Compound, Light-Emitting Material, and Light-Emitting Element

Abstract

To provide an excellent light-emitting material.SOLUTION: A compound represented by the following general formula is used as a light-emitting material. Any one of R1, R2, and R4 is a hydrogen atom or deuterium atom, and the others are donor groups where at least one is a carbazole-9-yl group having a condensed benzofuran ring, benzothiophene ring, indole ring, indene ring, or silaindene ring.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a compound useful as a light-emitting material and a light-emitting device using the same.

Background Art

[0002] Research is actively conducted to improve the luminous efficiency of light-emitting devices such as organic electroluminescence devices (organic EL devices). In particular, various efforts have been made to improve the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a light-emitting material, etc. constituting the organic electroluminescence device. Among them, research on organic electroluminescence devices using a delayed fluorescence material can also be seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after generating reverse intersystem crossing from the excited triplet state to the excited singlet state in the excited state. Fluorescence by such a path is observed later than fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence), and thus is called delayed fluorescence. Here, for example, when a luminescent compound is excited by carrier injection, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, there is a limit to the improvement of the luminous efficiency only with fluorescence from the directly generated excited singlet state. On the other hand, in the delayed fluorescence material, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the above-mentioned reverse intersystem crossing path, so that a higher luminous efficiency can be obtained compared with ordinary fluorescent materials.

[0004] Since such a principle was revealed, various studies have led to the discovery of various delayed fluorescence materials. However, just because a material emits delayed fluorescence does not necessarily mean it is immediately useful as a luminescent material. Among the delayed fluorescence materials, there are those in which reverse intersystem crossing occurs relatively rarely and those with a long lifetime of delayed fluorescence. There are also materials in which excitons accumulate in the high current density region, resulting in a decrease in luminous efficiency, or materials that rapidly deteriorate when driven for a long time. Therefore, in fact, there are extremely many delayed fluorescence materials that have room for improvement in terms of practicality. For this reason, it has been pointed out that there are problems even in benzonitrile-based compounds known as delayed fluorescence materials. For example, although 2CzPN having the following structure is a material that emits delayed fluorescence, it has problems such as low luminous efficiency and significant decrease in luminous efficiency in the high current density region (see Non-Patent Document 1).

[0005]

Chemical formula

Prior art documents

Non-Patent Documents

[0006]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] Despite being pointed out to have such problems, it is hard to say that the relationship between the chemical structure and properties of delayed fluorescence materials has been sufficiently elucidated. Therefore, it is currently difficult to generalize the chemical structure of compounds useful as luminescent materials, and there are many unclear points.

[0008] Under such circumstances, the present inventors have conducted extensive research with the aim of providing a more useful compound as a light-emitting material for light-emitting elements. Then, they have intensively studied to derive and generalize the general formula of a more useful compound as a light-emitting material.

Means for Solving the Problems

[0009] As a result of intensive studies to achieve the above object, the present inventors have found that among isophthalonitrile derivatives, a compound having a structure satisfying specific conditions is useful as a light-emitting material. The present invention has been proposed based on such findings, and specifically, has the following configurations.

[0010] [1] A compound represented by the following general formula (1).

Chemical Formula

[10] The remaining two and R 3At least one of them is a benzofuran-fused carbazole-9-yl group having a skeleton in which two benzofuran rings are condensed at the 2,3-positions to the carbazole ring, a benzothiophene-fused carbazole-9-yl group having a skeleton in which two benzothiophene rings are condensed at the 2,3-positions to the carbazole ring, an indole-fused carbazole-9-yl group having a skeleton in which two indole rings are condensed at the 2,3-positions to the carbazole ring, an indene-fused carbazole-9-yl group having a skeleton in which two indene rings are condensed at the 2,3-positions to the carbazole ring, or a silaindenefused carbazole-9-yl group having a skeleton in which two silaindenene rings are condensed at the 2,3-positions to the carbazole ring, the compound according to any one of [1] to [9].

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

[10] , having a symmetric structure.

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

[11] , comprising atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom.

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

[12] , wherein the benzofuran-fused carbazole-9-yl group has any of the following structures.

Chemical formula

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

[13] , wherein the benzothiophene-fused carbazole-9-yl group has any of the following structures.

Chemical formula

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

[14] .

[16] A light-emitting device characterized by containing the compound according to any one of [1] to

[14] .

[17] The light-emitting element according to

[16] , wherein the light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a host material.

[18] The light-emitting element according to

[16] , wherein the light-emitting element has a light-emitting layer, the light-emitting layer contains the compound and a light-emitting material, and mainly emits light from the light-emitting material. [Advantages of the Invention]

[0011] The compound of the present invention is useful as a light-emitting material. Further, among the compounds of the present invention, there are compounds that emit delayed fluorescence. Further, the compound of the present invention is also useful as a material for an organic light-emitting element. [Brief Description of the Drawings]

[0012]

Figure 1

[0013] Hereinafter, the content of the present invention will be described in detail. The description of the constituent elements described below may be based on typical embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In this specification, a numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. Further, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention can be substituted with deuterium atoms ( 2 H, deuterium D). In the chemical structural formulas in this specification, a hydrogen atom is represented as H or the representation is omitted. For example, when the representation of the atom bonded to the ring skeleton constituent carbon atom of the benzene ring is omitted, it is assumed that H is bonded to the ring skeleton constituent carbon atom at the location where the representation is omitted. In the chemical structural formulas in this specification, a deuterium atom is represented as D.

[0014] [Compound Represented by General Formula (1)] [Chemical Formula]

[0015] In general formula (1), R 1 , R 2 and R 4 Any one of them is a hydrogen atom or a deuterium atom. In a preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom. However, embodiments where R 2 is a hydrogen atom or a deuterium atom, or embodiments where R 4 is a hydrogen atom or a deuterium atom can also be adopted.

[0016] In general formula (1), two of R 1 , R 2 and R 4 that are other than a hydrogen atom and a deuterium atom and R 3 each independently represent a donor group. For example, when R 1 is a hydrogen atom or a deuterium atom, R 2 , R 3 and R 4 each independently represent a donor group, and it is preferable to adopt this embodiment. However, embodiments where R 2 is a hydrogen atom or a deuterium atom, and R 1 , R 3 and R 4 are each independently a donor group, or embodiments where R 4 is a hydrogen atom or a deuterium atom, and R 1 , R 2 and R 3 are each independently a donor group can also be adopted. In the following description, "two of R 1 , R 2 and R 4 that are other than a hydrogen atom and a deuterium atom and R 3 " will be collectively referred to as "three Rs that are donor groups".

[0017] Of the three Rs that are donor groups, at least one is a benzofuran-fused carbazol-9-yl group having a skeleton in which a benzofuran ring is condensed at the 2,3-positions to a carbazole ring (hereinafter abbreviated as "benzofuran-fused carbazol-9-yl group"), a benzothiophene-fused carbazol-9-yl group having a skeleton in which a benzothiophene ring is condensed at the 2,3-positions to a carbazole ring (hereinafter abbreviated as "benzothiophene-fused carbazol-9-yl group"), an indole-fused carbazol-9-yl group having a skeleton in which an indole ring is condensed at the 2,3-positions to a carbazole ring (hereinafter abbreviated as "indole-fused carbazol-9-yl group"), an indene-fused carbazol-9-yl group having a skeleton in which an indene ring is condensed at the 2,3-positions to a carbazole ring (hereinafter abbreviated as "indene-fused carbazol-9-yl group"), or a silainden-fused carbazol-9-yl group having a skeleton in which a silaindene ring is condensed at the 2,3-positions to a carbazole ring (hereinafter abbreviated as "silainden-fused carbazol-9-yl group").

[0018] In one aspect of the present invention, at least one of the three Rs which are donor groups is selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indole-fused carbazol-9-yl group. In one aspect of the present invention, at least one of the three Rs which are donor groups is selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indene-fused carbazol-9-yl group. In one aspect of the present invention, at least one of the three Rs which are donor groups is selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a silainden-fused carbazol-9-yl group. At least one of the three Rs which are donor groups is preferably a benzofuran-fused carbazol-9-yl group or a benzothiophene-fused carbazol-9-yl group, more preferably a benzofuran-fused carbazol-9-yl group. At least one of the three Rs which are donor groups may be a benzothiophene-fused carbazol-9-yl group. At least one of the three Rs which are donor groups may be an indole-fused carbazol-9-yl group. At least one of the three Rs which are donor groups may be an indene-fused carbazol-9-yl group. At least one of the three Rs which are donor groups may be a silainden-fused carbazol-9-yl group.

[0019] In one aspect of the present invention, at least two of the three Rs which are donor groups are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indole-fused carbazol-9-yl group. In one aspect of the present invention, at least two of the three Rs which are donor groups are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indene-fused carbazol-9-yl group. In one aspect of the present invention, at least two of the three Rs which are donor groups are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a sila-inden-fused carbazol-9-yl group. At least two of the three Rs which are donor groups are preferably a benzofuran-fused carbazol-9-yl group or a benzothiophene-fused carbazol-9-yl group, more preferably a benzofuran-fused carbazol-9-yl group. At least two of the three Rs which are donor groups may be a benzothiophene-fused carbazol-9-yl group. At least two of the three Rs which are donor groups may be an indole-fused carbazol-9-yl group. At least two of the three Rs which are donor groups may be an indene-fused carbazol-9-yl group. At least two of the three Rs which are donor groups may be a sila-inden-fused carbazol-9-yl group.

[0020] In one aspect of the present invention, all of the three Rs, which are donor groups, are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indole-fused carbazol-9-yl group. In one aspect of the present invention, all of the three Rs, which are donor groups, are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and an indene-fused carbazol-9-yl group. In one aspect of the present invention, all of the three Rs, which are donor groups, are selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a silainden-fused carbazol-9-yl group. All of the three Rs, which are donor groups, are preferably a benzofuran-fused carbazol-9-yl group or a benzothiophene-fused carbazol-9-yl group, more preferably a benzofuran-fused carbazol-9-yl group. All of the three Rs, which are donor groups, may be a benzothiophene-fused carbazol-9-yl group. All of the three Rs, which are donor groups, may be an indole-fused carbazol-9-yl group. All of the three Rs, which are donor groups, may be an indene-fused carbazol-9-yl group. All of the three Rs, which are donor groups, may be a silainden-fused carbazol-9-yl group.

