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

Abstract

According to the present invention, a compound represented by the following general formula is useful for an organic light-emitting element. R1 through R20 are each H, D, or a substituent; R21 and R22 are each H or D; X1 through X4 are each an aryl group, a heteroaryl group, a cycloalkyl group, or a nonaromatic heterocyclic 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 such compounds, and to organic light-emitting devices using such compounds. 【0002】 Research on organic light-emitting devices, such as organic electroluminescent elements, is actively being conducted. For example, Non-Patent Literature 1 describes how using a compound having a condensed polycyclic structure in which boron or nitrogen atoms with different numbers of valence electrons are introduced into a carbon-conjugated π-electron system, such as 5,9-diphenyl-5H,9H-[1,4]benzazavorino[2,3,4-kl]phenazavolin (DABNA-1), enables the expression of thermally activated delayed fluorescence through an inverse cross-system process, resulting in emission with a narrow full width at half maximum and high color purity. Such emission can achieve high luminescence efficiency and is therefore useful in display-oriented applications. Furthermore, Non-Patent Literature 1 and 2 describe how modifying DABNA-1 adjusts energy levels such as the highest transitioned molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO), and promotes the fluorescence emission process and inverse cross-system process that contribute to emission, thereby improving the electroluminescence quantum efficiency. 【0003】 Adv. Mater. 2016, 28, 2777-2781Angew. Chem. Int. Ed. 2018, 57, 11316-11320 【0004】 Although various studies have been conducted on compounds having polycyclic condensed structures incorporating boron and nitrogen atoms, many aspects of the relationship between their structure and properties remain unknown. To manufacture practical light-emitting devices, it is necessary to provide materials with even slightly superior properties. Therefore, the present inventors have diligently pursued research with the aim of generalizing structures that exhibit superior properties by investigating the relationship between derivatives of compounds having condensed polycyclic structures incorporating boron and nitrogen atoms and their properties. 【0005】As a result of intensive studies, the present inventors have found that those having a specific structure have excellent properties. The present invention has been proposed based on such findings and has the following constitution. [1] A compound represented by the following general formula (1). General formula (1) [In general formula (1), R ４ , ２２ , ４ , ４ , １ , １ , ２１ , １ ~R ２０ each independently represents a hydrogen atom, a deuterium atom or a substituent. 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 , R ６ and R ７ , 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 １８ and R １９ , R １９ and R ２０ may be bonded to each other to form a cyclic structure. R ２１ and R ２２ are each independently a hydrogen atom or a deuterium atom. X １ ~X ４ represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted non-aromatic heterocyclic group. ] [2] The compound according to [1], wherein X １ ~X ４ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted cycloalkyl group. [3] X １ ~X ４The compound according to [1] or [2], wherein at least one of is a substituted aryl group, and the aryl group is substituted with one or more selected from the group consisting of a deuterium atom, an alkyl group, an alkoxy group, a non-aromatic heterocyclic group, and a group having a structure in which two or more of these are bonded. [4] X １ ~X ４ However, each is an aryl group in which at least one tert-butyl group may be independently substituted with a deuterium atom, as described in any one of [1] to [3]. [5] R １ ~R ２０ The compound according to any one of [1] to [4], wherein each of them independently is a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyloxy group, or a substituted or unsubstituted non-aromatic heterocyclic group. [6] R １ ~R ２０ The compound according to any one of [1] to [5], wherein at least one of the alkyl groups may be substituted with a deuterium atom. [7] R ３ , R ６ , R １３ , R １６ The compound according to any one of [1] to [6], wherein at least one of the substituents is present. [8] R ３ , R ６ , R １３ , R １６ The compound according to any one of [1] to [7], wherein at least one of the members is a branched alkyl group which may be substituted with a deuterium atom. [9] R ９ and R １９A compound according to any one of [1] to [8], wherein each is a cycloalkyl group or a branched alkyl group that may be independently substituted with a deuterium atom.

[10] A compound according to any one of [1] to [9] having a deuterium atom.

[11] A compound according to any one of [1] to

[10] having a rotationally symmetric structure.

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

[11] .

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

[11] .

[14] An organic light-emitting element containing 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 containing the compound, and the layer also contains a host material.

[17] The organic light-emitting element according to

[16] , wherein the layer also includes a delayed fluorescence material in addition to the compound and the host material, and the lowest excitation singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound.

[18] The organic light-emitting element according to

[17] , wherein the amount of light emitted from the compound is the largest among the materials included in the organic electroluminescent element.

[19] The organic light-emitting element according to

[16] , wherein the layer also includes a phosphorescent material in addition to the compound and the host material.

