Compounds, luminescent materials and organic light-emitting elements

Abstract

The compounds represented by the following general formula exhibit excellent luminescent properties. Ar 1 Represents benzene ring, naphthalene ring, phenanthrene ring, etc.; D represents 5H-indol[3,2,1-de]phenazin-5-yl, etc.; A represents cyano, phenyl, pyrimidinyl, triazolyl, etc.; m represents 1 or 2; n represents 0 to 2; R 1 ~R 4 It represents H, aryl, cyano, etc.

Description

Technical Field

[0001] This invention relates to a compound with excellent luminescent properties. Furthermore, this invention also relates to a luminescent material and an organic light-emitting element using this compound. Background Technology

[0002] Organic light-emitting elements (OLEDs) are light-emitting devices that utilize organic materials. They can be manufactured through coating and have attracted considerable attention in recent years because they do not use rare elements. Organic electroluminescent elements (organic EL elements) are particularly advantageous because they emit light self-emittingly and do not require backlighting, allowing for the fabrication of lightweight and flexible devices. Furthermore, they exhibit fast response and high visibility, making them a promising next-generation light source. Therefore, research is actively underway related to the development of materials useful for organic light-emitting elements, particularly organic electroluminescent elements. In particular, research is actively being conducted on light-emitting materials (e.g., non-patent literature 1).

[0003] Previous technical documents

[0004] Non-patent literature

[0005] Non-patent literature 1: Chem. Soc. Rev., 2017, 46, 915 Summary of the Invention

[0006] The technical problem to be solved by the invention

[0007] On the other hand, there is still room for improvement in the light-emitting characteristics of organic light-emitting elements, and further improvements are needed.

[0008] Therefore, the inventors have conducted in-depth research in order to develop novel compounds that help improve the luminescence properties of organic light-emitting elements.

[0009] means for solving technical problems

[0010] Through in-depth research, the inventors discovered that compounds obtained by bonding groups with characteristic structures to a specific backbone are useful for light-emitting elements. This invention is based on this insight and has the following structure.

[0011] [1] A compound represented by the following general formula (1).

[0012] General formula (1)

[0013] [Chemical Formula 1]

[0014]

[0015] In general formula (1), Ar 1The symbol indicates a cyclic structure and represents a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring. D represents the group represented by the following general formula (2). A represents a group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl, and alkyl, or a combination of two or more groups (excluding substituted alkyl groups). m is 1 or 2, and n is 0, 1, or 2. When m is 2, the two Ds can be the same or different. When n is 2, the two As can be the same or different. R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a deuterium atom, or a group selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups, or a combination of two or more groups. R 1 and R 2 R 3 and R 4 They can bond with each other to form cyclic structures selected from the group consisting of benzene, naphthalene, and pyridine rings. The formed cyclic structure can be substituted by one or more groups selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups.

[0016] General formula (2)

[0017] [Chemical Formula 2]

[0018]

[0019] In general formula (2), R 5 ~R 15 Each can be used independently to represent a hydrogen atom, a deuterium atom, or a substituent. R 5 and R 6 R 6 and R 7 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 They can bond together to form a ring structure. X represents a single bond, an oxygen atom, or a sulfur atom. * indicates a bonding position.

[0020] [2] The compound according to [1] is represented by the following general formula (3).

[0021] General formula (3)

[0022] [Chemical Formula 3]

[0023]

[0024] In general formula (3), Ar 1 The symbol represents a cyclic structure and indicates a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring. D represents the group represented by the general formula (2). A represents a group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl, and alkyl, or a combination of two or more groups (excluding substituted alkyl groups). m is 1 or 2, and n is 0, 1, or 2. When m is 2, the two Ds can be the same or different. When n is 2, the two As can be the same or different. 2 Ar 3 It can independently form cyclic structures selected from the group consisting of benzene rings, naphthalene rings, and pyridine rings. The formed cyclic structures can be substituted by one or more groups selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups.

[0025] [3] The compound according to [1] has any of the following skeletons.

[0026] [Chemical Formula 4]

[0027]

[0028] Each of the above skeletons may have substituents within the range of general formula (1), but the rings and skeletons will not further fuse.

[0029] [4] The compound according to [1] is represented by any one of the following general formulas (4a) to (4f).

[0030] [Chemical Formula 5]

[0031]

[0032] In general formulas (4a) to (4f), R 21 ~R 28 R 41 ~R 44 R 51 R 52 R 61 ~R 68 R 81 ~R 84 R 101 ~R 104 R 111 ~R 114 R 119 R 120 Each can be independently represented by a hydrogen atom, a deuterium atom, or either D or A. Where R... 21 ~R 28One or two of them are D and 0 to 2 are A, R 41 ~R 44 R 51 and R 52 One or two of them are D and 0 to 2 are A, R 61 ~R 68 One or two of them are D and 0 to 2 are A, R 81 ~R 84 One or two of them are D and 0 to 2 are A, R 101 ~R 104 One or two of them are D and 0 to 2 are A, R 111 ~R 114 R 119 and R 120 One or two of them are D, and 0 to 2 are A. R 29 ~R 36 R 45 ~R 50 R 69 ~R 72 R 85 ~R 92 R 105 ~R 110 R 115 ~R 118 Each of these groups independently represents a hydrogen atom, a deuterium atom, or a group selected from the group consisting of alkyl, aryl, and cyano groups, or a combination of two or more groups.

[0033] [5] The compound according to any one of [1] to [4], wherein n is 0.

[0034] [6] A luminescent material comprising any one of the compounds described in [1] to [5].

[0035] [7] A membrane comprising any one of the compounds described in [1] to [5].

[0036] [8] An organic semiconductor device comprising any one of [1] to [5].

[0037] [9] An organic light-emitting element comprising any one of [1] to [5].

[0038]

[10] The organic light-emitting element according to [9], wherein the element has a layer comprising the compound, the layer further comprising a host material.

[0039]

[11] According to the organic light-emitting element of

[10] , in addition to the host material, the layer containing the compound also contains a delayed fluorescence material, wherein the minimum excitation singlet energy of the delayed fluorescence material is lower than that of the host material and higher than that of the compound.

[0040]

[12] The organic light-emitting element according to [9], wherein the element has a layer comprising the compound, the layer further comprising a light-emitting material having a structure different from that of the compound.

[0041]

[13] An organic light-emitting element according to any one of [9] to

[11] , wherein the amount of light emitted from the compound is the largest among the materials contained in the element.

[0042]

[14] According to the organic light-emitting element of

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

[0043]

[15] An organic light-emitting element according to any one of [9] to

[14] emits delayed fluorescence.

[0044] Invention Effects

[0045] The compounds of the present invention are useful for light-emitting elements. The compounds of the present invention can be used as light-emitting materials, and can be used to manufacture organic light-emitting elements. Organic light-emitting elements using the compounds of the present invention exhibit excellent properties in at least one of the following: luminous efficiency (especially, luminous efficiency at high concentrations), element durability, and improved color purity. Attached Figure Description

[0046] Figure 1 This is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent element. Detailed Implementation

[0047] The present invention will now be described in detail. The descriptions of the constituent elements described below are 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. Furthermore, in this document, the numerical range indicated by “~” refers to the range of values ​​described before and after “~” as the lower and upper limits. Also, in the compounds used in the present invention, some or all of the hydrogen atoms present within the molecule can be replaced by deuterium atoms (…). 2(H, Deuterium). In the chemical structural formulas described herein, the hydrogen atom is represented by H or its representation is omitted. For example, when the atom representing the carbon atom bonded to the ring skeleton of the benzene ring is omitted, it is assumed that H forms a carbon atom bond with the ring skeleton at the omitted position. In this document, the term "substituent" means an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" means that the hydrogen atom can be substituted by a deuterium atom or a substituent.

[0048] [Compounds represented by general formula (1)]

[0049] The compounds of the present invention are those represented by the following general formula (1).

[0050] [Chemical Formula 6]

[0051]

[0052] In general formula (1), Ar 1 This indicates a cyclic structure, specifically a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring. For example, in Ar... 1 When the benzene ring is represented, it becomes a quinoxaline structure formed by the fusion of a benzene ring and a pyrazine ring. In Ar 1 When representing a naphthalene ring, either the 1,2-naphthalene ring or the 2,3-naphthalene ring can be fused with a pyrazine ring. In the fusion of the 1,2-naphthalene ring and the pyrazine ring, the carbon atoms at positions 1 and 2 of the naphthalene ring are shared with the carbon atoms at positions 2 and 3 of the pyrazine ring, respectively. In Ar 1 When representing anthracene rings, the 2,3-anthracene ring is fused with a pyrazine ring. In Ar... 1 When representing a phenanthrene ring, any one of the 1,2-phenanthrene ring, 2,3-phenanthrene ring, 3,4-phenanthrene ring, and 9,10-phenanthrene ring can be fused with a pyrazine ring. In a preferred embodiment of the invention, any one of the benzene ring, 2,3-naphthyl ring, and 9,10-phenanthrene ring is fused with a pyrazine ring. In a more preferred embodiment of the invention, any one of the 2,3-naphthyl ring and 9,10-phenanthrene ring is fused with a pyrazine ring. For example, either the 2,3-naphthyl ring or the 9,10-phenanthrene ring can be fused.