[0021] The benzofuran-fused carbazol-9-yl group may be one in which only one benzofuran ring is fused at the 2,3-positions, or may be one in which two or more benzofuran rings are fused. Further, it may be one in which a benzofuran ring is fused at the 2,3-positions and another ring is fused. Examples of the fused ring include an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. Examples of the aromatic hydrocarbon ring include a benzene ring. Examples of the aromatic heterocyclic ring include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring. Examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. Examples of the aliphatic heterocyclic ring include a piperidine ring, a pyrrolidine ring, and an imidazoline ring. Specific examples of the fused ring constituting the aromatic hydrocarbon ring include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyran ring, and a tetracene ring. Further, specific examples of the fused ring containing a heteroatom include an indole ring, an isoindole ring, a benzimidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a cinnoline ring. In the present invention, as the benzofuran-fused carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be employed. Further, a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be employed. A preferred benzofuran-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzofuran ring is fused at the 2,3-positions and no other rings are fused. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably employed.

Chemical formula

[0022] A carbazol-9-yl group in which two benzofuran rings are fused at the 2,3-positions and no other rings are fused is also preferred. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably employed.

Chemical formula

[0023] The benzothiophene-fused carbazol-9-yl group may be one in which only one benzothiophene ring is fused at the 2,3-positions, or may be one in which two or more benzothiophene rings are fused. Further, it may be one in which a benzothiophene ring is fused at the 2,3-positions and another ring is also fused. Regarding the description and specific examples of the fused ring, reference can be made to the description and specific examples of the fused ring in the description of the benzofuran-fused carbazol-9-yl group above. In the present invention, as the benzothiophene-fused carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be adopted. Further, a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be adopted. A preferred benzothiophene-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzothiophene ring is fused at the 2,3-positions and no other ring is fused. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms, or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably adopted. [Chemical formula]

[0024] A carbazol-9-yl group in which two benzothiophene rings are condensed at the 2,3-positions and no other rings are condensed is also preferable. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms, or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably employed.

Chemical formula

[0025] The indole-fused carbazol-9-yl group may be one in which only one indole ring is condensed at the 2,3-positions, or one in which two or more indole rings are condensed. Further, it may be one in which an indole ring is condensed at the 2,3-positions and another ring is condensed. For the description of the condensed rings and specific examples, reference can be made to the description of the condensed rings and specific examples in the description of the benzofuran-fused carbazol-9-yl group above. In the present invention, as the indole-fused carbazol-9-yl group, a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl group can be employed. Further, a substituted or unsubstituted indolo[3,2-a]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted indolo[3,2-b]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted indolo[2,3-c]carbazol-9-yl group can also be employed. Further, a substituted or unsubstituted indolo[3,2-c]carbazol-9-yl group can also be employed. A preferred indole-fused carbazol-9-yl group is a carbazol-9-yl group in which only one indole ring is fused at the 2,3-positions and no other rings are fused. Specifically, it is a group having any of the following structures, where R in the following structures represents a hydrogen atom, a deuterium atom or a substituent (preferably R is a substituent). Also, the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms, or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably employed.

Chemical formula

[0026] The indene-condensed carbazol-9-yl group may have only one indene ring condensed at the 2,3-positions, or may have two or more indene rings condensed. Further, the indene ring may be condensed at the 2,3-positions and another ring may be condensed. For the description of the condensed ring and specific examples, reference can be made to the description of the condensed ring and specific examples in the description of the benzofuran-condensed carbazol-9-yl group above. When referring to the indene ring in the present invention, the description is based on 1H-indene (a double bond exists between the 2-position and the 3-position). On the other hand, when defining indeno carbazole, it is called indeno[2,3-x]carbazole or indeno[3,2-x]carbazole according to the IUPAC nomenclature (x is a, b or c). In the present invention, as the indene-condensed carbazol-9-yl group, a substituted or unsubstituted indeno[2,3-a]carbazol-9-yl group can be adopted. Further, a substituted or unsubstituted indeno[3,2-a]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted indeno[2,3-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted indeno[3,2-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted indeno[2,3-c]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted indeno[3,2-c]carbazol-9-yl group can also be adopted. A preferred indene-condensed carbazol-9-yl group is a carbazol-9-yl group in which only one indene ring is condensed at the 2,3-positions and no other ring is condensed. Specifically, it is a group having any of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms, or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably adopted. [Chemical formula]

[0027] The silaindenocondensed carbazol-9-yl group may be one in which only one silaindenocycle is condensed at the 2,3-positions, or one in which two or more silaindenocycles are condensed. Further, it may be one in which the silaindenocycle is condensed at the 2,3-positions and another ring is condensed. For the description of the condensed ring and specific examples, reference can be made to the description of the condensed ring and specific examples in the description of the benzofuran-condensed carbazol-9-yl group above. When referring to the silaindenocycle in the present invention, the description is based on 1H-silainden (a double bond exists between the 2-position and the 3-position). On the other hand, when defining silaindenocarbazole, it is called silaindenol[2,3-x]carbazole or silaindenol[3,2-x]carbazole according to the IUPAC nomenclature (x is a, b, or c). In the present invention, as the silaindenocondensed carbazol-9-yl group, a substituted or unsubstituted silaindenol[2,3-a]carbazol-9-yl group can be adopted. Further, a substituted or unsubstituted silaindenol[3,2-a]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted silaindenol[2,3-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted silaindenol[3,2-b]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted silaindenol[2,3-c]carbazol-9-yl group can also be adopted. Further, a substituted or unsubstituted silaindenol[3,2-c]carbazol-9-yl group can also be adopted. A preferred silainden-condensed carbazol-9-yl group is a carbazol-9-yl group in which only one silainden ring is condensed at the 2,3-positions and no other rings are condensed. Specifically, it is a group having any of the following structures, where R and R’ in the following structures each independently represent a hydrogen atom, a deuterium atom, or a substituent (preferably R and R’ are substituents). Also, the hydrogen atoms in the following structures may be substituted. For example, those in which some of the hydrogen atoms in the following structures are substituted with deuterium atoms, or those in which all of the hydrogen atoms in the following structures are substituted with deuterium atoms can be preferably exemplified. Those that are unsubstituted can also be preferably employed. R and R’ may be the same or different, and may also be bonded to each other to form a cyclic structure. [Chemical formula]

[0028] The benzofuran-condensed carbazol-9-yl group, benzothiophene-condensed carbazol-9-yl group, indole-condensed carbazol-9-yl group, indene-condensed carbazol-9-yl group, and silainden-condensed carbazol-9-yl group that can be employed in the general formula (1) may be substituted. Also, they may be unsubstituted. When substituted, they may be substituted with deuterium atoms or other substituents. Examples of the substituents here include an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, and a cyano group. These substituents may be further substituted with another substituent. For example, modes substituted with a deuterium atom, an alkyl group, an aryl group, an alkoxy group, or an alkylthio group can be mentioned. In one aspect of the present invention, the substituent is an aryl group that may be substituted with an alkyl group, or an alkyl group that may be substituted with an aryl group. The "alkyl group" referred to herein may be linear, branched, or cyclic. Further, two or more of a linear portion, a cyclic portion, and a branched portion may be mixed. Furthermore, the alkyl group may have a cage structure such as an adamantyl group. The number of carbon atoms of the alkyl group can be, for example, 1 or more, 2 or more, 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a norbornyl group, and an adamantyl group. The alkyl group as a substituent may be further substituted with a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. The "alkenyl group" may be linear, branched, or cyclic. Further, two or more of a linear portion, a cyclic portion, and a branched portion may be mixed. The number of carbon atoms of the alkenyl group can be, for example, 2 or more, 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, 4 or less. Specific examples of the alkenyl group include an ethenyl group, an n-propenyl group, an isopropenyl group, an n-butenyl group, an isobutenyl group, an n-pentenyl group, an isopentenyl group, an n-hexenyl group, an isohexenyl group, and a 2-ethylhexenyl group. The alkenyl group as a substituent may be further substituted. The "aryl group" and "heteroaryl group" may be monocyclic or a condensed ring in which two or more rings are fused. When it is a condensed ring, the number of fused rings is preferably 2 to 6, and can be selected, for example, from 2 to 4. Specific examples of the ring include benzene ring, pyridine ring, pyrimidine ring, triazine ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, quinoline ring, pyrazine ring, quinoxaline ring, and naphthyridine ring. Specific examples of the arylene group or heteroarylene group include phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-pyridyl group, 3-pyridyl group, and 4-pyridyl group. For the alkyl moieties of the "alkoxy group" and "alkylthio group", the descriptions and specific examples of the above alkyl groups can be referred to. For the aryl moieties of the "aryloxy group" and "arylthio group", the descriptions and specific examples of the above aryl groups can be referred to. For the heteroaryl moieties of the "heteroaryloxy group" and "heteroarylthio group", the descriptions and specific examples of the above heteroaryl groups can be referred to.

[0029] One or two of the three Rs that are donor groups may be a donor group other than a benzofuran-fused carbazole-9-yl group, a benzothiophene-fused carbazole-9-yl group, an indole-fused carbazole-9-yl group, an indene-fused carbazole-9-yl group, and a silainden-fused carbazole-9-yl group (hereinafter referred to as "other donor groups"). The other donor groups referred to here are groups with a negative Hammett σp value. Here, the "Hammett σp value" was proposed by L.P. Hammett and quantifies the influence of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following formula that holds between the substituent and the reaction rate constant or equilibrium constant in a para-substituted benzene derivative: log(k / k0) = ρσp or log(K / K0) = ρσp It is a constant (σp) specific to the substituent in [the relevant context]. In the above formula, k is the rate constant of a benzene derivative without a substituent, k0 is the rate constant of a benzene derivative substituted with a substituent, K is the equilibrium constant of a benzene derivative without a substituent, K0 is the equilibrium constant of a benzene derivative substituted with a substituent, and ρ represents a reaction constant determined by the type and conditions of the reaction. For the description of the "Hammett σp value" in the present invention and the numerical values of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165 - 195 (1991). A group with a negative Hammett σp value tends to show electron-donating (donor) properties, and a group with a positive Hammett σp value tends to show electron-withdrawing (acceptor) properties.