[20] The organic light-emitting element according to

[19] , wherein the amount of light emitted from the compound is the largest among the materials included in the organic electroluminescent element. 【0006】 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. 【0007】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 ( ２ It can be substituted with H (deuterium D). In the chemical structural formulas herein, hydrogen atoms are either represented as H or omitted. For example, when the representation of an atom bonded to a carbon atom in the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom in the ring skeleton where the representation is omitted. In this specification, the term "substituent" means an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that the hydrogen atom may be substituted with a deuterium atom or a substituent. 【0008】 [Compounds represented by general formula (1)] The compound represented by the general formula (1) below will be explained. General formula (1) 【0009】 In general formula (1), X １ ~X ４ X represents a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted non-aromatic heterocyclic group. In one embodiment of the present invention, X １ and X ３ Each of these is independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted non-aromatic heterocyclic group. In a preferred embodiment of the present invention, X １ ~X ４Each is independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted non-aromatic heterocyclic group, for example, each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted cycloalkyl group. In one embodiment of the present invention, X １ ~X ４ Each of these is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted cycloalkyl group, for example, a substituted or unsubstituted phenyl group, for example, a substituted or unsubstituted cycloalkyl group. １ ~X ４ The deuterium atoms or substituents that can be substituted for the aryl group, heteroaryl group, cycloalkyl group, or non-aromatic heterocyclic group may be selected from group A, group B, group C, group D, or group E described below. In one preferred embodiment of the present invention, one or more can be selected from the group consisting of deuterium atoms, alkyl groups, alkoxy groups, non-aromatic heterocyclic groups, and groups having a structure in which two or more of these are bonded together. For example, X １ and X ２ At least one of the following, and X ３ and X ４ At least one of these can be an alkyl group or aryl group which may be substituted with a deuterium atom, or an alkyl group or cycloalkyl group which may be substituted with a deuterium atom. For example, X １ ~X ４ For example, alkyl groups that may be substituted with deuterium atoms, aryl groups that may be substituted with deuterium atoms, alkyl groups that may be substituted with deuterium atoms, or cycloalkyl groups that may be substituted with deuterium atoms can be selected. １ ~X ４ As such, an aryl group substituted with at least one tert-butyl group can be selected, and specific examples include Y10, Y11, and Y12 described later. １ ~X４ Among the aryl groups that can be adopted, the phenyl group is a particularly noteworthy example. 【0010】 In this specification, an "aryl group" may be a monoring or a fused ring formed by the fusion of two or more rings. If it is a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of rings include a benzene ring, a naphthalene ring, anthracene ring, a phenanthrene ring, and a pyrene ring. Specific examples of aryl groups include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of constituent atoms of the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and can be selected from the range of 6 to 14 or from the range of 6 to 10. In this specification, a "heteroaryl group" may be a monoring or a fused ring formed by the fusion of two or more rings. If it is a fused ring, the number of rings after fusion is preferably 2 to 6, and can be selected from, for example, 2 to 4 or 2. Specific examples of heterocyclic groups constituting a heteroaryl group are given below. A heteroaryl group is a group in which any one hydrogen atom present in these heterocyclic groups is replaced by a bonding site, and may be bonded by a nitrogen atom or a carbon atom. It should be noted that the heteroaryl groups that can be adopted in the present invention are not limited to these specific examples. The hydrogen atoms of the heterocyclic group may be substituted, and in that case the substituent is not particularly limited, but it is preferable to adopt one or more atoms selected from the group consisting of a deuterium atom, a linear or branched aliphatic hydrocarbon having 10 or fewer carbon atoms, a cyclic aliphatic hydrocarbon group having 5 to 7 carbon atoms, a heterocyclic group, and a group having a structure in which two or more of these are bonded together. 【0011】In this specification, "alkyl group" is a saturated hydrocarbon group, which may be linear or branched. Furthermore, two or more linear and branched portions may be mixed. The number of carbon atoms in an alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. The range of carbon atoms may be selected, for example, within the range of 1 to 10, 1 to 6, or 1 to 4. Specific examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, and isodecanyl group. Alkyl groups may further be substituted with aryl groups, etc. In this specification, "cycloalkyl group" refers to a group bonded to carbon atoms constituting a saturated hydrocarbon ring. That is, a group bonded to carbon atoms constituting the ring skeleton. The number of carbon atoms in a cycloalkyl group can be, for example, 5 or more, 6 or more. Alternatively, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, or 7 or less. The range of carbon atoms may be selected, for example, within the range of 5 to 20, 5 to 10, or 5 to 8. Specific examples of cycloalkyl groups include cyclopentyl, cyclohexyl, cycloheptyl, and adamantyl groups. In one aspect of the present invention, a monocyclic cycloalkyl group is used as the cycloalkyl group. In one aspect of the present invention, a cycloalkyl group having a bicyclo or tricyclo structure is used as the cycloalkyl group. For example, a cycloalkyl group having a tricyclo structure is used. In this specification, "non-aromatic heterocyclic group" refers to a heterocyclic group that does not exhibit aromaticity, and contains at least one heteroatom as a ring skeleton constituent atom, and is bonded to carbon atoms or heteroatoms constituting the ring skeleton. Non-aromatic heterocyclic groups are also included in those in which at least one of the ring-constituting carbon atoms of the cyclic alkyl group described above is substituted with a heteroatom.The heteroatom constituting the non-aromatic heterocyclic group is preferably selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms constituting the ring is preferably 1 to 4, more preferably 1 to 3, for example, 1, for example, 2. Specific examples of the non-aromatic heterocyclic ring include a pyrrolidine ring, a pyrazolidine ring, an imidazolidine ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a dioxolane ring, a piperazine ring, a dioxane ring, a piperidine ring, a morpholine ring, a dithiane ring, a quinuclidine ring, an azadamantane ring, and examples of the non-aromatic heterocyclic group include a group bonded to these ring skeleton-constituting carbon atoms or ring skeleton-constituting nitrogen atoms. Regarding the alkyl portion of the "alkoxy group" in this specification, the definitions and explanations of the above alkyl group can be referred to. Regarding the cycloalkyl portion of the "cycloalkyloxy group" in this specification, the definitions and explanations of the above cycloalkyl group can be referred to. 【0012】 In one aspect of the present invention, X １ and X ２ are the same, and X ３ and X ４ are also the same. For example, X １ to X ４ are all the same. For example, all are unsubstituted aryl groups. For example, all are the same substituted aryl group. For example, all are the same unsubstituted cycloalkyl group. In one aspect of the present invention, X １ and X ２ are different, and X ３ and X ４ are also different. For example, X １ and X ３ are substituted aryl groups, and X ２ and X ４ are unsubstituted aryl groups. For example, X １ and X ３ are substituted aryl groups, and X ２ and X ４ are unsubstituted aryl groups different from X １ and X ３ . 【0013】 Hereinafter, X １ to X ４Specific examples of the bases that can be adopted are given below. However, X that can be adopted in the present invention １ ~X ４ The scope is not limited by the following specific examples. In the following specific examples, the methyl group is CH ３ The description has been omitted. Therefore, for example, methyl groups are present in Y2 to Y7. Also, Ph is a phenyl group (C ６ H ５ ) represents. 【0014】 【0015】 In one aspect of the present invention, X １ ~X ４ X is selected from the group consisting of Y1 to Y218. In one aspect of the present invention, X １ ~X ４ X is selected from the group consisting of Y1 to Y218. In one aspect of the present invention, X １ ~X ４ X is selected from the group consisting of Y1 to Y47 and Y110 to Y156. In one aspect of the present invention, X １ ~X ４ The group is selected from the groups Y1 to Y25 and Y110 to Y134. 【0016】 In general formula (1), 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 ４ and R ５ , R ５ and R ６ , R ６ and R ７ , 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 １８ and R １９ , R １９ and R ２０ These rings may be bonded to each other to form a cyclic structure. The formed cyclic structure may be an aromatic ring or a non-aromatic ring. It may also contain heteroatoms as constituent atoms of the ring skeleton, and may have one or more other rings fused to it. The heteroatoms referred to here are preferably selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms. Examples of the formed cyclic structure include a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, a triazole ring, an imidazoline ring, a furan ring, a thiophene ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycloheptatriene ring, a cycloheptadiene ring, a cycloheptene ring, and a ring in which one or more rings selected from the group consisting of these rings are further fused. In one preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted benzene ring, and the benzene ring may have further rings fused to it. For example, a benzene ring which may be substituted with an alkyl group or an aryl group. In a preferred embodiment of the present invention, the cyclic structure is a substituted or unsubstituted heteroaromatic ring, preferably a furan ring of benzofuran, a thiophene ring of benzothiophene, or a pyrrole ring of indole. The benzene rings constituting benzofuran, benzothiophene, and indole may be substituted with deuterium atoms or substituents, and the nitrogen atom at position 1 of indole may be bonded to, for example, a substituted or unsubstituted aryl group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４and R ５ , R ５ and R ６ , R ６ and R ７ , 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 １８ and R １９ , R １９ and R ２０ The number of combinations that are bonded to each other to form a ring structure may be 0, or it may be any of 1 to 6, for example. For example, it may be any of 1 to 4, and one can select 1, one can select 2, one can select 3 or one can select 4. In one aspect of the present invention, R １ and R ２ , R ２ and R ３ , R ３ and R ４ A pair selected from these is joined together to form a ring structure. In one aspect of the present invention, R ５ and R ６ , R ６ and R ７ Any one pair of these is joined together to form a ring structure. In one aspect of the present invention, R ８ and R ９ , R ９ and R １０ Any one pair of these is joined together to form a ring structure. In one aspect of the present invention, R ５ and R ６ , R １５ and R １６ All of them are bonded to each other to form a ring structure. Note that R in general formula (1) ２１ , R ２２ , X １ ~X ４ is nearby R ｍ(m = 1 to 22) and X １ ~X ４ They do not combine with each other to form a ring structure. 