[0053] In Ar 1 In the represented ring structure, m D and n A atoms act as substituents bonded to the ring backbone. In Ar 1When representing a naphthalene ring, anthracene ring, or phenanthrene ring, D and A can be bonded to any of the benzene rings constituting these rings. Furthermore, m Ds and n As can be bonded to only one benzene ring, or neither D nor A can be bonded to any other benzene ring. Alternatively, a portion of the m Ds and n As can be bonded to one benzene ring while the remainder is bonded to another. In a preferred embodiment of the invention, n is 0, and the m Ds are bonded to only one benzene ring. In another preferred embodiment of the invention, n is 0, and a portion of the m Ds are bonded to one benzene ring while the remainder is bonded to another benzene ring. In Ar 1 When representing a naphthalene ring, anthracene ring, or a phenanthrene ring, in a preferred embodiment of the invention, neither D nor A is bonded to the benzene ring directly fused with the pyrazine ring, so that m Ds and n As are bonded only to the remaining portion of the benzene ring (i.e., the benzene ring not directly fused with the pyrazine ring). In Ar 1 When representing a naphthalene ring, anthracene ring, or phenanthrene ring, in a preferred embodiment of the present invention, n is 0, and D is not bonded to the benzene ring directly fused with the pyrazine ring, so that m D are bonded only to the remaining portion of the benzene ring (i.e., the benzene ring not directly fused with the pyrazine ring).

[0054] In general formula (1), m is 1 or 2, and n is 0, 1, or 2. When m is 2, the two Ds can be the same or different, and the two Ds can be bonded to the same benzene ring or different benzene rings. When n is 2, the two As can be the same or different, and the two As can be bonded to the same benzene ring or different benzene rings. In a preferred embodiment of the invention, n is 0. For example, m is 1 and n is 0. For example, m is 2 and n is 0. In Ar 1 When n represents a naphthalene ring, anthracene ring, or phenanthrene ring and n is 1 or 2, in one embodiment of the present invention, A is not bonded to a benzene ring bonded to D, and D is not bonded to a benzene ring bonded to A.

[0055] In general formula (1), D represents the group represented by the following general formula (2).

[0056] General formula (2)

[0057] [Chemical Formula 7]

[0058]

[0059] In general formula (2), X represents a single bond, an oxygen atom, or a sulfur atom. In a preferred embodiment of the invention, X is a single bond. In a preferred embodiment of the invention, X is an oxygen atom. X can be an oxygen atom or a sulfur atom.

[0060] In general formula (2), * represents the bonding position.

[0061] In general formula (2), R 5 ~R 15Each can independently represent a hydrogen atom, a deuterium atom, or a substituent. Substituents can be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In a preferred embodiment of the invention, a substituent represents a group selected from the group consisting of alkyl (e.g., 1-20 carbon atoms), aryl (e.g., 6-22 carbon atoms), and cyano, or a combination of two or more groups. For example, a substituent can be a cyano or an aryl group that can be substituted by a group selected from the group consisting of cyano and alkyl, or a combination of two or more groups. In R 5 ~R 15 When two or more substituents are represented in R, these two or more substituents can be the same or different. 5 ~R 15 The 6 to 11 atoms in R are preferably hydrogen or deuterium atoms; for example, 8 to 11 atoms can be hydrogen or deuterium atoms. 5 ~R 15 It can consist entirely of hydrogen or deuterium atoms. Alternatively, it can consist of 8 to 10 hydrogen or deuterium atoms. For example, it can consist of 8 hydrogen or deuterium atoms, 9 hydrogen or deuterium atoms, or 10 hydrogen or deuterium atoms.

[0062] R 5 and R 6 R 6 and R 7 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15They can bond together to form a cyclic structure. The cyclic structure can be any of aromatic rings, heteroaromatic rings, aliphatic hydrocarbon rings, and aliphatic heterocycles, and can also be a ring formed by their fusion. Aromatic rings or heteroaromatic rings are preferred. Benzene rings are an example of aromatic rings. Heteroaromatic rings refer to aromatic rings containing heteroatoms as ring skeleton atoms, preferably 5- to 7-membered rings, for example, 5-membered or 6-membered rings. In one aspect of the invention, furan rings, thiophene rings, and pyrrole rings can be used as heteroaromatic rings. In a preferred embodiment of the invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole described herein may be unsubstituted, substituted, or substituted with substituents selected from substituent group A, B, C, D, or E. The nitrogen atom of the pyrrole ring constituting the indole is preferably bonded to a substituted or unsubstituted aryl group, and the substituents may, for example, include substituents selected from any one of substituent groups A through E. In R 5 and R 6 R 6 and R 7 R 8 and R 9 R 9 and R 10 R 10 and R 11 R 11 and R 12 R 12 and R 13 R 13 and R 14 R 14 and R 15 Preferably, 0 to 2 groups are bonded together to form a ring structure, more preferably 0 or 1 groups are bonded together to form a ring structure. One or two groups can be bonded together to form a ring structure. Furthermore, only one group can be bonded together to form a ring structure. Also, 0 groups can be bonded together to form a ring structure.

[0063] The following shows specific examples of D that can be used in general formula (1). D that can be used in general formula (1) can also be a group containing the following structure. For example, it can also be a group formed by fusion of a phenyl group or a ring (e.g., a benzene ring) substituted with a group having the following structure and a benzene ring in the following structure. The D that can be used in this invention is not to be limited by the following specific examples. Furthermore, in the following specific examples, wavy lines indicate bonding positions.

[0064] [Chemical Formula 8-1]

[0065]

[0066] [Chemical Formula 8-2]

[0067]

[0068] [Chemical Formula 8-3]

[0069]

[0070] [Chemical Formula 8-4]

[0071]

[0072] [Chemical Formula 8-5]

[0073]

[0074] [Chemical Formula 8-6]

[0075]

[0076] In general formula (1), A represents a group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl and alkyl, or a combination of two or more groups (except for substituted alkyl groups). That is, A is cyano, substituted or unsubstituted phenyl, substituted or unsubstituted pyrimidinyl or substituted or unsubstituted triazolyl, and the substituents of phenyl, pyrimidinyl and triazolyl are selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl and alkyl, or a combination of two or more groups, which can cause the benzene ring to condense with the phenyl and pyrimidinyl rings.

[0077] In a preferred embodiment of the invention, A is a cyano group or a cyano-substituted phenyl group. In another embodiment of the invention, A is a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazolyl group, preferably a substituted or unsubstituted phenyl-substituted pyrimidinyl group or a substituted or unsubstituted phenyl-substituted triazolyl group. In yet another embodiment of the invention, A is a substituted or unsubstituted pyrimidinyl-substituted phenyl group or a substituted or unsubstituted triazolyl-substituted phenyl group.

[0078] The following shows specific examples of A that can be used in general formula (1). A that can be used in general formula (1) can also be a group containing the following structure. For example, it can also be a group formed by fusion of a phenyl group or a ring (e.g., a benzene ring) substituted with a group having the following structure and a benzene ring in the following structure. The A that can be used in this invention is not limited by the following specific examples. Furthermore, in the following specific examples, * indicates a bonding position. And, methyl groups are omitted. For example, A15 is a group having two 4-methylphenyl groups.

[0079] [Chemical Formula 9-1]

[0080]

[0081] [Chemical Formula 9-2]

[0082]

[0083] R 1 ~R 4 Each of these groups independently represents a hydrogen atom, a deuterium atom, or a group selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups, or a combination of two or more groups. That is, R 1 ~R 4 Each of the following is independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a cyano group. The substituents of the alkyl, aryl, and heteroaryl groups are selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups, or combinations of two or more groups. In one embodiment of the invention, the substituent is an alkyl group that can be substituted by an aryl group or an aryl group that can be substituted by an alkyl group. In another embodiment of the invention, the substituent is a cyano group or an aryl or heteroaryl group substituted by a cyano group. In R 1 ~R 4 When two or more substituents are present in R, these substituents can be the same or different. 1 ~R 4 It can consist entirely of hydrogen atoms or deuterium atoms.

[0084] In a preferred embodiment of the invention, R 1 ~R 4 Each of the following is independently a hydrogen atom, a deuterium atom, or an aryl or pyridyl group that can be substituted with an alkyl or cyano group, preferably a hydrogen atom, a deuterium atom, or a phenyl or pyridyl group that can be substituted with an alkyl or cyano group. For example, hydrogen atom, deuterium atom, alkylphenyl, cyanophenyl, phenyl, or pyridyl group can be selected, or for example, hydrogen atom, deuterium atom, alkylphenyl, or phenyl group can be selected.

[0085] R 1 and R 2 R 3 and R 4 They can bond together to form a cyclic structure selected from the group consisting of benzene rings, naphthalene rings, and pyridine rings. The formed cyclic structure can be substituted by one or more groups selected from the group consisting of alkyl, aryl, and cyano groups. In one embodiment of the invention, R 1 and R 2 R 3 and R 4 One group of atoms in the ring bonds to each other to form a benzene ring, a naphthalene ring, and a pyridine ring. In one embodiment of the invention, R...1 and R 2 R 3 and R 4 These two bonds together to form benzene rings, naphthalene rings, and pyridine rings. At this point, R 1 and R 2 The formed ring and R 3 and R 4 The resulting rings can be the same or different. In one aspect of the invention, R 1 and R 2 R 3 and R 4 None of the atoms in the ring are bonded to each other to form a ring. In one aspect of the invention, the formed ring structure is a benzene ring or a naphthalene ring. In another aspect of the invention, the formed ring structure is a pyridine ring. The hydrogen atoms bonded to the benzene ring, naphthalene ring, and pyridine ring may be replaced by deuterium atoms or substituents. Examples of substituents include groups selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups, or combinations of two or more groups. In one aspect of the invention, the substituent is an alkyl group that can be replaced by an aryl group or an aryl group that can be replaced by an alkyl group. In another aspect of the invention, the substituent is a cyano group or an aryl group replaced by a cyano group. The hydrogen atoms bonded to the benzene ring, naphthalene ring, and pyridine ring may not be substituted.

