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

Abstract

Use a compound represented by the following general formula as a luminescent material. R 1 , R 2 , R 4 Any one of them is a hydrogen atom or a deuterium atom and the rest are donor groups, but at least one is a carbazol-9-yl fused with a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring or a silaindene ring.

Description

Technical Field

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

[0002] Research is actively being conducted to improve the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements). In particular, much effort has been made in improving the luminous efficiency by newly developing and combining an electron transport material, a hole transport material, a luminescent material, etc. constituting an organic electroluminescent element. Among them, research related to an organic electroluminescent element using a delayed fluorescence material has also been seen.

[0003] A delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after undergoing reverse intersystem crossing from the excited triplet state in the excited state. Fluorescence generated by this pathway 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, in the case of exciting a luminescent compound by injection of carriers, the generation probabilities of the excited singlet state and the excited triplet state are statistically 25%:75%. Therefore, if only fluorescence from the directly generated excited singlet state is used, there is a limit to the improvement of luminous efficiency. On the other hand, in a delayed fluorescence material, in addition to the excited singlet state, the excited triplet state can also be used for fluorescence emission through the above-mentioned reverse intersystem crossing pathway, and thus a high luminous efficiency can be obtained compared with ordinary fluorescence materials.

[0004] After this principle was clarified, various delayed fluorescence materials were discovered through various studies. However, not all materials that emit delayed fluorescence can be immediately useful as luminescent materials. Among delayed fluorescence materials, there are materials in which reverse intersystem crossing is relatively difficult to occur, and there are also materials with a long lifetime of delayed fluorescence. In addition, there are materials in which excitons accumulate in the high current density region and the luminous efficiency decreases, or rapid deterioration occurs if driven for a long time. Therefore, in fact, there are a great many delayed fluorescence materials that have room for improvement in terms of practicality. Therefore, it has been pointed out that problems also exist in benzonitrile-based compounds known as delayed fluorescence materials. For example, 2CzPN having the following structure is a material that emits delayed fluorescence, but there are problems such as low luminous efficiency and a significant decrease in luminous efficiency in the high current density region (see Non-Patent Document 1).

[0005] [Chemical formula 1]

[0006]

[0007] Prior Art Documents

[0008] Non-Patent Documents

[0009] Non-Patent Document 1: Organic Electronics 14(2013)2721–2726 Summary of the Invention

[0010] Technical Problem to be Solved by the Invention

[0011] Although such a problem has been pointed out, it is difficult to say that the relationship between the chemical structure and properties of delayed fluorescence materials has been fully elucidated. Therefore, it is currently difficult to broaden the chemical structure of compounds useful as luminescent materials, and there are many unclear points.

[0012] Under such circumstances, the present inventors repeatedly conducted research with the aim of providing a compound more useful as a luminescent material for a light-emitting element. Moreover, in-depth research was conducted with the aim of deriving and generalizing a general formula for a compound more useful as a luminescent material.

[0013] Means for Solving the Technical Problem

[0014] As a result of in-depth research to achieve the above object, the present inventors found that a compound having a structure satisfying specific conditions among isophthalonitrile derivatives is useful as a luminescent material. The present invention was proposed based on this finding, and specifically has the following structure.

[0015] [1] A compound represented by the following general formula (1).

[0016] [Chemical Formula 2]

[0017]

[0018] In the general formula (1),

[0019] R 1 、R 2 and R 4 Any one of them is a hydrogen atom or a deuterium atom,

[0020] The remaining two and R 3 Each independently represents a donor group, but at least one of them is a benzofuran-fused carbazol-9-yl having a skeleton formed by fusing a benzofuran ring to the 2- and 3-positions of a carbazole ring, a benzothiophene-fused carbazol-9-yl having a skeleton formed by fusing a benzothiophene ring to the 2- and 3-positions of a carbazole ring, an indole-fused carbazol-9-yl having a skeleton formed by fusing an indole ring to the 2- and 3-positions of a carbazole ring, an indene-fused carbazol-9-yl having a skeleton formed by fusing an indene ring to the 2- and 3-positions of a carbazole ring, or a silaindene-fused carbazol-9-yl having a skeleton formed by fusing a silaindene ring to the 2- and 3-positions of a carbazole ring.

[0021] [2] The compound according to [1], wherein the remaining two and R 3 both contain a carbazole ring.

[0022] [3] The compound according to [1] or [2], wherein R 3 is the benzofuran-fused carbazol-9-yl, the benzothiophene-fused carbazol-9-yl, the indole-fused carbazol-9-yl, the indene-fused carbazol-9-yl or the silaindene-fused carbazol-9-yl.

[0023] [4] The compound according to any one of [1] to [3], wherein R 2 and R 4 are each independently the benzofuran-fused carbazol-9-yl, the benzothiophene-fused carbazol-9-yl, the indole-fused carbazol-9-yl, the indene-fused carbazol-9-yl or the silaindene-fused carbazol-9-yl.

[0024] [5] The compound according to any one of [1] to [4], wherein R 2 and R 4 are the same.

[0025] [6] The compound according to any one of [1] to [5], wherein at least one of the remaining two and R 3 is the benzofuran-fused carbazol-9-yl or the benzothiophene-fused carbazol-9-yl.

[0026] [7] The compound according to any one of [1] to [5], wherein the remaining two and R 3 are each independently the benzofuran-fused carbazol-9-yl or the benzothiophene-fused carbazol-9-yl.

[0027] [8] The compound according to any one of [1] to [7], wherein R 1 is a hydrogen atom or a deuterium atom.

[0028] [9] The compound according to any one of [1] to [8], wherein the remaining two and R 3 are the same.

[0029]

[10] The compound according to any one of [1] to [9], wherein the remaining two and R 3At least one of them is a benzofuran-fused carbazol-9-yl having a skeleton formed by fusing two benzofuran rings to the 2- and 3-positions of the carbazole ring, a benzothiophene-fused carbazol-9-yl having a skeleton formed by fusing two benzothiophene rings to the 2- and 3-positions of the carbazole ring, an indole-fused carbazol-9-yl having a skeleton formed by fusing two indole rings to the 2- and 3-positions of the carbazole ring, an indene-fused carbazol-9-yl having a skeleton formed by fusing two indene rings to the 2- and 3-positions of the carbazole ring, or a silole-indene-fused carbazol-9-yl having a skeleton formed by fusing two silole-indene rings to the 2- and 3-positions of the carbazole ring.

[0030]

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

[10] has a symmetric structure.

[0031]

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

[11] is composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0032]

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

[12] , wherein the benzofuran-fused carbazol-9-yl has any one of the following structures,

[0033] [Chemical formula 3]

[0034]

[0035] [In each of the above structures, the hydrogen atom may be substituted, but the ring will not be further fused].

[0036]

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

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

[0037] [Chemical formula 4]

[0038]

[0039] [In each of the above structures, the hydrogen atom may be substituted, but the ring will not be further fused].

[0040]

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

[14] .

[0041]

[16] A light-emitting element, characterized by comprising the compound according to any one of [1] to

[14] .

[0042]

[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.

[0043]

[18] The light-emitting element according to

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

[0044] Advantages of the Invention

[0045] The compound of the present invention is useful as a light-emitting material. Further, the compound of the present invention contains a compound that emits delayed fluorescence. Moreover, the compound of the present invention is also useful as a material for an organic light-emitting element. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] Figure 1 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescent element. DETAILED DESCRIPTION OF THE INVENTION

[0047] The content of the present invention will be described in detail below. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. Further, in the present specification, the 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, part 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 formula of the present specification, a hydrogen atom is represented as H or its representation is omitted. For example, when an atom bonded to a ring skeleton constituting carbon atom of a benzene ring is omitted from representation, it is assumed that H is bonded to the ring skeleton constituting carbon atom at the omitted position. In the chemical structural formula of the present specification, a deuterium atom is represented as D.

[0048] [Compound represented by General Formula (1)]

[0049] [Chemical Formula 5]

[0050]

[0051] In General Formula (1), any one of R 1 , R 2 and R 4 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. Among them, a mode in which R 2 is a hydrogen atom or a deuterium atom or a mode in which R 4 is a hydrogen atom or a deuterium atom can also be adopted.

[0052] In General Formula (1), two of R 1 , R 2 and R 4 other than a hydrogen atom and a deuterium atom and R3 independently represent donor groups respectively. For example, when R 1 is a hydrogen atom or a deuterium atom, R 2 , R 3 and R 4 independently represent donor groups respectively, and this mode is preferably adopted. Among them, it is also possible to adopt the mode where R 2 is a hydrogen atom or a deuterium atom and R 1 , R 3 and R 4 are donor groups respectively, or the mode where R 4 is a hydrogen atom or a deuterium atom and R 1 , R 2 and R 3 are donor groups respectively. In the following description, "two of R 1 , R 2 and R 4 other than hydrogen atoms and deuterium atoms and R 3 " are collectively referred to as "three Rs as donor groups".

[0053] At least one of the three Rs as donor groups is a benzofuran-fused carbazol-9-yl having a skeleton formed by fusing a benzofuran ring to the 2- and 3-positions of a carbazole ring (hereinafter simply referred to as "benzofuran-fused carbazol-9-yl"), a benzothiophene-fused carbazol-9-yl having a skeleton formed by fusing a benzothiophene ring to the 2- and 3-positions of a carbazole ring (hereinafter simply referred to as "benzothiophene-fused carbazol-9-yl"), an indole-fused carbazol-9-yl having a skeleton formed by fusing an indole ring to the 2- and 3-positions of a carbazole ring (hereinafter simply referred to as "indole-fused carbazol-9-yl"), an indene-fused carbazol-9-yl having a skeleton formed by fusing an indene ring to the 2- and 3-positions of a carbazole ring (hereinafter simply referred to as "indene-fused carbazol-9-yl"), or a silole-fused carbazol-9-yl having a skeleton formed by fusing a silole ring to the 2- and 3-positions of a carbazole ring (hereinafter simply referred to as "silole-fused carbazol-9-yl").