[0030] Other donor groups in the present invention are preferably groups containing a substituted amino group. The substituent bonded to the nitrogen atom of the amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The donor group in the present invention may be a group bonded through the nitrogen atom of the substituted amino group, or a group bonded through a group to which the substituted amino group is bonded. The group to which the substituted amino group is bonded is preferably a π-conjugated group. More preferably, it is a group bonded through the nitrogen atom of the substituted amino group. For the alkyl group, alkenyl group, aryl group, and heteroaryl group as substituents mentioned here, reference can be made to the corresponding descriptions regarding the substituents of the aromatic hydrocarbon ring group and the aromatic heterocyclic ring group above. Particularly preferred as other donor groups in the present invention is a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group may be further condensed with a benzene ring or a heterocyclic ring (excluding a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring, and a silylindene ring). Examples of the substituent of the carbazol-9-yl group include a deuterium atom, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, and a substituted amino group. Preferred substituents include a deuterium atom, an alkyl group, an aryl group, and a substituted amino group. For the description of the substituted amino group, reference can be made to the description in the previous paragraph. The substituted amino group herein includes a substituted or unsubstituted carbazolyl group, for example, a substituted or unsubstituted carbazol-3-yl group and a substituted or unsubstituted carbazol-9-yl group. Other donor groups in the present invention preferably have 8 or more atoms other than hydrogen atoms and deuterium atoms, more preferably 12 or more atoms, and can be, for example, 16 or more atoms. Further, it is preferably 80 or less, more preferably 60 or less, and even more preferably 40 or less.

[0031] In the general formula (1), the three Rs, which are donor groups, may all be the same or different. Also, two of the Rs may be the same and one may be different. In a preferred embodiment of the present invention, the three Rs that are donor groups are the same. In another preferred embodiment of the present invention, two of the three Rs that are donor groups are the same, and one of them is a benzofuran-fused carbazole-9-yl group, a benzothiophene-fused carbazole-9-yl group, an indole-fused carbazole-9-yl group, an indene-fused carbazole-9-yl group, or a silainden-fused carbazole-9-yl group (hereinafter referred to as "the specific five types of fused carbazole-9-yl groups"), and the remaining one is a donor group other than the specific five types of fused carbazole-9-yl groups. In another preferred embodiment of the present invention, one of the three Rs that are donor groups is any one of the specific five types of fused carbazole-9-yl groups, and the remaining two are the same and are donor groups other than the specific five types of fused carbazole-9-yl groups. In a preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 2 , R 3 and R 4 are the same and are any one of the specific five types of fused carbazole-9-yl groups. In another preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 2 and R 4 are the same and are any one of the specific five types of fused carbazole-9-yl groups, and R 3 is another donor group. In another preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 3 is any one of the specific five types of fused carbazole-9-yl groups, and R 2 and R 4 are the same and are other donor groups. In another embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 3 and R 4 are the same and are any one of the specific five types of fused carbazole-9-yl groups, and R 2is another donor group.

[0032] Hereinafter, specific examples of the donor groups that the three Rs, which are donor groups, can take are shown. D1 to D12, D109 to D113, D150 to D179, D192 to D197, D240 to D244, D299, and D433 are specific examples of other donor groups, and D13 to D108, D114 to D149, D180 to D191, D198 to D239, D245 to D298, D300 to D432, and D434 to D839 are specific examples of benzofuran-fused carbazol-9-yl group, benzothiophene-fused carbazol-9-yl group, indole-fused carbazol-9-yl group, indene-fused carbazol-9-yl group, and silaindene-fused carbazol-9-yl group. In the following structural formulas, Ph represents a phenyl group, D represents a deuterium atom, tBu represents a tert-butyl group, and iPro represents an isopropyl group.

Chemical formula

[0033] The compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In a preferred embodiment of the present invention, the compound represented by the general formula (1) is composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Further, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and a sulfur atom. Furthermore, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, and a nitrogen atom. Additionally, the compound represented by the general formula (1) may be a compound that does not contain a hydrogen atom but contains a deuterium atom. For example, the compound represented by the general formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a deuterium atom, and a nitrogen atom. In a preferred embodiment of the present invention, the compound represented by the general formula (1) has a symmetric structure.

[0034] Specific examples of the compound represented by the general formula (1) are shown below. Among the following specific examples, Compounds 1 to 9800 and 20084 to 37803 are specific examples of compounds in which R 1 in the general formula (1) is a hydrogen atom. Compounds 9801 to 20083 are specific examples of compounds in which R 1 in the general formula (1) is a deuterium atom. The table shows the correspondence between the compound numbers and R 2 , R 3 , and R 4 . Among the following compounds, when there are rotational isomers, the mixture of rotational isomers and each separated rotational isomer are also considered to be those disclosed in this specification.

Table 1

[0035] When the compound represented by the general formula (1) is intended to be used by forming a film of an organic layer containing the compound represented by the general formula (1) by a vapor deposition method, for example, the molecular weight is preferably 1500 or less, more preferably 1200 or less, still more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1). The compound represented by the general formula (1) may be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight. The compound represented by the general formula (1) has the advantage of being easily dissolved in an organic solvent among cyanobenzene-based compounds. Therefore, the compound represented by the general formula (1) is easy to apply the coating method and is easy to purify and increase the purity.

[0036] Applying the present invention, it is also conceivable to use a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light-emitting material. For example, it is conceivable to use, as a light-emitting material, a polymer obtained by previously allowing a polymerizable group to be present in the structure represented by the general formula (1) and polymerizing the polymerizable group. Specifically, R of the general formula (1) 1 ~R 4 A monomer containing a polymerizable functional group in any of them is prepared, and this is polymerized alone or copolymerized with another monomer to obtain a polymer having a repeating unit, and it is conceivable to use the polymer as a light-emitting material. Alternatively, it is also conceivable to obtain dimers or trimers by coupling compounds having the structure represented by the general formula (1) and use them as light-emitting materials.

[0037] Examples of polymers having repeating units containing the structure represented by the general formula (1) include polymers containing the structure represented by the following general formula (2) or (3).

Chemical Formula

[0038] In the general formula (2) or (3), Q represents a group containing the structure represented by the general formula (1), and L 1 and L 2 represent linking groups. 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 preferably has a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L 11 represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. In the general formula (2) or (3), R 101 , R 102 , R 103 and R 104 each independently represent a substituent. Preferably, they 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 an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms or an unsubstituted alkoxy group having 1 to 3 carbon atoms. The linking groups represented by L 1 and L 2 can be bonded to any one of R 1 to R 4 in the general formula (1) that constitutes Q. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.

[0039] As specific structural examples of the repeating unit, the structures represented by the following formulas (4) to (7) can be cited.

Chemical formula

[0040] A polymer having a repeating unit containing these formulas (4) to (7) has a hydroxy group introduced into any one of R 1 ~R 4 and can be synthesized by reacting the following compound using it as a linker to introduce a polymerizable group and polymerizing the polymerizable group.

Chemical formula

[0041] The polymer containing the structure represented by the general formula (1) in the molecule may be a polymer composed only of the repeating unit having the structure represented by the general formula (1), or may be a polymer containing a repeating unit having another structure. Further, the repeating unit having the structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. Examples of the repeating unit not having the structure represented by the general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond such as ethylene and styrene can be cited.

[0042] In a certain embodiment, the compound represented by the general formula (1) is a luminescent material. In a certain embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence. In a certain embodiment of the present disclosure, when the compound represented by the general formula (1) is excited by thermal or electronic means, it can emit light in the UV region, the blue, green, yellow, orange, or red region (for example, about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) of the visible spectrum, or the near-infrared region. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the red or orange region (e.g., about 620 nm to about 780 nm, about 650 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the orange or yellow region (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the blue region (e.g., about 400 nm to about 490 nm, about 475 nm) of the visible spectrum. In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the ultraviolet spectral region (e.g., 280 - 400 nm). In certain embodiments of the present disclosure, when the compound represented by general formula (1) is excited by thermal or electronic means, it can emit light in the infrared spectral region (e.g., 780 nm to 2 μm).

[0043] The electronic properties of the small molecule chemical substance library can be calculated using known ab initio quantum chemical calculations. For example, based on the basis of 6 - 31G*, and using time-dependent density functional theory with a function group known as Becke's three-parameter, Lee-Yang-Parr hybrid functional, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) is analyzed to screen for molecular fragments (portions) having a HOMO above a specific threshold and a LUMO below a specific threshold. Thereby, for example, when there is a HOMO energy (e.g., ionization potential) of -6.5 eV or higher, a donor moiety ("D") can be selected. Also, for example, when there is a LUMO energy (e.g., electron affinity) of -0.5 eV or lower, an acceptor moiety ("A") can be selected. The bridge moiety ("B") is, for example, a strong conjugated system that can severely restrict the acceptor and donor moieties to a specific steric configuration, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties. In certain embodiments, the compound library is selected using one or more of the following properties. 1. Emission near a specific wavelength 2. Calculated triplet state above a specific energy level 3. ΔE below a specific value ST Value 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In certain embodiments, the difference (ΔE ST ) between the lowest singlet excited state and the lowest triplet excited state at 77 K 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 certain embodiments, the ΔE ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by general formula (1) exhibits a quantum yield of greater than 25%, such as about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95%, or more.

[0044] [Synthesis method of the compound represented by general formula (1)] The compound represented by general formula (1) is a novel compound. The compound represented by the general formula (1) can be synthesized by combining known reactions. For example, it can be synthesized by reacting Donor-H (a donor group bonded to a hydrogen atom) with trifluoroisophthalonitrile in which the position where three donor groups Donor are to be introduced is substituted with a fluorine atom in tetrahydrofuran in the presence of sodium hydride. When introducing a plurality of types of donor groups, the reaction with the donor groups may be carried out in two steps. For specific reaction conditions and reaction procedures, reference can be made to the synthesis examples described below.