[0086] Specific examples of aryl groups that can be substituted with alkyl groups are shown below. However, the aryl groups that can be substituted with alkyl groups that can be used in this invention are not to be interpreted as limiting the scope of the following examples. In the following examples, * indicates a bonding position. Furthermore, the methyl group is omitted. For example, N4 is 4-methylphenyl. Preferably, N5, N8, N10, and N11 are used.

[0087] [Chemical Formula 10]

[0088]

[0089] R as general formula (1) 1 ~R 4 More preferably, N5 and tert-butyl, especially N5.

[0090] The compound represented by general formula (1) can be the compound represented by general formula (3) below.

[0091] General formula (3)

[0092] [Chemical Formula 11]

[0093]

[0094] In general formula (3), Ar 1The symbol represents a cyclic structure and indicates a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring. D represents the group represented by the general formula (2). A represents a group selected from the group consisting of cyano, phenyl, pyrimidinyl, triazolyl, and alkyl, or a combination of two or more groups (excluding substituted alkyl groups). m is 1 or 2, and n is 0, 1, or 2. When m is 2, the two Ds can be the same or different. When n is 2, the two As can be the same or different. 2 Ar 3 They can independently form cyclic structures selected from the group consisting of benzene ring, naphthalene ring, and pyridine ring. The formed cyclic structures can be replaced by one or more groups selected from the group consisting of alkyl, aryl, heteroaryl, and cyano groups.

[0095] Regarding Ar of general formula (3) 1 For details and preferred ranges of Ar, D, A, m, and n, please refer to the corresponding record of the above general formula (1). 2 Ar 3 For details and preferred ranges of the benzene ring, naphthalene ring, and pyridine ring represented, please refer to R in the above general formula (1). 1 and R 2 R 3 and R 4 The description of benzene rings, naphthalene rings and pyridine rings formed by mutual bonding.

[0096] In one embodiment of the invention, D in general formula (3) is a substituted or unsubstituted 5H-indol[3,2,1-de]phenazin-5-yl, A is a cyano, phenyl, pyrimidinyl, triazolyl, or benzonitrile, n is 0 or 1, and Ar is... 2 Ar 3 Each ring can be independently a benzene ring, a naphthalene ring, a pyridine ring, or a benzene ring substituted with a cyano group.

[0097] The compound represented by general formula (1) preferably has any of the following skeletal structures. At least one hydrogen atom in the following skeletal structure can be replaced by a deuterium atom or a substituent within the range of general formula (1). Other rings do not fuse. In addition, since D is always present in general formula (1), only one D is described in the following ring skeletal structure.

[0098] [Chemical Formula 12]

[0099]

[0100] In a preferred embodiment of the invention, the compound represented by general formula (1) has any one of the following ring skeletons in group 1.

[0101] [Chemical Formula 13]

[0102] In a preferred embodiment of the invention, the compound represented by general formula (1) has any one of the following ring skeletons in group 2.

[0103] [Chemical Formula 14]

[0104]

[0105] In a preferred embodiment, A is not present in the molecule in ring skeleton group 1 and ring skeleton group 2. In one embodiment of the invention, the aromatic ring is bonded to a hydrogen atom, a deuterium atom, an unsubstituted alkyl group, or an aryl group that can be substituted by an alkyl group, and the aromatic ring is fused to the lower part of the pyrazine ring in ring skeleton group 1 and ring skeleton group 2. In a preferred embodiment of the invention, the aromatic ring is bonded to a hydrogen atom, a deuterium atom, or an unsubstituted alkyl group, and the aromatic ring is fused to the lower part of the pyrazine ring in ring skeleton group 1 and ring skeleton group 2.

[0106] The compound represented by general formula (1) can be any of the compounds represented by general formulas (4a) to (4f) below.

[0107] [Chemical Formula 15]

[0108]

[0109] In general formulas (4a) to (4f), R 21 ~R 28 R 41 ~R 44 R 51 R 52 R 61 ~R 68 R 81 ~R 84 R 101 ~R 104 R 111 ~R 114 R 119 R 120 Each can be independently represented by a hydrogen atom, a deuterium atom, or either D or A. Where R... 21 ~R 28 One or two of them are D and 0 to 2 are A, R 41 ~R 44 R 51 and R 52 One or two of them are D and 0 to 2 are A, R 61 ~R 68 One or two of them are D and 0 to 2 are A, R 81 ~R 84 One or two of them are D and 0 to 2 are A, R 101 ~R 104One or two of them are D and 0 to 2 are A, R 111 ~R 114 R 119 and R 120 One or two of them are D and 0 to 2 are A, R 29 ~R 36 R 45 ~R 50 R 69 ~R 72 R 85 ~R 92 R 105 ~R 110 R 115 ~R 118 Each of these groups independently represents a hydrogen atom, a deuterium atom, or a group selected from the group consisting of alkyl, aryl, and cyano groups, or a combination of two or more groups. In general formulas (4a) to (4f), the ring does not further fuse with the described ring skeleton.

[0110] For details and preferred ranges of general formulas (4a) to (4f), please refer to the corresponding description of general formula (1). In one aspect of the present invention, a compound represented by general formula (4a) is selected. In one aspect of the present invention, a compound represented by general formula (4b) is selected. In one aspect of the present invention, a compound represented by general formula (4c) is selected. In one aspect of the present invention, a compound represented by general formula (4d) is selected. In one aspect of the present invention, a compound represented by general formula (4e) is selected. In one aspect of the present invention, a compound represented by general formula (4f) is selected.

[0111] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 12 below. Specific examples of compounds represented by general formula (4a') are shown in Tables 1 and 2; specific examples of compounds represented by general formula (4b') are shown in Tables 3 and 4; specific examples of compounds represented by general formula (4c') are shown in Tables 5 and 6; specific examples of compounds represented by general formula (4d') are shown in Tables 7 and 8; specific examples of compounds represented by general formula (4e') are shown in Tables 9 and 10; and specific examples of compounds represented by general formula (4f') are shown in Tables 11 and 12. The compounds represented by general formula (1) that can be used in this invention should not be interpreted limitingly by these specific examples.

[0112] [Table 1-1]

[0113]

[0114] [Table 1-2]

[0115]

[0116] The compounds represented by general formula (4a') are further illustrated in Table 2 below. In Table 2, structures obtained by further substituting a portion of the structure determined by the compound number are further assigned compound numbers. For example, in Table 2, compounds 101–150 (represented as No. 101–150 in the table) are further used with the R of compounds 1–50. 22 (Represented as R22 in the table) corresponds to the substituents of compounds 1-50, R. 27 (In the table, it is represented as R27). Compound 101 is the compound used as R in compound 1. 22 D1 further replaces R in compound 1 27 The obtained compound, compound 102, is used as R in compound 2. 22 D2 further replaces R in compound 2 27 The obtained compounds. The structures of each compound listed in Table 2 and in Tables 4, 6, 8, 10, and 12 were determined using this method. The structures of each numbered compound in Tables 2, 4, 6, 8, 10, and 12 were determined individually and are disclosed in detail herein. Furthermore, "t-Bu" in the tables indicates tert-butyl group.

[0117] [Table 2]

[0118]

[0119] [Table 3-1]

[0120]

[0121] [Table 3-2]

[0122]

[0123] [Table 4]

[0124]

[0125] [Table 5-1]

[0126]

[0127] [Table 5-2]

[0128]

[0129] [Table 6]

[0130]

[0131] [Table 7-1]

[0132]

[0133] [Table 7-2]

[0134]

[0135] [Table 8]

[0136]

[0137] [Table 9-1]

[0138]

[0139] [Table 9-2]

[0140]

[0141] [Table 10]

[0142]

[0143] [Table 11-1]

[0144]

[0145] [Table 11-2]

[0146]

[0147] [Table 12]

[0148]

[0149] Furthermore, compounds 1d to 22600d are disclosed in which all hydrogen atoms present in the molecules of compounds 1 to 22600 are replaced with deuterium atoms. In addition, in the case where the compounds illustrated above contain rotational isomers, mixtures of rotational isomers and isolated rotational isomers are disclosed herein.

[0150] In one aspect of the invention, a compound having a linearly symmetric structure is selected as the compound represented by general formula (1). In another aspect of the invention, a compound having an asymmetric structure is selected as the compound represented by general formula (1).

[0151] In one embodiment of the present invention, compounds 1 to 3200 and 1d to 3200d are selected as compounds represented by general formula (1). In one embodiment of the present invention, compounds 3201 to 5800 and 3201d to 5800d are selected as compounds represented by general formula (1). In one embodiment of the present invention, compounds 5801 to 7800 and 5801d to 7800d are selected as compounds represented by general formula (1). In one embodiment of the present invention, compounds 7801 to 11000 and 7801d to 11000d are selected as compounds represented by general formula (1). In one embodiment of the present invention, compounds 11001 to 13600 and 11001d to 13600d are selected as compounds represented by general formula (1). In one embodiment of the present invention, compounds 13601 to 16200 and 13601d to 16200d are selected as compounds represented by general formula (1). In one aspect of the present invention, compounds 16201 to 18200 and 16201d to 18200d are selected as compounds represented by general formula (1). In another aspect of the present invention, compounds 18201 to 22600 and 18201d to 22600d are selected as compounds represented by general formula (1).

[0152] The compound represented by general formula (1) can be a compound in which the acceptor group is not bonded to the skeleton of general formula (1). The acceptor group mentioned here is a group with a positive Hammett σp value. The compound represented by general formula (1) can be a compound in which there is no group having a Hammett σp value of 0.2 or higher.

[0153] Regarding the molecular weight of the compound represented by general formula (1), for example, when attempting to form an organic layer containing the compound represented by 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 of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1).

[0154] Compounds represented by general formula (1) can be coated to form films regardless of their molecular weight. Even compounds with relatively large molecular weights can be coated to form films. Compounds represented by general formula (1) are readily soluble in organic solvents. Therefore, compounds represented by general formula (1) are easily adapted to the coating method and are easily purified to improve purity.

