL) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 43.2 mL, 43.2 mmol) was added over 15 minutes. After stirring for 1 hour, zinc chloride solution (1 M hexane / THF solution, 46.8 mL, 46.8 mmol) was added, and the mixture was stirred for another hour. The reaction solution was heated to room temperature, and 2-chloro-4,6-bis(phenyl-d) ５)-1,3,5-triazine (10.0 g, 36.0 mmol), palladium acetate (0.40 g, 1.80 mmol), and Sphos (1.47 g, 3.60 mmol) were added and the mixture was heated and stirred at 80°C for 18 hours. After cooling to room temperature, aqueous ammonium chloride solution was added, and the organic phase was separated. The aqueous phase was then extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (toluene / hexane = 5 / 5) to obtain 2.8 g (7.35 mmol, yield 20%) of intermediate bf. APCI-MS: Calculated value 381.18 (C 22 H3D 10 F2N4), Observed value 381.16 ([M+H] + ).

[0365] Synthesis of compound AM

[0366] A mixture of intermediate be (1.0 g, 2.63 mmol), intermediate an (2.1 g, 2.89 mmol), potassium carbonate (1.8 g, 13.1 mmol), and NMP (52 mL) was heated and stirred at 150°C for 3 hours under a nitrogen atmosphere. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 6:4) to obtain 1.30 g (1.21 mmol, yield 46%) of the yellow solid compound AM. 1 H NMR (400 MHz, CDCl3): d 8.51-8.48 (m, 2H), 8.40-8.31 (m, 3H), 7.82-7.78 (m, 1H), 7.73-7.67 (m, 3H), 7.62 (d, J = 2.0 Hz, 1H), 7.48 (d, J = 8.8 Hz, 1H), 7.41 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 7.25-7.14 (m, 3H). APCI-MS: Calculated value 1073.58 (C 76 H 17 D 30 N6), Observed value 1073.88 ([M+H] + ).

[0367] (Synthesis Example 40) Synthesis of intermediate bg of compound AN

[0368] A mixture of intermediate ab (3.26 g, 10.0 mmol), 3'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1'-biphenyl]-4-carbonitrile (3.05 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.572 g, 0.495 mmol), potassium carbonate (4.15 g, 30.0 mmol), THF (75 mL), and water (25 mL) was stirred at 80°C for 14 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water. The crude product was dissolved in dichloromethane, filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 2.71 g (5.77 mmol, yield 58%) of the white solid intermediate bg. 1 H NMR (400 MHz, CDCl3): d 8.90 (t, J = 1.6 Hz, 1H), 8.75 (dt, J = 7.6, 1.6 Hz, 1H), 7.84-7.78 (m, 5H), 7.68 (t, J = 7.2 Hz, 1H), 6.89-6.84 (m, 2H). APCI-MS: Calculated value 470.17 (C 28 H 11 D5F3N4), Observed value 470.50 ([M+H] + ).

[0369] Synthesis of compound AN

[0370] A mixture of intermediate bg (2.70 g, 5.75 mmol), intermediate r (2.75 g, 4.79 mmol), tripotassium phosphate (5.08 g, 23.9 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 24 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 3:1) to obtain 1.74 g (1.77 mmol, yield 37%) of compound AN as a pale yellowish-green solid.1 H NMR (400 MHz, CDCl3): d 8.17 (dd, J = 7.8, 1.4 Hz, 2H), 8.11 (t, J = 1.6 Hz, 1H), 8.06 (t, J = 1.6 Hz, 1H), 7.97 (dd, J = 7.8, 0.9 Hz, 2H), 7.89 (d, J = 7.8 Hz, 2H), 7.74 (d, J = 8.2 Hz, 2H), 7.58 (d, J= 8.2 Hz, 2H), 7.55 (dt, J = 7.5, 1.6 Hz, 1H), 7.50-7.46 (m, 2H), 7.43-7.29 (m, 10H), 7.25-7.18 (m, 5H), 7.15 (d, J = 1.4 Hz, 2H), 7.13-7.09 (m, 2H). APCI-MS: Calculated value 983.37 (C 70 H 35 D5N7), Observed value 983.42 ([M+H] + ).