[0045] [Composition using the compound represented by the general formula (1)] In one embodiment, it is used in combination with the compound represented by the general formula (1), and one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond with, coat, support, or associate with the same compound are used to form a solid film or layer. For example, a film can be formed by combining the compound represented by the general formula (1) with an electroactive material. In some cases, the compound represented by the general formula (1) may be combined with a hole-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with an electron-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by the general formula (1) may be combined with a copolymer having both a hole-transporting part and an electron-transporting part. According to the above embodiments, electrons and / or holes formed in the solid film or layer can be made to interact with the compound represented by the general formula (1).

[0046] [Formation of film] In one embodiment, a film containing the compound of the present invention represented by the general formula (1) can be formed by a wet process. In the wet process, a solution in which a composition containing the compound of the present invention is dissolved is applied to a surface, and a film is formed after removing the solvent. Examples of the wet process include, but are not limited to, spin coating method, slit coating method, inkjet method (spray method), gravure printing method, offset printing method, and flexographic printing method. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, a substituent (for example, an alkyl group) that increases the solubility in an organic solvent can be introduced into the compound contained in the composition. In one embodiment, a film containing the compound of the present invention can be formed by a dry process. In one embodiment, a vacuum evaporation method can be employed as the dry process, but it is not limited thereto. When the vacuum evaporation method is employed, the compounds constituting the film may be co-evaporated from individual evaporation sources, or may be co-evaporated from a single evaporation source in which the compounds are mixed. When using a single evaporation source, a mixed powder obtained by mixing the compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting each compound and then cooling may be used. In one embodiment, by performing co-evaporation under the condition that the evaporation rates (weight loss rates) of a plurality of compounds contained in a single evaporation source are the same or substantially the same, a film having a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the evaporation source can be formed. If a plurality of compounds are mixed at the same composition ratio as the composition ratio of the formed film to form an evaporation source, a film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-evaporated compound has the same weight loss rate can be specified and adopted as the temperature during co-evaporation.

[0047] [Examples of use of the compound represented by the general formula (1)] Organic light-emitting diode: One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In certain embodiments, the compound represented by the general formula (1) of the present invention can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In certain embodiments, the compound represented by the general formula (1) includes a delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In certain embodiments, the present invention provides a delayed phosphor having the structure represented by the general formula (1). In certain embodiments, the present invention relates to the use of the compound represented by the general formula (1) as a delayed phosphor. In certain embodiments, the compound represented by the general formula (1) can be used as a host material and can be used together with one or more light-emitting materials, and the light-emitting materials can be fluorescent materials, phosphorescent materials, or TADF. In certain embodiments, the compound represented by the general formula (1) can also be used as a hole transport material. In certain embodiments, the compound represented by the general formula (1) can be used as an electron transport material. In certain embodiments, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In certain embodiments, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In certain embodiments, the light-emitting layer contains the compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In certain embodiments, the substrate is a film-forming surface. In certain embodiments, the orientation of the compound represented by the general formula (1) with respect to the film-forming surface affects or determines the propagation direction of the light emitted by the compound that aligns it. In certain embodiments, by aligning the propagation direction of the light emitted by the compound represented by the general formula (1), the light extraction efficiency from the light-emitting layer is improved. One aspect of the present invention relates to an organic light-emitting device. In certain embodiments, the organic light-emitting device includes a light-emitting layer. In certain embodiments, the light-emitting layer includes a compound represented by the general formula (1) as a light-emitting material. In certain embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device). In certain embodiments, the organic light-emitting device is an organic electroluminescence device (organic EL device). In certain embodiments, the compound represented by the general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In certain embodiments, the compound represented by the general formula (1) contained in the light-emitting layer is at its lowest excited singlet energy level and is included 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 certain embodiments, the organic photoluminescence device includes at least one light-emitting layer. In certain embodiments, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In certain embodiments, the organic layer includes at least a light-emitting layer. In certain embodiments, the organic layer includes only a light-emitting layer. In certain embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an exciton barrier layer. In certain embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. An example of the organic electroluminescence device is shown in FIG. 1.

[0048] Light-emitting layer: In certain embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and the cathode, respectively, recombine to form excitons. In certain embodiments, the layer emits light. In one embodiment, only the luminescent material is used as the light-emitting layer. In one embodiment, the light-emitting layer includes a luminescent material and a host material. In one embodiment, the luminescent material is one or more compounds of general formula (1). In one embodiment, in order to improve the light emission efficiency of the organic electroluminescence device and the organic photoluminescence device, singlet excitons and triplet excitons generated in the luminescent material are confined within the luminescent material. In one embodiment, a host material is used in addition to the luminescent material in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has singlet excitation energy and triplet excitation energy, and at least one of them is higher than those of the luminescent material of the present invention. In one embodiment, singlet excitons and triplet excitons generated in the luminescent material of the present invention are confined within the molecules of the luminescent material of the present invention. In one embodiment, singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In one embodiment, although a high light emission efficiency can still be obtained, singlet excitons and triplet excitons are not sufficiently confined, that is, a host material capable of achieving a high light emission efficiency can be used in the present invention without particular limitation. In one embodiment, light emission occurs in the luminescent material in the light-emitting layer of the device of the present invention. In one embodiment, the emitted light includes both fluorescence and delayed fluorescence. In one embodiment, the emitted light includes the emitted light from the host material. In one embodiment, the emitted light consists of the emitted light from the host material. In one embodiment, the emitted light includes the emitted light from the compound represented by general formula (1) and the emitted light from the host material. In one embodiment, a TADF molecule and a host material are used. In one embodiment, TADF is an assist dopant.

[0049] When using the compound represented by the general formula (1) as an assist dopant, various compounds can be employed as the luminescent material (preferably a fluorescent material). Such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. These exemplified skeletons may or may not have substituents. Also, these exemplified skeletons may be combined with each other. In the following, luminescent materials that can be used in combination with the assist dopant represented by the general formula (1) are exemplified.

[0050]

Chemical formula

[0051] Also, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can be particularly preferably employed as the luminescent material used together with the assist dopant represented by the general formula (1).

[0052] In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 0.1 wt% or more. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 1 wt% or more. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 50 wt% or less. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 20 wt% or less. In certain embodiments, when using a host material, the amount of the compound of the present invention as a luminescent material contained in the light-emitting layer is 10 wt% or less. In certain embodiments, the host material of the light-emitting layer is an organic compound having a hole-transporting function and an electron-transporting function. In certain embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of the emitted light from increasing. In certain embodiments, the host material of the light-emitting layer is an organic compound having a high glass transition temperature.

[0053] In some embodiments, the host material is selected from the group consisting of: [Chemical formula] JPEG0007716743000248.jpg150170In certain embodiments, the light-emitting layer contains two or more TADF molecules having different structures. For example, a light-emitting layer containing these three materials can be formed in which the singlet excitation energy levels are in the order of the host material, the first TADF molecule, and the second TADF molecule, with the highest energy level for the host material. At this time, both the first TADF molecule and the second TADF molecule have a difference ΔE between the lowest singlet excitation energy level and the lowest triplet excitation energy level at 77K STIt is preferably 0.3 eV or less, more preferably 0.25 eV or less, still more preferably 0.2 eV or less, even more preferably 0.15 eV or less, further preferably 0.1 eV or less, even further preferably 0.07 eV or less, still further preferably 0.05 eV or less, even still further preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The content of the first TADF molecule in the light-emitting layer is preferably more than the content of the second TADF molecule. Also, the content of the host material in the light-emitting layer is preferably more than the content of the second TADF molecule. The content of the first TADF molecule in the light-emitting layer may be more than, less than, or the same as the content of the host material. In one embodiment, the composition in the light-emitting layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecule, and 0.1 to 30% by weight of the second TADF molecule. In one embodiment, the composition in the light-emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule. In one embodiment, the photoluminescence quantum yield φPL1(A) of the co-evaporated film of the first TADF molecule and the host material (the content ratio of the first TADF molecule in this co-evaporated film = A% by weight) upon photoexcitation and the photoluminescence quantum yield φPL2(A) of the co-evaporated film of the second TADF molecule and the host material (the content ratio of the second TADF molecule in this co-evaporated film = A% by weight) upon photoexcitation satisfy the relational expression φPL1(A)>φPL2(A). In one embodiment, the photoluminescence quantum yield φPL2(B) of the co-evaporated film of the second TADF molecule and the host material (the content ratio of the second TADF molecule in this co-evaporated film = B% by weight) upon photoexcitation and the photoluminescence quantum yield φPL2(100) of the single film of the second TADF molecule upon photoexcitation satisfy the relational expression φPL2(B)>φPL2(100). In one embodiment, the light-emitting layer can contain three types of TADF molecules with different structures. The compound of the present invention can be any of the plurality of TADF compounds contained in the light-emitting layer. In one embodiment, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain a metal element. In one embodiment, the light-emitting layer can be composed of a material consisting of only atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. Alternatively, the light-emitting layer can also be composed of a material consisting of only atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Alternatively, the light-emitting layer can also be composed of a material consisting of only atoms selected from the group consisting of a carbon atom, a hydrogen atom, a nitrogen atom, and an oxygen atom. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescence material. Preferred delayed fluorescence materials include compounds included in the general formulas described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, paragraphs 0008 to 0071 and 0118 to 0133 of WO2013 / 081088, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO2013 / 133359, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013 / 161437, paragraphs 0007 to 0041 and 0060 to 0069 of JP 2014-9352 A, paragraphs 0008 to 0048 and 0067 to 0076 of JP 2014-9224 A, paragraphs 0013 to 0025 of JP 2017-119663 A, paragraphs 0013 to 0026 of JP 2017-119664 A, paragraphs 0012 to 0025 of JP 2017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds capable of emitting delayed fluorescence are included.In addition, here, a luminescent material described in JP-A-2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP-A-2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, WO2015 / 159541, which can emit delayed fluorescence, can preferably be employed. The above-mentioned publications described in this paragraph are hereby incorporated herein by reference as part of this specification.