[0155] Alternatively, the present invention may be applied to use compounds containing multiple structures represented by general formula (1) within the molecule as luminescent materials.

[0156] For example, a polymer obtained by pre-existing a polymeric group in the structure represented by general formula (1) and then polymerizing that polymeric group can be considered as a luminescent material. Specifically, it is possible to prepare any of the structures represented by general formula (1) (e.g., Ar...). 1 D, A, R 1 ~R 4 Monomers containing polymerizable functional groups (any one of the monomers in formula (1)) are polymerized individually or copolymerized with other monomers to obtain polymers with repeating units, and these polymers are used as luminescent materials. Alternatively, dimers or trimers can be obtained by coupling compounds represented by general formula (1) to each other, and these can be used as luminescent materials.

[0157] Examples of polymers having repeating units that include the structure represented by general formula (1) may include polymers that include the structure represented by either of the following two general formulas.

[0158] [Chemical Formula 16]

[0159]

[0160] In the above general formula, Q represents a group containing the structure represented by general formula (1), and L 1 and L 2 This indicates a linking group. The linking group preferably has 0 to 20 carbon atoms, more preferably 1 to 15, and even more preferably 2 to 10. The linking group preferably has a -X symbol. 11 -L 11 - The linking group representing the structure. Here, X 11 Represents an oxygen atom or a sulfur atom, preferably an oxygen atom. L 11 The linking group is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted aryl group, more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms.

[0161] R 201 R 202 R 203 and R 204 Each substituent is represented independently. Preferably, it is an alkyl group with 1 to 6 substituted or unsubstituted carbon atoms, an alkoxy group with 1 to 6 substituted or unsubstituted carbon atoms, or a halogen atom; more preferably, it is an alkyl group with 1 to 3 unsubstituted carbon atoms, an alkoxy group with 1 to 3 unsubstituted carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, it is an alkyl group with 1 to 3 unsubstituted carbon atoms or an alkoxy group with 1 to 3 unsubstituted carbon atoms.

[0162] L 1 and L 2The linking group can be attached to any position in the structure represented by the general formula (1) constituting Q (e.g., Ar). 1 D, A, R 1 ~R 4 (Any one of them) is bonded. Two or more linking groups can be linked to one Q to form a cross-linked structure or a network structure.

[0163] Specific structural examples of repeating units may include the structure represented by the following formula.

[0164] [Chemical Formula 17]

[0165]

[0166] Polymers having repeating units containing these formulas can be synthesized by: [the following is an example of a synthesis of polymers containing repeating units of general formula (1)] (e.g., Ar). 1 D, A, R 1 ~R 4 A hydroxyl group is introduced into any one of the compounds to act as a linking group, thereby introducing a polymerizable group and causing the polymerizable group to polymerize.

[0167] [Chemical Formula 18]

[0168]

[0169] Polymers containing the structure represented by general formula (1) within their molecules can be polymers composed solely of repeating units having the structure represented by general formula (1), or polymers containing repeating units having structures other than those represented by general formula (1). Furthermore, the repeating units containing the structure represented by general formula (1) in the polymer can be a single type or two or more types. As repeating units that do not have the structure represented by general formula (1), examples include repeating units derived from monomers commonly used for copolymerization. For example, repeating units derived from monomers such as ethylene and styrene that have vinyl unsaturated bonds can be cited.

[0170] The compound represented by general formula (1) preferably does not contain metal atoms. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms can be selected. For example, as a compound represented by general formula (1), a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, and nitrogen atoms can be selected.

[0171] In this document, "alkyl" can be any of the following: straight-chain, branched, or cyclic. Furthermore, two or more of the straight-chain, cyclic, and branched moieties can be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isohexyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decyl, isododecyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group may be further substituted with an aryl group.

[0172] The "alkenyl" group can be any of the following: linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched groups can be mixed. The number of carbon atoms in the alkenyl group can be, for example, 2 or more, or 4 or more. The number of carbon atoms can also be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkenyl groups include vinyl, propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl. The alkenyl group of the substituent can be further substituted with substituents.

[0173] "Aryl" and "heteroaryl" can be monocyclic or fused rings composed of two or more rings. When fused rings are used, the number of fused rings is preferably 2 to 6, for example, selected from 2 to 4. Specific examples of rings include benzene rings, pyrazinidine rings, pyrimidine rings, triazine rings, naphthyl rings, anthracene rings, phenanthrene rings, triphenylene rings, quinoline rings, pyrazine rings, quinoxaline rings, and naphthidine rings, or these fused rings. Specific examples of aryl or heteroaryl groups include phenyl, 1-naphthyl, 2-naphthyl, 1-anthrayl, 2-anthrayl, 9-anthrayl, 2-pyridyl, 3-pyridyl, and 4-pyridyl. The number of atoms constituting the aryl ring skeleton is preferably 6 to 40, more preferably 6 to 20, and can be selected from the range of 6 to 14 or from the range of 6 to 10. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and can be selected in the range of 5 to 14 or in the range of 5 to 10. "Arylidene" and "heteroaryl" can be defined as groups in which the valence number in the description of aryl and heteroaryl is replaced from 1 to 2.

[0174] In this document, "substituent group A" means selected from hydroxyl, halogen atom (e.g., fluorine, chlorine, bromine, iodine), alkyl (e.g., 1-40 carbon atoms), alkoxy (e.g., 1-40 carbon atoms), alkylthio (e.g., 1-40 carbon atoms), aryl (e.g., 6-30 carbon atoms), aryloxy (e.g., 6-30 carbon atoms), arylthio (e.g., 6-30 carbon atoms), heteroaryl (e.g., 5-30 atoms in the ring skeleton), and heteroaryloxy (e.g., 5-30 atoms in the ring skeleton). A group consisting of one or more of the following groups: 30, heteroarylthio (e.g., 5 to 30 atoms in the ring skeleton), acyl (e.g., 1 to 40 carbon atoms), alkenyl (e.g., 1 to 40 carbon atoms), alkoxycarbonyl (e.g., 1 to 40 carbon atoms), aryloxycarbonyl (e.g., 1 to 40 carbon atoms), heteroaryloxycarbonyl (e.g., 1 to 40 carbon atoms), silyl (e.g., trialkylsilyl with 1 to 40 carbon atoms), and nitro.

[0175] In this document, "substituent group B" means a group selected from one or more of the group consisting of alkyl (e.g., 1 to 40 carbon atoms), alkoxy (e.g., 1 to 40 carbon atoms), aryl (e.g., 6 to 30 carbon atoms), aryloxy (e.g., 6 to 30 carbon atoms), heteroaryl (e.g., 5 to 30 atoms forming the ring skeleton), heteroaryloxy (e.g., 5 to 30 atoms forming the ring skeleton), and diarylamino (e.g., 0 to 20 carbon atoms).

[0176] In this document, “substituent group C” means a group selected from one or more of the group consisting of alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms), heteroaryl (e.g., 5 to 20 cyclic skeleton atoms), and diarylamino (e.g., 12 to 20 carbon atoms).

[0177] In this document, "substituent group D" means a group selected from one or more groups composed of alkyl (e.g., 1 to 20 carbon atoms), aryl (e.g., 6 to 22 carbon atoms), and heteroaryl (e.g., 5 to 20 cyclic skeleton atoms).

[0178] In this document, “substituent group E” means a group selected from one or more groups composed of alkyl (e.g., 1 to 20 carbon atoms) and aryl (e.g., 6 to 22 carbon atoms).

[0179] In this document, a substituent described as "substituent" or "substituted or unsubstituted" may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0180] In one embodiment, the compound represented by general formula (1) is a luminescent material.

[0181] In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence.

[0182] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the UV region, the blue, green, yellow, orange, and red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region when excited by a thermal or electronic device.

[0183] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm) when excited by a thermal or electronic device.

[0184] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm) when excited by a thermal or electronic device.

[0185] In one embodiment of the invention, the compound represented by general formula (1) is able to emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by a thermal or electronic device.

[0186] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by a thermal or electronic device.

[0187] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the ultraviolet spectral region (e.g., 280–400 nm) when excited by a thermal or electronic device.

[0188] In one embodiment of the present invention, the compound represented by general formula (1) is able to emit light in the infrared spectral region (e.g., 780 nm to 2 μm) when excited by a thermal or electronic device.

[0189] In one embodiment of the present invention, an organic semiconductor device using a compound represented by general formula (1) can be fabricated. For example, a CMOS (complementary metal oxide semiconductor) or the like using a compound represented by general formula (1) can be fabricated. In one embodiment of the present invention, an organic light-emitting element or a solid-state imaging element (e.g., a CMOS image sensor) or the like can be fabricated using a compound represented by general formula (1).

[0190] The electronic properties of a small molecule chemical library can be calculated using quantum chemical calculations based on well-known ab initio. For example, as a basis, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be analyzed using density functional theory that utilizes the time dependence of a set of functions known as the three-parameter Lee-Yang-Parr hybrid density functional as 6-31G* and Becke, and molecular fragments (partially) with HOMOs above a specific threshold and LUMOs below a specific threshold can be screened.

[0191] Thus, for example, when a HOMO energy (e.g., ionization potential) above -6.5 eV is present, the donor portion (“D”) can be selected. And, for example, when a LUMO energy (e.g., electron affinity) below -0.5 eV is present, the acceptor portion (“A”) can be selected. The bridging portion (“B”) is, for example, a strongly conjugated system that strictly restricts the acceptor and donor portions to specific stereostructures, thereby preventing repetition between the π-conjugated systems of the donor and acceptor portions.

[0192] In one embodiment, the compound library is screened using more than one of the following properties.