[0054] In one embodiment of the present invention, at least one of the three Rs as donor groups may be 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 embodiment of the present invention, at least one of the three Rs as donor groups may be 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 embodiment of the present invention, at least one of the three Rs as donor groups may be selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a silolene-fused carbazol-9-yl group. At least one of the three Rs as donor groups is preferably a benzofuran-fused carbazol-9-yl group or a benzothiophene-fused carbazol-9-yl group, and more preferably a benzofuran-fused carbazol-9-yl group. At least one of the three Rs as donor groups may be a benzothiophene-fused carbazol-9-yl group. At least one of the three Rs as donor groups may be an indole-fused carbazol-9-yl group. At least one of the three Rs as donor groups may be an indene-fused carbazol-9-yl group. At least one of the three Rs as donor groups may be a silolene-fused carbazol-9-yl group.

[0055] In one embodiment of the present invention, at least two of the three Rs as donor groups may be 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 embodiment of the present invention, at least two of the three Rs as donor groups may be 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 embodiment of the present invention, at least two of the three Rs as donor groups may be selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a silolene-fused carbazol-9-yl group. At least two of the three Rs as donor groups are preferably a benzofuran-fused carbazol-9-yl group or a benzothiophene-fused carbazol-9-yl group, and more preferably a benzofuran-fused carbazol-9-yl group. At least two of the three Rs as donor groups may be a benzothiophene-fused carbazol-9-yl group. At least two of the three Rs as donor groups may be an indole-fused carbazol-9-yl group. At least two of the three Rs as donor groups may be an indene-fused carbazol-9-yl group. At least two of the three Rs as donor groups may be a silolene-fused carbazol-9-yl group.

[0056] In one embodiment of the present invention, all of the three Rs as donor groups can be 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 embodiment of the present invention, all of the three Rs as donor groups can be 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 embodiment of the present invention, all of the three Rs as donor groups can be selected from a benzofuran-fused carbazol-9-yl group, a benzothiophene-fused carbazol-9-yl group, and a silaindene-fused carbazol-9-yl group. All of the three Rs as 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 as donor groups can be a benzothiophene-fused carbazol-9-yl group. All of the three Rs as donor groups can be an indole-fused carbazol-9-yl group. All of the three Rs as donor groups can be an indene-fused carbazol-9-yl group. All of the three Rs as donor groups can be a silaindene-fused carbazol-9-yl group.

[0057] The benzofuran-fused carbazol-9-yl group may be formed by fusing only one benzofuran ring at the 2- and 3-positions, or may be formed by fusing two or more benzofuran rings. Further, it may be formed by fusing a benzofuran ring at the 2- and 3-positions and other rings. 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.

[0058] In the present invention, as the benzofuran-fused carbazol-9-yl group, a substituted or unsubstituted benzofuran[2,3-a]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzofluoro[3,2-a]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzofluoro[2,3-b]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzofluoro[3,2-b]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzofluoro[2,3-c]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzofluoro[3,2-c]carbazol-9-yl group can be used.

[0059] Preferably, the benzofuran-fused carbazol-9-yl group is a carbazol-9-yl group in which only one benzofuran ring is fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, it is possible to preferably exemplify a case where a part of the hydrogen atoms in the following structures is substituted with deuterium atoms or a case where all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also possible to preferably use an unsubstituted one.

[0060] [Chemical formula 6]

[0061]

[0062] Also preferably, the carbazol-9-yl group is one in which two benzofuran rings are fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, it is possible to preferably exemplify a case where a part of the hydrogen atoms in the following structures is substituted with deuterium atoms or a case where all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also possible to preferably use an unsubstituted one.

[0063] [Chemical formula 7]

[0064]

[0065] The benzothiophene-fused carbazol-9-yl group may be one in which only one benzothiophene ring is fused at the 2- and 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- and 3-positions and another ring is fused. Regarding the description and specific examples of the fused rings, reference can be made to the description and specific examples of the fused rings 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 used. Further, a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can be used. Further, a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can be used.

[0066] The preferred benzo[b]thiophene-fused carbazol-9-yl is a carbazol-9-yl in which only one benzo[b]thiophene ring is fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, it is preferably exemplified that a part of the hydrogen atoms in the following structures are substituted with deuterium atoms or all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also preferably unsubstituted.

[0067] [Chemical Formula 8]

[0068]

[0069] Also preferred is a carbazol-9-yl in which two benzo[b]thiophene rings are fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, it is preferably exemplified that a part of the hydrogen atoms in the following structures are substituted with deuterium atoms or all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also preferably unsubstituted.

[0070] [Chemical Formula 9]

[0071]

[0072] The indole-fused carbazol-9-yl may be formed by fusing only one indole ring at the 2- and 3-positions, or may be formed by fusing two or more indole rings. Further, it may be formed by fusing an indole ring at the 2- and 3-positions and other rings. Regarding the description and specific examples of the fused rings, reference can be made to the description and specific examples of the fused rings in the description of the benzofuran-fused carbazol-9-yl above. In the present invention, as the indole-fused carbazol-9-yl, a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl may be used. Further, a substituted or unsubstituted indolo[3,2-a]carbazol-9-yl may be used. Further, a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl may be used. Further, a substituted or unsubstituted indolo[3,2-b]carbazol-9-yl may be used. Further, a substituted or unsubstituted indolo[2,3-c]carbazol-9-yl may be used. Further, a substituted or unsubstituted indolo[3,2-c]carbazol-9-yl may be used.

[0073] The preferred indole-fused carbazol-9-yl is a carbazol-9-yl in which only one indole ring is fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one 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, it is possible to preferably exemplify those in which a part of the hydrogen atoms in the following structures are substituted with deuterium atoms or all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also possible to preferably use those that are unsubstituted.

[0074] [Chemical formula 10]

[0075]

[0076] The indene-fused carbazol-9-yl may be one in which only one indene ring is fused at the 2- and 3-positions, or may be one in which two or more indene rings are fused. Also, it may be one in which an indene ring is fused at the 2- and 3-positions and another ring is fused. For the description and specific examples of the fused rings, reference can be made to the description and specific examples of the fused rings in the description of the benzofuran-fused carbazol-9-yl above. In addition, when an indene ring is mentioned in the present invention, it is described on the premise of 1H-indene (a double bond exists between the 2- and 3-positions). On the other hand, when defining indeno[2,3-x]carbazole or indeno[3,2-x]carbazole (x is a, b or c) according to the IUPAC nomenclature. In the present invention, as the indene-fused carbazol-9-yl, a substituted or unsubstituted indeno[2,3-a]carbazol-9-yl may be used. Also, a substituted or unsubstituted indeno[3,2-a]carbazol-9-yl may be used. Also, a substituted or unsubstituted indeno[2,3-b]carbazol-9-yl may be used. Also, a substituted or unsubstituted indeno[3,2-b]carbazol-9-yl may be used. Also, a substituted or unsubstituted indeno[2,3-c]carbazol-9-yl may be used. Also, a substituted or unsubstituted indeno[3,2-c]carbazol-9-yl may be used.

[0077] The preferred indene-fused carbazol-9-yl is a carbazol-9-yl in which only one indene ring is fused at the 2- and 3-positions and no other rings are fused thereto. Specifically, it is a group having any one of the following structures, where the hydrogen atoms in the following structures may be substituted. For example, it is possible to preferably exemplify those in which a part of the hydrogen atoms in the following structures are substituted with deuterium atoms or all of the hydrogen atoms in the following structures are substituted with deuterium atoms. It is also possible to preferably use those that are unsubstituted.

[0078] [Chemical formula 11]

[0079]

[0080] The silaindene-fused carbazol-9-yl may be formed by fusing only one silaindene ring at the 2- and 3-positions, or may be formed by fusing two or more silaindene rings. Further, it may be formed by fusing a silaindene ring at the 2- and 3-positions and another ring. 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 above. In addition, when referring to the silaindene ring in the present invention, the description is based on 1H-silaindene (a double bond exists between the 2- and 3-positions). On the other hand, when defining silaindeno[2,3-x]carbazole or silaindeno[3,2-x]carbazole (x is a, b, or c) according to the IUPAC nomenclature. In the present invention, as the silaindene-fused carbazol-9-yl, a substituted or unsubstituted silaindeno[2,3-a]carbazol-9-yl can be used. Further, a substituted or unsubstituted silaindeno[3,2-a]carbazol-9-yl can be used. Further, a substituted or unsubstituted silaindeno[2,3-b]carbazol-9-yl can be used. Further, a substituted or unsubstituted silaindeno[3,2-b]carbazol-9-yl can be used. Further, a substituted or unsubstituted silaindeno[2,3-c]carbazol-9-yl can be used. Further, a substituted or unsubstituted silaindeno[3,2-c]carbazol-9-yl can be used.

[0081] A preferred silaindene-fused carbazol-9-yl is a carbazol-9-yl in which only one silaindene ring is fused at the 2- and 3-positions and no other ring is fused. Specifically, it is a group having any one 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). Further, the hydrogen atoms in the following structures may be substituted. For example, it is preferably exemplified that a part of the hydrogen atoms in the following structures is substituted with deuterium atoms or all of the hydrogen atoms in the following structures are substituted with deuterium atoms. An unsubstituted one may also be preferably used. R and R’ may be the same or different, and may be bonded to each other to form a cyclic structure.

[0082] [Chemical formula 12]

[0083]

[0084] The benzofuran-fused carbazol-9-yl, benzothiophene-fused carbazol-9-yl, indole-fused carbazol-9-yl, indene-fused carbazol-9-yl, and silaindene-fused carbazol-9-yl that can be used in the general formula (1) may be substituted. Further, they may be unsubstituted. In the case of being substituted, they may be substituted with a deuterium atom or with a substituent other than this. Examples of the substituent described herein 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, substitution patterns with a deuterium atom, an alkyl group, an aryl group, an alkoxy group, and an alkylthio group can be mentioned. In one embodiment 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.