[0371] (Synthesis Example 41) Synthesis of bh, an intermediate for the synthesis of compound AO

[0372] A mixture of intermediate ab (3.13 g, 9.58 mmol), 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzothiophene (3.71 g, 9.60 mmol), tetrakis(triphenylphosphine)palladium (0) (0.557 g, 0.482 mmol), potassium carbonate (4.00 g, 28.9 mmol), THF (75 mL), and water (25 mL) was stirred at 80°C for 12 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water. The crude product was dissolved in dichloromethane, filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 2.99 g (5.43 mmol, yield 57%) of the white solid intermediate bh. 1H NMR (400 MHz, CDCl3): d 9.08-9.07 (m, 1H), 8.76 (ddd, J = 7.8, 1.6, 1.1 Hz, 1H), 8.22 (dt, J = 6.6, 2.2 Hz, 2H), 8.00 (ddd, J = 7.7, 1.9, APCI-MS: Calculated value 551.16 (C 33 H 14 D5F3N3S), Observed value 551.61 ([M+H] + ).

[0373] Synthesis of compound AO

[0374] A mixture of intermediate bh (2.64 g, 4.79 mmol), intermediate r (2.28 g, 3.97 mmol), tripotassium phosphate (4.22 g, 20.0 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 20 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 0.879 g (0.826 mmol, yield 21%) of compound AO as a yellow-green solid. 1H NMR (400 MHz, CDCl3): d 8.20-8.11 (m, 5H), 8.10 (t, J = 1.6 Hz, 1H), 7.92 (dd, J= 7.9, 1.3 Hz, 2H), 7.88 (d, J = 7.6 Hz, 2H), 7.80-7.78 (m, 1H), 7.73-7.70 (m, 1H), 7.57 (t, J = 7.7 Hz, 1H), 7.49-7.44 (m, 4H), 7.39-7.26 (m, 13H), 7.23 (d, J = 8.2 Hz, 1H), 7.14 (t, J = 7.6 Hz, 2H), 7.09 (d, J = 1.6 Hz, 2H), 7.08-7.04 (m, 2H). APCI-MS: Calculated value 1064.36 (C 75 H 38 D5N6S), Observed value 1064.60 ([M+H] + ).

[0375] (Synthesis Example 42) Synthesis of bi, an intermediate for the synthesis of compound AP

[0376] Intermediate ab (3.25 g, 9.95 mmol), 9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbazole-d ８ A mixture of (3.77 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.578 g, 0.500 mmol), potassium carbonate (4.14 g, 30.0 mmol), THF (75 mL), and water (25 mL) was stirred at 80°C for 12 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water. The crude product was dissolved in dichloromethane, filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 3.09 g (5.71 mmol, yield 58%) of the white solid intermediate bi. 1 H NMR (400 MHz, CDCl3): d 8.92 (t, J = 1.7 Hz, 1H), 8.79 (ddd, J = 6.4, 2.4, 1.6 Hz, 1H), 7.83-7.78 (m, 2H), 6.87-6.82 (m, 2H). APCI-MS: Calculated value 542.25 (C33 H7D 13 F3N4), Observed value 542.46 ([M+H] + ).

[0377] Synthesis of compound AP

[0378] A mixture of intermediate bi (2.61 g, 4.82 mmol), intermediate r (2.29 g, 3.99 mmol), potassium phosphate (4.25 g, 20.0 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 20 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 1.65 g (1.56 mmol, yield 39%) of compound AP as a yellow-green solid. 1 H NMR (400 MHz, CDCl3): d 8.12 (dt, J = 7.9, 1.1 Hz, 2H), 8.02 (t, J = 1.6 Hz, 1H), 7.85-7.82 (m, 4H), 7.70 (s, 1H), 7.58 (d, J = 7.8 Hz, 1H), 7.54 (ddd, J = 7.9, 2.2, 1.2 Hz, 1H), 7.47-7.27 (m, 9H), 7.23-7.17 (m, 5H), 7.07 (d, J = 1.6 Hz, 2H), 7.02-6.97 (m, 4H). APCI-MS: Calculated value 1055.45 (C 75 H 31 D 13 N7), Observed value 1055.64 ([M+H] + ).

[0379] (Synthesis Example 43) Synthesis of intermediate bj of compound AQ

[0380] 1,3,5-trifluorobenzene-d ３A mixture of (2.42 g, 17.9 mmol) and THF (90 mL) was cooled to -85°C, and LDA (1.01 MTHF solution, 19.5 mL, 19.7 mmol) was added and stirred for 1 hour. Zinc chloride (approximately 1 MTHF solution, 22.5 mL, 22.5 mmol) was added to the mixture and stirred at -85°C for 1 hour, then stirred at room temperature for 1 hour. Palladium(II) acetate (0.168 g, 0.748 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.432 g, 1.49 mmol), and 2-chloro-4,6-bis(phenyl-d) were added to the reaction mixture. ５ )-1,3,5-triazine (4.17 g, 15.0 mmol) was added and the mixture was stirred at 80°C for 12 hours. After the mixture cooled to room temperature, water was added and the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (dichloromethane:hexane = 1:4) to obtain 4.99 g (12.7 mmol, yield 85%) of the white solid intermediate bj. APCI-MS: Calculated value 376.18 (C 21 HD 12 F3N3), Observed value 376.39 ([M+H] + ).