[0193] 1. Emission near a specific wavelength

[0194] 2. Triplets above the calculated specific energy level

[0195] 3. ΔE below a specific value ST value

[0196] 4. Quantum yield above a certain value

[0197] 5. HOMO level

[0198] 6. LUMO level

[0199] In one embodiment, the difference (ΔE) between the lowest singlet excited state and the lowest triplet excited state in 77K ST Less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, ΔE ST Values ​​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.

[0200] In one embodiment, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0201] [Synthetic methods for compounds represented by general formula (1)]

[0202] The compound represented by general formula (1) is a novel compound.

[0203] The compounds represented by general formula (1) can be synthesized by combining known reactions. For example, they can be synthesized by using ring-closing reactions or substitution reactions. For specific synthetic conditions, please refer to the synthetic examples described later.

[0204] [Using the structure of a compound represented by general formula (1)]

[0205] In one embodiment, a solid film or layer is formed by dispersing the compound in combination with a compound represented by general formula (1), covalently bonding the compound with the compound, coating the compound, or using the compound or one or more materials associated with the compound (e.g., small molecules, polymers, metals, metal complexes, etc.). For example, the compound represented by general formula (1) can be combined with an electroactive material to form a film. In some cases, the compound represented by general formula (1) can be combined with a hole-transporting polymer. In some cases, the compound represented by general formula (1) can be combined with an electron-transporting polymer. In some cases, the compound represented by general formula (1) can be combined with both a hole-transporting polymer and an electron-transporting polymer. In some cases, the compound represented by general formula (1) can be combined with a copolymer having both a hole-transporting portion and an electron-transporting portion. Through the above embodiments, electrons and / or positive pores formed in the solid film or layer can interact with the compound represented by general formula (1).

[0206] [Membrane formation]

[0207] In one embodiment, a film containing a compound of the present invention represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition comprising a compound of the present invention is applied to a surface, and the film is formed after the solvent is removed. Examples of wet processes include spin coating, slot coating, inkjet printing, gravure printing, offset printing, and flexographic printing, but are not limited to these. In the wet process, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected. In one embodiment, a substituent (e.g., an alkyl group) that improves solubility in an organic solvent can be introduced into the compound contained in the composition.

[0208] In one embodiment, a film containing the compound of the present invention can be formed by a dry process. In one embodiment, vacuum evaporation can be used as the dry process, but it is not limited to this. When using vacuum evaporation, the compound constituting the film can be co-deposited from a single evaporation source, or co-deposited from a single evaporation source containing the compound. When using a single evaporation source, a mixture of powders containing the compound can be used, a compression molded body of the mixed powder can be used, or a mixture in which the compounds are heated, melted, and cooled can be used. In one embodiment, co-depositing is performed under conditions where the evaporation rates (weight loss rates) of the multiple compounds contained in a single evaporation source are consistent or substantially consistent, thereby forming a film with a component ratio corresponding to the component ratio of the multiple compounds contained in the evaporation source. If multiple compounds are mixed as evaporation sources with the same component ratio as the component ratio of the formed film, a film with the desired component ratio can be easily formed. In one embodiment, the temperature at which the co-deposited compounds achieve the same weight loss rate can be determined, and this temperature is used as the temperature during co-depositing.

[0209] [Examples of the use of compounds represented by general formula (1)]

[0210] The compound represented by general formula (1) is useful as a material for organic light-emitting elements. It is especially preferred for organic light-emitting diodes and the like.

[0211] Organic light-emitting diodes (OLEDs):

[0212] One aspect of the present invention relates to the use of the compound represented by general formula (1) of the present invention in the form of a luminescent material of an organic light-emitting element. In one embodiment, the compound represented by general formula (1) of the present invention can be effectively used as a luminescent material in the luminescent layer of an organic light-emitting element. In one embodiment, the compound represented by general formula (1) comprises a delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having the structure represented by general formula (1). In one embodiment, the present invention relates to the use of the compound represented by general formula (1) as a delayed phosphor. In one embodiment, the compound represented by general formula (1) of the present invention can be used as a host material and can be used together with one or more luminescent materials, which may be fluorescent materials, phosphorescent materials, or TADF. In one embodiment, the compound represented by general formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by general formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from the compound represented by general formula (1). In one embodiment, an organic light-emitting element comprising the compound as a luminescent material emits delayed fluorescence and exhibits high luminous efficiency.

[0213] In one embodiment, the light-emitting layer comprises a compound represented by general formula (1), which is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) on the film-forming surface influences or determines the propagation direction of light emitted by the arranged compounds. In one embodiment, by aligning the compounds in the propagation direction of light emitted by the compound represented by general formula (1), the light extraction efficiency from the light-emitting layer is improved.

[0214] One aspect of the present invention relates to an organic light-emitting element. In one embodiment, the organic light-emitting element comprises a light-emitting layer. In one embodiment, the light-emitting layer comprises a compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting element is an organic photoluminescent element (organic PL element). In one embodiment, the organic light-emitting element is an organic electroluminescent element (organic EL element). In one embodiment, the compound represented by general formula (1) assists in the luminescence of other light-emitting materials contained in the light-emitting layer (as a so-called auxiliary dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer is at its lowest excited singlet state energy level, which is contained between the lowest excited singlet state energy level of the host material contained in the light-emitting layer and the lowest excited singlet state energy level of another light-emitting material contained in the light-emitting layer.

[0215] In one embodiment, the organic photoluminescent element includes at least one light-emitting layer. In one embodiment, the organic electroluminescent element includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least one light-emitting layer. In one embodiment, the organic layer includes only one light-emitting layer. In one embodiment, the organic layer includes more than one organic layer other than the light-emitting layer. Examples of organic layers include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers, and exciton blocking layers. In one embodiment, the hole transport layer can be a hole injection and transport layer with hole injection functionality, and the electron transport layer can be an electron injection and transport layer with electron injection functionality. Examples of organic electroluminescent elements are shown in... Figure 1 middle.

[0216] Emissive layer:

[0217] In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, are rebonded to form excitons. In one embodiment, the layer emits light.

[0218] In one embodiment, only a luminescent material is used as the luminescent layer. In one embodiment, the luminescent layer comprises a luminescent material and a host material. In one embodiment, the luminescent material is a compound represented by general formula (1). In one embodiment, to enable organic electroluminescent elements and organic photoluminescent elements to exhibit high luminous efficiency, singlet and triplet excitons generated in the luminescent material are confined within the luminescent material. In one embodiment, a host material is used in addition to the luminescent material in the luminescent layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has an excitation singlet energy and an excitation triplet energy, at least one of which is higher than those energies of the luminescent material of the present invention. In one embodiment, singlet and triplet excitons generated in the luminescent material of the present invention are confined within the molecules of the luminescent material of the present invention. In one embodiment, the singlet and triplet excitons are sufficiently confined to promote luminous efficiency. In one embodiment, the singlet and triplet excitons are not sufficiently confined, but a high luminous efficiency is still obtained; that is, a host material capable of achieving high luminous efficiency can be used in the present invention without particular limitation. In one embodiment, luminescence occurs in the luminescent material within the luminescent layer of the element of the present invention. In one embodiment, the emitted light comprises both fluorescence and delayed fluorescence. In one embodiment, the emitted light comprises 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 comprises light emitted from the compound represented by general formula (1) and light emitted from the host material. In one embodiment, TADF molecules and the host material are used. In one embodiment, TADF is an auxiliary dopant, and the excited singlet state energy is lower than that of the host material in the luminescent layer and higher than that of the luminescent material in the luminescent layer.

[0219] When the compound represented by general formula (1) is used as an auxiliary dopant, various compounds can be used as luminescent materials (preferably fluorescent materials). Such luminescent materials can be derived from anthracene derivatives, tetraphenylene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, etc. Derivatives, including rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthracene derivatives, pyrrole methylene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, juulolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn), etc. These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons can be combined with each other.

[0220] The following examples illustrate luminescent materials that can be used in combination with auxiliary dopants having the structure represented by general formula (1).

[0221] [Chemical Formula 19-1]

[0222]

[0223] [Chemical Formula 19-2]

[0224]

[0225] [Chemical Formula 19-3]

[0226]

[0227] [Chemical Formula 19-4]

[0228]

[0229] Furthermore, compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 or compounds having a pyrrole methylene boron skeleton as described in WO2021 / 015177 may be used, particularly preferably, as luminescent materials used together with auxiliary dopants having the structure represented by general formula (1).

[0230] In one embodiment, when using the host material, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 0.1% by weight or more. In one embodiment, when using the host material, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 1% by weight or more. In one embodiment, when using the host material, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 50% by weight or less. In one embodiment, when using the host material, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 20% by weight or less. In one embodiment, when using the host material, the amount of the compound of the present invention in the form of a luminescent material contained in the luminescent layer is 10% by weight or less.

[0231] In one embodiment, the host material of the light-emitting layer is an organic compound that incorporates both hole transport and electron transport functions. In another embodiment, the host material of the light-emitting layer is an organic compound that prevents an increase in the wavelength of the emitted light. In yet another embodiment, the host material of the light-emitting layer is an organic compound with a high glass transition temperature.