[0054] Hereinafter, each member of the organic electroluminescence element and each layer other than the light-emitting layer will be described.

[0055] Substrate: In some embodiments, the organic electroluminescence element of the present invention is held by a substrate, and the substrate is not particularly limited, and any material formed of, for example, glass, transparent plastic, quartz, and silicon, which is generally used in an organic electroluminescence element, may be used.

[0056] Anode: In some embodiments, the anode of the organic electroluminescence device is manufactured from a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material such as IDIXO (In2O3-ZnO) that can form a transparent conductive film 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, when high precision of the pattern is not required (for example, about 100 μm or more), the pattern may be formed using a mask having a shape suitable for vapor deposition or sputtering on the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film forming method such as a printing method or a coating method is used. In some embodiments, when the emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms 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.

[0057] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal having 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 selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron injection metal and a second metal, which is a stable metal having a work function higher than that of the electron injection metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves the electron injection characteristics and the resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by evaporation 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, in order to transmit the emitted light, either the anode or the cathode of the organic electroluminescence device is transparent or semi-transparent. In some embodiments, the transparent or semi-transparent electroluminescence device improves the light emission luminance. In some embodiments, the cathode is formed of the conductive transparent material described above with respect to the anode, thereby forming a transparent or semi-transparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semi-transparent.

[0058] 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 emission luminance. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the light-emitting layer or the hole transport layer, and between the cathode and the light-emitting layer or the electron transport layer. In some embodiments, an injection layer exists. In some embodiments, no injection layer exists. Examples of preferable compounds that can be used as the hole injection material are given below.

[0059]

Chemical formula

[0060] Next, examples of preferable compounds that can be used as the electron injection material are given.

Chemical formula

[0061] Barrier layer: The barrier layer is a layer that can prevent the charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, the electron barrier layer exists between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer and reaching the hole transport layer. In some embodiments, the hole barrier layer exists between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer and reaching the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. The term "electron barrier layer" or "exciton barrier layer" as used herein includes a layer having both the functions of an electron barrier layer and an exciton barrier layer.

[0062] Hole barrier layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during the transport of electrons, the hole blocking layer prevents holes from reaching the electron transport layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material used for the hole blocking layer may be the same as the material described above for the electron transport layer. Examples of preferable compounds that can be used for the hole blocking layer are given below.

[0063]

Chemical formula

[0064]

Chemical formula

[0065] Electron blocking layer: The electron blocking layer transports holes. In some embodiments, during the transport of holes, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material used for the electron blocking layer may be the same as the material described above for the hole transport layer. Specific examples of preferable compounds that can be used as the electron blocking material are given below.

[0066]

Chemical formula

[0067] Exciton blocking 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 light emission efficiency of the device is improved. In some embodiments, the exciton barrier layer is on either the anode side or the cathode side, and adjacent to the light-emitting layer on both sides. In some embodiments, when the exciton barrier layer is present on the anode side, the layer is present between the hole transport layer and the light-emitting layer and may be adjacent to the light-emitting layer. In some embodiments, when the exciton barrier layer is present on the cathode side, the layer is present between the light-emitting layer and the cathode and may be adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron barrier layer, or a similar layer is present 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, an electron barrier layer, a hole barrier layer, or a similar layer is present between the cathode and the exciton barrier layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton barrier layer includes singlet excitation energy and triplet excitation energy, at least one of which is higher than the singlet excitation energy and the triplet excitation energy of the light-emitting material, respectively.

[0068] Hole transport layer: The hole transport layer includes 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, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from 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 the hole transport material are given below.

[0069]

Chemical formula

[0070]

Chemical formula

[0071]

Chemical formula

[0072] Electron transport layer: The electron transport layer contains 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 the electron transport layer that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as the electron transport material are given below.

[0073] [Chemical formula]

[0074] [Chemical formula]

[0075] [Chemical formula]

[0076] [Chemical formula]

[0077] Furthermore, examples of preferred compounds as materials that can be added to each organic layer are given. For example, adding as a stabilizing material, etc. can be considered.

[0078] [Chemical formula]

[0079] Although preferred materials that can be used in the organic electroluminescent element have been specifically exemplified, the materials that can be used in the present invention should not be construed as being limited to the following exemplified compounds. Further, even the compounds exemplified as materials having specific functions can be diverted as materials having other functions.

[0080] Device: In some embodiments, the light-emitting layer is incorporated into the device. For example, the device includes, but is not limited to, an OLED bulb, an OLED lamp, a display for a television, a monitor for a computer, a mobile phone, and a tablet. In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the composition can be useful for promoting charge transfer or energy transfer within the device and / or as a hole transport material. Examples of the device include, for example, an organic light-emitting diode (OLED), an organic integrated circuit (OIC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detection device, an organic photoreceptor, an organic magnetic field-quench (O-FQD) device, a light-emitting fuel cell (LEC), or an organic laser diode (O-laser).

[0081] Valve or lamp: In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including 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 including 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 that are not red, green, or blue (e.g., orange and yellow - green). In some embodiments, the combination of OLEDs is a combination of two colors, four colors, or more colors. In some embodiments, the device is a circuit board having a first surface with an attachment surface and a second surface opposite thereto, and defining at least one opening, at least one OLED on the attachment surface, the at least one OLED having a light - emitting configuration including 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 disposed at an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. The device is an OLED light. In some embodiments, the OLED light has a plurality of OLEDs attached to the circuit board such that light is emitted in a plurality of directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0082] Display or screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or a display. In some embodiments, the compounds according to the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful in two-sided etching that provides pixels with a unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern enables the arrangement of very sharp narrow tippers between the pixels in the vertical direction and a large wide range of angled openings in the horizontal direction. This enables a fine pattern configuration of the pixels required for a high-resolution display while optimizing chemical vapor deposition onto the TFT backplane. Internal patterning of the pixels enables the formation of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Further, the use of imaged "stripes" or halftone circles in the pixel region protects the etching in specific regions until these specific patterns are undercut and removed from the substrate. At that time, all pixel regions are processed at the same etching rate, but the depth varies with the halftone pattern. By changing the size and spacing of the halftone pattern, etching with different protection rates within the pixel becomes possible, enabling localized deep etching necessary to form a sharp vertical bevel. A preferred material for the evaporation mask is Invar. Invar is a metal alloy cold-rolled in a long thin sheet form at a steelworks. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming an opening region in the evaporation mask is a method 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 processed 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.

[0083] Method for manufacturing a device: An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and a encapsulation layer over time, and then cutting from the mother panel. An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin-film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and a encapsulation layer over time, and then cutting from the mother panel.

[0084] In another aspect of the present invention, there is provided a method for manufacturing an organic light-emitting diode (OLED) display, the method comprising: 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; A step of applying an organic film to the interface portion between the cell panels is included. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the end portion of the barrier layer is coated with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists the mother panel to be cut softly in cell panel units. In some embodiments, the thin film transistor (TFT) layer has a light emitting layer, a gate electrode, and a source / drain electrode. 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. The organic film applied to the interface portion is formed of the same material as the material of 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 therebetween, and a encapsulation layer that covers and protects the light emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0085] Each of the organic film and the planarization film may include any one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method further includes a step of attaching a carrier substrate formed of a glass material to the other surface of the base substrate before forming a barrier layer on one surface of the base substrate formed of polyimide, and a step of separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer 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 is formed of polyimide or acrylic, similar to the organic film formed at the end of the barrier layer. In some embodiments, during the manufacture of the OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film may be formed at the end of the barrier layer, whereby a part of the organic film directly contacts the base substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the end of the barrier layer.

[0086] 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 electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, whereby the organic light-emitting layer emits light, and thereby an image is formed. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin-film encapsulation structure in which an organic film and an inorganic film 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 disposed at intervals from each of the plurality of display units. In some embodiments, the organic film is formed in such a manner that a part of the organic film directly contacts the base substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the end of the barrier layer.

[0087] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide. In some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated. In some embodiments, the barrier layer is formed on the surface of the base substrate on the opposite side of the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, whereby grooves are formed in the interface portion between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0088] 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, at least a part of the organic film is formed by the groove, and the groove does not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and the passivation layer which is an inorganic film and the planarization film which is an organic film are disposed on the TFT layer to cover the TFT layer. For example, when 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 cracks from occurring by allowing the generated impact to be absorbed by the organic film when each cell panel is cut along the groove at the interface portion. That is, when all the barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the generated impact is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between the barrier layers is covered with an organic film to absorb the impact that could be transmitted to the barrier layer without the organic film, so that each cell panel may be cut softly to prevent cracking in the barrier layer. In one embodiment, the organic film covering the groove in the interface portion and the planarization film are spaced apart from each other. For example, when the organic film and the planarization film are connected to each other as one layer, there is a risk that external moisture may enter the display unit through the remaining portions of the planarization film and the organic film. Therefore, the organic film and the planarization film are spaced apart from each other such that the organic film is disposed at a distance from the display unit.

[0089] In some embodiments, the display unit is formed by the formation of the light-emitting unit, and the encapsulation layer is disposed on the display unit to cover the display unit. Thereby, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. 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 the coefficient of thermal expansion between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface portion between the cell panels using a cutter. In some embodiments, since the groove of the interface portion along which the mother panel is cut is covered with an organic film, the organic film absorbs the impact during cutting. In some embodiments, the formation of cracks in 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 aspect 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 applied to an end portion of the barrier layer.

Examples

[0090] The features of the present invention will be described more specifically with reference to synthesis examples and examples below. The materials, processing contents, processing procedures, etc. shown below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The evaluation of the light-emitting characteristics was performed using a source meter (manufactured by Keithley Instruments, Inc.: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies, Inc.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), an optical spectrometer (manufactured by Ocean Optics, Inc.: USB2000), a spectro-radiometer (manufactured by Topcon Corporation: SR-3), and a streak camera (model C4334 manufactured by Hamamatsu Photonics K.K.).