[0381] Synthesis of compound AQ

[0382] Intermediate bj (1.80 g, 4.79 mmol), intermediate r (2.29 g, 3.99 mmol), tripotassium phosphate (4.27 g, 20.1 mmol), 1,3-dimethyl-2-imidazolidinone (DMI, 20 mL), DMSO-d ６ The mixture (5 mL) was stirred at 230°C for 1 hour. After cooling to room temperature, ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:3) to obtain 0.733 g (0.824 mmol, yield 21%) of compound AQ as a pale yellowish-green solid. 1H NMR (400 MHz, CDCl3): d 8.17 (dd, J = 7.8, 1.1 Hz, 2H), 8.03 (t, J = 1.6 Hz, 1H), 8.00 (dd, J = 7.8, 1.1 Hz, 2H), 7.91 (d, J = 7.8 Hz, 2H), 7.50-7.23 (m, 13H), 7.18-7.13 (m, 4H). APCI-MS: Calculated value 889.39 (C 63 H 25 D 12 N6), Observed value 889.39 ([M+H] + ).

[0383] (Synthesis Example 44) Synthesis of intermediate bk of compound AR

[0384] A mixture of intermediate ab (2.70 g, 8.26 mmol), (3-(2-methylbenzo[d]thiazolo-5-yl)phenyl)boronic acid (2.69 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium (0) (0.579 g, 0.501 mmol), potassium carbonate (4.21 g, 30.5 mmol), THF (74 mL), and water (25 mL) was stirred at 80°C for 12 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water. The crude product was dissolved in dichloromethane, filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 1.84 g (3.57 mmol, yield 43%) of the pale yellow solid intermediate bk. 1 H NMR (400 MHz, CDCl3): d 9.00 (t, J = 1.7 Hz, 1H), 8.71-8.69 (m, 1H), 8.31 (d, J= 1.8 Hz, 1H), 7.94 (d, J = 8.2 Hz, 1H), 7.92-7.90 (m, 1H), 7.72 (dd, J= 8.4, 1.7 Hz, 1H), 7.67 (t, J = 7.6 Hz, 1H), 6.90-6.83 (m, 2H), 2.89 (s, 3H). APCI-MS: Calculated value 516.15 (C 29 H 13 D5F3N4S), Observed value 516.37 ([M+H] + ).

[0385] Synthesis of compound AR

[0386] A mixture of intermediate bk (2.80 g, 5.59 mmol), intermediate r (2.59 g, 4.51 mmol), tripotassium phosphate (4.78 g, 22.5 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 22 mL) was stirred at 230°C for 2 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene) to obtain 1.25 g (1.21 mmol, yield 27%) of compound AR as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.27 (s, 1H), 8.17 (dd, J = 7.8, 0.9 Hz, 2H), 8.13 (d, J= 1.4 Hz, 1H), 8.09 (t, J = 1.6 Hz, 1H), 7.97 (dd, J = 7.8, 0.9 Hz, 2H), 7.91-7.87 (m, 3H), 7.66-7.63 (m, 1H), 7.53-7.47 (m, 3H), 7.43-7.40 (m, 6H), 7.37-7.21 (m, 9H), 7.14 (d, J = 1.4 Hz, 2H), 7.07 (t, J = 7.2 Hz, 2H), 2.89 (s, 3H). APCI-MS: Calculated value 1029.36 (C 71 H 37 D5N7S), Observed value 1029.32 ([M+H] + ).

[0387] (Synthesis Example 45) Synthesis of intermediate bl of compound AS

[0388] Under a nitrogen atmosphere, a mixture of 1,3,5-trifluorobenzene (9.2 g, 70 mmol) and THF (200 mL) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 73.5 mL, 73.5 mmol) was added over 15 minutes. After stirring for 1 hour, zinc chloride solution (1 M hexane / THF solution, 77.0 mL, 77.0 mmol) was added, and the mixture was stirred for another hour. The reaction solution was heated to room temperature, and 4,6-dichloro-2-(phenyl-d) ５ Pyrimidine (16.9 g, 73.5 mmol) and tetrakis(triphenylphosphine)palladium (0) (4.0 g, 3.50 mmol) were added, and the mixture was heated and stirred at 80°C for 16 hours. After cooling to room temperature, aqueous ammonium chloride solution and dichloromethane were added, and the organic phase was separated. The aqueous phase was then extracted three times with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated to obtain the crude product. This was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 13.7 g (42.3 mmol, yield 60%) of intermediate bl. APCI-MS: Calculated value 326.07 (C 16 H4D5ClF3N2), Observed value 326.52 ([M+H] + ).