[0232] In some embodiments, the body material is selected from the group consisting of:

[0233] [Chemical Formula 20-1]

[0234]

[0235] [Chemical Formula 20-2]

[0236]

[0237] In one embodiment, the luminescent layer comprises two or more TADF molecules with different structures. For example, it can be configured as a luminescent layer comprising three materials with high excitation singlet energy levels in the order of host material, first TADF molecule, and second TADF molecule. In this case, the difference ΔE between the lowest excitation singlet energy level of the first TADF molecule and the second TADF molecule and the lowest excitation triplet energy level at 77K is... STThe concentrations are preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecule in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. Furthermore, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecule. The concentration of the first TADF molecule in the light-emitting layer can be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the light-emitting layer can be set as follows: the host material is set to 10-70% by weight, the first TADF molecule is set to 10-80% by weight, and the second TADF molecule is set to 0.1-30% by weight. In one embodiment, the composition of the light-emitting layer can be set as follows: the host material is set to 20-45% by weight, the first TADF molecule is set to 50-75% by weight, and the second TADF molecule is set to 5-20% by weight. In one embodiment, the light emission quantum yield φPL1(A) caused by photoexcitation of the co-deposited film of the first TADF molecule and the host material (the concentration of the first TADF molecule in the co-deposited film = A% by weight) and the light emission quantum yield φPL2(A) caused by photoexcitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-deposited film = A% by weight) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the luminescence quantum yield φPL2(B) induced by photoexcitation of the co-deposited film of the second TADF molecule and the host material (the concentration of the second TADF molecule in the co-deposited film = B wt%) and the luminescence quantum yield φPL2(100) induced by photoexcitation of the film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In one embodiment, the luminescent layer can contain three TADF molecules with different structures. The compound of the present invention can be any one of a plurality of TADF compounds contained in the luminescent layer.

[0238] In one embodiment, the light-emitting layer may be composed of a material selected from the group consisting of a host material, an auxiliary dopant, and a light-emitting material. In one embodiment, the light-emitting layer does not contain any metallic elements. In one embodiment, the light-emitting layer may be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer may also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer may also be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

[0239] When the luminescent layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescence material. Preferred delayed fluorescence materials may include segments 0008-0048 and 0095-0133 of WO2013 / 154064, segments 0007-0047 and 0073-0085 of WO2013 / 011954, segments 0007-0033 and 0059-0066 of WO2013 / 011955, and segments 0008-007 of WO2013 / 081088. Paragraphs 1 and 0118–0133, paragraphs 0009–0046 and 0093–0134 of Japanese Patent Application Publication No. 2013-256490, paragraphs 0008–0020 and 0038–0040 of Japanese Patent Application Publication No. 2013-116975, paragraphs 0007–0032 and 0079–0084 of Japanese Patent Application Publication No. WO2013 / 133359, and paragraph 0008 of Japanese Patent Application Publication No. WO2013 / 161437. Paragraphs 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of Japanese Patent Application Publication No. 2014-9352, paragraphs 0008 to 0048 and 0067 to 0076 of Japanese Patent Application Publication No. 2014-9224, paragraphs 0013 to 0025 of Japanese Patent Application Publication No. 2017-119663, and paragraphs 0013 to 0026 of Japanese Patent Application Publication No. 2017-119664. Compounds contained in the general formulas described in Japanese Patent Application Publication No. 2017-222623 (paragraphs 0012-0025), Japanese Patent Application Publication No. 2017-226838 (paragraphs 0010-0050), Japanese Patent Application Publication No. 2018-100411 (paragraphs 0012-0043), and Japanese Patent Application Publication No. WO2018 / 047853 (paragraphs 0016-0044), especially exemplary compounds capable of emitting delayed fluorescence.Furthermore, Japanese Patent Application Publication Nos. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, and WO2014 / 133121 may be preferred. Communiqués, WO2014 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008580, WO2014 / 203840, WO2015 / 002213, WO2015 / 016200, WO2015 Japanese Publication No. / 019725, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, Japanese Patent Application Publication No. 2015-129240, WO2015 / 129714, WO2015 / 12971 Materials that emit delayed fluorescence as described in Publications No. 5, WO2015 / 133501, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. Furthermore, the aforementioned publications described in this paragraph are incorporated herein by reference as part of this document.

[0240] The following describes the components of an organic electroluminescent element and its layers other than the light-emitting layer.

[0241] Substrate:

[0242] In some embodiments, the organic electroluminescent element of the present invention is supported by a substrate, wherein the substrate is not particularly limited and may be any of those substrates commonly used in organic electroluminescent elements, such as those formed of glass, transparent plastic, quartz and silicon.

[0243] anode:

[0244] In some embodiments, the anode of the organic electroluminescent device is made of a metal, alloy, 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), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, when high precision (e.g., above about 100 μm) may not be required for the pattern, the pattern can be formed by vapor deposition or sputtering of the electrode material using a mask with the desired shape. In some embodiments, when a coating material (such as an organic conductive compound) can be applied, wet film formation methods, such as printing and coating, are used. In some embodiments, when emitted light passes through the anode, the transmittance of the anode is greater than 10%, and the sheet resistance of the anode is less than several hundred ohms per square meter. In some embodiments, the thickness of the anode is 10–1,000 nm. In some embodiments, the thickness of the anode is 10–200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0245] cathode:

[0246] In some embodiments, the cathode is made of a metal (below 4 eV) (referred to as an electron-injecting metal), alloy, conductive compound, or combination thereof, with an electrode material having a low work function. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al2O3) mixtures, indium, lithium-aluminum mixtures, and rare earth metals. In some embodiments, a mixture of the electron-injecting metal and a second metal is used, the second metal being a stable metal with a work function greater than that of the electron-injecting metal. In some embodiments, the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-alumina (Al2O3) mixtures, lithium-aluminum mixtures, and aluminum. In some embodiments, the mixture increases electron-injection characteristics and durability against oxidation. In some embodiments, the cathode is manufactured by forming the electrode material into a thin film using vapor deposition or sputtering. In some embodiments, the film resistivity of the cathode is below several hundred ohms per square meter. In some embodiments, the thickness of the cathode is in the range of 10 nm to 5 μm. In some embodiments, the thickness of the cathode is in the range of 50–200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent element is transparent or translucent in order to transmit the emitted light. In some embodiments, transparent or translucent electroluminescent elements enhance the luminous brightness.

[0247] In some embodiments, the cathode is formed using a conductive transparent material as described for the anode to form a transparent or translucent cathode. In some embodiments, the element comprises a uniformly transparent or translucent anode and cathode.

[0248] Injection layer:

[0249] The injection layer is a layer located between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the luminous intensity. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the luminescent layer or hole transport layer, and between the cathode and the luminescent layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present.

[0250] The following are examples of preferred compounds that can be used as hole injection materials.

[0251] [Chemical Formula 21]

[0252]

[0253] Next, preferred examples of compounds that can be used as electron injection materials will be given.

[0254] [Chemical Formula 22]

[0255]

[0256] Barrier layer:

[0257] A blocking layer is a layer capable of suppressing 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, an electron blocking layer is located between the light-emitting layer and the hole transport layer, and suppresses electrons from passing through the light-emitting layer toward the hole transport layer. In some embodiments, a hole blocking layer is located between the light-emitting layer and the electron transport layer, and suppresses holes from passing through the light-emitting layer toward the electron transport layer. In some embodiments, the blocking layer suppresses exciton diffusion to the outside of the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that function as both electron blocking layers and exciton blocking layers.

[0258] Cavity blocking layer:

[0259] The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer suppresses holes from reaching the electron transport layer while transporting electrons. In some embodiments, the hole blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the hole blocking layer can be the same material described for the electron transport layer.

[0260] The following are examples of preferred compounds that can be used in hole-blocking layers.

[0261] [Chemical Formula 23]

[0262]

[0263] Electron blocking layer:

[0264] Holes are transported by an electron blocking layer. In some embodiments, the electron blocking layer suppresses electrons from reaching the hole transport layer while transporting holes. In some embodiments, the electron blocking layer enhances the probability of rebonding between electrons and holes in the light-emitting layer. The material used for the electron blocking layer can be the same material described for the hole transport layer.

[0265] The following are specific examples of preferred compounds that can be used as electron blocking materials.

[0266] [Chemical Formula 24]

[0267]

[0268] Exciton blocking layer:

[0269] An exciton blocking layer suppresses the diffusion of excitons generated via the rebonding of holes and electrons in the light-emitting layer into the electron transport layer. In some embodiments, the exciton blocking layer enables the effective confinement of excitons within the light-emitting layer. In some embodiments, it enhances the luminous efficiency of the device. In some embodiments, the exciton blocking layer is adjacent to the light-emitting layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is on the anode side, the layer may be located between and adjacent to the hole transport layer and the light-emitting layer. In some embodiments, when the exciton blocking layer is on the cathode side, the layer may be located between and adjacent to the light-emitting layer and the cathode. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is located between the anode and the exciton blocking layer, with the exciton blocking layer 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 a similar layer is located between the cathode and the exciton blocking layer, with the exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer includes an excitation singlet energy and an excitation triplet energy, at least one of which is higher than the excitation singlet energy and excitation triplet energy of the luminescent material, respectively.

[0270] Hole transport layer:

[0271] The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers.

[0272] In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in this invention include (but are not limited to) triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkyl derivatives, pyrazoline derivatives, dihydropyrazolone derivatives, phenylenediamine derivatives, aromatic amine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-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 styrene amine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are included below.

[0273] [Chemical Formula 25]

[0274]

[0275] Electron transport layer:

[0276] The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers.

[0277] In some embodiments, the electron transport material only needs to have the function of transporting electrons injected from the cathode into the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples that can be used in the electron transport layer of the present invention include (but are not limited to) nitro-substituted fluorene derivatives, dibenzoquinone derivatives, thiopiperanoxide derivatives, carbodiimide, fluorenemethane derivatives, anthraquinone dimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, aziridine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are included below.

[0278] [Chemical Formula 26]

[0279]

[0280] Furthermore, compounds that are preferred as materials that can be added to each organic layer are included. For example, they can be considered as stabilizing materials.

[0281] [Chemical Formula 27]

[0282]

[0283] Preferred materials that can be used in organic electroluminescent devices are specifically exemplified, but the materials that can be used in this invention are not limited to the compounds exemplified below. Furthermore, even compounds exemplified as materials with specific functions can be converted into materials with other functions.