[0085] The "alkyl group" described 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. In addition, 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. Further, 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, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a n-hexyl group, an isohexyl group, a 2-ethylhexyl group, a n-heptyl group, an isoheptyl group, a n-octyl group, an isooctyl group, a n-nonyl group, an isononyl group, a n-decyl group, an isododecyl 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.

[0086] 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. Further, 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 a vinyl group, a n-propenyl group, an isopropenyl group, a n-butenyl group, an isobutenyl group, a n-pentenyl group, an isopentenyl group, a n-hexenyl group, an isohexenyl group, and a 2-ethylhexenyl group. The alkenyl group as a substituent may be further substituted.

[0087] "Aryl" and "heteroaryl" can be monocyclic or polycyclic fused by two or more rings. In the case of polycyclic, the number of fused rings is preferably 2 to 6, for example, it can be selected 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, naphthyridine ring. Specific examples of arylene or heteroarylene include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 2-pyridyl, 3-pyridyl, 4-pyridyl.

[0088] Regarding the alkyl moiety of "alkoxy" and "alkylthio", the descriptions and specific examples of the above alkyl can be referred to. Regarding the aryl moiety of "aryloxy" and "arylthio", the descriptions and specific examples of the above aryl can be referred to. Regarding the heteroaryl moiety of "heteroaryloxy" and "heteroarylthio", the descriptions and specific examples of the above heteroaryl can be referred to.

[0089] One or two of the three Rs as donor groups can be donor groups other than benzofuran-fused carbazol-9-yl, benzothiophene-fused carbazol-9-yl, indole-fused carbazol-9-yl, indene-fused carbazol-9-yl and silaindene-fused carbazol-9-yl (hereinafter referred to as "other donor groups"). The other donor groups herein are groups with a negative Hammett σp value. Herein, the "Hammett σp value" was proposed by L.P. Hammett to quantify the influence of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, it is the following formula established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

[0090] log(k / k0) = ρσp

[0091] Or

[0092] log(K / K0) = ρσp

[0093] The constant (σp) specific to the substituent in. In the above formula, k represents the rate constant of the benzene derivative without substituents, k0 represents the rate constant of the benzene derivative substituted with substituents, K represents the equilibrium constant of the benzene derivative without substituents, k0 represents the equilibrium constant of the benzene derivative substituted with substituents, and ρ represents the reaction constant determined by the type and conditions of the reaction. Regarding the description related to the "Hammett σp value" in the present invention and the values of each substituent, the description related to the σp value in Hansch, C. et al., Chem. Rev., 91, 165–195 (1991) can be referred to. There is a tendency that groups with a negative Hammett σp value show electron-donating properties (donor properties), and groups with a positive Hammett σp value show electron-withdrawing properties (acceptor properties).

[0094] 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, 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 to the nitrogen atom of the substituted amino group or a group bonded to a group bonded with a substituted amino group. The group bonded with a substituted amino group is preferably a π-conjugated group. More preferably, it is a group bonded to the nitrogen atom of the substituted amino group. Regarding the alkyl group, alkenyl group, aryl group, and heteroaryl group as substituents described herein, reference can be made to the corresponding descriptions related to the substituents of the aromatic hydrocarbon ring group and the aromatic heterocyclic ring group.

[0095] Particularly preferred groups as other donor groups in the present invention are substituted or unsubstituted carbazol-9-yl groups. A benzene ring or a heterocyclic ring (excluding benzofuran ring, benzothiophene ring, indole ring, indene ring, silaindene ring) may be further fused to the carbazol-9-yl group. 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. Regarding the description of the substituted amino group, reference can be made to the previous paragraph. And the substituted amino group described herein includes a substituted or unsubstituted carbazolyl group, for example, a substituted or unsubstituted carbazol-3-yl group or a substituted or unsubstituted carbazol-9-yl group.

[0096] The number of atoms other than hydrogen atoms and deuterium atoms of other donor groups in the present invention is preferably 8 or more, more preferably 12 or more, and can also be set to 16 or more, for example. And it is preferably 80 or less, more preferably 60 or less, and further preferably 40 or less.

[0097] The three Rs as donor groups in the general formula (1) may all be the same or different. Further, two of the Rs may be the same or one may be different. In a preferred embodiment of the present invention, the three Rs as donor groups are the same. In another preferred embodiment of the present invention, two of the three Rs as donor groups are the same and are each any one of a benzofuran-fused carbazol-9-yl, a benzothiophene-fused carbazol-9-yl, an indole-fused carbazol-9-yl, an indene-fused carbazol-9-yl, and a silaindene-fused carbazol-9-yl (hereinafter referred to as "the specific five fused carbazol-9-yls"), and the remaining one is a donor group other than the specific five fused carbazol-9-yls. In another preferred embodiment of the present invention, one of the three Rs as donor groups is any one of the specific five fused carbazol-9-yls, and the remaining two are the same and are donor groups other than the specific five fused carbazol-9-yls.

[0098] 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 each any one of the specific five fused carbazol-9-yls. In another preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, R 2 and R 4 are each any one of the specific five fused carbazol-9-yls, 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, R 3 is any one of the specific five fused carbazol-9-yls, 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, R 3 and R 4 are each any one of the specific five fused carbazol-9-yls, and R 2 is another donor group.

[0099] In the following, specific examples of donor groups that the three Rs as donor groups can adopt 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, benzothiophene-fused carbazol-9-yl, indole-fused carbazol-9-yl, indene-fused carbazol-9-yl, and silaindene-fused carbazol-9-yl. 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.

[0100] [Chemical Formula 13-1]

[0101]

[0102] [Chemical Formula 13-2]

[0103]

[0104] [Chemical Formula 13-3]

[0105]

[0106] [Chemical Formula 13-4]

[0107]

[0108] [Chemical Formula 13-5]

[0109]

[0110] [Chemical Formula 13-6]

[0111]

[0112] [Chemical Formula 13-7]

[0113]

[0114] [Chemical Formula 13-8]

[0115]

[0116] [Chemical Formula 13-9]

[0117]

[0118] [Chemical Formula 13-10]

[0119]

[0120] [Chemical Formula 13-11]

[0121]

[0122] [Chemical Formula 13-12]

[0123]

[0124] [Chemical Formula 13-13]

[0125]

[0126] [Chemical Formula 13-14]

[0127]

[0128] [Chemical Formula 13-15]

[0129]

[0130] [Chemical Formula 13-16]

[0131]

[0132] [Chemical Formula 13-17]

[0133]

[0134] [Chemical Formula 13-18]

[0135]

[0136] [Chemical Formula 13-19]

[0137]

[0138] [Chemical Formula 13-20]

[0139]

[0140] [Chemical Formula 13-21]

[0141]

[0142] [Chemical Formula 13-22]

[0143]

[0144] [Chemical Formula 13-23]

[0145]

[0146] [Chemical Formula 13-24]

[0147]

[0148] [Chemical Formula 13-25]

[0149]

[0150] [Chemical Formula 13-26]

[0151]

[0152] [Chemical Formula 13-27]

[0153]

[0154] [Chemical Formula 13-28]

[0155]

[0156] [Chemical Formula 13-29]

[0157]

[0158] [Chemical Formula 13-30]

[0159]

[0160] [Chemical Formula 13-31]

[0161]

[0162] [Chemical Formula 13-32]

[0163]

[0164] [Chemical Formula 13-33]

[0165]

[0166] [Chemical Formula 13-34]

[0167]

[0168] [Chemical Formula 13-35]

[0169]

[0170] [Chemical Formula 13-36]

[0171]

[0172] [Chemical Formula 13-37]

[0173]

[0174] The compound represented by 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 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 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. In addition, the compound represented by 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. In addition, the compound represented by General Formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, and a nitrogen atom. In addition, the compound represented by General Formula (1) may be a compound containing a deuterium atom and not containing a hydrogen atom. For example, the compound represented by 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.

[0175] In a preferred embodiment of the present invention, the compound represented by General Formula (1) has a symmetric structure.

[0176] Specific examples of the compound represented by General Formula (1) are shown below. The following specific examples are for the case where R 1 in General Formula (1) is a hydrogen atom.

[0177] Compound numbers and R 2 、R 3 、R 4 are shown in Table 1 in a corresponding relationship.

[0178] In addition, when there are rotational isomers in the following compounds, both the mixture of rotational isomers and each separated rotational isomer are disclosed in this specification.

[0179] [Table 1-1]

[0180]

[0181] [Table 1-2]

[0182]

[0183] [Table 1-3]

[0184]

[0185] [Table 1-4]

[0186]

[0187] In Tables 2 and 3 below, specific examples of the compounds represented by the general formula (1) are further illustrated in tabular form. In Tables 2 and 3, a compound number is further assigned to a structure obtained by further substituting a part of the structure determined by the compound number. For example, in Table 2, Compounds 721 to 1440 (represented as No. 721 to 1440 in the table) represent the compounds in which R 2 (represented as R2 in the table) of Compounds 1 to 720 is substituted with D1. Compound 721 is the compound in which R 2 of Compound 1 is substituted with D1, and Compound 722 is the compound in which R 2 of Compound 2 is substituted with D1. The structures of the respective compounds described in Table 2 and the respective compounds described in Table 3 are determined in this manner. In Tables 2 and 3, each compound assigned a number has its structure determined individually and is specifically disclosed one by one in this specification.