[0389] Synthesis of intermediate bm

[0390] A mixture of intermediate bl (4.9 g, 15.00 mmol), 4-cyanophenylboronic acid (3.3 g, 22.50 mmol), tetrakis(triphenylphosphine)palladium (0) (0.87 g, 0.75 mmol), sodium carbonate (4.7 g, 45.00 mmol), toluene (50 mL), ethanol (30 mL), and deionized water (30 mL) was stirred at 90°C for 15 hours under a nitrogen atmosphere. After the mixture cooled to room temperature, the precipitated solid was washed with deionized water, methanol, and hexane in that order. The obtained solid was washed with hot toluene, cooled to room temperature, filtered, and washed with toluene and hexane in that order. 5.4 g (13.7 mmol, yield 92%) of the white solid intermediate bm was obtained. APCI-MS: Calculated value 393.14 (C 23H8D5F3N3), Observed value 393.51 ([M+H] + ).

[0391] Synthesis of compound AS

[0392] A mixture of intermediate bm (0.94 g, 2.40 mmol), intermediate r (1.1 g, 1.92 mmol), potassium carbonate (3.3 g, 24.00 mmol), and NMP (12 mL) was heated and stirred at 230°C for 1 hour under a nitrogen atmosphere. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 6:4) to obtain 0.65 g (0.71 mmol, yield 37%) of the yellow solid compound AS. 1 H NMR (400 MHz, CDCl3): d 8.18 (d, J = 7.6 Hz, 2H), 8.05-7.98 (m, 5H), 7.54-7.20 (m, 20H), 7.12 (t, J = 2.0 Hz, 2H), 7.03-6.97 (m, 2H). APCI-MS: Calculated value 906.34 (C 65 H 32 D5N6), Observed value 906.70 ([M+H] + ).

[0393] (Synthesis Example 46) Synthesis of bn, a synthetic intermediate of compound AT

[0394] 1-Bromo-2,4,6-trifluorobenzene (4.24 g, 20.1 mmol), phenylboronic acid-d ５A mixture of (2.82 g, 22.2 mmol), tetrakis(triphenylphosphine)palladium (0) (1.15 g, 0.996 mmol), potassium carbonate (8.31 g, 60.1 mmol), 1,4-dioxane (75 mL), and water (25 mL) was stirred at 110°C for 12 hours. After the mixture cooled to room temperature, the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate, and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was purified by flash column chromatography (hexane) to obtain 3.94 g (18.5 mmol, 92% yield) of the white solid intermediate bn. 1 H NMR (400 MHz, CDCl3): d 6.80-6.72 (m, 2H).

[0395] Synthesis of intermediate bo

[0396] A mixture of intermediate bn (3.87 g, 18.1 mmol) and THF (90 mL) was cooled to -85°C, and LDA (1.01 MTHF solution, 20 mL, 20.2 mmol) was added and the mixture was stirred for 1 hour. Zinc chloride (approximately 1 MTHF solution, 23 mL, 23.0 mmol) was added to the mixture and stirred at -85°C for 1 hour, then stirred at room temperature for 4 hours. Palladium(II) acetate (0.172 g, 0.766 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.442 g, 1.52 mmol), and 2-chloro-4,6-bis(phenyl-d) were added to the reaction mixture. ５ )-1,3,5-triazine (4.20 g, 15.1 mmol) was added and the mixture was stirred at 80°C for 14 hours. After the mixture cooled to room temperature, water was added and the reaction mixture was separated into an organic phase and an aqueous phase. The aqueous phase was extracted with ethyl acetate and the combined organic phase was washed with saturated brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was filtered through silica gel and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 6.10 g (13.4 mmol, yield 89%) of the pale orange solid intermediate bo. 1 H NMR (400 MHz, CDCl3): d 6.97 (td, J = 9.6, 1.9 Hz, 1H). APCI-MS: Calculated value 455.23 (C27 H2D 15 F3N3), Observed value 455.42 ([M+H] + ).