[0284] Device:

[0285] In some embodiments, the light-emitting layer is incorporated into the device. For example, the device includes, but is not limited to, OLED bulbs, OLED lights, television screens, computer monitors, mobile phones, and tablet computers.

[0286] In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer containing a light-emitting layer between the anode and the cathode.

[0287] 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 facilitating charge transfer or energy transfer within the device and / or for use as hole transport materials. Such 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).

[0288] Light bulb or lamp:

[0289] In some embodiments, the electronic device includes an OLED, the OLED including an anode, a cathode and at least one organic layer containing a light-emitting layer between the anode and the cathode.

[0290] In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array comprising combinations of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors.

[0291] In some embodiments, the device is an OLED light, the OLED light comprising:

[0292] The circuit board has a first surface having a mounting surface and a second surface opposite thereto, and at least one opening is defined thereon;

[0293] At least one OLED is disposed on the mounting surface and has a structure in which the at least one OLED includes an anode, a cathode and at least one organic layer containing a light-emitting layer between the anode and the cathode and emits light.

[0294] Housing, used for circuit board; and

[0295] At least one connector is disposed at an end of the housing, and the housing and the connector define an encapsulation suitable for mounting to a lighting device.

[0296] In some embodiments, the OLED lamp includes a plurality of OLEDs mounted on a circuit board to emit light 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.

[0297] Monitor or screen:

[0298] In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compound involved in the present invention is deposited onto a substrate using methods including (but not limited to) vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photographic plate structure suitable for double-sided etching, providing pixels with a unique aspect ratio. The screen (which may also be referred to as a mask) is used in methods for manufacturing OLED displays. The corresponding artwork pattern design promotes extremely steep and narrow tie-bars between pixels in the vertical direction and promotes large swept-bevel openings in the horizontal direction. This allows for tight patterning of pixels required for high-definition displays while optimizing chemical vapor deposition onto the TFT substrate.

[0299] Internal patterning of pixels allows for the construction of 3D pixel openings with varying aspect ratios in both the horizontal and vertical directions. Furthermore, imaging "strips" or halftone circles within the pixel region suppress etching in specific areas until these specific patterns are undercut and leave the substrate. At this point, all pixel regions are processed at the same etching rate, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows etching to be suppressed at different rates within the pixel, enabling locally deeper etching to create steep vertical bevels.

[0300] The preferred material for deposition masks is invar steel. Invar steel is a metal alloy that is cold-rolled into long thin sheets in a steel mill. Invar steel cannot be used as a nickel mask for electrodeposition onto a spin mandrel. A suitable and low-cost method for forming opening regions within a vapor deposition mask is a wet chemical etching method.

[0301] 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 other embodiments, the screen or display pattern is fabricated using plasma etching.

[0302] Method for manufacturing the device:

[0303] OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit cells. Generally, each unit cell on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate, applying a planarization film onto the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0304] OLED displays are typically manufactured by forming a large motherboard and then cutting the motherboard into unit cells. Generally, each unit cell on the motherboard is formed by: forming a thin-film transistor (TFT) including an active layer and source / drain electrodes on a substrate, applying a planarization film onto the TFT, and sequentially forming a pixel electrode, a light-emitting layer, a counter electrode, and an encapsulation layer, and then cutting it from the motherboard.

[0305] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method comprising:

[0306] The process of forming a barrier layer on the substrate of the motherboard;

[0307] The process of forming multiple display units from unit board units on the barrier layer;

[0308] The process of forming an encapsulation layer on each of the display units of the unit board; and

[0309] The process of coating an organic film on the interface portion between the unit plates.

[0310] In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edge portions of the barrier layer are covered with an organic film formed of polyimide or acryloyl groups. In some embodiments, the organic film facilitates the gentle cutting of the motherboard into unit panels.

[0311] In some embodiments, the thin-film transistor (TFT) layer has a light-emitting layer, a gate electrode, and a source / drain electrode. Each of the plurality of display units may 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 an organic film coated on the interface portion is formed of the same material as the planarization film and is formed at the same time as the planarization film is formed. 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 neither contacts the display unit nor the encapsulation layer.

[0312] Each of the organic film and the planarization film may comprise either polyimide or acryloyl groups. 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 another surface of the substrate 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.

[0313] 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 acrylamide, as in the case of an organic film formed on an edge portion of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously when manufacturing an OLED display. In some embodiments, the organic film may be formed on an edge portion of the barrier layer such that a portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0314] 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 / drain electrode of the TFT layer.

[0315] 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 opposite electrode, thereby causing the organic light-emitting layer to emit light and thus forming an image. Hereinafter, the image forming unit having a TFT layer and light-emitting units will be referred to as a display unit.

[0316] In some embodiments, the encapsulation layer covering the display units and preventing external moisture penetration can be formed as a film encapsulation structure having organic and inorganic films alternately stacked. In some embodiments, the encapsulation layer has a film encapsulation structure having multiple thin films 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 portion of the organic film directly contacts the substrate, and the remaining portion of the organic film contacts the barrier layer while surrounding the edge portion of the barrier layer.

[0317] In one embodiment, the OLED display is flexible and uses a soft 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.

[0318] In some embodiments, a barrier layer is formed on the surface of the substrate opposite to the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each unit plate. For example, while forming the substrate over the entire surface of the motherboard, the barrier layer is formed according to the size of each unit plate, thereby forming a groove at the interface portion between the unit plate barrier layers. Each unit plate can be cut along the groove.

[0319] In some embodiments, the manufacturing method further includes a step of cutting along the interface portion, wherein a groove is formed in the barrier layer, at least a portion of an organic film is formed in the groove, and the groove does not penetrate into the substrate. In some embodiments, a TFT layer is formed for each unit panel, 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. The groove at the interface portion is covered with an organic film, such as a polyimide or acrylamide, while a planarization film formed of, for example, polyimide or acrylamide is formed. This is to prevent cracking by allowing the organic film to absorb shocks generated when cutting each unit panel along the groove at the interface portion. That is, if the entire barrier layer is completely exposed without the organic film, the shock generated when cutting each unit panel along the groove at the interface portion is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, because the grooves at the interface portions between the barrier layers are covered with an organic film, and this organic film absorbs impacts that would otherwise be transferred to the barrier layers, each unit panel can be cut gently, and cracking in the barrier layers can be prevented. In one embodiment, the organic film covering the grooves at the interface portions is spaced apart from the planarization film. For example, if the organic film and the planarization film are connected as a single layer, then because external moisture may penetrate into the display unit through the planarization film and a portion of the residual organic film, the organic film and the planarization film are spaced apart from each other so that the organic film is separated from the display unit.

[0320] In some embodiments, a display unit is formed by forming light-emitting units, and an encapsulation layer is disposed on the display unit to cover it. Thus, after the motherboard is fully manufactured, a 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 separates from the substrate due to the difference in thermal expansion coefficients between the carrier substrate and the substrate.

[0321] In some embodiments, the motherboard is cut into unit panels. In some embodiments, the motherboard is cut along the interface portion between the unit panels using a cutting machine. In some embodiments, because the grooves at the interface portion along which the motherboard is cut are covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking can be prevented from occurring in the barrier layer during cutting.

[0322] In some embodiments, the method reduces the defect rate of the product and stabilizes its quality.

[0323] Another approach is an OLED display having: 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 the edge portion of the barrier layer.

[0324] Example

[0325] The following examples and embodiments further illustrate the features of the present invention. The materials, processing methods, and processing steps shown below can be appropriately modified without departing from the spirit of the invention. Therefore, the scope of the present invention should not be limited by the specific examples shown below. Furthermore, the evaluation of luminescence characteristics was performed using a source meter (Keithley 2400 series), a semiconductor parameter analyzer (Agilent Technologies Japan, Ltd. E5273A), an optical power meter (Newport Corporation 1930C), a spectrometer (Ocean Optics USB2000), a spectrophotometer (TOPCON CORPORATION SR-3), and a streak camera (Hamamatsu Photonics KK C4334).

[0326] (Synthetic Example 1) Synthesis of Compound 53

[0327] [Chemical Formula 28]

[0328]

[0329] 3-fluoro-4-nitrobenzyl nitrile (1.38 g, 10.0 mmol) and 1-fluorocarbazole (0.93 g, 5.0 mmol) were reacted in dimethylformamide (30 mL) under a nitrogen stream in the presence of potassium carbonate at 50 °C for 2.5 h. The reaction was then stopped at room temperature with water. The precipitated solid was filtered, and the filtrate was dissolved in ethyl acetate, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The reaction mixture was purified by silica gel column chromatography (ethyl acetate / hexane = 4 / 1) and reprecipitation (ethyl acetate / hexane) to give compound b (1.67 g, 99% yield) as a yellow solid.

[0330] 1 H NMR (400MHz, CDCl3, δ): 8.29 (d, J = 10Hz, 1H), 8.11 (d, J = 10Hz, 1H), 8.0 (s, 1H), 7.95 (d, J = 10Hz, 1H), 7.89 (d, J = 1 0Hz,1H),7.44(t,J=10Hz,1H),7.35(t,J=10Hz,1H),7.24(m,1H),7.12(t,J=10.0Hz,1H),7.07(t,J=10.0Hz,1H).

[0331] MS(ASAP): 331.08 (M+H) + ).Calcd for C 50 H 37 N5:332.17.