[0188] [Table 2-1]

[0189]

[0190] [Table 2-2]

[0191]

[0192] [Table 2-3]

[0193]

[0194] [Table 2-4]

[0195]

[0196] [Table 2-5]

[0197]

[0198] [Table 2-6]

[0199]

[0200] [Table 2-7]

[0201]

[0202] [Table 2-8]

[0203]

[0204] [Table 2-9]

[0205]

[0206] [Table 2-10]

[0207]

[0208] [Table 2-11]

[0209]

[0210] [Table 2-12]

[0211]

[0212] [Table 2-13]

[0213]

[0214] [Table 2-14]

[0215]

[0216] [Table 2-15]

[0217]

[0218] [Table 2-16]

[0219]

[0220] [Table 3-1]

[0221]

[0222] [Table 3-2]

[0223]

[0224] [Table 3-3]

[0225]

[0226] [Table 3-4]

[0227]

[0228] [Table 3-5]

[0229]

[0230] [Table 3-6]

[0231]

[0232] [Table 3-7]

[0233]

[0234] [Table 3-8]

[0235]

[0236] [Table 3-9]

[0237]

[0238] [Table 3-10]

[0239]

[0240] [Table 3-11]

[0241]

[0242] [Table 3-12]

[0243]

[0244] [Table 3-13]

[0245]

[0246] [Table 3-14]

[0247]

[0248] [Table 3-15]

[0249]

[0250] [Table 3-16]

[0251]

[0252] Regarding the molecular weight of the compound represented by the general formula (1), for example, when attempting to form a film of an organic layer containing the compound represented by the general formula (1) by vapor deposition, it is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and even more preferably 900 or less. The lower limit value of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1).

[0253] The compound represented by the general formula (1) can be formed into a film by a coating method regardless of its molecular weight. If the coating method is used, even a compound with a relatively large molecular weight can be formed into a film. The compound represented by the general formula (1) has the advantage of being easily soluble in an organic solvent among cyanobenzene-based compounds. Therefore, the compound represented by the general formula (1) is easily applicable to the coating method and is easily purified to improve the purity.

[0254] The present invention can also be considered applicable, and a compound containing a plurality of structures represented by the general formula (1) within a molecule can be used as a luminescent material.

[0255] For example, a polymer obtained by pre-existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group can be considered as a luminescent material. Specifically, it can be considered to prepare a monomer containing a polymerizable functional group in any one of R 1 ~R 4 in the general formula (1), polymerize it alone or copolymerize it with other monomers to obtain a polymer having a repeating unit, and use this polymer as a luminescent material. Alternatively, it can also be considered to obtain a dimer or trimer by coupling compounds having the structure represented by the general formula (1) with each other, and use these as luminescent materials.

[0256] Examples of polymers having a repeating unit containing the structure represented by the general formula (1) may include polymers containing the structure represented by the following general formula (2) or (3).

[0257] [Chemical formula 14]

[0258]

[0259] 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 a linking group. The number of carbon atoms of the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. The linking group is preferably a linking group having a structure represented by -X 11 -L 11 -. Here, X 11 represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

[0260] In the general formula (2) or (3), R 101 、R 102 、R 103 and R 104 each independently represent a substituent. It is preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and further preferably an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.

[0261] L 1 and L 2 The linking group represented can bond to any one of R in the general formula (1) constituting Q 1 ~R 4 Among them. Two or more linking groups can be connected to one Q to form a crosslinked structure or a network structure.

[0262] Specific structural examples of the repeating unit can include the structures represented by the following formulas (4) to (7).

[0263] [Chemical formula 15]

[0264]

[0265] A polymer having repeating units containing these formulas (4) to (7) can be synthesized as follows: Hydroxyl groups are introduced into any one of R 1 ~R 4 Among them in advance, and it is used as a linking group to react the following compounds to introduce a polymerizable group, and the polymerizable group is polymerized.

[0266] [Chemical formula 16]

[0267]

[0268] The polymer containing the structure represented by the general formula (1) in the molecule can be a polymer composed only of repeating units having the structure represented by the general formula (1), or can be a polymer containing repeating units having other structures. And, the repeating units having the structure represented by the general formula (1) contained in the polymer can be a single type, or two or more types. As the repeating units not having the structure represented by the general formula (1), repeating units derived from monomers commonly used for copolymerization can be cited. For example, repeating units derived from monomers having an ethylenic unsaturated bond such as ethylene and styrene can be cited.

[0269] In one embodiment, the compound represented by the general formula (1) is a luminescent material.

[0270] In one embodiment, the compound represented by the general formula (1) is a compound capable of emitting delayed fluorescence.

[0271] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by heat or an electronic device, it can emit light in the UV region, the blue, green, yellow, orange, red regions (for example, about 420 nm to about 500 nm, about 500 nm to about 600 nm or about 600 nm to about 700 nm) in the visible spectrum, or the near-infrared region.

[0272] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, 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.

[0273] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, 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.

[0274] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, it can emit light in the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum.

[0275] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, it can emit light in the blue region (e.g., about 400 nm to about 490 nm, about 475 nm) of the visible spectrum.

[0276] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, it can emit light in the ultraviolet spectral region (e.g., 280 - 400 nm).

[0277] In one embodiment of the present invention, when the compound represented by the general formula (1) is excited by a thermal or electronic device, it can emit light in the infrared spectral region (e.g., 780 nm to 2 μm).

[0278] The electronic properties of a chemical library of small molecules can be calculated using well-known ab initio quantum chemical calculations. For example, as a basis set, time-dependent density functional theory using a functional group known as 6-31G* and the three-parameter Becke and Lee-Yang-Parr hybrid functional is used to analyze the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*), and molecular fragments (parts) having a HOMO above a specific threshold and a LUMO below a specific threshold can be screened, and the triplet state of this part can be calculated to exceed 2.75 eV.

[0279] Thus, for example, when there is a HOMO energy (e.g., ionization potential) above -6.5 eV, a donor moiety ("D") can be selected. And, for example, when there is a LUMO energy (e.g., electron affinity) below -0.5 eV, an acceptor moiety ("A") can be selected. The bridge moiety ("B") is, for example, a strong conjugated system capable of strictly confining the acceptor and donor moieties to a unique three-dimensional structure, thereby preventing overlap between the π-conjugated systems of the donor and acceptor moieties.

[0280] In one embodiment, a compound library is screened using one or more of the following properties.

[0281] 1. Emission near a specific wavelength

[0282] 2. A triplet state above a calculated specific energy level

[0283] 3. A ΔE below a specific value ST Value

[0284] 4. A quantum yield above a specific value

[0285] 5. HOMO level

[0286] 6. LUMO level

[0287] In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, 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.

[0288] In one embodiment, the compound represented by the general formula (1) exhibits a quantum yield of more 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.

[0289] [Synthesis method of the compound represented by the general formula (1)]

[0290] The compound represented by the general formula (1) is a novel compound.

[0291] 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 positions where three donor groups Donor are to be introduced are substituted with fluorine atoms in tetrahydrofuran in the presence of sodium hydride. When multiple donor groups are to be introduced, the reaction with the donor groups can be carried out in two stages. Regarding the specific conditions and reaction steps of the reaction, reference can be made to the synthesis examples described later.

[0292] [Structure using the compound represented by the general formula (1)]

[0293] In one embodiment, one or more materials (such as small molecules, polymers, metals, metal complexes, etc.) that are combined with the compound represented by the general formula (1) to disperse the compound, covalently bond to the compound, coat the compound, support the compound, or associate with the compound are used together 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) can also be combined with a hole-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by the general formula (1) can also be combined with a copolymer having both a hole-transporting part and an electron-transporting part. Through the above embodiments, electrons and / or holes formed in the solid film or layer can interact with the compound represented by the general formula (1).

[0294] [Formation of the film]

[0295] 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 obtained by dissolving a composition containing the compound of the present invention is coated on the surface, and after removing the solvent, a film is formed. Examples of the wet process include spin coating, slot coating, inkjet printing (spray coating), gravure printing, offset printing, and flexographic printing, but are not limited thereto. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected. In one embodiment, substituents (such as alkyl groups) that improve the solubility in the organic solvent can be introduced into the compound contained in the composition.

[0296] In one embodiment, a thin film containing the compound of the present invention can be formed by a dry process. In one embodiment, as the dry process, a vacuum evaporation method can be employed, but it is not limited thereto. In the case of using the vacuum evaporation method, the compounds constituting the thin film can be co-evaporated from separate evaporation sources, or can be co-evaporated from a single evaporation source in which the compounds are mixed. In the case of using a single evaporation source, a mixed powder in which the compound powder is mixed can be used, a compression molded body obtained by compressing the mixed powder can be used, or a mixture obtained by heating and melting each compound and then cooling can be used. In one embodiment, co-evaporation is performed under the condition that the evaporation rates (weight reduction rates) of the plurality of compounds contained in the single evaporation source are the same or substantially the same, whereby a thin 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 as an evaporation source in the same composition ratio as the composition ratio of the formed thin film, a thin film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each compound for co-evaporation has the same weight reduction rate can be determined, and this temperature can be adopted as the temperature during co-evaporation.

[0297] [Example of use of the compound represented by the general formula (1)]

[0298] Organic light-emitting diode:

[0299] One aspect of the present invention relates to the use of the compound represented by the general formula (1) of the present invention in the form of a light-emitting material of an organic light-emitting device. In one embodiment, 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 one embodiment, the compound represented by the general formula (1) includes delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having the structure represented by the general formula (1). In one embodiment, the present invention relates to the use of the compound represented by the general formula (1) as a delayed phosphor. In one embodiment, the compound represented by the general formula (1) of the present invention 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 one embodiment, the compound represented by the general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by the general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from the compound represented by the general formula (1). In one embodiment, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high luminous efficiency.

[0300] In one embodiment, the light-emitting layer contains a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) on the film-forming surface affects or determines the propagation direction of the light emitted by the arranged compounds. In one embodiment, by arranging in 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.

[0301] One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes a light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by the general formula (1) assists the luminescence of other light-emitting materials contained in the light-emitting layer (as a so-called co-dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is in its lowest excited singlet energy level, and this energy level is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of another light-emitting material contained in the light-emitting layer.

[0302] In one embodiment, the organic photoluminescence device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least a light-emitting layer. In one embodiment, the organic layer only includes a light-emitting layer. In one embodiment, the organic layer includes more than one organic layer other than the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer can be a hole injection and transport layer having a hole injection function, and the electron transport layer can be an electron injection and transport layer having an electron injection function. Examples of the organic electroluminescence device are shown in Figure 1 in.