[0091] (Synthesis Example 1) Synthesis of Compound 1131 [ka]

[0092] Under a nitrogen stream, sodium hydride (0.44 g, 11.0 mmol) and benzofuro[3,2-c]carbazole (2.83 g, 11.0 mmol) were stirred in tetrahydrofuran (20 mL) at 0°C for 30 minutes, followed by the addition of 4,5,6-trifluoroisophthalonitrile. The mixture was then warmed to room temperature and reacted for 5 hours. The reaction was then quenched with water and methanol. The precipitated yellow solid was filtered, and the residue was purified by silica gel column chromatography (toluene / hexane / chloroform = 11 / 2 / 1) and reprecipitation (o-dichlorobenzene / methanol) to obtain compound 1131 (0.91 g, 1.02 mmol, 37% yield) as a yellow solid. 1 H NMR (400MHz, CDCl3,δ): 8.62 (s, 0.3H), 8.61 (s, 0.7H), 8.15-8.10 (m, 2H), 7.88-7.77 (s, 2H), 7.73-7.54 (m, 6H), 7.40-7.25 (m, 6H), 7.23-7.11 (m, 8H), 7.09-6.93 (m, 2H), 6.90-6.78 (m, 3H), 6.69-6.51 (m, 1H). MS (ASAP): 894.43 (M+H + ). Calcd for C62H31N5O3: 893.24.

[0093] (Synthesis Example 2) Synthesis of Compound 1313 [ka]

[0094] It was synthesized in the same manner as in Synthesis Example 1 with a yield of 80%. 11H NMR (400 MHz, CDCl3, δ): 8.66 (s, 1H), 8.22 (s, 0.7H), 8.17 (s, 0.3H), 8.08 (s, 0.7H), 8.05 (s, 0.3H), 7.92 - 7.87 (m, 1H), 7.79 (d, J = 8.4 Hz, 1H), 7.74 - 7.69 (m, 2H), 7.66 - 7.63 (m, 2H), 7.53 - 7.37 (m, 5H), 7.35 - 7.27 (m, 4H), 7.23 - 7.17 (m, 2H), 7.15 - 7.08 (m, 2H), 7.06 - 6.98 (m, 3H), 6.95 - 6.86 (m, 3H), 6.80 - 6.68 (m, 2H), 6.57 - 6.53 (m, 1H). MS (ASAP): 894.44 (M+H + ). Calcd for C62H31N5O3: 893.24.

[0095] (Synthesis Example 3) Synthesis of Compound 1404

Chemical Structure

[0096] Under a nitrogen stream, potassium carbonate (1.20 g, 8.69 mmol) and benzofuro[2,3 - c]carbazole (1.99 g, 7.72 mmol) were stirred in dimethylformamide (20 mL) at room temperature for 30 minutes. Then, 4,5,6 - trifluoroisonicotrinitrile (0.35 mmol, 1.92 mmol) was added, and the temperature was raised to 60 °C followed by reaction for 5 hours. After that, the reaction was returned to room temperature and quenched with water and methanol. The precipitated yellow solid was filtered, and the filtrate was purified by silica gel column chromatography (toluene) and reprecipitation (toluene / methanol) to obtain yellow solid Compound 1404 (1.35 g, 1.51 mmol, 79% yield). 11H NMR (400 MHz, CDCl3, δ): 8.65 (s, 1H), 8.35 - 8.28 (m, 5H), 7.98 - 7.95 (m, 1H), 7.81 - 7.78 (m, 1H), 7.57 - 7.50 (m, 2H), 7.47 - 7.28 (m, 11H), 7.23 - 7.10 (m, 5H), 7.02 - 6.79 (m, 4H), 6.72 - 6.60 (m, 1H). MS (ASAP): 894.50 (M + H + ). Calcd for C62H31N5O3: 893.24.

[0097] (Synthesis Example 4) Synthesis of Compound 3861

Chemical Structure

[0098] Synthesized in the same manner as in Synthesis Example 3 with a yield of 63%. 1 1H NMR (400 MHz, CDCl3, δ): 8.43 (d, J = 8.0 Hz, 1H), 8.38 - 8.35 (m, 3H), 8.17 - 8.13 (m, 2H), 8.10 - 8.03 (m, 3H), 7.88 - 7.82 (m, 1H), 7.13 - 7.77 (m, 4H), 7.70 - 7.64 (m, 4H), 7.58 - 7.43 (m, 5H), 7.38 - 7.32 (m, 3H), 7.24 (t, J = 7.2 Hz, 1H), 7.14 - 7.21 (m, 2H), 6.88 (t, J = 7.6 Hz, 1H), 6.78 (t, J = 8.4 Hz, 1H). MS (ASAP): 942.15 (M + H + ). Calcd for C62H31N5S3: 941.17.

[0099] (Synthesis Example 5) Synthesis of Compound 11795

Chemical Structure

[0100] It was synthesized in a yield of 92% by the same method as in Synthesis Example 1. 1 H NMR (400 MHz, CDCl3, δ): 9.67 - 9.64 (m, 1H), 8.24 - 8.03 (m, 6-H), 7.94 - 7.87 (m, 3H), 7.81 - 7.74 (m, 3H), 7.71 - 7.22 (m, 13H), 7.16 - 7.03 (m, 0.5H), 7.16 - 7.03 (m, 0.5H), 6.81 - 6.79 (m, 0.5H), 6.64 - 6.61 (m, 0.5H), 6.47 - 6.44 (m, 0.5H). MS (ASAP): 1137.68 (M+H + ). Calcd for C80H28D15N5O3: 1136.43.

[0101] (Synthesis Example 6) Synthesis of Compound 1222

Chemical Structure

[0102] It was synthesized in a yield of 69% by the same method as in Synthesis Example 3. MS (ASAP): 894.43 (M+H + ). Calcd for C 62 [HH 31 N5O3: 893.24.

[0103] (Synthesis Example 7) Synthesis of Compound 1040

Chemical Structure

[0104] It was synthesized in a yield of 69% by the same method as in Synthesis Example 3. MS (ASAP): 894.46 (M+H + ). Calcd for C 62 [HH 31 N5O3: 893.24.

[0105] (Synthesis Example 8) Synthesis of Compound 3

Chem.

[0106] Under a nitrogen atmosphere, a solution of 5H-benzo[f]chromeno[3,2-c]carbazole (14.1 g, 54.8 mmol) and NaH (60%, 2.2 g, 55 mmol) in tetrahydrofuran (150 mL) was stirred at room temperature for 30 minutes. Then, a solution of 4,5,6-trifluoroisophthalonitrile (5 g, 27.5 mmol) in tetrahydrofuran (275 mL) cooled to -10 °C was added dropwise thereto over 20 minutes, and the mixture was stirred for 4 hours. The reaction mixture was neutralized by adding a saturated aqueous NH4Cl solution, and the reaction was stopped by returning to room temperature. The mixture was extracted with ethyl acetate, and the organic layer was dried over Mg2SO4. After separating the inorganic substances by filtration, the solvent was distilled off under reduced pressure, and the obtained mixture was purified by column chromatography (toluene / hexane / CHCl3 = 6 / 3.5 / 0.5) and reprecipitation (CHCl3 / hexane) to obtain yellow solid Compound 1a (16.5 g, 25.2 mmol, 91.7%). 1 H NMR (400 MHz, CDCl3, δ): 8.54 (d, J = 7.6 Hz, 2H), 8.23 (s, 1H), 8.00 (d, J = 8.8 Hz, 2H), 7.97 (d, J = 7.6 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.567 - 7.443 (m, 6H), 7.38 (t, J = 8.0 Hz, 2H), 7.28 - 7.25 (m, 2H), 7.20 - 7.17 (m, 2H). MS (ASAP): 657.25 [M+H] + . Calcd for. C 44 H 21 FN4O2: 656.16

Chem.

[0107] Under a nitrogen atmosphere, a solution of compound 1a (16.5 g, 252.2 mmol), carbazole (7.9 g, 47.2 mmol), and K2CO3 (8.17 g, 59.1 mmol) in dimethylformamide (280 mL) was stirred at room temperature for 15 hours. 200 mL of methanol and 150 mL of water were added to the reaction mixture to quench the reaction. The precipitate was then filtered, and the solid was recovered. The resulting filtrate was purified by column chromatography (toluene / hexane / CHCl3 = 6 / 3.5 / 0.5) and reprecipitation (toluene / hexane) to obtain compound 3 (16.0 g, 19.9 mmol, 84.2%) as a yellow solid. 1 H NMR (400MHz, CDCl3, δ): 8.60 (s, 1H), 8.19-8.15 (m, 2H), 7.87 (t, J=8.4Hz, 2H), 7.90-7.86 (m,4H), 7.44-7.39 (m, 2H), 7.36-7.31 (m, 2H), 7.22-7.02 (m, 10H), 6,83-6.66 (m, 4H), 6.62-6.46 (m, 2H). MS (ASAP): 804.25 [M+H] + .Calcd for.C 56 H 29 N5O2: 803.23

[0108] (Synthesis Example 9) Synthesis of Compound 159 [ka]

[0109] It was synthesized in a yield of 68% in the same manner as in the second reaction of Synthesis Example 8. 11H NMR (400 MHz, CDCl3, δ): 8.52 (s, 1H), 8.20 - 8.17 (m, 2H), 7.87 (t, J = 6.8 Hz, 2H), 7.65 - 7.59 (m, 4H), 7.42 - 7.36 (m, 2H), 7.34 - 7.30 (m, 2H), 7.25 - 7.19 (m, 2H), 7.18 - 6.92 (m, 6H), 6.95 (s, 2H), 6.70 - 6.62 (m, 2H), 6.38 - 6.27 (m, 2H), 2.05 (s, 6H). MS (ASAP): 832.41 [M + H] + . Calcd for. C58H33N5O2 : 831.26

[0110] (Synthesis Example 10) Synthesis of Compound 4

Chemical Structure

[0111] Synthesized in a yield of 56% by the same method as the first reaction of Synthesis Example 8. 1 1H NMR (400 MHz, CDCl3, δ): 8.64 (s, 2H), 8.45 (s, 1H), 8.23 (d, J = 8.0 Hz, 2H), 8.06 (d, J = 6.8 Hz, 2H), 7.59 - 7.35 (m, 1H), 7.29 - 7.24 (m, 2H). MS (ASAP): 657.35 [M + H] + . Calcd for. C 44 H 21 FN4O2: 656.16