【0017】 Adjacent R ｎ (n=1 to 20) and R that are not connected to each other １ ~R ２０ Each of these is independently a hydrogen atom, a deuterium atom, or a substituent. The deuterium atom or substituent referred to here may be selected from group A, group B, group C, group D, or group E described below. １ ~R ２０ The preferred substituents that can be adopted are substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted cycloalkyloxy groups, or substituted or unsubstituted non-aromatic heterocyclic groups. For example, a substituted or unsubstituted alkyl group, and for example, a substituted or unsubstituted cycloalkyl group. The alkyl group, aryl group, heteroaryl group, cycloalkyl group, and non-aromatic heterocyclic group referred to here may each be substituted with a deuterium atom or a substituent, and the deuterium atom or substituent may be selected from group A, group B, group C, group D, or group E described below. More preferably, it is selected from substituent group E, and it may be unsubstituted. In addition, as the cycloalkyl group referred to here, a cycloalkyl group having a tricyclo structure may be selected in particular. For example, an adamantyl group may be selected. In one embodiment of the present invention, R １ ~R ４ At least one of them is a substituent. In one aspect of the present invention, R ５ ~R ７ At least one of them is a substituent. In one aspect of the present invention, R ８ ~R １０ At least one of them is a substituent. In one aspect of the present invention, R １ ~R４ At least one of and R １１ ~R １４ At least one of them is a substituent. In one aspect of the present invention, R ５ ~R ７ At least one of and R １５ ~R １７ At least one of them is a substituent. In one aspect of the present invention, R ８ ~R １０ At least one of and R １８ ~R ２０ At least one of them is a substituent. In one aspect of the present invention, R ３ , R ６ , R １３ , R １６ At least one of them is a substituent, for example R ３ and R １３ is a substituent, for example R ６ and R １６ is a substituent, for example R ３ , R ６ , R １３ , R １６ All of them are substituents. In one aspect of the present invention, R ９ and R １９ At least one of them is a substituent, for example R ９ and R １９ Both are substituents. In this paragraph, the substituents are alkyl groups or cycloalkyl groups which may be substituted with a deuterium atom, for example, a methyl group which may be substituted with a deuterium atom, or a tert-butyl group which may be substituted with a deuterium atom, for example, a cyclohexyl group which may be substituted with a deuterium atom. In one aspect of the present invention, R １ ~R ２０ R is an alkyl group in which at least one of the atoms may be substituted with a deuterium atom. In one aspect of the present invention, R ９ and R １９Each of these is a cycloalkyl group or a branched alkyl group which may be independently substituted with a deuterium atom, for example, a cycloalkyl group which may be both substituted with a deuterium atom, or a branched alkyl group which may be both substituted with a deuterium atom. An example of a cycloalkyl group is a cyclohexyl group which may be substituted with a deuterium atom, and an example of a branched alkyl group is a tert-butyl group which may be substituted with a deuterium atom. 【0018】 In general formula (1), R ２１ and R ２２ Each of these is independently either a hydrogen atom or a deuterium atom. For example, R ２１ and R ２２ R is a hydrogen atom. For example, R ２１ and R ２２ It is a deuterium atom. 【0019】 In the following, R in general formula (1) １ ~R ２０ Specific examples of the groups that can be adopted are given below. However, the R that can be adopted in the present invention is １ ~R ２０ The scope is not limited by the following specific examples. In the following specific examples, the methyl group is CH ３ The description is omitted. For example, Z1 is a methyl group and Z5 is a methoxy group. Also, Ph is a phenyl group (C ６ H ５ ) represents a 1-adamantyl group, and Z33 represents a 1-adamantyl group. 【0020】 【0021】 In one aspect of the present invention, R １ ~R ２０ R is selected from the group consisting of hydrogen atoms, deuterium atoms and Z1 to Z80. In one aspect of the present invention, R １ ~R ２０R is selected from the group consisting of hydrogen atoms, deuterium atoms and Z1 to Z32 and Z41 to Z72. In one embodiment of the present invention, R １ ~R ２０ R is selected from the group consisting of hydrogen atoms, deuterium atoms, Z1 to Z21 and Z41 to Z61. In one embodiment of the present invention, R １ ~R ２０ The elements are selected from the group consisting of hydrogen atoms, deuterium atoms, Z1-Z4, Z9-Z15, Z41-Z44, and Z49-Z55. 【0022】 In general formula (1), B is a boron atom and N is a nitrogen atom. 【0023】In this specification, "Group A" means: deuterium atom; hydroxyl group: halogen atom such as fluorine, chlorine, bromine, or iodine; alkyl group having, for example, 1 to 40 carbon atoms; alkoxy group having, for example, 1 to 40 carbon atoms; alkylthio group having, for example, 1 to 40 carbon atoms; aryl group having, for example, 6 to 30 carbon atoms; aryloxy group having, for example, 6 to 30 carbon atoms; arylthio group having, for example, 6 to 30 carbon atoms; heteroaryl group having, for example, 5 to 30 constituent atoms of the ring skeleton; heteroaryl group having, for example, 5 to 30 constituent atoms of the ring skeleton This group consists of aryloxy groups; heteroarylthio groups having, for example, 5 to 30 constituent atoms in the ring skeleton; acyl groups having, for example, 1 to 40 carbon atoms; alkenyl groups having, for example, 1 to 40 carbon atoms; alkynyl groups having, for example, 1 to 40 carbon atoms; alkoxycarbonyl groups having, for example, 1 to 40 carbon atoms; aryloxycarbonyl groups having, for example, 1 to 40 carbon atoms; heteroaryloxycarbonyl groups having, for example, 1 to 40 carbon atoms; silyl groups such as trialkylsilyl groups having, for example, 1 to 40 carbon atoms; and nitro groups. The alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups, alkenyl groups, alkynyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups referred to here may be substituted with substituents having a structure in which one or more of the deuterium atoms constituting group A and any of the substituents listed above are bonded. In this specification, "Group B" refers to the group consisting of a deuterium atom, an alkyl group having, for example, 1 to 40 carbon atoms; an alkoxy group having, for example, 1 to 40 carbon atoms; an aryl group having, for example, 6 to 30 carbon atoms; an aryloxy group having, for example, 6 to 30 carbon atoms; a heteroaryl group having, for example, 5 to 30 constituent atoms of the ring skeleton; a heteroaryloxy group having, for example, 5 to 30 constituent atoms of the ring skeleton; and a diarylaminoamino group having, for example, 0 to 20 carbon atoms.The alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heteroaryl groups, heteroaryloxy groups, and diarylaminoamino groups referred to herein may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to a deuterium atom constituting group B. In this specification, "group C" refers to the group consisting of a deuterium atom, an alkyl group having, for example, 1 to 20 carbon atoms; an aryl group having, for example, 6 to 22 carbon atoms; a heteroaryl group having, for example, 5 to 20 atoms in its ring skeleton; and a diarylamino group having, for example, 12 to 20 carbon atoms. The alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups referred to herein may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to a deuterium atom constituting group C. In this specification, "group D" refers to the group consisting of a deuterium atom, an alkyl group having, for example, 1 to 20 carbon atoms; an aryl group having, for example, 6 to 22 carbon atoms; and a heteroaryl group having, for example, 5 to 20 atoms in its ring skeleton. The alkyl groups, aryl groups, and heteroaryl groups referred to herein may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to a deuterium atom constituting group D. In this specification, "group E" refers to a group consisting of a deuterium atom, alkyl groups having, for example, 1 to 20 carbon atoms, and aryl groups having, for example, 6 to 22 carbon atoms. The alkyl groups and aryl groups referred to herein may be substituted with substituents having a structure in which one or more of the substituents listed above are bonded to a deuterium atom constituting group E. In this specification, when it is stated that a deuterium atom or substituent is substituted, it may be selected from, for example, group A, group B, group C, group D, or group E. 【0024】 As compound group 1 of the present invention, X of general formula (1) １ and X ２ At least one of them is a substituted or unsubstituted aryl group, X ３ and X ４A group of compounds in which at least one of the groups is a substituted or unsubstituted aryl group can be listed. Compound group 1 is the X of general formula (1) １ and X ２ Compound group 1a, in which both are identical substituted or unsubstituted aryl groups; and X of general formula (1) １ and X ２ Compound group 1b, in which each of the aryl groups is different from the others, either substituted or unsubstituted; and X of general formula (1) １ ~X ４ Compound group 1c, in which all are identical substituted or unsubstituted aryl groups; and X of general formula (1) １ ~X ４ All of them are substituted or unsubstituted aryl groups, but X １ ~X ４ This includes compound group 1d, in which not all compounds have the same structure. Examples of substituted or unsubstituted aryl groups in this paragraph include substituted or unsubstituted alkylaryl groups. For each of these compound groups 1a to 1d, further embodiments satisfying the following addition conditions can be exemplified. One of the addition conditions is the R of general formula (1). １ ~R ２０ At least one, for example two or more, for example four or more, are substituents. One additional condition is that R in general formula (1) １ ~R ２０ At least one of the alkyl groups, for example, two or more, or for example, four or more, is a substituted or unsubstituted alkyl group, for example, an alkyl group that may be substituted with a deuterium atom. One additional condition is the R of general formula (1) ３ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ３ and R ６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ３ and R １３R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ６ and R １６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ６ and R １３ and R １６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ３ and R １３ and R １６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ３ and R ６ and R １３ and R １６ R is a substituent, for example, a substituted or unsubstituted alkyl group, preferably an alkyl group that may be substituted with a deuterium atom. One of the addition conditions is R of general formula (1) ９ R is a substituent, for example, a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted cycloalkyl group, for example, a substituted or unsubstituted aryl group. One of the addition conditions is R of general formula (1) ９ and R １９ R is a substituent, for example, a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted cycloalkyl group, for example, a substituted or unsubstituted aryl group. One of the addition conditions is R of general formula (1) ８ and R １０ and R １８ and R ２０ is a substituent, for example, a substituted or unsubstituted alkyl group, for example, a substituted or unsubstituted cycloalkyl group, for example, a substituted or unsubstituted aryl group. One of the addition conditions is R ９ and R １９ Each is independently a cycloalkyl group or a branched alkyl group. One additional condition is that general formula (1) has a rotationally symmetric structure. Another additional condition is that R in general formula (1) ２１ and R ２２This is a hydrogen atom. One additional condition is that R in general formula (1) １ ~R ２０ The number of carbon atoms of the substituent being substituted is 0 to 4, for example 1 to 4, for example 3 to 4. One additional condition is R in general formula (1) ８ and R １０ and R １８ and R ２０ R is a hydrogen atom or a deuterium atom. One additional condition is that the general formula (1) contains at least one deuterium atom. Another additional condition is that R is not a substituent. ２ ~R ７ and R １１ ~R １７ This is a deuterium atom. 【0025】 As compound group 2 of the present invention, X of general formula (1) １ and X ２ At least one of them is a substituted or unsubstituted cycloalkyl group, X ３ and X ４ A group of compounds in which at least one of the elements is a substituted or unsubstituted cycloalkyl group can be listed. Group 2 of compounds is X of general formula (1) １ and X ２ Compound group 2a, in which both are the same substituted or unsubstituted cycloalkyl group; and X of general formula (1) １ and X ２ Compound group 2b consists of two different substituted or unsubstituted cycloalkyl groups; and X of general formula (1) １ ~X ４ Compound group 2c, in which all are identical substituted or unsubstituted cycloalkyl groups; and X of general formula (1) １ ~X ４ All of them are substituted or unsubstituted cycloalkyl groups, but X １ ~X ４ This includes a group of compounds 2d in which not all compounds have the same structure. For each of these groups of compounds 2a to 2d, examples can be given in which the additional conditions described in groups 1a to 1d are also satisfied. 【0026】The compound represented by general formula (1) preferably does not contain metal atoms. Here, the metal atoms do not include boron atoms. The compound represented by general formula (1) may also be composed of only atoms selected from the group consisting of boron atoms, carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In one aspect of the present invention, the compound represented by general formula (1) is composed of only atoms selected from the group consisting of boron atoms, carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be composed of only atoms selected from the group consisting of boron atoms, carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) may also be composed of only atoms selected from the group consisting of boron atoms, carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. Moreover, the compound represented by general formula (1) may not contain hydrogen atoms but may contain deuterium atoms. 