[0303] Light-emitting layer:

[0304] In one embodiment, the light-emitting layer is a layer in which holes and electrons respectively injected from the anode and the cathode are re-bonded to form excitons. In one embodiment, the layer emits light.

[0305] In one embodiment, only a luminescent material is used as the light-emitting layer. In one embodiment, the light-emitting layer contains 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 make the organic electroluminescent device and the organic photoluminescent device exhibit high luminous efficiency, singlet excitons and triplet excitons generated in the luminescent material are confined in the luminescent material. In one embodiment, in addition to the luminescent material, a host material is also used in the light-emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excited singlet energy and an excited triplet energy, at least one of which 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 in the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are confined sufficiently to promote the luminous efficiency. In one embodiment, the singlet excitons and triplet excitons are not confined sufficiently, but still a high luminous efficiency is obtained, that is, a host material capable of achieving a high luminous 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 contains both fluorescence and delayed fluorescence. In one embodiment, the emitted light contains light emitted from the host material. In one embodiment, the emitted light consists of light emitted from the host material. In one embodiment, the emitted light contains light emitted from the compound represented by general formula (1) and light emitted from the host material. In one embodiment, a TADF molecule and a host material are used. In one embodiment, the TADF is a co-dopant.

[0306] When the compound represented by general formula (1) is used as the co-dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Such luminescent materials can be those using anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives having metals (Al, Zn), etc. These exemplified skeletons may or may not have substituents. And these exemplified skeletons can be combined with each other.

[0307] The following exemplifies luminescent materials that can be used in combination with the co-dopant represented by the general formula (1).

[0308] [Chemical formula 17-1]

[0309]

[0310] [Chemical formula 17-2]

[0311]

[0312] [Chemical formula 17-3]

[0313]

[0314] Furthermore, it is particularly preferable to use the compound described in paragraphs 0220 to 0239 of WO2015 / 022974 as the luminescent material used together with the co-dopant represented by the general formula (1).

[0315] In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 0.1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 50% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 20% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention in the form of a luminescent material contained in the light-emitting layer is 10% by weight or less.

[0316] In one embodiment, the host material in the light-emitting layer is an organic compound having a hole-transporting function and an electron-transporting function. In one embodiment, the host material in the light-emitting layer is an organic compound that prevents an increase in the wavelength of the emitted light. In one embodiment, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0317] In some embodiments, the host material is selected from the group consisting of:

[0318] [Chemical formula 18-1]

[0319]

[0320] [Chemical formula 18-2]

[0321]

[0322] In one embodiment, the light-emitting layer contains two or more TADF molecules having different structures. For example, a light-emitting layer can be provided that contains these three materials in which the singlet excitation energy levels are in the order of the host material, the first TADF molecule, and the second TADF molecule being higher. At this time, the difference δE between the lowest singlet excitation energy level of the first TADF molecule and the second TADF molecule and the lowest triplet excitation energy level at 77K ST is preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, further preferably 0.1 eV or less, still more preferably 0.07 eV or less, still further preferably 0.05 eV or less, yet 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 can be more than the content of the host material, less than the content of the host material, or the same. In one embodiment, the composition within the light-emitting layer can be set as follows: the host material is 10 to 70% by weight, the first TADF molecule is 10 to 80% by weight, and the second TADF molecule is 0.1 to 30% by weight. In one embodiment, the composition within the light-emitting layer can be set as follows: the host material is 20 to 45% by weight, the first TADF molecule is 50 to 75% by weight, and the second TADF molecule is 5 to 20% by weight. In one embodiment, the luminescence quantum yield caused by photoexcitation of the co-evaporated film of the first TADF molecule and the host material (the content rate of the first TADF molecule in this co-evaporated film = A% by weight) and the luminescence quantum yield caused by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the content rate of the second TADF molecule in this co-evaporated film = A% by weight) satisfy the relational expression. In one embodiment, the luminescence quantum yield caused by photoexcitation of the co-evaporated film of the second TADF molecule and the host material (the content rate of the second TADF molecule in this co-evaporated film = B% by weight) and the luminescence quantum yield caused by photoexcitation of the single film of the second TADF molecule satisfy the relational expression. In one embodiment, the light-emitting layer can contain three TADF molecules having different structures. The compound of the present invention can be any one of the plurality of TADF compounds contained in the light-emitting layer.

[0323] In one embodiment, the light-emitting layer can be composed of materials selected from the group consisting of a host material, a co-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 materials consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can also be composed of materials consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can also be composed of materials consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0324] 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 may include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, paragraphs 0008 to 0071 and 0118 to 0133 of WO2013 / 081088, paragraphs 0009 to 0046 and 0093 to 0134 of Japanese Patent Laid-Open No. 2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of Japanese Patent Laid-Open No. 2013-116975, 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 Japanese Patent Laid-Open No. 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of Japanese Patent Laid-Open No. 2014-9224, paragraphs 0013 to 0025 of Japanese Patent Laid-Open No. 2017-119663, paragraphs 0013 to 0026 of Japanese Patent Laid-Open No. 2017-119664, paragraphs 0012 to 0025 of Japanese Patent Laid-Open No. 2017-222623, paragraphs 0010 to 0050 of Japanese Patent Laid-Open No. 2017-226838, paragraphs 0012 to 0043 of Japanese Patent Laid-Open No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, compounds contained in the general formulas described therein, particularly exemplified compounds capable of emitting delayed fluorescence.Furthermore, it is preferable to use a luminescent material that can emit delayed fluorescence and is described in Japanese Patent Application Laid-Open No. 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, Japanese Patent Application Laid-Open No. 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, WO2015 / 159541. Additionally, the above-mentioned gazettes described in this paragraph are incorporated herein by reference as part of this text.

[0325] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0326] Substrate:

[0327] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, where the substrate is not particularly limited and can be any of those substrates commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz, and silicon.

[0328] Anode:

[0329] In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a large work function (above 4 eV). 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 capable of forming a transparent conductive film such as IDIXO (In2O3-ZnO) etc. is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by evaporation or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when high precision of the pattern is not required (for example, above about 100 μm), the pattern can be formed using a mask with a desired shape during evaporation or sputtering of the electrode material. In some embodiments, when a coating material (such as an organic conductive compound) can be coated, wet film forming methods such as printing and coating are used. In some embodiments, when the emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is several hundred ohms per square or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies according to the material used.

[0330] Cathode:

[0331] In some embodiments, the cathode is made of a metal having a relatively low work function of the electrode material (below 4 eV) (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 metals. In some embodiments, a mixture of an electron injection metal and a second metal is used, where the second metal is a stable metal having a larger work function than the electron injection metal. 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 enhances the electron injection characteristics and the durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film by evaporation or sputtering. In some embodiments, the sheet resistance of the cathode is several hundred ohms per square or less. In some embodiments, the thickness of the cathode ranges from 10 nm to 5 μm. In some embodiments, the thickness of the cathode ranges from 50 to 200 nm. In some embodiments, in order to transmit the emitted light, either the anode or the cathode of the organic electroluminescent element is transparent or semi-transparent. In some embodiments, the transparent or semi-transparent electroluminescent element enhances the emission luminance.

[0332] In some embodiments, the cathode is formed of a conductive transparent material as described for the anode to form a transparent or semi-transparent cathode. In some embodiments, the element includes both a transparent or semi-transparent anode and a cathode.

[0333] Injection layer:

[0334] 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 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, there is an injection layer. In some embodiments, there is no injection layer.

[0335] The following includes preferred compound examples that can be used as hole injection materials.

[0336] [Chemical formula 19]

[0337]

[0338] Next, preferred compound examples that can be used as electron injection materials are given.

[0339] [Chemical formula 20]

[0340]

[0341] Blocking layer:

[0342] The blocking layer is a layer that can inhibit the diffusion of charges (electrons or holes) and / or excitons in the light-emitting layer to the outside of the light-emitting layer. In some embodiments, the electron blocking layer is between the light-emitting layer and the hole transport layer, and inhibits electrons from passing through the light-emitting layer towards the hole transport layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron transport layer, and inhibits holes from passing through the light-emitting layer towards the electron transport layer. In some embodiments, the blocking layer inhibits the diffusion of excitons to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer form an exciton blocking layer. As used herein, the term "electron blocking layer" or "exciton blocking layer" includes a layer having the functions of both an electron blocking layer and an exciton blocking layer.

[0343] Hole blocking layer:

[0344] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer inhibits holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer increases the probability of rebonding of electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material as that described for the electron transport layer.

[0345] The following includes preferred compound examples that can be used for the hole blocking layer.

[0346] [Chemical formula 21]

[0347]

[0348] [Chemical formula 22]

[0349]

[0350] Electron blocking layer:

[0351] Holes are transported by the electron blocking layer. In some embodiments, the electron blocking layer inhibits electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer increases the probability of rebonding of electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material as that described for the hole transport layer.

[0352] The following includes specific examples of preferred compounds that can be used as electron blocking materials.

[0353] [Chemical formula 23]

[0354]

[0355] Exciton blocking layer:

[0356] The exciton blocking layer suppresses the diffusion of excitons generated by the rebonding of holes and electrons in the light-emitting layer into the charge transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons in the light-emitting layer. In some embodiments, the light-emitting efficiency of the device is enhanced. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side and the cathode side or on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be between the light-emitting layer and the cathode and adjacent to the light-emitting layer. In some embodiments, a hole injection layer, an electron blocking layer, or the same layer is between the anode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or the same layer is between the cathode and the exciton blocking layer, and the exciton blocking layer is adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer contains 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.

[0357] Hole transport layer:

[0358] The hole transport layer contains 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.

[0359] In some embodiments, the hole transport material has one of the properties of hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include (but are not limited to) triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, chalcone derivatives substituted with amino groups, oxazole derivatives, styryl anthracene 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 amines, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. The following includes specific examples of preferred compounds that can be used as hole transport materials.

[0360] [Chemical formula 24]

[0361]

[0362] [Chemical Formula 25]

[0363]

[0364] [Chemical Formula 26]

[0365]

[0366] Electron transport layer:

[0367] 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.