Chemical Structure

[0112] Synthesized in a yield of 67% by the same method as the second reaction of Synthesis Example 8. 1H NMR (400MHz, CDCl3, δ): 8.62 (s, 1H), 8.24 (d, J = 10.8 Hz, 2H), 7.95-7.90 (m, 2H), 7.81-7.76 (m, 2H),7.52-7.30 (m, 7H), 7.21-7.00 (m, 7H), 6.92-6.54 (m, 8H). MS (ASAP): 804.37 [M+H] + .Calcd for.C 56 H 29 N5O2: 803.23

[0113] (Synthesis Example 11) Synthesis of Compound 33 [ka]

[0114] It was synthesized in a yield of 80% in the same manner as in the first reaction of Synthesis Example 8. MS (ASAP): 689.43 [M+H] + . Calcd for. C44H21FN4S2: 688.12 [ka]

[0115] It was synthesized in a yield of 89% in the same manner as in the second reaction of Synthesis Example 8. 1 H NMR (400MHz, CDCl3, δ): 8.61 (s, 1H), 8.08 (t, J = 8.4 Hz, 2H), 7.90-7.81 (m, 7H), 7.48-7.40 (m, 2H),7.30-7.02 (m, 10H), 6.80-6.43 (m, 7H). MS (ASAP): 836.14 [M+H] + . Calcd for. C56H29N5S2: 835.19

[0116] (Synthesis example 12) Compound 34 synthesis [ka]

[0117] It was synthesized in a yield of 79% in the same manner as in the first reaction of Synthesis Example 8. 1 H NMR (400MHz, CDCl3, δ): 9.53 (s, 1H), 8.46 (t, J = 7.6 Hz, 4H), 7.40 (d, J = 8.0 Hz, 4H), 8.02 (d, J = 7.6Hz, 2H), 7.40 (d, J = 8.0 Hz, 2H), 7.62-748 (m, 8H). MS (ASAP): 688.97 [M+H] + . Calcd for. C44H21FN4S2: 688.12 [ka]

[0118] It was synthesized in a yield of 48% in the same manner as in the second reaction of Synthesis Example 8. 1 H NMR (400MHz, DMSO, δ): 9.75 (s, 1H), 8.24 (d, J = 7.2 Hz, 2H), 8.13 (d, J = 7.2 Hz, 2H), 7.99 (d, J = 7.6Hz, 2H), 7.89 (d, J = 8.4 Hz, 2H), 7.81 (d, J = 7.2 Hz, 2H), 7.61 (d, J = 7.2 Hz, 2H), 7.47 (d, J = 8.8 Hz, 4H), 7.26-7.22 (m, 2H), 7.11-7.06 (m, 5H), 6.90 (d, J = 8.0 Hz, 1H), 6.67 (t, J = 7.6 Hz, 1H), 6.44 (t, J = 7.2 Hz, 1H), 6.08 (t, J = 8.0 Hz, 1H), 5.16 (t, J = 8.4 Hz, 1H). MS (ASAP): 836.20 [M+H] + . Calcd for. C56H29N5S2: 835.19

[0119] (Synthesis Example 13) Synthesis of Compound 21 [Chemical Formula]

[0120] It was synthesized in a yield of 90% by the same method as the first reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.77 (s, 2H), 8.37 (s, 1H), 8.08 (d, J = 8.8 Hz, 2H), 8.01 (d, J = 7.6 Hz, 2H), 7.82 - 7.75 (m, 9H), 7.55 - 7.47 (m, 6H), 7.43 - 7.37 (m, 6H), 7.28 - 7.25 (m, 1H). MS (ASAP): 809.33 [M+H] + . Calcd for. C56H29FN4O2: 808.23 [Chemical Formula]

[0121] It was synthesized in a yield of 94% by the same method as the second reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.63 (s, 1H), 8.35 (d, J = 10.4 Hz, 2H), 7.92 - 7.86 (m, 2H), 7.74 (d, J = 8.4 Hz, 1H), 7.66 - 7.57 (m, 7H), 7.48 - 7.31 (m, 11H), 7.29 - 7.10 (m, 8H), 6.84 - 6.46 (m, 5H). MS (ASAP): 956.43 [M+H] + . Calcd for. C68H37N5O2: 955.29

[0122] (Synthesis Example 14) Synthesis of Compound 20098 [Chemical Formula]

[0123] It was synthesized in a yield of 89% by the same method as the first reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.77 (s, 2H), 8.38 (s, 1H), 8.09 (d, J = 8.4 Hz, 2H), 8.01 (d, J = 6.4 Hz, 2H), 7.83 - 7.76 (m, 4H) 7.49 (t, J = 7.2 Hz, 2H), 7.43 - 7.38 (m, 4H) 7.28 - 7.25 (m, 2H). MS (ASAP): 819.45 [M + H] + . Calcd for. C56H19D10FN4O2: 818.29

Chemical Structure

[0124] It was synthesized in a yield of 89% by the same method as the second reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.63 (s, 1H), 8.35 (d, J = 8.8 Hz, 2H), 7.93 - 7.86 (m, 2H), 7.74 (d, J = 8.8 Hz, 1H), 7.68 - 7.61 (m, 3H), 7.46 - 7.32 (m, 5H) 7.27 - 7.10 (m, 7H), 6.84 - 6.46 (m, 6H). MS (APCI): 966 [M + H] + . Calcd for. C68H27D10N5O2: 965.36 TG0112

[0125] (Synthesis Example 15) Synthesis of Compound 69

Chemical Structure

[0126] It was synthesized in a yield of 64% by the same method as the first reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.52 (d, J = 8.0 Hz, 2H), 8.34 (s, 1H), 7.91 - 7.88 (m, 2H), 7.76 - 7.74 (m, 2H), 7.54 - 7.44 (m, 6H), 7.38 - 7.32 (m, 4H), 7.25 - 7.21 (m, 4H), 1.91 (s, 6H), 1.86 (s, 6H). MS (ASAP): 709.26[M + H] + . Calcd for. C50H33FN4: 708.27

Chem.

[0127] It was synthesized in a yield of 69% by the same method as the second reaction of Synthesis Example 8. 1 H NMR (400 MHz, CDCl3, δ): 8.62 (s, 1H), 8.04 (t, J = 8.0 Hz, 2H), 7.62 - 7.57 (m, 2H), 7.46 (d, J = 8.0 Hz, 2H), 7.44 - 7.27 (m, 8H), 7.19 - 6.99 (m, 10H), 6.92 (t, J = 8.0 Hz, 1H), 6.70 - 6.43 (m, 6H), 1.54 (s, 6H), 1.49 (s, 6H). MS (ASAP): 856.49 [M + H] + . Calcd for. C62H41N5: 855.34

[0128] (Synthesis Example 16) Synthesis of Compound 7962

Chem.

[0129] It was synthesized in a yield of 63% by the same method as the first reaction of Synthesis Example 8. 11H NMR (400 MHz, DMSO, δ): 9.35 (s, 1H), 8.42 (d, J = 8.4 Hz, 4H), 8.25 (d, J = 8.4 Hz, 4H), 7.97 (d, J = 8.4 Hz, 4H), 7.84 (d, J = 6.8 Hz, 4H), 7.59 (t, J = 6.8 Hz, 4H), 7.46 (t, J = 7.2 Hz, 4H), 7.23 - 7.10 (m, 4H). MS (ASAP): 837.33 [M+H] + . Calcd for. C56H25FN4O4: 836.19

Chem.

[0130] It was synthesized in a yield of 61% by the same method as the second reaction of Synthesis Example 8. 1 1H NMR (400 MHz, DMSO, δ): 9.64 (s, 1H), 8.12 (d, J = 8.4 Hz, 4H), 7.99 (d, J = 8.4 Hz, 4H), 7.84 (d, J = 8.4 Hz, 8H), 7.53 - 7.47 (m, 6H), 7.39 (t, J = 6.8 Hz, 4H), 7.23 (m, 2H), 6.64 - 6.58 (m, 4H). MS (ASAP): 984.45 [M+H] + . Calcd for. C68H33N5O4: 983.25

[0131] (Synthesis Example 17) Synthesis of Compound 22

Chem.

[0132] It was synthesized in a yield of 83% by the same method as the first reaction of Synthesis Example 8. 11H NMR (400 MHz, CDCl3, δ): 8.42 (s, 1H), 8.37 (s, 2H), 8.15 (d, J = 8.0 Hz, 2H), 8.06 (d, J = 7.6 Hz, 2H), 8.06 (d, J = 8.4 Hz, 2H), 7.69 - 7.36 (m, 20H). MS (ASAP): 809.55[M+H] + . Calcd for. C56H29FN4O2: 808.23

Chem.

[0133] It was synthesized in a yield of 60% by the same method as the second reaction of Synthesis Example 8. 1 1H NMR (400 MHz, CDCl3, δ): 8.70 (s, 1H), 7.92 (s, 2H), 7.89 - 7.85 (m, 2H), 7.70 - 7.64 (m, 4H), 7.54 (d, J = 7.6 Hz, 4H), 7.46 - 7.38 (m, 6H), 7.33 - 7.22 (m, 11H), 6.95 (d, J = 8.8 Hz, 1H), 6.78 (t, J = 8.8 Hz, 2H), 6.64 (d, J = 8.8 Hz, 1H), 6.54 (t, J = 8.8 Hz, 1H), 6.12 (t, J = 8.8 Hz, 1H), 5.40 (t, J = 8.8 Hz, 1H),. MS (ASAP): 956.57 [M+H] + . Calcd for. C68H37N5O2: 955.29

[0134] (Synthesis Example 18) Synthesis of Compound 24

Chem.

[0135] It was synthesized in a yield of 56% by the same method as the first reaction of Synthesis Example 8. 11H NMR (400 MHz, CDCl3, δ): 8.92 (s, 2H), 8.64 (d, J = 6.8 Hz, 2H), 8.39 (s, 1H), 7.84 - 7.79 (m, 8H), 7.72 (d, J = 8.4 Hz, 2H), 7.58 - 7.52 (m, 8H), 7.46 - 7.36 (m, 6H). MS (ASAP): 809.44[M + H] + . Calcd for. C56H29FN4O2: 808.23

Chem.