【0027】 Tables 1 to 3 below illustrate specific examples of compounds represented by general formula (1). Here, among the compounds represented by general formula (1), compounds represented by general formula (1a) are particularly illustrated. However, the compounds represented by general formula (1) that can be used in the present invention should not be interpreted as being limited by these specific examples. General formula (1a) 【0028】 X １ ~X ４ The combinations when X is one of Y1 to Y218 are shown in Table 1 below as Q1 to Q218. In Table 1, X １ and X ３ They are identical, X ２ and X ４ They are identical. In the first row of Table 1, X １ and X ３ Y1 is X ２ and X ４ The combination where Y1 is shown as Q1. In the second row of Table 1, X １ and X ３ Y1 is X ２ and X ４The combination where Y2 is shown as Q2. The same method is used for the third row and beyond. １ ~X ４ This shows the combinations. 【0029】 【0030】 Table 2 contains X １ ~X ４ The combinations where Y1 to Y218 is one of the following are shown as Q1 to Q47524. １ and X ３ They are identical, X ２ and X ４ They are identical. In the first row of Table 2, X １ and X ３ Y1 is X ２ and X ４ The combinations where Y1 to Y218 are grouped together as Q1 to Q218. That is, the first row of Table 2 displays all of the Q1 to Q218 specified in Table 1 in one row. The second row of Table 2 is X １ and X ３ Y2 is X ２ and X ４ The combinations where Y1 to Y218 are grouped together as Q219 to Q436. The third row of Table 2 is X １ and X ３ Y3 is X ２ and X ４ The combinations where Y1 to Y218 are shown in order as Q437 to Q654. The combinations in subsequent rows are identified in the same manner. 【0031】 【0032】 In Table 3, R of the compound represented by general formula (1a) ３ , R ６ , R ９ , R １３ , R １６ , R １９ , X １ ~X ４By identifying R, the structures of compounds 1 to 923914084 are shown. In Table 3, R ３ and R １３ They are identical, R ６ and R １６ They are identical, R ９ and R １９ They are identical. Also, X １ ~X ４ This is identified by the combinations (Q1 to Q47524) specified in Table 2. In the first row of Table 3, R ３ , R ６ , R ９ , R １３ , R １６ , R １９ All of them are hydrogen atoms (H), X １ ~X ４ The combinations identified by 1 to Q47524 are listed in order as compounds 1 to 47524. In the second row, R ３ , R ６ , R １３ , R １６ All are identical and are one of Z1 to Z80, R ９ and R １９ is a hydrogen atom (H), and X １ ~X ４ The combinations identified by Q1 to Q47524 are shown as compounds 47525 to 3849444. Here, first R ３ , R ６ , R １３ , R １６ All are fixed to Z1, X １ ~X ４ Compounds whose values ​​are Q1 to Q47524 are designated as compounds 47525 to 95048 in order. Next, R ３ , R ６ , R １３ , R １６ All are fixed to Z2, X １ ~X ４ Compounds where Q1 to Q47524 are designated as compounds 95049 to 142572 in order. Next, R ３ , R ６ , R １３ , R １６ All are fixed to Z3, X １ ~X４ Compounds whose values ​​are Q1 to Q47524 are designated as compounds 142573 to 190098 in order. Subsequent compounds are identified in the same manner, and finally R ３ , R ６ , R １３ , R １６ All of them are fixed to the Z80, X １ ~X ４ Compounds where Q1 to Q47524 are, in order, designated as compounds 3801921 to 3849444. ３ , R １３ The column displays Z1 to Z80, and also R ６ , R １６ In the column, each row labeled Z1 to Z80 specifies the structure of the compound. 【0033】 Compounds obtained by substituting all hydrogen atoms in each of compounds 1 to 923914084 with deuterium atoms are designated as compounds 1(D) to 923914084(D), respectively. In each of compounds 1 to 923914084, R other than the substituent in general formula (1) １ ~R ７ and R １１ ~R １７ Compounds in which all atoms are replaced with deuterium atoms are designated as Compound 1(D') to 923914084(D'), in order. Compounds 1 to 923914084, Compounds 1(D) to 923914084(D), and Compounds 1(D') to 923914084(D') are individually identified and their structures are disclosed herein. 【0034】 Examples of preferred compounds represented by general formula (1) include the compounds synthesized in the synthesis examples described later. Other examples of compounds represented by general formula (1) include the following compounds. 【0035】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. 【0036】 Compounds represented by general formula (1), particularly those represented by general formula (1a), 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) exhibit excellent device durability and a long device lifespan. Furthermore, organic light-emitting devices using compounds represented by general formula (1) tend to have a low initial drive voltage. Additionally, organic light-emitting devices using compounds represented by general formula (1) tend to have high luminous efficiency. Moreover, compounds represented by general formula (1) can be effectively used in organic light-emitting devices. 【0037】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. 【0038】 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. 【0039】 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. 【0040】 As a concrete example of a repeating unit structure, we can cite the structure represented by the following formula. 【0041】 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. 【0042】 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. 【0043】In some embodiments, the compound represented by general formula (1) is a light-emitting material. Among the compounds represented by general formula (1) are compounds with a long luminescence lifetime. 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) are compounds that can extend the device lifetime when used in organic light-emitting devices. In some embodiments, the compound represented by general formula (1) is a compound that can emit delayed fluorescence. Among the compounds represented by general formula (1) 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, when excited by thermal or electronic means, the compound represented by general formula (1) can emit light in the UV region, the blue, green, yellow, orange, and 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. In some embodiments of this disclosure, a compound represented by general formula (1) may emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, 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 region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, 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) can emit light in the ultraviolet spectral region (e.g., 280–400 nm) when excited by thermal or electronic means.In some embodiments of this disclosure, a compound represented by general formula (1) can emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. 【0044】 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. 【0045】 [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. 【0046】[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). 【0047】[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. 【0048】[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 and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of a compound represented by general formula (1) as a light-emitting material for an organic light-emitting device. 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, for example, by using a combination of a phosphorescent material and the compound represented by general formula (1) in the light-emitting layer. Examples of phosphorescent materials include compounds containing Ir. In this case, one or two additional host materials may be used in the light-emitting layer. In one embodiment, the present invention provides a delayed phosphor having a structure represented by general formula (1). In one embodiment, the present invention relates to the use of the compound represented by general formula (1) as a delayed phosphor. In one embodiment, the present invention can be used as a host material and can be used with one or more light-emitting materials, the light-emitting materials may be fluorescent materials, phosphorescent materials or TADF materials (delayed fluorescence materials). In one embodiment, the compound represented by general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from the compound represented by general formula (1).In one embodiment, an organic light-emitting element containing a compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In one embodiment, the light-emitting layer contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) with respect to the film-forming surface affects or determines the direction of propagation of light emitted by the aligned compound. In one embodiment, the light extraction efficiency from the light-emitting layer is improved by aligning the direction of propagation of light emitted by the compound represented by general formula (1). One aspect of the present invention relates to an organic light-emitting element. In one embodiment, the organic light-emitting element includes a light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). 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. 【0049】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 the compound represented by general formula (1) and a host material also contains a delayed fluorescence material, the lowest excitation singlet energy of the delayed fluorescence material being lower than that of the host material and higher than that of the compound represented by general formula (1). In this embodiment, when the organic electroluminescent element is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent element has a layer containing the compound represented by general formula (1) and a light-emitting material having a structure outside the range of general formula (1) (this layer may further contain a host material). In 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). 【0050】 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. 【0051】 In some embodiments, the host material is selected from the group consisting of the following: 【0052】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 wt%) 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. 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 includes a TADF material, 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. 【0053】 The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer. 【0054】 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. 【0055】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. 【0056】 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. 【0057】 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. 【0058】 【0059】 Next, we will list some examples of preferred compounds that can be used as electron injection materials. 【0060】 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. 【0061】 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. 【0062】 【0063】 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. 【0064】 【0065】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. 【0066】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. 【0067】 【0068】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 inducer or 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. 【0069】 【0070】 Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials. 【0071】 【0072】 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. 【0073】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). 【0074】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. 【0075】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. 【0076】 Device manufacturing method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. 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, a light-emitting layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel. 【0077】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. 【0078】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. 【0079】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. 【0080】 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. 【0081】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. 【0082】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. 【0083】 The features of the present invention will be described in more detail below with reference to examples. 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 Corporation: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In addition, the energy of HOMO and LUMO was measured by atmospheric photoelectron spectroscopy (RIKEN Instruments Co., Ltd.: AC-3, etc.). 