[0368] In some embodiments, the electron transport material only needs to have the function of transporting electrons, which are injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include (but are not limited to) fluorene derivatives substituted with nitro groups, quinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenediylmethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, oxazole derivatives, pyrazine derivatives, or combinations 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 polymeric material. The following includes specific examples of preferred compounds that can be used as electron transport materials.

[0369] [Chemical Formula 27]

[0370]

[0371] [Chemical Formula 28]

[0372]

[0373] [Chemical Formula 29]

[0374]

[0375] [Chemical Formula 30]

[0376]

[0377] In addition, examples of more preferred compounds of materials that can be added to each organic layer are included. For example, addition as a stabilizing material can be considered, etc.

[0378] [Chemical Formula 31]

[0379]

[0380] Specific examples of preferred materials that can be used in organic electroluminescent elements are illustrated, but the materials that can be used in the present invention are not to be construed as being limited to the following exemplified compounds. Moreover, even compounds exemplified as materials having specific functions can be used as materials having other functions.

[0381] Device:

[0382] In some embodiments, a light-emitting layer is incorporated into the device. By way of example, the device includes an OLED bulb, an OLED lamp, a television screen, a computer monitor, a mobile phone, and a tablet computer, but is not limited thereto.

[0383] In some embodiments, an 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.

[0384] In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or photovoltaic devices. In some embodiments, the compositions can be suitable for promoting charge transfer or energy transfer within the device and / or can be used as hole transport materials. The devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic photodetectors, organic photosensors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), or organic laser diodes (O-lasers).

[0385] Bulb or lamp:

[0386] In some embodiments, an electronic device includes an OLED including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode.

[0387] 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 other than red, green, or blue (e.g., orange and yellowish green). In some embodiments, the combination of OLEDs is a combination of two, four, or more than four colors.

[0388] In some embodiments, the device is an OLED lamp having:

[0389] A circuit board having a first side with a mounting surface and a second side opposite thereto, and defining at least one opening;

[0390] At least one OLED disposed on the mounting surface and having a structure in which the at least one OLED includes an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode and emits light;

[0391] A housing for the circuit board; and

[0392] At least one connector disposed at an end of the housing, and the housing and the connector define a package adapted to be mounted to a lighting device.

[0393] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is deflected to be emitted in a second direction. In some embodiments, a reflector is used to deflect the light emitted in the first direction.

[0394] A display or screen:

[0395] In some embodiments, the light-emitting layer of the present invention can be used in a screen or a display. In some embodiments, methods including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD) are used to deposit the compounds involved in the present invention onto a substrate. In some embodiments, the substrate is a photoplate structure suitable for double-sided etching, providing unique aspect ratio pixels. A screen (which can also be referred to as a mask) is used in the method for manufacturing an OLED display. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and larger sweep bevel openings in the horizontal direction. Thereby, it allows for tight patterning of pixels required for a high-definition display while optimizing chemical vapor deposition onto a TFT substrate.

[0396] Internal patterning of the pixels allows for the construction of three-dimensional pixel openings with aspect ratio variations in the horizontal and vertical directions. Additionally, imaging "strips" or halftone circles are used within the pixel area to inhibit etching in specific areas until these specific patterns are undercut and removed from the substrate. At this time, all pixel areas are processed at the same etching rate, but the depth varies depending on the halftone pattern. Changing the size and spacing of the halftone pattern allows etching to be inhibited at different rates within the pixel, allowing for local deeper etching required to form steep vertical bevels.

[0397] A preferred material for the evaporation mask is invar. Invar is a metal alloy that is cold-rolled into thin sheets in a steel mill. 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 wet chemical etching-based method.

[0398] In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In additional embodiments, the screen or display pattern is fabricated using plasma etching.

[0399] Method for manufacturing a device:

[0400] OLED displays are generally manufactured by forming a large mother board and then cutting the mother board into unit board units. Generally, each unit board on the mother board is formed by: forming a thin film transistor including an active layer and source / drain electrodes on a base substrate, coating a planarization film on the TFT, and sequentially forming a pixel electrode, a light emitting layer, a counter electrode, and an encapsulation layer, and then cutting from the mother board.

[0401] OLED displays are generally manufactured by forming a large mother board and then cutting the mother board into unit board units. Generally, each unit board on the mother board is formed by: forming a thin film transistor including an active layer and source / drain electrodes on a base substrate, coating a planarization film on the TFT, and sequentially forming a pixel electrode, a light emitting layer, a counter electrode, and an encapsulation layer, and then cutting from the mother board.

[0402] In another aspect of the present invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising:

[0403] a step of forming a barrier layer on a base substrate of a mother board;

[0404] a step of forming a plurality of display units in unit board units on the barrier layer;

[0405] a step of forming an encapsulation layer on each of the display units of the unit board; and

[0406] a step of coating an organic film on an interface portion between the unit boards.

[0407] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and an edge portion of the barrier layer is covered with an organic film formed of polyimide or acryloyl. In some embodiments, the organic film helps to gently cut the mother board into unit board units.

[0408] In some embodiments, the thin film transistor (TFT) layer has a light emitting layer, a gate electrode, and a source electrode / drain electrode. Each of the plurality of display units may include a thin film transistor (TFT), a planarization film formed on the TFT layer, and a light emitting unit formed on the planarization film, wherein the organic film coated on the interface portion is formed of the same material as the material of the planarization film and is formed at the same time as the formation of the planarization film. In some embodiments, the light emitting unit is connected to the TFT layer, with a passivation layer, a planarization film, and an encapsulation layer therebetween, and the encapsulation layer covers and protects the light emitting unit. In some embodiments of the manufacturing method, the organic film does not contact either the display unit or the encapsulation layer.

[0409] Each of the organic film and the planarization film may include either polyimide or acryloyl. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the substrate may be formed of polyimide. The method may further include mounting a carrier substrate formed of a glass material onto the other surface of the substrate formed of polyimide before forming the barrier layer on one surface of the substrate formed of polyimide, and separating the carrier substrate from the substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible display.

[0410] In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acryloyl, as is the organic film formed on the edge portion of the barrier layer. In some embodiments, when manufacturing an OLED display, the planarization film and the organic film are formed simultaneously. In some embodiments, the organic film may be formed on the edge portion of the barrier layer such that a part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0411] In some embodiments, the light emitting layer has 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 electrode / drain electrode of the TFT layer.

[0412] In some embodiments, when a voltage is applied to the pixel electrode via the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, whereby the organic light-emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit is referred to as a display unit.

[0413] In some embodiments, an encapsulation layer that covers the display unit and prevents external moisture from penetrating may be formed to have a thin film encapsulation structure in which an organic film and an inorganic film are alternately stacked. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are stacked. In some embodiments, the organic film coated on the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a part of the organic film directly contacts the substrate, and the remaining part of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0414] In one embodiment, the OLED display is flexible and uses a flexible substrate formed of polyimide. In some embodiments, the substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

[0415] In some embodiments, a barrier layer is formed on the surface of the substrate on the side opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit panel. For example, while the substrate is formed over the entire surface of the mother board, the barrier layer is formed according to the size of each unit panel, thereby forming a groove at the interface portion between the unit panel barrier layers. Each unit panel can be cut along the groove.

[0416] In some embodiments, the manufacturing method further includes a process 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 in the groove, and the groove does not penetrate into the substrate. In some embodiments, the TFT layer of each unit plate is formed, and a passivation layer (i.e., an inorganic film) and a planarization film (i.e., an organic film) are disposed on the TFT layer to cover the TFT layer. While forming the planarization film formed of, for example, polyimide or acrylate, the groove at the interface portion is covered with an organic film formed of, for example, polyimide or acrylate. This is when cracking is prevented from occurring by allowing the organic film to absorb the impact, which is generated when cutting each unit plate along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the impact generated when cutting each unit plate along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, since the groove at the interface portion between the barrier layers is covered with an organic film, and the organic film absorbs the impact that would otherwise be transferred to the barrier layer, each unit plate can be gently cut, and cracking in the barrier layer can be prevented. In one embodiment, the organic film covering the groove at the interface portion is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected to each other as a single layer, since external moisture may penetrate into the display unit via the planarization film and a part where the organic film remains, the organic film is spaced apart from the planarization film so that the organic film is spaced apart from the display unit.

[0417] In some embodiments, a display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother board is completely manufactured, the carrier substrate supporting the substrate is separated from the substrate. In some embodiments, when a laser beam is emitted toward the carrier substrate, the carrier substrate is separated from the substrate due to the difference in the coefficient of thermal expansion between the carrier substrate and the substrate.

[0418] In some embodiments, the mother board is cut into unit plate units. In some embodiments, the mother board is cut along the interface portion between the unit plates by using a cutting machine. In some embodiments, since the groove at the interface portion along which the mother board is cut is covered with an organic film, the organic film absorbs the impact during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting.

[0419] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0420] Another way is an OLED display, which has: a barrier layer formed on a substrate; a display unit formed on the barrier layer; an encapsulation layer formed on the display unit; and an organic film coated on an edge portion of the barrier layer.

[0421] Examples

[0422] Synthesis examples and examples are given below to further specifically illustrate the features of the present invention. The materials, treatment contents, treatment steps, etc. shown below can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. In addition, for the evaluation of the light emission characteristics, a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies Japan, Ltd.: E5273A), an optical power meter measuring device (manufactured by Newport Corporation: 1930C), a spectrometer (manufactured by Ocean Optics: USB2000), a spectro-radiometer (manufactured by TOPCON CORPORATION: SR-3), and a streak camera (type C4334 manufactured by Hamamatsu Photonics K.K.) were used.