[0397] Synthesis of compound AT

[0398] A mixture of intermediate bo (2.18 g, 4.80 mmol), intermediate r (2.30 g, 4.01 mmol), tripotassium phosphate (4.27 g, 20.1 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 20 mL) was stirred at 230°C for 3 hours. After cooling to room temperature, ammonium chloride aqueous solution was added to reprecipitation. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 1:1) to obtain 1.54 g (1.59 mmol, yield 40%) of compound AT as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.17 (t, J = 1.7 Hz, 1H), 8.07 (dd, J = 7.8, 1.1 Hz, 1H), 8.03 (d, J = 7.8 Hz, 1H), 7.99 (dd, J = 7.8, 1.1 Hz, 1H), 7.90 (d, J= 7.8 Hz, 1H), 7.87 (dd, J = 7.8, 1.1 Hz, 1H), 7.73-7.70 (m, 2H), 7.47-7.27 (m, 9H), 7.24-7.11 (m, 7H), 6.99-6.95 (m, 1H). APCI-MS: Calculated value 968.44 (C 69 H 26 D 15 N6), Observed value 968.46 ([M+H] + ).

[0399] (Synthesis Example 47) Synthesis of Compound AU Synthesis of Compound AU

[0400] A mixture of intermediate az (1.65 g, 31.67 mmol), benzothio[2,3-a]carbazole (0.546 g, 2.0 mmol), potassium carbonate (0.692 g, 5 mmol), and NMP (41 mL) was stirred at 170°C for 18 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 1.05 g (0.85 mmol, yield 50.9%) of compound AU as a yellow solid. APCI-MS: Calculated value 1236.52 (C 84 H 30 D 20 FN9S), Observed value 1236.19 ([M+H] + ).

[0401] (Synthesis Example 48) Synthesis of bp, a synthetic intermediate for compound AV

[0402] In a 100 mL three-necked flask, add 2,6-difluorobenzonitrile (2.18 g, 15.7 mmol) and THF (15 mL), cool to -78°C, then add lithium diisopropylamide (1 M hexane solution, 16.5 mL, 16.5 mmol) and stir for 1 hour. Add zinc chloride (1 M THF solution, 17.2 mL, 17.2 mmol) and stir for another 1 hour. 2-chloro-4,6-bis(phenyl-d ５ Pyrimidine (4.15 g, 15.0 mmol), palladium acetate (33.6 mg, 150 μmol), and Sphos (123 mg, 300 μmol) were added, and the mixture was heated under reflux. After the reaction was complete, the mixture was poured into water (60 mL), THF was removed by distillation using a rotary evaporator, and the precipitate was filtered off. The resulting crude product was purified by silica gel column chromatography to obtain 3.36 g of the intermediate bp (orange solid) (yield 59.0%). 1 H NMR (400 MHz, CDCl3): d 8.74-8.67(m, 1H), 8.11(s, 1H), 7.26-7.19 (m, 1H). APCI-MS: Calculated value 380.18 (C 23 H3D 10 F2N3), Observed value 380.20 ([M+H]+ ).

[0403] Synthesis of intermediate bq

[0404] In a 100 mL three-necked flask, add intermediate bp (1.89 g, 5.0 mmol) and THF (50.0 mL), cool to -78°C, then add lithium diisopropylamide (1 M hexane solution, 5.25 mL, 5.25 mmol) and stir for 1 hour. Add zinc chloride (1 M THF solution, 5.50 mL, 5.50 mmol) and stir for a further 2 hours. 2-chloro-4,6-bis(phenyl-d ５ Pyrimidine (1.45 g, 5.25 mmol), palladium acetate (112 mg, 500 μmol), and Sphos (410 mg, 1.0 mmol) were added, and the mixture was heated under reflux. After the reaction was complete, the mixture was poured into water (60 mL), and the precipitate was filtered off. The resulting crude product was purified by silica gel column chromatography to obtain 0.885 g of intermediate bq (white solid) (yield 28.6%). 1 H NMR (400 MHz, CDCl3): d 9.94(t, 1H), 8.16(s, 2H). APCI-MS: Calculated value 620.33(C 39 H4D 20 F2N5), Observed value 620.49 ([M+H] + ).

[0405] Synthesis of intermediate br

[0406] Intermediate br was synthesized using the same method as for intermediate an. APCI-MS: Calculated value 590.20 (C 42 H 25 N2O2), observed value 590.30 ([M+H] + ).

[0407] Synthesis of compound AV

[0408] In a 50 mL round-bottom flask, intermediate bq (867 mg, 1.40 mmol), intermediate br (824 mg, 1.40 mmol), potassium carbonate (1.15 g, 8.39 mmol), and NMP (7.0 mL) were added and the mixture was stirred at 150°C. After the reaction was complete, the mixture was poured into water (30 mL) and the precipitate was filtered off. The resulting crude product was washed with acetonitrile and then purified by column chromatography to obtain 0.134 g of compound AV (white solid) (yield 8.22%). 1 H NMR (400 MHz, CDCl3): d 9.20 (s, 1H), 8.50(d, 2H), 7.93(d, 2H), 7.87(s, 2H), 7.79(s, 2H), 7.74-7.69(m, 3H), 7.55-7.34(m, 10H), 7.24(d, 2H). APCI-MS: Calculated value 1168.50(C 81 H 26 D 20 N7O2), Observed value 1168.61 ([M+H] + ).