【0084】(Synthesis Example 1) Synthetic intermediate (1) of compound A 【0085】 Under a nitrogen atmosphere, a solution (221 mL) of carbazole (21.82 g, 48.8 mmol), 3,6-di-tert-butylcarbazole (21.82 g, 48.8 mmol), 1,4-dibromo-2,5-difluorobenzene (12.0 g, 44.3 mmol), and potassium phosphate (28.2 g, 133 mmol) in N,N-dimethylformamide (DMF) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for about 15 minutes, and the precipitated crystals were filtered. The filtrate was purified by column chromatography to obtain a white solid intermediate (1) (18.5 g, 26.7 mmol, yield 33%). MS (ASAP): (M + ). Calcd for. C 38 H 34 Br2N2: 692.8 【0086】 Intermediate (a) 【0087】 A solution of 2,6-dibromo-4-methylaniline (25 g, 94.3 mmol), (2,4,6-trimethylphenyl)boronic acid (15.4 g, 94.3 mmol), tetrakis(triphenylphosphine)palladium (5.44 g, 4.71 mmol), and sodium carbonate (19.9 g, 188 mmol) in toluene (470 ml), ethanol (90 ml), and water (90 ml) was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (a) (28.1 g, 92.2 mmol, yield 97.9%). MS (ASAP): (M + ). Calcd for. C 16 H 18 BrN: 304.5 【0088】 Intermediate (b) 【0089】Intermediate (a) (28 g, 92.0 mmol), phenylboronic acid (13.4 g, 110 mmol), tetrakis(triphenylphosphine)palladium (5.31 g, 4.60 mmol), and sodium carbonate (29.2 g, 276 mmol) were dissolved in toluene (300 ml), ethanol (75 ml), and water (75 ml). This mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (b) (15.6 g, 51.7 mmol, yield 56.3%). MS (ASAP): (M + ). Calcd for. C 22 H 23 N: 301.7 【0090】 Intermediate (2) 【0091】 Intermediate (b) (5.12 g, 16.9 mmol) and potassium iodide (8.39 g, 50.6 mmol) were dissolved in 80 mL of acetonitrile and cooled to -10°C. To this solution, a solution of p-toluenesulfonic acid (9.62 g, 50.6 mmol) and sodium nitrite (2.91 g, 42.2 mmol) in 40 mL of water was added dropwise. After the addition was complete, the reaction was carried out overnight in an oil bath at 50°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (2) (5.16 g, 12.5 mmol, yield 74%). MS (ASAP): (M + ). Calcd for. C 22 H 21 I: 412.5 【0092】 Compound A 【0093】Under a nitrogen atmosphere, 25 mL of toluene solution of intermediate (1) (0.9 g, 1.38 mmol) was mixed with n-BuLi (1.51 mol / L hexane solution, 2.6 mL, 4.2 mmol) in an external bath at 50°C and stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (0.33 mL, 3.5 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (2) (2.0 g, 4.85 mmol) and n-BuLi (3.0 mL, 4.9 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound A as a yellow solid (0.3 g, 0.27 mmol, yield 19.6%). 1 H-NMR (400 MHz, CDCl3): δ 9.32-9.21 (m, 2H), 8.43-8.36 (m, 2H), 8.22-8.19 (m, 2H), 8.17-7.99 (m, 4H), 7.96-7.83 (m, 4H), 7.79-7.63 (m, 4H), 7.57-7.37 (m, 4H), 7.24-7.09 (m, 2H), 6.85 (t, 1H), 6.67-6.59 (m, 4H), 6.54-6.47 (m, 2H), 6.44-6.35 (m, 3H), 6.26 (d, 1H), 2.10-2.06 (m, 4H), 2.03-1.99 (m, 3H), 1.84-1.79 (m, 3H), 1.59-1.49 (m, 18H), 1.48-1.37 (m, 12H), 1.30-1.26 (m, 3H) MS (ASAP): (M + ). Calcd for. C 82 H 74 B2N2:1110.07 【0094】 (Synthesis Example 2) Synthetic intermediate of compound B (3) 【0095】Under a nitrogen atmosphere, a 170 mL DMF solution of carbazole-1,2,3,4,5,6,7,8-d8 (19.8 g, 113 mmol), 1,4-dibromo-2,5-difluorobenzene (14.0 g, 51.4 mmol), and tripotassium phosphate (32.6 g, 154 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction solution was quenched by adding water. The mixture was stirred for about 15 minutes, and the precipitated crystals were filtered. Methanol was added to the filtrate and stirred for 30 minutes, and these crystals were filtered. The filtered crystals were heated under reflux in toluene, cooled, and filtered to obtain a white solid intermediate (3) (24.5 g, 42.0 mmol, yield 82%). MS (SAP): (M + ). Calcd for. C 38 H 34 Br2N2: 580.2 【0096】 Compound B 【0097】 Under a nitrogen atmosphere, 7.5 mL of n-BuLi (1.51 mol / L hexane solution, 12.0 mmol) was added to 80 mL of a toluene solution of intermediate (3) (2.32 g, 4.00 mmol) in an external bath at 50°C, and the mixture was stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (1.13 mL, 12.0 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (2) (6.6 g, 16.0 mmol) and n-BuLi (10.2 mL, 16.4 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound B as a yellow solid (1.0 g, 0.99 mmol, yield 24.7%). 1H-NMR (400 MHz, CDCl3): δ9.26 (dd, 2H), 8.17-8.08 (m, 1H), 7.93-7.80 (m, 4H), 7.73 (tdd, 2H), 7.69-7.61 (m, 2H), 7.18 (d, 2H), 6.84 (d, 1H), 6.57 (s, 1H), 6.51 (d, 2H), 6.41 (s, 1H), 6.38 (d, 2H), 2.07 (d, 6H), 1.78 (d, 6H), 1.44 (s, 3H), 1.34 (d, 3H), 1.24 (d, 6H) MS (ASAP) : (M + ). Calcd for. C 74 H 44 D 14 B2N2:1012.01 【0098】 (Synthesis Example 3) Synthetic intermediate (c) of compound C 【0099】 Intermediate (a) (12.8 g, 42.0 mmol), 3,5-di-tert-butylphenylboronic acid (19.6 g, 84.0 mmol), tetrakis(triphenylphosphine)palladium (4.85 g, 4.20 mmol), and sodium carbonate (13.3 g, 126 mmol) were dissolved in toluene (140 ml), ethanol (90 ml), and water (90 ml). The mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (c) (8.7 g, 21.0 mmol, yield 50.0%). MS (ASAP): (M + ). Calcd for. C 30 H 39 N: 413.8 【0100】 Intermediate (4) 【0101】Intermediate (c) (6.78 g, 16.3 mmol) and potassium iodide (8.11 g, 48.9 mmol) were dissolved in 80 mL of acetonitrile and cooled to -10°C. To this solution, a solution of p-toluenesulfonic acid (9.30 g, 48.9 mmol) and sodium nitrite (2.80 g, 40.7 mmol) in 40 mL of water was added dropwise. After the addition was complete, the mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (4) (5.5 g, 10.5 mmol, yield 65%). MS (ASAP): (M + ). Calcd for. C 30 H 37 I: 524.7 【0102】 Compound C 【0103】 Under a nitrogen atmosphere, 10.5 mL of n-BuLi (1.51 mol / L hexane solution, 16.9 mmol) was added to a toluene solution (147 mL) of intermediate (3) (3.3 g, 5.7 mmol) in an external bath at 50°C, and the mixture was stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (1.60 mL, 16.9 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (4) (11.8 g, 22.6 mmol) and n-BuLi (21.3 mL, 32.3 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound C as a yellow solid (0.4 g, 0.3 mmol, yield 5.7%). 1H-NMR (400 MHz, CDCl3): δ8.73 (d, 2H), 7.65 (d, 2H), 7.24-7.22 (m, 2H), 6.89-6.87 (m, 4H), 6.72-6.70 (m, 2H), 6.60 (t, 2H), 6.18 (s, 2H), 2.73 (s, 6H), 2.53 (s, 6H), 1.95 (s, 6H), 1.33 (d, 6H), 0.33-0.23 (m, 36H) MS (ASAP) : (M + ). Calcd for. C 90 H 76 D 14 B2N2:1236.30 【0104】 (Synthesis Example 4) Synthetic intermediate of compound D (5) 【0105】 Under an ambient atmosphere, a 200 mL DMF solution of 3-tert-butyl-9H-carbazole (30 g, 134 mmol), 1,4-dibromo-2,5-difluorobenzene (16.5 g, 60.9 mmol), and tripotassium phosphate (38.6 g, 182 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction solution was quenched by adding water. The mixture was stirred for about 15 minutes, and the precipitated crystals were filtered. Methanol was added to the filtrate and stirred for 30 minutes, and these crystals were filtered. The filtered crystals were heated under reflux in toluene, cooled, and filtered to obtain a white solid intermediate (5) (34.28 g, 50.5 mmol, yield 83%). MS (ASAP): (M + ). Calcd for. C 38 H 34 Br2N2: 678.7 【0106】 Intermediate (d) 【0107】2,6-Dibromo-4-methylaniline (20 g, 75.4 mmol), (3,5-di-tert-butylphenyl)boronic acid (40.5 g, 173 mmol), tetrakis(triphenylphosphine)palladium (871 mg, 0.754 mmol), and sodium carbonate (31.9 g, 301 mmol) in toluene (250 ml), ethanol (45 ml), and water (45 ml) were heated under reflux in an oil bath at 100 °C overnight. The reaction was confirmed to be complete, and the organic layer was separated through a celite-silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (d) (32.5 g, 67.2 mmol, 89% yield). MS (ASAP): (M + ). Calcd for. C 35 H 49 N: 483.5 【0108】 Intermediate (6) 【0109】 Intermediate (d) (15 g, 31.0 mmol) and potassium iodide (6.2 g, 37.1 mmol) were dissolved in 60 mL of acetonitrile and cooled to -10 °C. A solution of p-toluenesulfonic acid (2.4 g, 15.5 mmol) and sodium nitrite (4.3 g, 62.0 mmol) in water (15 ml) was added dropwise to this solution. After the addition was complete, the mixture was stirred and heated in an oil bath at 50 °C overnight. The reaction was confirmed to be complete, and the organic layer was separated through a celite-silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (6) (12.0 g, 20.1 mmol, 65.2% yield). MS (ASAP): (M + ). Calcd for. C 35 H 47 I: 594.8 【0110】 Compound D 【0111】Under a nitrogen atmosphere, n-BuLi (1.51 mol / L hexane solution, 17.4 mL, 26.4 mmol) was added to a toluene solution (180 mL) of intermediate (5) (6.0 g, 8.8 mmol) at an external bath temperature of 50 °C, and the mixture was stirred for 2 hours. The reaction mixture was cooled to -80 °C, boron tribromide (2.50 mL, 26.4 mmol) was added, the temperature was raised to room temperature, and the mixture was stirred for 30 minutes. Then, the temperature was further raised to 50 °C in the external bath and stirred for 30 minutes. A solution prepared by mixing intermediate (6) (21.0 g, 35.3 mmol) and n-BuLi (25.6 mL, 38.8 mmol) in toluene was added to this reaction solution, and the temperature was further raised and stirred at 70 °C overnight. This mixture was filtered using celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane: hexane) to obtain yellow solid compound D (2.3 g, 1.6 mmol, yield 18.0%). 1 H-NMR (400 MHz, CDCl3): δ 9.08 - 9.04 (m, 2H), 8.22 - 7.78 (m, 8H), 7.65 - 7.58 (m, 6H), 7.43 - 7.16 (m, 2H), 7.08 - 7.03 (m, 8H), 6.71 - 6.63 (m, 4H), 2.77 - 2.73 (m, 6H), 1.56 (d, J = 0.7 Hz, 12H), 1.33 - 1.29 (m, 6H), 0.64 - 0.57 (m, 72H) 【0112】 (Synthesis Example 5) Intermediate (e) for the synthesis of compound E 【0113】 Under a nitrogen atmosphere, N-bromosuccinimide (NBS, 83.1 g, 467 mmol) was gradually added to a solution of 4-cyclohexylaniline (40.0 g, 228 mmol) in tetrahydrofuran (760 mL) under cooling, and the mixture was stirred for 1 hour after the addition was completed. After confirming the completion of the reaction, sodium thiosulfate was added to the reaction solution to quench it. The solvent was distilled off under reduced pressure, the residue was extracted with hexane and washed with water. The solvent was distilled off, and the obtained residue was purified by column chromatography to obtain intermediate (e) (76.3 g, 100 mmol). MS (ASAP): (M + ). Calcd for. C 12 H 15Br2N: 331.0 【0114】 Intermediate (f) 【0115】 Intermediate (e) (20 g, 75.4 mmol), (3,5-di-tert-butylphenyl)boronic acid (40.5 g, 173 mmol), tetrakis(triphenylphosphine)palladium (871 mg, 0.754 mmol), sodium carbonate (31.9 g, 301 mmol) were mixed in toluene (250 ml), ethanol (45 ml), and water (45 ml). The mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (f) (32.5 g, 67.2 mmol, yield 89%). MS (ASAP): (M + ). Calcd for. C 40 H 57 N: 551.5 【0116】 Intermediate (7) 【0117】 Intermediate (f) (15 g, 62.0 mmol) and potassium iodide (12.8 g, 77.5 mmol) were dissolved in 150 mL of acetonitrile and cooled to -10°C. To this solution, a solution of p-toluenesulfonic acid (6.48 g, 34.1 mmol) and sodium nitrite (8.55 g, 124 mmol) in water (124 mL) was added dropwise. After the addition was complete, the mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (7) (32.5 g, 67.2 mmol, yield 89%). MS (ASAP): (M + ). Calcd for. C 40 H 55 I: 662.5 【0118】 Compound E 【0119】Under a nitrogen atmosphere, 147 mL of toluene solution of intermediate (5) (5.0 g, 7.36 mmol) was mixed with n-BuLi (1.51 mol / L hexane solution, 14.5 mL, 22.0 mmol) in an external bath at 50°C and stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (2.08 mL, 22.0 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (7) (19.4 g, 29.4 mmol) and n-BuLi (21.3 mL, 32.3 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound E (1.7 g, 1.05 mmol, yield 14.4%), a yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 9.04-8.98 (m, 2H), 8.22-7.82 (m, 8H), 7.66-7.40 (m, 4H), 7.20-7.13 (m, 4H), 7.08-6.98 (m, 8H), 6.70-6.63 (m, 4H), 2.95-2.83 (m, 2H), 2.37-2.19 (m, 7H), 2.04-2.01 (m, 4H), 1.90-1.74 (m, 6H), 1.69-1.56 (m, 4H), 1.53 (s, 18H), 1.49-1.23 (m, 9H), 0.97-0.40 (m, 72H) MS (ASAP): (M + ). Calcd for. C 118 H 142 B2N2: 1610.3 【0120】 (Synthesis Example 6) Synthetic intermediate of compound F (8) 【0121】Under a nitrogen atmosphere, a 100 mL DMF solution of 4-(3,5-di-tert-butylphenyl)-9H-carbazole (10 g, 28.1 mmol), 1,4-dibromo-2,5-difluorobenzene (3.6 g, 13.3 mmol), and tripotassium phosphate (8.51 g, 40.1 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction solution was quenched by adding water. The mixture was stirred for about 15 minutes, and the precipitated crystals were filtered. Methanol was added to the filtrate and stirred for 30 minutes, and these crystals were filtered. The filtered crystals were heated under reflux in toluene, cooled, and filtered to obtain a white solid intermediate (8) (11.4 g, 12.0 mmol, yield 91.2%). MS (ASAP): (M + ). Calcd for. C 58 H 58 Br2N2: 943.0 【0122】 Compound F 【0123】 Under a nitrogen atmosphere, 3.5 mL of n-BuLi (1.51 mol / L hexane solution, 5.3 mmol) was added to a toluene solution (40 mL) of intermediate (8) (2.0 g, 2.1 mmol) in an external bath at 50°C, and the mixture was stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (0.5 mL, 5.3 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (7) (5.6 g, 8.4 mmol) and n-BuLi (5.6 mL, 8.4 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound F as a yellow solid (0.7 g, 0.4 mmol, yield 17.6%). 