[0136] It was synthesized in a yield of 71% by the same method as the second reaction of Synthesis Example 8. 1 1H NMR (400 MHz, CDCl3, δ): 8.66 (s, 1H), 8.52 (s, 2H), 8.40 (d, J = 7.2 Hz, 2H), 7.65 - 7.61 (m, 6H), 7.54 - 7.48 (m, 6H), 7.46 - 7.38 (m, 5H), 7.36 - 7.25 (m, 7H), 7.19 (d, J = 7.6 Hz, 2H), 6.86 - 6.80 (m, 2H), 6.76 - 6.51 (m, 4H). MS (ASAP): 956.57 [M + H] + . Calcd for. C68H37N5O2: 955.29

[0137] (Synthesis Example 19) Synthesis of Compound 30870

Chem.

[0138] It was synthesized in a yield of 32% by the same method as Compound 1a. 11H NMR (400 MHz, CDCl3, δ): 8.61 (d, J = 8.0 Hz, 2H), 8.38 (s, 1H), 7.99 (d, J = 7.6 Hz, 2H), 7.94 (d, J = 8.0 Hz, 2H), 7.77 - 7.72 (m, 9H), 7.59 - 7.40 (m, 13H). MS (ASAP): 809.44[M+H] + . Calcd for. C56H29FN4O2: 808.23

Chem.

[0139] It was synthesized in a yield of 64% by the same method as the second reaction of Synthesis Example 8. 1 1H NMR (400 MHz, CDCl3, δ): 8.62 (s, 0.5H), 8.58 (s, 0.5H), 8.24 (d, J = 8.0 Hz, 1H), 8.18 (d, J = 8.0 Hz, 1H), 8.02 - 7.99 (m, 1.5H), 7.90 (d, J = 6.8 Hz, 1H), 7.70 - 7.60 (m, 2H), 7.51 - 7.26 (m, 13H), 7.21 - 7.14 (m, 7H), 6.95 - 6.62 (m, 5.5H), 6.58 (t, J = 8.0 Hz, 0.5H), 6.46 - 6.38 (m, 1.5H). MS (ASAP): 956.57 [M+H] + . Calcd for. C68H37N5O2: 955.29

[0140] (Synthesis Example 20) Synthesis of Compound 37027

Chem.

[0141] Under a nitrogen atmosphere, potassium carbonate (1.47 g, 10.35 mmol) and 5H-benzofuro[3,2-c]carbazole (1.95 g, 7.59 mmol) were stirred in dimethylformamide (60 mL) at room temperature for 30 minutes, and then 4,5,6-trifluoroisopropylnitrile (0.35 mmol, 1.92 mmol) was added and the mixture was allowed to react at room temperature for 5 hours. The reaction was then quenched with water and methanol, and the precipitated yellow solid was filtered. The residue was purified by silica gel column chromatography (toluene) and reprecipitation (toluene / methanol) to give compound 2a (0.90 g, 1.17 mmol, 34% yield) as a yellow solid. 1 H NMR (400MHz, CDCl3, δ): 8.31 (s, 1H), 8.13-8.06 (m, 2H), 7.90-7.87 (m, 0.5H), 7.79-7.76 (m, 1.5H), 7.69-7.65 (m, 0.5H), 7.59-7.53 (m, 3.5H), 7.41-7.34 (m, 2H), 7.30-7.25 (m, 2H), 7.23-7.09 (m, 4H), 7.04-6.99 (m, 2), 6.93-6.86 (m, 2H). MS (ASAP): 765.27 (M+H + ). Calcd for C44H21IN4O2: 764.07. [ka]

[0142] Under a nitrogen atmosphere, a dimethylformamide solution (20 mL) of compound 2a (0.75 g, 0.98 mmol), carbazole (0.33 g, 1.96 mmol), and K2CO3 (0.35 g, 2.45 mmol) was heated and stirred at 120 °C for 5 hours. Methanol and water were added to the reaction mixture to quench the reaction. The precipitate was then filtered, and the solid was recovered. The resulting filtrate was purified by column chromatography (toluene / hexane / CHCl3 = 7 / 2.5 / 0.5) and reprecipitation (toluene / hexane) to obtain compound 37027 (0.45 g, 0.56 mmol, 57%) as a yellow solid. 1 1H NMR (400 MHz, CDCl3, δ): 8.58 (s, 1H), 8.13 (d, J = 8.0 Hz, 1H), 7.86 - 7.78 (m, 2H), 7.74 - 7.55 (m, 6H), 7.45 - 7.42 (m, 1H), 7.39 - 6.97 (m, 14H), 6.93 - 6.74 (m, 3H), 6.66 - 6.55 (m, 1H). MS (ASAP): 804.43 [M+H] + . Calcd for. C 56 H 29 N5O2: 803.23

[0143] (Examples 1 - 3, Comparative Example 1) Fabrication and Evaluation of Thin Films On a quartz substrate, Compound 1131 and mCBP were deposited from different evaporation sources by vacuum evaporation under a condition of a vacuum degree of less than 1 × 10 -3 Pa to form a thin film with a thickness of 100 nm and a concentration of Compound 1131 of 20 wt%, which was used as the doped thin film of Example 1. Instead of Compound 1131, Compound 1313, Compound 1404, and Comparative Compound A were used respectively to obtain the thin films of Example 2, Example 3, and Comparative Example 1. When each of the obtained thin films was irradiated with 300 - nm excitation light, photoluminescence was observed for all the thin films. From the transient decay curve of the luminescence, the lifetime (τ d ) of the delayed fluorescence was obtained. The results were as shown in the following table. It was confirmed that the delayed fluorescence lifetimes (τ d ) of Examples 1 - 3 were short.

Table 2

[0144] (Example 4) Fabrication of Organic Electroluminescence Device On a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 100 nm was formed, each thin film was deposited by vacuum evaporation under a vacuum degree of 1 × 10 -6The layers were laminated by Pa. First, HATCN was formed on ITO to a thickness of 10 nm, and NPD was formed thereon to a thickness of 30 nm. Next, TrisPCz was formed thereon to a thickness of 10 nm, and Host1 was further formed thereon to a thickness of 5 nm. Next, Compound 1131 and Host1 were co-deposited from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the concentration of Compound 1131 was 35 wt %. SF3TRZ was formed thereon to a thickness of 10 nm, and SF3TRZ and Liq were further co-deposited thereon from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the SF3TRZ:Liq (weight ratio) was 7:3. Next, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode. By the above procedure, the organic electroluminescent device of Example 1 was fabricated.

[0145] (Comparative Example 2) An organic electroluminescence device of Comparative Example 2 was prepared in the same manner as in Example 1, except that Comparative Compound A was used instead of Compound 1131.

[0146] (evaluation) The x and y CIE chromaticity coordinates were measured for the light emitted from each of the organic electroluminescent elements of Example 1 and Comparative Example 2. In addition, the luminance of each organic electroluminescent element was 12.6 mA / cm 2 The time (LT95) until the luminous intensity at 100% decreased to 95% was measured, and the relative value was calculated with the LT95 of Comparative Example 2 set to 100%. The results are shown in the table below. The organic electroluminescent element of Example 1 had good chromaticity and significantly improved element life (element durability).

[0147] [Table 3]

[0148] [ka] [Explanation of symbols]

[0149] 1 Substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1). 【Chemical 1】 [In general formula (1), R １ is a hydrogen atom or a deuterium atom, R ２ to R ４ each independently represents a donor group, among which R2 and R4 are a benzofuran-fused carbazole-9-yl group having a skeleton in which a benzofuran ring is condensed at the 2- and 3-positions of the carbazole ring, or a benzothiophene-fused carbazole-9-yl group having a skeleton in which a benzothiophene ring is condensed at the 2- and 3-positions of the carbazole ring, and R3 is a substituted or unsubstituted carbazole-9-yl group (the carbazole-9-yl group herein may have a benzene ring or a hetero ring condensed thereto, provided that the condensed ring is not a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring, or a silainden ring).]

2. R ２ and R ４ are the same, the compound according to claim 1.

3. At least one of R2 and R4 is a benzofuran-fused carbazole-9-yl group having a skeleton in which two benzofuran rings are condensed at the 2,3-positions to the carbazole ring, or a benzothiophene-fused carbazole-9-yl group having a skeleton in which two benzothiophene rings are condensed at the 2,3-positions to the carbazole ring. The compound according to claim 1 or 2.

4. R ２ and R ４ are different, the compound according to claim 1.

5. One of R2 and R4 is a carbazole-9-yl group in which two selected from the group consisting of a benzofuran ring and a benzothiophene ring are each condensed at the 2,3-positions, and the other of R2 and R4 is a carbazole-9-yl group in which a benzofuran ring or a benzothiophene ring is condensed at the 2,3-positions. The compound according to claim 4.

6. The compound according to any one of claims 1 to 3, having a symmetric structure.

7. The compound according to any one of claims 1 to 6, consisting of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom.

8. The compound according to any one of claims 1 to 7, wherein the benzofuran-fused carbazole-9-yl group has any of the following structures. [Chemical Formula 2] [In each of the above structures, the hydrogen atom may be substituted, but is not further condensed.]

9. The compound according to any one of claims 1 to 8, wherein the benzothiophene-fused carbazole-9-yl group has any of the following structures. 【Chemical Formula 3】 [In each of the above structures, the hydrogen atom may be substituted, but is not further condensed.]

10. A light-emitting material comprising the compound according to any one of claims 1 to 9.

11. A light-emitting device comprising the compound according to any one of claims 1 to 9.

12. The light-emitting device according to claim 11, wherein the light-emitting device has a light-emitting layer, and the light-emitting layer contains the compound and a host material.

13. The light-emitting device according to claim 11 or 12, wherein the light-emitting device has a light-emitting layer, the light-emitting layer contains the compound and a light-emitting material, and emits light mainly from the light-emitting material.

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