[0423] (Synthesis Example 1) Synthesis of Compound 3

[0424] [Chemical Formula 32]

[0425]

[0426] Under a nitrogen stream, sodium hydride (0.44 g, 11.0 mmol) and benzo[f] [3,2-c] carbazole (2.83 g, 11.0 mmol) were stirred in tetrahydrofuran (20 mL) at 0 °C for 30 minutes, then 4,5,6-trifluoroisophthalonitrile was added. After warming to room temperature, the reaction was carried out at room temperature for 5 hours. Then, the reaction was stopped with water and methanol. The precipitated yellow solid was filtered, and the filtrate was purified by silica gel column chromatography (toluene / hexane / chloroform = 11 / 2 / 1) and reprecipitation (o-dichlorobenzene / methanol) to obtain yellow solid Compound 3 (0.91 g, 1.02 mmol, yield 37%).

[0427] 11H NMR (400 MHz, 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).

[0428] MS (ASAP): 894.43 (M + H + ). Calcd for C62H31N5O3: 893.24.

[0429] (Synthesis Example 2) Synthesis of Compound 5

[0430] [Chemical Formula 33]

[0431]

[0432] Synthesis was carried out in the same manner as in Synthesis Example 1 with a yield of 80%.

[0433] 1 1H 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).

[0434] MS (ASAP): 894.44 (M + H + ). Calcd for C62H31N5O3: 893.24.

[0435] (Synthesis Example 3) Synthesis of Compound 6

[0436] [Chemical Formula 34]

[0437]

[0438] Under a nitrogen stream, potassium carbonate (1.20 g, 8.69 mmol) and benzo[f]carbazole (1.99 g, 7.72 mmol) were stirred in dimethylformamide (20 mL) at room temperature for 30 minutes, then 4,5,6-trifluoroisophthalonitrile (0.35 mmol, 1.92 mmol) was added, and the reaction was carried out at 60 °C for 5 hours. Then, it was returned to room temperature, and the reaction was stopped 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 the yellow solid compound 6 (1.35 g, 1.51 mmol, yield 79%).

[0439] 1 H NMR (400 MHz, CDCl3, δ): 8.65 (s, 1H), 8.35 - 8.28 (m, 5H), 7.98 - 7.7.95 (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).

[0440] MS (ASAP): 894.50 (M+H + ). Calcd for C62H31N5O3: 893.24.

[0441] (Synthesis Example 4) Synthesis of Compound 33

[0442] [Chemical Formula 35]

[0443]

[0444] Synthesis was carried out in the same manner as in Synthesis Example 3 with a yield of 63%.

[0445] 1 H 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).

[0446] MS(ASAP): 942.15 (M+H + ). Calcd for C62H31N5S3: 941.17.

[0447] (Synthesis Example 5) Synthesis of Compound 159

[0448] [Chemical Formula 36]

[0449]

[0450] Synthesis was carried out by the same method as in Synthesis Example 1 with a yield of 92%.

[0451] 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).

[0452] MS(ASAP): 1137.68 (M+H + ). Calcd for C80H28D15N5O3: 1136.43.

[0453] (Synthesis Example 6) Synthesis of Compound 4

[0454] [Chemical Formula 37]

[0455]

[0456] Synthesis was carried out by the same method as in Synthesis Example 3 with a yield of 69%.

[0457] MS(ASAP): 894.43 (M+H + ). Calcd for C 62 H 31 N5O3: 893.24.

[0458] (Synthesis Example 7) Synthesis of Compound 2

[0459] [Chemical Formula 38]

[0460]

[0461] Synthesis was carried out by the same method as in Synthesis Example 3 with a yield of 69%.

[0462] MS(ASAP): 894.46 (M + H + ). Calcd for C 62 H 31 N5O3: 893.24.

[0463] (Synthesis Example 8) Synthesis of Compound 570243

[0464] [Chemical Formula 39]

[0465]

[0466] 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 over 20 minutes, and the mixture was stirred for 4 hours. After adding a saturated aqueous NH4Cl solution to the reaction mixture to neutralize it, the reaction was stopped by returning to room temperature, and the mixture was extracted with ethyl acetate. 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 Compound 1a as a yellow solid (16.5 g, 25.2 mmol, 91.7%).

[0467] 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).

[0468] MS(ASAP): 657.25 [M + H] + . Calcd for.C 44 H 21 FN4O2: 656.16

[0469] [Chemical Formula 40]

[0470]

[0471] In a nitrogen atmosphere, a dimethylformamide solution (280 mL) of compound 1a (16.5 g, 252.2 mmol), carbazole (7.9 g, 47.2 mmol), and K2CO3 (8.17 g, 59.1 mmol) was stirred at room temperature for 15 hours. 200 mL of methanol and 150 mL of water were added to the reaction mixture, and the reaction was stopped. Thereafter, the precipitated precipitate was filtered, and the solid was recovered. The obtained filtrate was purified by column chromatography (toluene / hexane / CHCl3 = 6 / 3.5 / 0.5) and reprecipitation (toluene / hexane) to obtain compound 570243 as a yellow solid (16.0 g, 19.9 mmol, 84.2%).

[0472] 1 H NMR (400 MHz, CDCl3, δ): 8.60 (s, 1H), 8.19 - 8.15 (m, 2H), 7.87 (t, J = 8.4 Hz, 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).

[0473] MS (ASAP): 804.25 [M+H] + .Calcd for.C 56 H 29 N5O2: 803.23

[0474] (Synthesis Example 9) Synthesis of compound 571683

[0475] [Chemical formula 41]

[0476]

[0477] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 68%.

[0478] 1 H 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).

[0479] MS(ASAP): 832.41 [M+H] + .Calcd for.C58H33N5O2: 831.26

[0480] (Synthesis Example 10) Synthesis of Compound 570244

[0481] [Chemical Formula 42]

[0482]

[0483] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 56%.

[0484] 1 H 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, 12H), 7.29 - 7.24(m, 2H).

[0485] MS(ASAP): 657.35 [M+H] + .Calcd for.C 44 H 21 FN4O2: 656.16

[0486] [Chemical Formula 43]

[0487]

[0488] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 67%.

[0489] 1 H NMR(400 MHz, 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).

[0490] MS(ASAP): 804.37 [M+H] + .Calcd for.C 56 H 29 N5O2: 803.23

[0491] (Synthesis Example 11) Synthesis of Compound 570273

[0492] [Chemical Formula 44]

[0493]

[0494] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 80%.

[0495] MS(ASAP): 689.43 [M+H] + .Calcd for.C44H21FN4S2: 688.12

[0496] [Chemical formula 45]

[0497]

[0498] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 89%.

[0499] 1 H NMR(400MHz, CDCl3, δ): 8.61(s, 1H), 8.08(t, J = 8.4Hz, 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).

[0500] MS(ASAP): 836.14 [M+H] + .Calcd for.C56H29N5S2: 835.19

[0501] (Synthesis Example 12) Synthesis of Compound 570274

[0502] [Chemical formula 46]

[0503]

[0504] Synthesis was carried out in the same manner as the first reaction of Synthesis Example8 with a yield of 79%.

[0505] 1 H NMR(400MHz, CDCl3, δ): 9.53(s, 1H), 8.46(t, J = 7.6Hz, 4H), 7.40(d, J = 8.0Hz, 4H), 8.02(d, J = 7.6Hz, 2H), 7.40(d, J = 8.0Hz, 2H), 7.62 - 748(m, 8H).

[0506] MS(ASAP): 688.97 [M+H] + .Calcd for.C44H21FN4S2: 688.12

[0507] [Chemical formula 47]

[0508]

[0509] Synthesis was carried out by the same method as the second reaction of Synthesis Example 8 with a yield of 48%.

[0510] 1 H NMR (400 MHz, 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 = 7.6 Hz, 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).

[0511] MS (ASAP): 836.20 [M + H] + .Calcd for.C56H29N5S2: 835.19

[0512] (Synthesis Example 13) Synthesis of Compound 570261

[0513] [Chemical Formula 48]

[0514]

[0515] Synthesis was carried out by the same method as the first reaction of Synthesis Example 8 with a yield of 90%.

[0516] 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).

[0517] MS (ASAP): 809.33 [M + H] + .Calcd for.C56H29FN4O2: 808.23

[0518] [Chemical Formula 49]

[0519]

[0520] Synthesis was carried out by the same method as the second reaction of Synthesis Example 8 in a yield of 94%.

[0521] 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).

[0522] MS (ASAP): 956.43 [M + H] + . Calcd for.C68H37N5O2: 955.29

[0523] (Synthesis Example 14) Synthesis of Compound 570399

[0524] [Chemical Formula 50]

[0525]

[0526] Synthesis was carried out by the same method as the first reaction of Synthesis Example 8 in a yield of 89%.

[0527] 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).

[0528] MS (ASAP): 819.45 [M + H] + . Calcd for.C56H19D10FN4O2: 818.29

[0529] [Chemical Formula 51]

[0530]

[0531] Synthesis was carried out by the same method as the second reaction of Synthesis Example 8 in a yield of 89%.

[0532] 11H 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).

[0533] MS (APCI): 966 [M+H] + .Calcd for.C68H27D10N5O2: 965.36

[0534] TG0112

[0535] (Synthesis Example 15) Synthesis of Compound 570309

[0536] [Chemical Formula 52]

[0537]

[0538] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 64%.

[0539] 1 1H 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).

[0540] MS (ASAP): 709.26 [M+H] + .Calcd for.C50H33FN4: 708.27

[0541] [Chemical Formula 53]

[0542]

[0543] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 69%.

[0544] 11H 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).

[0545] MS (ASAP): 856.49 [M+H] + .Calcd for.C62H41N5: 855.34

[0546] (Synthesis Example 16) Synthesis of Compound 570378

[0547] [Chemical Formula 54]

[0548]

[0549] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 63%.

[0550] 1 1H 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).

[0551] MS (ASAP): 837.33 [M+H] + .Calcd for.C56H25FN4O4: 836.19

[0552] [Chemical Formula 55]

[0553]

[0554] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 61%.

[0555] 11H 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).

[0556] MS (ASAP): 984.45 [M+H] + .Calcd for.C68H33N5O4: 983.25

[0557] (Synthesis Example 17) Synthesis of Compound 570262

[0558] [Chemical Formula 56]

[0559]

[0560] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 83%.