[0409] (Synthesis Example 49) Synthesis of intermediate bs of compound AW

[0410] Intermediate bl (2.9 g, 9.0 mmol), phenylboronic acid-d ５ A mixture of (1.7 g, 13.5 mmol), tetrakis(triphenylphosphine)palladium (0) (0.52 g, 0.45 mmol), sodium carbonate (2.8 g, 27.0 mmol), toluene (30 mL), ethanol (18 mL), and water (18 mL) was stirred at 90°C for 22 hours under a nitrogen atmosphere. After the mixture was cooled to room temperature, aqueous ammonium chloride solution and dichloromethane were added, and the organic phase was separated. The aqueous phase was extracted three times with ethyl acetate. The combined organic phase was purified by flash column chromatography (toluene), and the solvent was removed by distillation. The resulting solid was washed with methanol and hexane to obtain 3.0 g (8.07 mmol, yield 89%) of intermediate bs. APCI-MS: Calculated value 373.18 (C 22 H4D 10 F3N2), Observed value 373.55 ([M+H] + ).

[0411] Synthesis of intermediate bt

[0412] Under a nitrogen atmosphere, a mixture of 1,3,5-phenyltriboronic acid tris(pinacol) ester (6.8 g, 15.0 mmol), 6-bromo-5H-benzofl[3,2-c]carbazole (15.6 g, 46.5 mmol), tetrakis(triphenylphosphine)palladium (0) (0.86 g, 0.75 mmol), potassium carbonate (10.3 g, 75.0 mmol), N,N-dimethylacetamide (50 mL), and water (5 mL) was stirred at 110°C for 16 hours under a nitrogen atmosphere. After the mixture cooled to room temperature, the organic phase and aqueous phase were separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated. The crude product was dissolved in heated THF, acetonitrile was added, and the mixture was cooled to obtain a precipitate. The resulting precipitate was filtered and washed with THF / acetonitrile solution to obtain 8.6 g (10.2 mmol, 68% yield) of intermediate bt. APCI-MS: Calculated value 844.26 (C 60 H 34 N3O3), Observed value 844.61 ([M+H] + ).

[0413] Synthesis of compound AW

[0414] A mixture of intermediate bs (3.0 g, 8.0 mmol), intermediate bt (5.4 g, 6.4 mmol), potassium carbonate (11.0 g, 80.0 mmol), and DMI (40 mL) was heated and stirred at 230°C for 2 hours under a nitrogen atmosphere. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 5:5) to obtain 0.80 g (0.69 mmol, yield 10%) of the yellow solid compound AW. 1 H NMR (400 MHz, CDCl3): d 8.66 (s, 1H), 8.41 (s, 2H), 8.17 (s, 1H), 8.05-6.95 (m, 29H). APCI-MS: Calculated value 1156.41 (C 82 H34 D 10 N5 O3), Observed value 1156.93 ([M+H] + ).

[0415] (Synthesis Example 50) Synthesis of bu, an intermediate for the synthesis of compound AX

[0416] Under a nitrogen atmosphere, a THF solution (100 mL) of 1,2,3,5-tetrafluorobenzene (3.00 g, 19.9 mmol) was cooled to -78°C, and lithium diisopropylamide solution (1 M hexane / THF solution, 19.9 mL, 19.9 mmol) was added over 15 minutes. After stirring for 1 hour, zinc chloride solution (1 M hexane / THF solution, 19.9 mL, 19.9 mmol) was added, and the mixture was stirred for a further 2 hours. The reaction solution was heated to room temperature, and 2-chloro-4,6-bis(phenyl-d) ５ )-1,3,5-triazine (4.58 g, 16.5 mmol) and tetrakis(triphenylphosphine)palladium (0) (957 mg, 0.829 mmol) were added and the mixture was heated and stirred at 75°C for 18 hours. After the mixture cooled to room temperature, the precipitated solid was washed with water, methanol, and hexane in that order. The obtained solid was washed with hot toluene, cooled to room temperature, and the solid was filtered off and washed with toluene and hexane in that order to obtain 5.5 g (14.0 mmol, yield 85%) of the white solid intermediate bu. APCI-MS: Calculated value 391.15 (C 21 HD 10 F4N3), Observed value 391.40 (M + ).