1H-NMR (400 MHz, CDCl3): δ 9.07 (s, 2H), 8.00 (dd, J = 46.0, 7.8 Hz, 4H), 7.70 (d, J = 8.0 Hz, 2H), 7.55-7.53 (m, 6H), 7.45-7.39 (m, 6H), 7.19-7.13 (m, 4H), 7.04-6.98 (m, 8H), 6.64 (s, 4H), 2.86-2.80 (m, 2H), 2.25 (d, J = 11.9 Hz, 4H), 1.99 (d, J = 11.4 Hz, 4H), 1.87-1.72 (m, 6H), 1.60-1.57 (m, 2H), 1.43-1.26 (m, 36H), 0.92-0.49 (m, 72H) MS (ASAP) : (M + ). Calcd for. C 138 H 166 B2N2: 1873.4 【0124】 (Synthesis Example 7) Synthetic intermediate of compound G (9) 【0125】 Under a nitrogen atmosphere, a 50 mL DMF solution of 3,6-di-tert-butyl-9H-carbazole-1,2,4,5,7,8-d6 (9.0 g, 31.5 mmol), 1,4-dibromo-2,5-difluorobenzene (4.1 g, 15.0 mmol), and tripotassium phosphate (12.7 g, 60.0 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature, and the reaction solution was quenched by adding water. The mixture was stirred for about 15 minutes, and the precipitated crystals were filtered. Methanol was added to the filtrate and stirred for 30 minutes, and these crystals were filtered. The filtered crystals were heated under reflux in toluene, cooled, and filtered to obtain a white solid intermediate (9) (10.5 g, 13.0 mmol, yield 88%). MS (SAP): (M + ). Calcd for. C 46 H 38 D 12 Br2N2: 800.5 【0126】 Compound G 【0127】Under a nitrogen atmosphere, 7.4 mL, 11.1 mmol of n-BuLi (1.51 mol / L hexane solution) was added to 80 mL of a toluene solution of intermediate (9) (3.0 g, 3.7 mmol) in an external bath at 50°C, and the mixture was stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (1.0 mL, 11.1 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (7) (9.8 g, 14.8 mmol) and n-BuLi (10.7 mL, 16.3 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound G as a yellow solid (1.4 g, 0.8 mmol, yield 21.7%). 1 H-NMR (400 MHz, CDCl3) δ 7.62-7.66 (s,4H), 7.01-7.11 (d, 8H), 6.66-6.71 (m, 4H), 2.81-3.00 (m, 2H), 2.25-2.44 (m, 4H), 1.96-2.12 (m, 4H), 1.71-1.96 (m, 8H), 1.35-1.71 (m, 4H), 1.18-1.34 (s, 36H), 0.37-0.66 (s,72H) MS (ASAP) : (M + ). Calcd for. C 126 H 158 B2N2: 1734.5 【0128】 (Synthesis Example 8) Synthetic intermediate of compound H (10) 【0129】Under a nitrogen atmosphere, a 100 mL solution of DMF containing (1,2,3,4,5,6,7,8-d8)-9H-carbazole (26.8 g, 153.0 mmol), 3,6-di-tert-butyl(1,2,4,5,7,8-d6)-9H-carbazole (23.3 g, 81.6 mmol), 1,4-dibromo-2,5-difluorobenzene (27.4 g, 101 mmol), and potassium phosphate (64.9 g, 306 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for about 15 minutes, and the precipitated crystals were filtered. The filtrate was purified by column chromatography to obtain a white solid intermediate (10) (18.5 g, 26.7 mmol, yield 33%). MS (ASAP): (M + ). Calcd for. C 38 H 20 D 14 Br2N2: 690.5 【0130】 Compound H 【0131】 Under a nitrogen atmosphere, 120 mL of toluene solution of intermediate (10) (4.3 g, 6.2 mmol) was mixed with n-BuLi (1.51 mol / L hexane solution, 12.3 mL, 18.6 mmol) in an external bath at 50°C and stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (1.8 mL, 18.6 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 50°C and stirred for 30 minutes. To this reaction mixture, a solution prepared by mixing intermediate (7) (16.4 g, 24.8 mmol) and n-BuLi (18.0 mL, 27.2 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound H as a yellow solid (1.7 g, 1.06 mmol, yield 17.2%). 1H-NMR (400 MHz, CDCl3) δ 7.62-7.66 (s,4H), 7.01-7.11 (d, 8H), 6.66-6.71 (m, 4H), 2.81-3.00 (m, 2H), 2.25-2.44 (m, 4H), 1.96-2.12 (m, 4H), 1.71-1.96 (m, 8H), 1.35-1.71 (m, 4H), 1.18-1.34 (s, 18H), 0.37-0.66 (s,72H) MS (ASAP) : (M + ). Calcd for. C 82 H 74 B2N2: 1109.3 【0132】 (Synthesis Example 9) Synthesis of Compound I 【0133】 Intermediate (2) was changed to intermediate (6), and compound I was synthesized in the same manner as compound B. 1 H-NMR (400 MHz, CDCl3) δ 8.98-9.17 (2H), 7.54-7.68 (4H), 6.93-7.08 (8H), 6.52-6.75 (4H), 2.51-2.86 (6H), 0.39-0.81 (72H) MS (ASAP): (M + ). Calcd for. C 100 H 96 D 14 B2N2: 1375.18 【0134】 (Synthesis Example 10) Synthetic intermediate (g) of compound J 【0135】 Under a nitrogen atmosphere, NBS (171 g, 961 mmol) was gradually added to a solution of 4-tert-butylaniline (70 g, 469 mmol) in tetrahydrofuran (1563 mL) under cooling, and the mixture was stirred for 1 hour after the addition was complete. After confirming the completion of the reaction, sodium thiosulfate was added to the reaction mixture and quenched. The solvent was removed under reduced pressure, and the residue was extracted with hexane and washed with water. The solvent was removed, and the obtained residue was purified by column chromatography to obtain the intermediate (g) (152.1 g, 495 mmol, 106%). MS (ASAP): (M + ). Calcd for. C10 H 13 Br2N: 306.5 【0136】 Intermediate (h) 【0137】 Intermediate (g) (72 g, 234 mmol), 3,5-di-tert-butylphenylboronic acid (120 g, 514 mmol), tetrakis(triphenylphosphine)palladium (5.4 g, 4.68 mmol), tripotassium phosphate (198 g, 936 mmol) in toluene (640 ml) and water (125 ml) were heated under reflux overnight in an oil bath at 100 °C. The completion of the reaction was confirmed, and the organic layer was separated by passing through a celite-silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain Intermediate (h) (85.9 g, 163 mmol, 69.8%). MS (ASAP): (M + ). Calcd for. C 38 H 55 N: 525.3 【0138】 Intermediate (11) 【0139】 Intermediate (h) was dissolved in 540 mL of acetonitrile and cooled to -10 °C. A solution of hydrochloric acid (41.2 mL, 486 mmol) and sodium nitrite (22.36 g, 324 mmol) in water (324 ml) and a solution of potassium iodide (64.5 g, 389 mmol) in water (324 ml) were added dropwise thereto. After completion of the dropwise addition, the mixture was reacted overnight in an oil bath at 50 °C. The completion of the reaction was confirmed, and the mixture was filtered. The filtrate was purified by silica gel column chromatography (dichloromethane:hexane) to obtain Intermediate (11) (67.1 g, 105.37 mmol, 65%). MS (ASAP): (M + ). Calcd for. C 38 H 53 I: 636.2 【0140】 Compound J 【0141】 Intermediate (6) was changed to Intermediate (11), and Compound J was synthesized in the same manner as Compound D. 1H-NMR (400 MHz, CDCl3) δ 8.95-9.12 (2H), 8.07-8.24 (4H), 7.31-8.02 (10H), 6.92-7.12 (8H), 6.60-6.75 (4H), 1.61-1.74 (18H), 1.40-1.53 ​​(9H), 1.16-1.43 (9H), 0.53-0.66 (72H) MS (ASAP): (M + ). Calcd for. C 114 H 138 B2N2: 1557.47 【0142】 (Synthesis Example 11) Synthetic intermediate of compound K (12) 【0143】 Intermediate (12) was synthesized by replacing 3,6-di-tert-butyl-9H-carbazole-1,2,4,5,7,8-d6 with 3,6-di-tert-butyl-9H-carbazole using the same synthetic method as intermediate (9). 【0144】 Compound K 【0145】 Under a nitrogen atmosphere, 252 mL of a toluene solution of intermediate (12) (10.0 g, 12.6 mmol) was mixed with n-BuLi (1.51 mol / L hexane solution, 25.0 mL, 37.8 mmol) in an external bath at 50°C and stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (3.57 mL, 37.8 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 70°C and stirred for 1 hour. To this reaction mixture, a solution prepared by mixing intermediate (7) (33.4 g, 50.4 mmol) and n-BuLi (36.6 mL, 55.4 mmol) in toluene was added and stirred at 70°C for 2 hours. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound K as a yellow solid (9.13 g, 5.3 mmol, yield 42.0%). 1HNMR (400 MHz, CDCl3, δ):δ 8.97 (s, 2H), 8.23 ​​(d, J = 1.8 Hz, 2H), 8.12 (d, J = 1.8 Hz, 2H), 7.98 (d, J = 8.7 Hz, 2H), 7.86 (d, J = 1.8 Hz, 2H), 7.65-7.62 (m, 6H), 7.08-7.03 (m, 8H), 6.70 (s, 4H), 2.92 (t, J = 11.9 Hz, 2H), 2.36 (d, J = 11.9 Hz, 4H), 2.04 (d, J = 12.8 Hz, 4H), 1.90-1.81 (m, 6H), 1.65 (q, J = 13.1 Hz, 4H), 1.55 (s, 18H), 1.49-1.39 (m, 2H), 1.35-1.25 (m, 18H), 0.65-0.51 (m, 72H) MS (ASAP): (M + ). Calcd for. C 126 H 158 B2N2: 1722.26 【0146】 (Synthesis Example 12) Synthetic intermediate of compound L (13) 【0147】 Under a nitrogen atmosphere, a DMF solution (36.3 mL) containing 2-phenyl-5H-benzofl[3,2-c]carbazole (5 g, 14.9 mmol), 1,4-dibromo-2,5-difluorobenzene (1.97 g, 7.26 mmol), and potassium phosphate (4.62 g, 21.8 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for about 15 minutes, and the precipitated crystals were filtered. The filtrate was suspended under reflux of toluene, cooled, and filtered to obtain a white solid intermediate (13) (3.2 g, 3.56 mmol, yield 49%). MS (ASAP): (M + ). Calcd for. C 54 H 30 Br2N2O2: 898.2 【0148】 Compound L 【0149】Intermediate (9) was changed to intermediate (13), and compound L was synthesized in the same manner as compound G. 1 H-NMR (400 MHz, CDCl3) δ 9.17-9.26 (2H), 8.73-8.84 (2H), 8.44-8.52 (2H), 7.86-8.30 (10H), 7.61-7.78 (10H), 7.35-7.52 (6H), 7.06-7.16 (8H), 6.52-6.65 (4H), 2.16-2.50 (4H), 1.34-2.17 (18H), 0.41-0.77 (72H) MS (ASAP): (M + ). Calcd for. C 134 H 138 B2N2O2: 1829.69 【0150】 (Synthesis Example 13) Synthetic intermediate of compound M (14) 【0151】 Under a nitrogen atmosphere, a 73.5 mL solution of DMF containing 3,6-bis(2-(methyl-d3)propan-2-yl-1,1,1,3,3,3-d6)-9H-carbazole-1,2,4,5,7,8-d6 (6.3 g, 32.3 mmol), 1,4-dibromo-2,5-difluorobenzene (4 g, 14.7 mmol), and potassium phosphate (9.36 g, 44.1 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for about 15 minutes, and the precipitated crystals were filtered. The filtrate was suspended under reflux of toluene, cooled, and filtered to obtain a white solid intermediate (14) (9.5 g, 11.3 mmol, yield 77.2%). MS (ASAP): (M + ). Calcd for. C 20 HD 24 N: 838.5 【0152】 Compound M 【0153】 Intermediate (9) was changed to intermediate (14), and compound M was synthesized in the same manner as compound G. 1H-NMR (400 MHz, CDCl3) δ 9.01 (dd, J = 10.0, 7.9 Hz, 2H), 7.64-7.60 (m, 4H), 7.04-6.99 (m, 8H), 6.67-6.64 (m, 4H), 2.53 (d, J = 7.3 Hz, 2H), 2.31 (d, J = 10.5 Hz, 4H), 2.09-2.02 (m, 4H), 1.90-1.75 (m, 8H), 1.69-1.56 (m, 2H), 1.50-1.37 (m, 2H), 0.69-0.53 (m, 72H) MS (ASAP) : (M + ). Calculated for. C 126 H 112 D 46 B2N2: 1768.05 【0154】 (Synthesis Example 14) Synthesis of Compound N 【0155】 Intermediate (7) and Intermediate (11) are the same, compound G is the same as compound N, and compound N is synthesized by the same method. 1 H-NMR (400 MHz, CDCl3) δ 8.90-9.05 (2H), 7.74-7.84 (4H), 7.01-7.14 (8H), 6.62-6.76 (4H), 1.63-1.76 (18H), 1.37-1.53 ​​(18H), 1.22-1.39 (18H), 0.46-0.70 (72H) MS (ASAP) : (M + ). Calculated for. C 122 H 144 D 10 B2N2: 1679.75 【0156】 (Synthesis Example 15) Synthesis intermediate (i) of compound O 【0157】A solution of 2,4,6-tribromoaniline (12.5 g, 37.8 mmol), 3,5-di-tert-butylphenylboronic acid (28 g, 120 mmol), tetrakis(triphenylphosphine)palladium (2.18 g, 1.89 mmol), and potassium carbonate (15 g, 113 mmol) in toluene (151 ml), ethanol (54 ml), and water (54 ml) was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (i) (16.05 g, 24.3 mmol, 64.5%). MS (ASAP): (M + ). Calcd for. C 48 H 67 N: 657.6 【0158】 Intermediate (15) 【0159】 Intermediate (i) (16.05 g, 24.3 mmol) was dissolved in acetonitrile (81 mL) and cooled to -10°C. To this solution, hydrochloric acid (6.17 mL, 72.9 mmol), a solution of sodium nitrite (3.35 g, 48.6 mmol) in water (24.3 mL), and a solution of potassium iodide (9.67 g, 58.3 mmol) in water (24.3 mL) were added dropwise. After the addition was complete, the reaction was carried out overnight in an oil bath at 50°C. After confirming the completion of the reaction, the filtrate was filtered, and the filtrate was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (15) (14.04 g, 17.1 mmol, 70.4%). MS (ASAP): (M + ). Calcd for. C 48 H 65 I: 768.4 【0160】 Compound O 【0161】 Intermediate (7) was changed to intermediate (15), and compound O was synthesized in the same manner as compound G. 1H-NMR (400 MHz, CDCl3) δ 9.04-9.20 (2H), 8.03-8.07 (4H), 7.80-7.84 (4H), 7.53-7.65 (2H), 7.13-7.21 (8H), 6.67-6.83 (4H), 1.36-1.51 (54H), 1.26-1.36 (18H), 0.53-0.70 (72H) MS (ASAP) : (M + ). Calcd for. C 142 H 168 D 10 B2N2: 1944.16 【0162】 (Synthesis Example 16) Synthesis of Compound P 【0163】 Under a nitrogen atmosphere, 29.8 mL of a toluene solution of intermediate (14) (2.5 g, 2.98 mmol) was mixed with n-BuLi (1.51 mol / L hexane solution, 4.93 mL, 7.45 mmol) in an external bath at 50°C and stirred for 2 hours. The reaction mixture was cooled to -80°C, boron tribromide (0.7 mL, 7.45 mmol) was added, and the mixture was heated to room temperature and stirred for 30 minutes. Then, the mixture was further heated in an external bath at 70°C and stirred for 1 hour. To this reaction mixture, a solution prepared by mixing intermediate (11) (4.74 g, 7.45 mmol) and n-BuLi (4.93 mL, 7.45 mmol) in toluene was added, and the mixture was further heated and stirred overnight at 70°C. The mixture was filtered using Celite and silica, and the filtrate was concentrated. This residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound P as a yellow solid (1.56 g, 0.9 mmol, yield 30.5%). 