[0561] 1 1H 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).

[0562] MS (ASAP): 809.55 [M+H] + .Calcd for.C56H29FN4O2: 808.23

[0563] [Chemical Formula 57]

[0564]

[0565] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 60%.

[0566] 11H 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),.

[0567] MS (ASAP): 956.57 [M + H] + .Calcd for.C68H37N5O2: 955.29

[0568] (Synthesis Example 18) Synthesis of Compound 570264

[0569] [Chemical Formula 58]

[0570]

[0571] Synthesis was carried out in the same manner as the first reaction of Synthesis Example 8 with a yield of 56%.

[0572] 1 1H 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).

[0573] MS (ASAP): 809.44 [M + H] + .Calcd for.C56H29FN4O2: 808.23

[0574] [Chemical Formula 59]

[0575]

[0576] Synthesis was carried out in the same manner as the second reaction of Synthesis Example 8 with a yield of 71%.

[0577] 11H 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).

[0578] MS (ASAP): 956.57 [M+H] + .Calcd for.C68H37N5O2: 955.29

[0579] (Synthesis Example 19) Synthesis of Compound 570507

[0580] [Chemical Formula 60]

[0581]

[0582] Synthesis was carried out by the same method as that of Compound 1a with a yield of 32%.

[0583] 1 1H 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).

[0584] MS (ASAP): 809.44 [M+H] + .Calcd for.C56H29FN4O2: 808.23

[0585] [Chemical Formula 61]

[0586]

[0587] Synthesis was carried out by the same method as the second reaction of Synthesis Example 8 with a yield of 64%.

[0588] 11H 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).

[0589] MS (ASAP): 956.57[M + H] + .Calcd for.C68H37N5O2: 955.29

[0590] (Synthesis Example 20) Synthesis of Compound 723

[0591] [Chemical Formula 62]

[0592]

[0593] Under a nitrogen stream, potassium carbonate (1.47 g, 10.35 mmol) and 5H - benzofluoro[3,2 - c]carbazole (1.95 g, 7.59 mmol) were stirred in dimethylformamide (60 mL) at room temperature for 30 minutes. Then, 4,5,6 - trifluoroisophthalonitrile (0.35 mmol, 1.92 mmol) was added, and the reaction was carried out at room temperature for 5 hours. After that, the reaction was stopped 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 the yellow solid compound 2a (0.90 g, 1.17 mmol, yield 34%).

[0594] 1 1H NMR (400 MHz, 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).

[0595] MS (ASAP): 765.27(M + H +).Calcd for C44H21IN4O2: 764.07.

[0596] [Chemical formula 63]

[0597]

[0598] 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 stop the reaction. Thereafter, the precipitated precipitate was filtered, and the solid was recovered. The obtained filtrate was purified by column chromatography (toluene / hexane / CHCl3 = 7 / 2.5 / 0.5) and reprecipitation (toluene / hexane) to obtain compound 37027 as a yellow solid (0.45 g, 0.56 mmol, 57%).

[0599] 1 H 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).

[0600] MS (ASAP): 804.43 [M + H] + .Calcd for.C 56 H 29 N5O2: 803.23

[0601] (Examples 1 to 3, Comparative Example 1) Fabrication and Evaluation of Thin Films

[0602] By vacuum evaporation, compound 3 and mCBP were evaporated onto a quartz substrate from different evaporation sources under a condition of a vacuum degree less than 1 × 10 -3 Pa to form a thin film with a thickness of 100 nm and a concentration of compound 3 of 20 wt%, which was set as the doped thin film of Example 1.

[0603] Compound 5, compound 6, and comparative compound A were used to replace compound 3, respectively, whereby the thin films of Example 2, Example 3, and Comparative Example 1 were obtained.

[0604] When 300 nm excitation light was irradiated to each of the obtained thin films, photoluminescence was observed for each thin film. The lifetime (τ of delayed fluorescence was obtained from the transient decay curve of the luminescenced )。The results are shown in the following table. The delayed fluorescence lifetimes (τ d ) of Examples 1 to 3 were confirmed to be short.

[0605] [Table 4]

[0606] <![CDATA[τ d (μs)]]> Example 1 1.68 Example 2 1.99 Example 3 1.89 Comparative Example 1 2.99

[0607] (Example 4) Fabrication of an organic electroluminescent element

[0608] By vacuum evaporation, each thin film layer was laminated on a glass substrate having an anode made of indium / tin oxide (ITO) with a film thickness of 100 nm under a vacuum degree of 1×10 -6 Pa. First, HATCN with a thickness of 10 nm was formed on the ITO, and NPD with a thickness of 30 nm was formed thereon. Then, TrisPCz with a thickness of 10 nm was further formed thereon, and Host1 with a thickness of 5 nm was further formed thereon. Then, Compound 3 and Host1 were co-evaporated from different evaporation sources to form a light-emitting layer with a thickness of 30 nm. At this time, the concentration of Compound 3 was set to 35 wt%. SF3TRZ with a thickness of 10 nm was formed thereon, and SF3TRZ and Liq were co-evaporated from different evaporation sources to further form a layer with a thickness of 30 nm thereon. At this time, the SF3TRZ:Liq (weight ratio) was set to 7:3. In addition, 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. Through the above steps, the organic electroluminescent element of Example 1 was fabricated.

[0609] (Comparative Example 2)

[0610] The organic electroluminescent element of Comparative Example 2 was fabricated by the same steps as in Example 1, using Comparative Compound A instead of Compound 3.

[0611] (Evaluation)

[0612] Regarding the light emission of each organic electroluminescent element of Example 1 and Comparative Example 2, the x and y of the CIE chromaticity coordinates were measured. And, the time (LT95) until the light emission intensity at 12.6 mA / cm 2 was reduced to 95% was measured for each organic electroluminescent element, and the relative value was calculated with the LT95 of Comparative Example 2 set to 100%. The results are shown in the following table. The chromaticity of the organic electroluminescent element of Example 1 was good, and the element lifetime (element durability) was greatly improved.

[0613] [Table 5]

[0614]

[0615] [Chemical Formula 64]

[0616]

[0617] Symbol Explanation

[0618] 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 formula 1] General formula (1) In general formula (1), R 1 is a hydrogen atom or a deuterium atom, R 2 ~R 4 At least one of them is a benzofuran-fused carbazol-9-yl having a skeleton formed by fusing a benzofuran ring at the 2,3-positions to a carbazole ring, a benzothiophene-fused carbazol-9-yl having a skeleton formed by fusing a benzothiophene ring at the 2,3-positions to a carbazole ring, an indole-fused carbazol-9-yl having a skeleton formed by fusing an indole ring at the 2,3-positions to a carbazole ring, an indene-fused carbazol-9-yl having a skeleton formed by fusing an indene ring at the 2,3-positions to a carbazole ring, or a silaindene-fused carbazol-9-yl having a skeleton formed by fusing a silaindene ring at the 2,3-positions to a carbazole ring, and the remaining R 2 ~R 4 is a substituted or unsubstituted carbazol-9-yl, and the carbazol-9-yl may be further fused with a benzene ring or a heterocyclic ring, provided that the heterocyclic ring does not include a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring, and a silaindene ring.

2. The compound according to claim 1, wherein, R 3 is the benzofuran-fused carbazol-9-yl, the benzothiophene-fused carbazol-9-yl, the indole-fused carbazol-9-yl, the indene-fused carbazol-9-yl or the silaindene-fused carbazol-9-yl.

3. The compound according to claim 1, wherein, R 2 and R 4 are each independently the benzofuran-fused carbazol-9-yl, the benzothiophene-fused carbazol-9-yl, the indole-fused carbazol-9-yl, the indene-fused carbazol-9-yl or the silaindene-fused carbazol-9-yl.

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

5. The compound according to claim 1, wherein, R 2 ~R 4 At least one of them is the benzofuran-fused carbazol-9-yl or the benzothiophene-fused carbazol-9-yl.

6. The compound according to claim 1, wherein, R 2 ~R 4 Each is independently the benzofuran-fused carbazol-9-yl or the benzothiophene-fused carbazol-9-yl.

7. The compound according to any one of claims 1 to 6, wherein, R 2 ~R 4 Same 8. The compound according to any one of claims 1 to 6, wherein, R 2 to R 4 at least one of which is a benzofuran-fused carbazol-9-yl having a skeleton formed by fusing two benzofuran rings to a carbazole ring at the 2,3-positions, a benzothiophene-fused carbazol-9-yl having a skeleton formed by fusing two benzothiophene rings to a carbazole ring at the 2,3-positions, an indole-fused carbazol-9-yl having a skeleton formed by fusing two indole rings to a carbazole ring at the 2,3-positions, an indene-fused carbazol-9-yl having a skeleton formed by fusing two indene rings to a carbazole ring at the 2,3-positions, or a silaindene-fused carbazol-9-yl having a skeleton formed by fusing two silaindene rings to a carbazole ring at the 2,3-positions.

9. The compound according to any one of claims 1 to 6, which has a symmetric structure.

10. The compound according to any one of claims 1 to 6, which is composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms and sulfur atoms.

11. The compound according to any one of claims 1 to 6, wherein, The benzofuran-fused carbazol-9-yl has any one of the following structures, [Chemical formula 2] In each of the above structures, the hydrogen atom is substituted or unsubstituted, but no further fusion occurs.

12. The compound according to any one of claims 1 to 6, wherein, The benzothiophene-fused carbazol-9-yl has any one of the following structures, [Chemical formula 3] In each of the above structures, the hydrogen atom is substituted or unsubstituted, but no further fusion occurs.

13. Use of the compound according to any one of claims 1 to 12 as a luminescent material.

14. A light-emitting element, characterized in that, Comprising the compound according to any one of claims 1 to 12.

15. The light-emitting element according to claim 14, wherein, The light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a host material.

16. The light-emitting element according to claim 14, wherein, The light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a luminescent material, and mainly emits light from the luminescent material.

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