[0417] Synthesis of intermediate bv

[0418] A mixture of intermediate bu (2 g, 5.08 mmol), intermediate r (3.19 g, 5.56 mmol), potassium carbonate (3.51 g, 25.4 mmol), and NMP (6.3 mL) was stirred at 220°C for 3 hours. After cooling to room temperature, water was added and reprecipitation was performed. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 0.92 g (1.02 mmol, yield 20.1%) of the yellow solid intermediate bv. APCI-MS: Calculated value 905.36 (C 63 H 26 D 10 FN6), Observed value 905.19 ([M+H] + ).

[0419] Synthesis of compound AX

[0420] A mixture of intermediate bv (1.7 g, 1.87 mmol), imidazole (0.381 g, 5.61 mmol), potassium carbonate (1.29 g, 9.35 mmol), and N-methylpyrrolidone (47 mL) was stirred at 120°C for 18 hours. After cooling to room temperature, water was added and reprecipitation was performed. The resulting solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 0.774 g (0.813 mmol, yield 43.5%) of compound AX as a yellow solid. APCI-MS: Calculated value 953.39 (C 66 H 29 D 10 N8), Observed value 953.19 ([M+H] + ).

[0421] (Synthesis Example 51) Synthesis of Compound AY Synthesis of Compound AY

[0422] A mixture of 2,4,6-trifluorobenzonitrile (1.73 g, 11.0 mmol), intermediate r (5.74 g, 10.0 mmol), tripotassium phosphate (10.8 g, 50.9 mmol), and 1,3-dimethyl-2-imidazolidinone (DMI, 50 mL) was stirred at 100°C for 1 hour and at 230°C for 1.5 hours. After cooling to room temperature, aqueous ammonium chloride solution was added to reprecipitation. The obtained solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was filtered through silica gel, and the silica gel was washed with dichloromethane. The obtained filtrate was concentrated to obtain 1.56 g (2.32 mmol, yield 23%) of the yellow solid compound AY. 1 H NMR (400 MHz, CDCl3): d 8.18-8.13 (m, 6H), 7.49-7.30 (m, 15H), 7.20 (d, J = 7.8 Hz, 2H), 7.17 (d, J = 8.2 Hz, 1H), 7.08 (d, J = 1.8 Hz, 2H). APCI-MS: Calculated value 671.23 (C 49 H 27 N4), Observed value 671.87 ([M+H] + ).

[0423] (Synthesis Example 52) Synthesis of intermediate bw of compound AZ

[0424] A mixture of 2,4-difluorobenzonitrile (1.67 g, 12.0 mmol) and THF (60 mL) was cooled to -85°C, and LDA (0.88 MTHF solution, 15 mL, 13.2 mmol) was added and stirred for 1 hour. Zinc chloride (approximately 1 MTHF solution, 15 mL, 15.0 mmol) was added to the mixture and stirred at -85°C for 0.5 hours, then stirred at room temperature for 2 hours. Tetrakis(triphenylphosphine)palladium (0) (0.581 g, 0.503 mmol) and 2-chloro-4,6-bis(phenyl-d) were added to the reaction mixture. ５)-1,3,5-triazine (2.78 g, 10.0 mmol) was added and the mixture was stirred at 80°C for 17 hours. After the mixture cooled to room temperature, the precipitated solid was filtered off and washed with water, methanol, and hexane in that order. The crude product was filtered through silica gel, and the silica gel was washed with dichloromethane. The resulting filtrate was concentrated to obtain 3.15 g (8.28 mmol, yield 83%) of the pale yellow solid intermediate bw. 1 H NMR (400 MHz, CDCl3): d 7.81 (ddd, J = 10.6, 5.0, 3.8 Hz, 1H), 7.22 (td, J = 8.7, 1.6 Hz, 1H). APCI-MS: Calculated value 381.18 (C 22 H3D 10 F2N4), Observed value 381.40 ([M+H] + ).

[0425] Synthesis of compound AZ

[0426] A mixture of intermediate bw (1.49 g, 3.92 mmol), intermediate c (1.22 g, 2.99 mmol), potassium phosphate (2.07 g, 15.0 mmol), and NMP (15 mL) was stirred at 180°C for 2 hours. After cooling to room temperature, ammonium chloride aqueous solution was added and reprecipitation was performed. The obtained solid was filtered off and washed with deionized water, methanol, and hexane in that order. The crude product was purified by flash column chromatography (toluene:hexane = 2:1) to obtain 0.893 g (1.19 mmol, yield 40%) of compound AZ as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): d 8.38 (s, 1H), 8.05-8.01 (m, 2H), 7.96-7.92 (m, 2H), 7.56 (dd, J= 8.1, 1.1 Hz, 1H), 7.35-7.28 (m, 11H), 7.19-7.14 (m, 3H). APCI-MS: Calculated value 749.33 (C 52 H 21 D 10 N6), Obse...