1 H NMR (400 MHz, CDCl3, δ): δ 8.90-9.05 (2H), 7.74-8.02 (4H), 6.98-7.16 (8H), 6.62-6.77 (4H), 1.63-1.74 (18H), 0.52-0.68 (72H) MS (ASAP): (M + ). Calcd for. C 126 H 146 D 12 B2N2: 1717.53 【0164】(Synthesis Example 17) Synthetic intermediate of compound Q (16) 【0165】 Under a nitrogen atmosphere, a 160 mL DMF solution of 9H-carbazole (39.0 g, 233 mmol), 3,6-di-tert-butyl-9H-carbazole (34.6 g, 124 mmol), 1,4-dibromo-2,5-difluorobenzene (42.1 g, 155 mmol), and potassium phosphate (98.4 g, 464 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for 1 hour, and the precipitated crystals were filtered. The obtained crystals were dispersed in toluene and filtered to remove unwanted materials. Finally, methanol was added to the resulting filtrate and stirred for 30 minutes, and filtered to obtain a white solid intermediate (16) (79.4 g, 117 mmol, yield 76%). MS(ASAP): (M + ). Calcd for. C 38 H 34 Br2N2: 678.0 【0166】 Compound Q 【0167】 Intermediate (10) was changed to intermediate (16), and compound Q was synthesized in the same manner as compound H. 1 H-NMR (400 MHz, CDCl3) δ 8.94-9.10 (2H), 7.77-8.29 (8H), 7.56-7.70 (5H), 7.32-7.56 (2H), 7.11-7.23 (1H), 6.92-7.11 (8H), 6.56-6.76 (4H), 2.78-2.99 (2H), 2.20-2.42 (4H), 1.95-2.12 (4H), 1.68-1.95 (6H), 1.56-1.68 (4H), 1.53-1.56 (9H), 1.35-1.49 (2H), 1.22-1.35 (9H), 0.37-0.88 (72H) 【0168】 (Synthesis Example 18) Synthetic intermediate (j) of compound R 【0169】Under a nitrogen atmosphere, iodine (40.8 g, 161 mmol) and silver sulfate (50.1 g, 161 mmol) were suspended in ethanol (585 mL) and slowly added to the solution at room temperature with 4-tert-butylaniline (12.5 mL, 79.0 mmol). After stirring for 2.5 hours, the reaction mixture was filtered through a glass filter. After removing the solvent under reduced pressure, the residue was dissolved in methylene chloride (200 mL), the organic layer was washed with 5% sodium hydroxide aqueous solution (100 mL) and water (100 mL), dried over anhydrous magnesium sulfate, and concentrated. The resulting residue was purified by neutral silica gel column chromatography (hexane / ethyl acetate = 50:1) to obtain intermediate (j) (14.19 g, 35.3 mmol, yield 44.6%). MS (ASAP): (M + ). Calcd for. C 10 H 13 I2N: 400.5 【0170】 Intermediate (k) 【0171】 Intermediate (j) (10.7 g, 26.7 mmol), (3-tert-butylenyl)boronic acid (10 g, 56.1 mmol), tetrakis(triphenylphosphine)palladium (1.53 g, 1.33 mmol), potassium carbonate (11 g, 80.1 mmol) were dissolved in toluene (267 ml), ethanol (66.7 ml), and water (66.7 ml). This mixture was heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (k) (7 g, 16.9 mmol, 63.6%). MS (ASAP): (M + ). Calcd for. C 30 H 39 N: 413.1 【0172】 Intermediate (17) 【0173】Intermediate (k) (7 g, 16.9 mmol) was dissolved in acetonitrile (56.3 mL) and cooled to -10°C. To this solution, hydrochloric acid (4.28 mL, 50.6 mmol), sodium nitrite (2.33 g, 33.8 mmol) in water (16.9 mL), and potassium iodide (6.72 g, 40.5 mmol) in water (16.9 mL) were added dropwise. After the addition was complete, the reaction was carried out overnight in an oil bath at 50°C. After confirming the completion of the reaction, the solution was filtered, and the filtrate was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (17) (8.05 g, 15.3 mmol, 90.8%). MS (ASAP): (M + ). Calcd for. C 30 H 37 I: 524.0 【0174】 Compound R 【0175】 Intermediate (7) was changed to intermediate (17), and compound R was synthesized in the same manner as compound K. 1 H-NMR (400 MHz, CDCl3) δ 8.79-8.94 (2H), 8.18-8.32 (2H), 8.04-8.18 (2H), 7.69-7.92 (8H), 7.33-7.57 (2H), 7.13-7.24 (4H), 6.89-7.05 (4H), 6.79-6.89 (4H), 6.66-6.79 (4H), 1.58-1.90 (18H), 1.41-1.51 (18H), 1.11-1.41 (19H), 0.15-0.58 (36H) 【0176】 (Synthesis Example 19) Synthetic intermediate of compound S (18) 【0177】Under a nitrogen atmosphere, a 248 mL DMF solution containing 3-tert-butyl-9H-carbazole (20 g, 89.5 mmol), 3,6-di-tert-butyl-9H-carbazole (16.6 g, 59.6 mmol), 1,4-dibromo-2,5-difluorobenzene (20.2 g, 74.5 mmol), and potassium phosphate (47.3 g, 223 mmol) was stirred at 150°C for 16 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered. Methanol was added to the resulting filtrate and stirred for about 15 minutes, and the precipitated crystals were filtered. The filtrate was suspended under reflux of toluene, cooled, and filtered to obtain a white solid intermediate (18) (25.84 g, 35.17 mmol, yield 47.2%). MS (ASAP): (M + ). Calcd for. C 42 H 42 Br2N2: 734.1 【0178】 Compound S 【0179】 Intermediate (10) was changed to intermediate (18), and compound S was synthesized in the same manner as compound H. 1 H-NMR (400 MHz, CDCl3) δ 8.90-9.09 (2H), 7.75-8.29 (8H), 7.11-7.72 (7H), 6.92-7.11 (8H), 6.55-6.78 (4H), 2.78-3.01 (2H), 2.21-2.45 (4H), 1.95-2.13 (4H), 1.72-1.95 (6H), 1.55-1.72 (4H), 1.53-1.55 (9H), 1.33-1.50 (3H), 1.30-1.33 (9H), 0.37-0.89 (72H) 【0180】 (Synthesis Example 20) Synthetic intermediate (l) of compound T 【0181】Intermediate (e) (72 g, 234 mmol), 3-tert-butylphenylboronic acid (91.5 g, 514 mmol), tetrakis(triphenylphosphine)palladium (5.4 g, 4.68 mmol), and tripotassium phosphate (198 g, 936 mmol) were dissolved in toluene (640 ml) and water (125 ml) and heated overnight under reflux in an oil bath at 100°C. After confirming the completion of the reaction, the organic layer was separated by passing it through a Celite silica pad. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (dichloromethane:hexane) to obtain intermediate (l) (71.8 g, 163 mmol, 69.8%). MS (ASAP): (M+). Calcd for. C 32 H 41 N: 439.33 【0182】 Intermediate (19) 【0183】 Intermediate (l) was dissolved in acetonitrile (540 mL) and cooled to -10°C. To this solution, a solution of hydrochloric acid (41.2 mL, 486 mmol), sodium nitrite (22.36 g, 324 mmol) in water (324 mL), and a solution of potassium iodide (64.5 g, 389 mmol) in water (324 mL) were added dropwise. After the addition was complete, the reaction was carried out overnight in an oil bath at 50°C. After confirming the completion of the reaction, the filtrate was filtered, and the filtrate was purified by silica gel column chromatography (dichloromethane:hexane) to obtain compound (19) (67.1 g, 105.37 mmol, 65%). MS(ASAP): (M + ). Calcd for. C 32 H 39 I: 550.46 【0184】 Compound T Intermediate (7) was replaced with intermediate (19), and compound T was synthesized in the same manner as compound K. MS (ASAP): (M + ). Calcd for. C 110 H 126 B2N2: 1497.21 【0185】 (Synthesis Example 21) Synthesis of Compound U 【0186】Intermediate (7) was changed to intermediate (11), and compound U was synthesized in the same manner as compound Q. MS (ASAP): (M + ). Calcd for. C 114 H 138 B2N2: 1557.27 【0187】 (Example 1) Fabrication and evaluation of organic electroluminescent elements. On a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 50 nm was formed, each thin film was deposited by vacuum deposition at a vacuum of 5.0 × 10⁻⁶. －５ The layers were laminated with Pa. First, the compound HAT-CN described later was formed to a thickness of 10 nm on ITO, then the compound NPD described later was formed to a thickness of 30 nm on top of it, then the compound TrisPCz described later was formed to a thickness of 10 nm on top of that, and then the compound H1 described later was formed to a thickness of 5 nm on top of that. Next, the compound H2 described later, the compound T1 described later, and the compound G described later were co-deposited from different deposition sources to form a 40 nm thick layer which served as the light-emitting layer. The concentration of compound H2 in the light-emitting layer was 65 mass%, the concentration of compound T1 was 34 mass%, and the concentration of compound G was 1 mass%. Next, the compound SF3-TRZ described later was formed to a thickness of 10 nm, and then the compound Liq described later and SF3-TRZ were co-deposited from different deposition sources to form a 30 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 mass% and 70 mass%, respectively. Furthermore, a cathode was formed by creating a 2 nm thick layer of Liq, followed by a 100 nm thick layer of aluminum (Al), thus creating an organic electroluminescent element. Organic electroluminescent elements were fabricated using the same procedure with compound H and comparative compound 1 instead of compound G. Each organic electroluminescent element was subjected to a current of 6.3 mA / cm². ２When the external quantum efficiency (EQE) was measured while driving the devices, all showed high values ​​exceeding 25%. Furthermore, the driving voltage was confirmed to be low, less than 3.8V. Each organic electroluminescent element was continuously emitted at 1000 nits, and the time until the luminescence intensity decreased to 95% of the initial level (LT95) was measured. The results are shown in the table below. The data in the table are relative values, with the measurement time of the element using comparative compound 1 set to 1. Compared to the element using comparative compound 1, the LT95 of the elements using compounds G and H was more than 20% longer. This confirms that by using the compound represented by general formula (1), the lifespan of the element can be further extended while maintaining the excellent luminescence efficiency and low driving voltage of the element. 【0188】 【0189】 (Example 2) Fabrication and Evaluation of Another Organic Electroluminescent Element An organic electroluminescent element was fabricated using the same procedure as in Example 1, except that the 40 nm thick light-emitting layer was formed by co-depositing compound H1, compound T1, and compound D from different deposition sources. The concentration of compound H1 in the fabricated light-emitting layer was 54% by mass, the concentration of compound T1 was 45% by mass, and the concentration of compound D was 1% by mass. Organic electroluminescent elements were fabricated using the same procedure as in Example 1, with compounds E, G-J, and comparative compound 1 used instead of compound D. The LT95 of each organic electroluminescent element was measured under the same conditions as in Example 1, and the results are shown in the table below. The data in the table are relative values ​​with the measurement time of the element using comparative compound 1 set to 1. It was confirmed that even when the material and composition of the light-emitting layer are changed, the lifespan of the element can be extended by using the compound represented by general formula (1). 【0190】 【0191】(Example 3) Fabrication and evaluation of another organic electroluminescent element. Each thin film was deposited on a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 100 nm was formed, using a vacuum deposition method at a vacuum of 5.0 × 10⁻⁶. －５ The layers were laminated with Pa. First, the compound HAT-CN described later was formed to a thickness of 10 nm on ITO, and then the compound HT2 described later was formed to a thickness of 20 nm on top of it. Next, the compounds H3, H4, Ir(ppy)3, and K described later were co-deposited from different deposition sources to form a 40 nm thick layer which served as the light-emitting layer. The concentrations of compound H3, H4, Ir(ppy)3, and D in the light-emitting layer were 45% by mass, 45% by mass, 10% by mass, and 2% by mass respectively. Next, after forming the compound H3 described later to a thickness of 10 nm, the compounds ET2 and Liq described later were co-deposited from different deposition sources to form a 20 nm thick layer. The concentrations of ET2 and Liq in this layer were 50% by mass each. Furthermore, a cathode was formed by creating a 1.5 nm thick layer of Liq, followed by a 100 nm thick layer of aluminum (Al) deposition, creating an organic electroluminescent element, which was designated as Inventive Element 1. An organic electroluminescent element was fabricated using Comparative Compound 1 instead of Compound K, following the same procedure, and was designated as Comparative Element 1. In addition, an organic electroluminescent element was fabricated using the same procedure as in Example 1, except that a 40 nm thick light-emitting layer was formed by co-depositing Compound H3, Compound H4, and Ir(ppy)3 from different deposition sources, and was designated as Comparative Element 2. The concentrations of Compound H3, Compound H4, and Ir(ppy)3 in the fabricated light-emitting layer were 45% by mass, 45% by mass, and 10% by mass, respectively. Each organic electroluminescent element was set to 2 mA / cm². ２The external quantum efficiency (EQE) was measured by driving the device. LT95 was measured under the same conditions as in Example 1. The results are shown in the table below. In the table, LT95 is shown as a relative value with the measurement time of the device using comparative compound 1 set to 1. Compared to comparative device 1 using comparative compound 1 and comparative device 2, which is a phosphorescent device, the inventive device 1 using the compound represented by general formula (1) showed higher luminous efficiency and a longer device lifespan. In particular, it was confirmed that using the compound represented by general formula (1) for the phosphorescent device clearly improved both luminous efficiency and device lifespan. 【0192】 【0193】 【0194】 The compound of the present invention, represented by general formula (1), exhibits excellent performance as a compound for organic light-emitting devices. Therefore, the present invention has high potential for industrial application.

Claims

A compound represented by the following general formula (1). General form (1) [In general formula (1), R １ ~R ２０ each independently represents a hydrogen atom, a deuterium atom or a substituent. 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 , R ６ and R ７ , 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 １８ and R １９ , R １９ and R ２０ may be bonded to each other to form a cyclic structure. R ２１ and R ２２ are each independently a hydrogen atom or a deuterium atom. X １ ~X ４ represent a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted non-aromatic heterocyclic group. ] X １ ~X ４ The compound according to claim 1, wherein each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted cycloalkyl group. X １ ~X ４ The compound according to claim 1, wherein at least one of the molecules is a substituted aryl group, and the aryl group is substituted with one or more molecules selected from the group consisting of a deuterium atom, an alkyl group, an alkoxy group, a non-aromatic heterocyclic group, and a group having a structure in which two or more of these are bonded. X １ ~X ４ The compound according to claim 1, wherein each is an aryl group in which at least one tert-butyl group may be independently substituted with a deuterium atom. R １ ~R ２０ The compound according to claim 1, wherein each of them is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted cycloalkyloxy group, or a substituted or unsubstituted non-aromatic heterocyclic group. R １ ~R ２０ The compound according to claim 1, wherein at least one of the alkyl groups may be substituted with a deuterium atom. R ３ , R ６ , R １３ , R １６ The compound according to claim 1, wherein at least one of the substituents is a substituent. R ３ , R ６ , R １３ , R １６ The compound according to claim 1, wherein at least one of the members is a branched alkyl group which may be substituted with a deuterium atom. R ９ and R １９ The compound according to claim 1, wherein each is a cycloalkyl group or a branched alkyl group that may be independently substituted with a deuterium atom. The compound according to claim 1, having a deuterium atom. 　 The compound according to claim 1, having a rotationally symmetric structure. 　 A light-emitting material comprising the compound according to any one of claims 1 to 11. 　 A film comprising the compound according to any one of claims 1 to 11. 　 An organic light-emitting element comprising the compound according to any one of claims 1 to 11. 　 The organic light-emitting element according to claim 14, which is an organic electroluminescent element. 　 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. 　 The organic light-emitting element according to claim 16, wherein the layer includes a delayed fluorescence material in addition to the compound and the host material, and the lowest excitation singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound. 　 The organic light-emitting element according to claim 17, wherein the material contained in the organic electroluminescent element has the greatest amount of light emitted from the compound. 　 The organic light-emitting element according to claim 16, wherein the layer also includes a phosphorescent material in addition to the compound and the host material. 　 The organic light-emitting element according to claim 19, wherein the compound emits the maximum amount of light among the materials contained in the organic electroluminescent element.

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