Claims

1. A compound represented by the following general formula (1). General formula (1) [In general formula (1), ａ Y ｅ to Y ａ each independently represents N or C, and a hydrogen atom, a deuterium atom or a substituent is bonded to the C. One of Y ｃ to Y ２ represents C bonded to D ａ One of the remaining Y ｅ to Y ａ represents C bonded to Acp. One of the remaining Y ｅ to Y ３ may be C bonded to a linking group D ａ linked to Ar. Further, one of the remaining Y ｅ to Y ４ may be C bonded to a linking group D ａ linked to Ar. Finally, one of the remaining Y ｅ to Y ５ may be C bonded to a linking group D １ linked to Ar. D ５ each independently represents a group represented by the following general formula (2). D in general formula (1) １ to D ５ The shortest number of connecting atoms in the cyclic structure formed by two of them and ring B and Ar is each independently 10 to 14. The minimum number of linked atoms is the number of ring-constituting atoms when the ring-constituting atoms are selected in such a way that the number of atoms constituting the ring in the cyclic structure is minimized. Ar represents an aromatic ring which may contain nitrogen atoms as ring-skeleton constituent atoms, and the aromatic ring may be substituted or fused with other rings. a represents an integer from 1 to 3. When a is 2 or more, multiple Y ａ ~Y ｅ , D １ ~D ５ And Ar may be the same or different. Acp represents an α-valent acceptor group. ] General formula (2) [In general formula (2), R １１ ~R １９ Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, or 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 １７ , R １７ and R １８ , R １８ and R １９ They bond to each other to form a ring structure. １４ and R １５ When they bond with each other, they are called single bonds, -O-, -S-, -N(R) ２０ )-,-C(R ２１ ) (Caution ２２ )-,-Si(R ２３ ) (Caution ２４ ) - forms one of the following. ２０ ~R ２４ Each of the asterisks (*) independently represents a hydrogen atom, a deuterium atom, or a substituent. The asterisk (*) represents a bonding site, and either of the two asterisks may be bonded to ring B.

2. D １ ~D ５ The compound according to claim 1, wherein at least one of the atoms is bonded to ring B by a nitrogen atom.

3. D １ ~D ５ The compound according to claim 1, wherein the shortest number of linked atoms in the cyclic structure formed by two of these atoms, ring B, and Ar is 12.

4. D １ ~D ５ The compound according to claim 1, wherein the linking group has the same structure.

5. D ３ ~D ５ When D does not exist, １ and D ２ The number of constituent atoms of the ring skeleton of ring B that connects them in the shortest possible way, and D １ and D ２ The compound according to claim 1, wherein the number of constituent atoms of the Ar ring skeleton that connects them in the shortest possible way is the same.

6. The compound according to claim 1, wherein Acp is bonded to ring B in a six-membered heteroaromatic ring containing a nitrogen atom as a ring skeleton constituent atom.

7. The compound according to claim 6, wherein the six-membered heteroaromatic ring is substituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

8. The compound according to claim 1, wherein a is 1.

9. The compound according to claim 1, wherein a is 2 or 3.

10. The remaining Y ａ ~Y ｅ One of them is a linking group D that connects to Ar. ３ The compound according to claim 1, wherein C is bonded to.

11. a is 1, Y ａ ~Y ｃ One of them is C to which Acp is bonded, and the other Y ａ ~Y ｅ The compound according to claim 1, wherein at least one of them is a carbon to which a group having the same structure as Acp is bonded.

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

13. A film comprising the compound described in any one of claims 1 to 11.

14. An organic light-emitting element comprising the compound described in any one of claims 1 to 11.

15. The organic light-emitting element according to claim 14, which is an organic electroluminescent element.

16. The organic light-emitting element according to claim 15, wherein the organic electroluminescent element has a layer containing the compound, and the layer also contains a host material.

17. The organic light-emitting element according to claim 16, wherein the layer also includes a light-emitting material in addition to the compound and the host material, and the lowest excitation singlet energy of the compound is lower than that of the host material and higher than that of the light-emitting material.

18. The organic light-emitting element according to claim 17, wherein the layer further comprises a delayed fluorescence material.

19. The organic light-emitting element according to claim 15, which emits fluorescence or delayed fluorescence.

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