[0332] Compound b (1.38 g, 10.0 mmol), activated carbon (0.18 g, 15.0 mmol), and ferric chloride (0.135 g, 0.5 mmol) were dissolved in a mixed solvent of toluene (150 mL) and ethanol (150 mL) under a nitrogen stream, and an aqueous solution of hydrazine (4 mL, 125 mmol) was added. The reaction mixture was reacted at 90 °C for 2 hours, then cooled to room temperature and filtered through diatomaceous earth. The organic layer was separated by distillation under reduced pressure, followed by extraction with water and ethyl acetate. The mixture was dried over magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The filtrate was dissolved in ethyl acetate, dried over magnesium sulfate, and the solvent was distilled under reduced pressure. The reaction mixture was purified by silica gel column chromatography (ethyl acetate / hexane = 1 / 1) and reprecipitation (ethyl acetate / hexane) to give compound c (1.35 g, 90% yield) as a white solid.

[0333] 1H NMR (400MHz, CDCl3, δ): 8.21 (d, J = 10Hz, 1H), 8.02 (m, 1H), 7.40 (t, J = 10Hz, 1H), 7.26 ( d,J=10Hz,2H),7.18(m,3H),6.97(d,J=10Hz,1H),7.93(d,J=10.0Hz,1H),5.48(s,1H).

[0334] MS(ASAP): 301.10(M+H) + ).Calcd for C 50 H 37 N5:302.17.

[0335] [Chemical Formula 29]

[0336]

[0337] Compound c (0.75 g, 2.5 mmol), compound d (1.0 g, 2.17 mmol), tris(tert-butyl)phosphonium tetrafluoroborate (95 mg, 0.325 mmol), cesium carbonate (1.41 g, 4.34 mmol), and tris(dibenzylacetone) bispalladium (100 mg, 0.168 mmol) were reacted in toluene (200 mL) under a nitrogen stream at 130 °C for 24 h. The reaction was stopped by injecting the reaction solution into water at room temperature. After adding dichloromethane and separating the organic layer by extraction, the mixture was dried with magnesium sulfate, and the solvent was removed by vacuum distillation. The residue obtained was purified by column chromatography (toluene) to give compound e (0.7 g, 63%) as a yellow solid.

[0338] 1 H NMR (400MHz, CDCl3, δ): 9.46 (m, 3H), 9.32 (d, J = 10Hz, 1H), 8.87 (t, J = 10Hz, 3H), 8.54 (m, 1H), 8.46 (s, 1H), 8.25 (d, J = 10 Hz,1H),8.10(d,J=10.0Hz,1H),7.97(s,1H),7.88(m,8H),7.70(d,J=10.0Hz,1H),7.46(t,J=10.0Hz,1H),7.28(m,3H).

[0339] MS(ASAP): 679.22 (M+H) + ).Calcd for C 50 H 37 N5:680.35.

[0340] Compound e (0.7 g, 1.02 mmol) and sodium hydride (45 mg, 1.1 mmol) were reacted in dimethylformamide (50 mL) at 150 °C for 24 hours. The reaction solution was returned to room temperature, and the solid obtained after adding water was filtered off. The solid was washed and dissolved in toluene, dried over magnesium sulfate, and the solvent was concentrated by vacuum distillation. The residue was purified by column chromatography (toluene) and reprecipitation (chloroform / methanol) to give compound 53 (0.27 g, 57%) as a yellow solid.

[0341] MS(ASAP): 659.21(M+H) + ).Calcd for C 50 H 37 N5:660.09.

[0342] (Synthetic Example 2) Synthesis of Compound 3054

[0343] [Chemical Formula 30]

[0344]

[0345] Under a nitrogen stream, N-methyl-2-pyrrolidone (NMP, 900 mL) was added to a mixture of 2-(6-bromo-1-fluoro-9H-carbazole-9-yl)aminobenzene (19.0 g, 53.5 mmol) and copper cyanide (I) (14.4 g, 161 mmol), and the mixture was stirred at 170 °C for 48 h. The reaction solution was returned to room temperature, water was added, and the mixture was filtered. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to give compound f as a white solid of 12.0 g (39.8 mmol, yield 74%).

[0346] 1 H-NMR (400MHz, DMSO-d6): δ8.87(s,1H),8.21-8.17(m,1H),7.33-7.28(m,2H),7.25(t ,J=8Hz,1H),7.14(d,J=8Hz,1H),6.93(d,J=8Hz,1H),6.67(t,J=8Hz,1H),5.05(s,1H).

[0347] MS(ASAP): 302.48 (M+H) + ).Calcd for C 19 H 12 FN3:301.10.

[0348] [Chemical Formula 31]

[0349]

[0350] Under a nitrogen stream, potassium carbonate (8.3 g, 60 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.26 g, 0.4 mmol) were added to a solution of 4,5-dibromo-1,2-phenylenediamine (4.0 g, 15 mmol), 4-tert-butylphenylboronic acid (6.7 g, 38 mmol) in toluene (130 mL), ethanol (10 mL), and water (20 mL), and the mixture was stirred at 90 °C for 24 h. The reaction solution was returned to room temperature, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off and purified by silica gel column chromatography to give 4.5 g (12 mmol, 80% yield) of the compound as a white solid.

[0351] MS(ASAP): 373(M+H) + ).Calcd for C 26 H 32 N2:372.

[0352] Under a nitrogen stream, acetic acid (200 mL) was added to a mixture of compound g (5.00 g, 13.4 mmol) and 3-bromophenanthrene-9,10-dione (3.85 g, 13.4 mmol), and the mixture was stirred at 130 °C for 24 hours. The reaction solution was returned to room temperature, methanol was added, and the mixture was filtered. The crude product was washed with methanol and chloroform to give compound h (7.5 g, 12 mmol, 90% yield) as a white-yellow solid.

[0353] MS(ASAP): 623(M+H) + ).Calcd for C 40 H 35 BrN2:622.

[0354] Under a nitrogen stream, tri-tert-butylphosphine tetrafluoroborate (0.56 g, 1.2 mmol), cesium carbonate (4.0 g, 12 mmol), and tris(dibenzylacetone)dipalladium(0) (0.56 g, 0.61 mmol) were added to a toluene (160 mL) solution of compound h (3.8 g, 6.1 mmol) and compound f (2.0 g, 6.7 mmol), and the mixture was stirred at 120 °C for 15 hours. The reaction solution was returned to room temperature, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off and purified by silica gel column chromatography (hexane:toluene = 3:7) to give compound i (1.0 g, 1.2 mmol, 19% yield) as a yellow solid.

[0355] 1H-NMR (400MHz, CDCl3): δ9.390 (dd, J=7.2Hz, 3.2Hz, 2H), 9.187 (d, J=8.8Hz, 1H), 8.418(s,1H),8.335-8.300(m,3H),8.030(s,1H),7.903(dd,J=8.0Hz,1.2Hz,1H) ,7.760-7.718(m,3H),7.695(dd,J=8.0Hz,1.2Hz,1H),7.557(td,J=8.8Hz,1.6Hz ,1H),7.450(d,J=7.6Hz,1H),7.331-7.212(m,13H),5.705(s,1H),1.334(s,18H).

[0356] MS(ASAP): 844.30(M+H) + ).Calcd for C 59 H 46 FN5:843.37.

[0357] ASAP MS spectral analysis: C 59 H 46 FN5: Theoretical value 843.37, observed value 844.30 [M+H] + ]

[0358] A mixture of 50 mL of NaH (28 mg, 0.69 mmol) in N,N-dimethylformamide and compound i (0.53 g, 0.63 mmol) was stirred at 150 °C for 15 hours. The mixture was then cooled to room temperature, quenched with water, and the precipitated solid was filtered off and washed with methanol. The obtained solid was purified by silica gel column chromatography to give compound 3054 (0.45 g, 0.55 mmol, 87% yield).

[0359] 1H-NMR (400MHz, CDCl3): δ9.725(d,J=8.0Hz,1H),9.484(d,J=8.8Hz,1H),8.635(s,1H), 8.524(d,J=9.2Hz,1H),8.418(d,J=3.2Hz,2H),8.353(s,1H),8.084(d,J=9.2Hz,1H),7 .833-7.755(m,4H),7.722(d,J=8.4Hz,1H),7.336(d,J=8.4Hz,4H),7.275-7.259(m,5H ),6.902-6.746(m,3H),6.304(d,J=8.4Hz,1H),5.946(d,J=7.6Hz,1H),1.352(s,18H).

[0360] MS(ASAP): 824.52 (M+H) + ).Calcd for C 59 H 45 N5:823.37.

[0361] (Synthetic Example 2) Synthesis of Compound 17254

[0362] [Chemical Formula 32]

[0363]

[0364] Compound J (1.83 g, 5.74 mmol), compound K (1.85 g, 5.74 mmol), triethylamine (3.4 mL), acetic acid (100 mL), and ethanol (25 mL) were stirred at 130 °C for 6 hours under a nitrogen stream. After the mixture was cooled to room temperature, the precipitated solid was filtered off. The residue was washed with methanol to give compound l (2.25 g, 3.95 mmol, 70% yield).

[0365] MS(ASAP): 570. Calculated for C 36 H 31 BrN2:570.

[0366] [Chemical Formula 33]

[0367]

[0368] Under a nitrogen stream, Pd2dba3 (0.16 g, 0.17 mmol) was added to a toluene (300 mL) solution of compound l (2.0 g, 3.4 mmol), compound m (1.2 g, 3.8 mmol), tBu3PHBF4 (0.1 g, 0.34 mmol), and tBuONa (0.8 g, 6.8 mmol), and the mixture was heated under reflux overnight. After the reaction solution was returned to room temperature, it was quenched with water and extracted with dichloromethane. The solvent was distilled using a still, and the solution was purified by silica gel column chromatography to obtain compound n (2.2 g, 2.8 mmol, 82% yield).

[0369] MS(ASAP): 791. Calculated for C 55 H 42 FN5:791.

[0370] [Chemical Formula 34]

[0371]

[0372] Under a nitrogen stream, NaH (0.3 g, 7.6 mmol) was added to a solution of compound n (2.0 g, 2.5 mmol) in N,N-dimethylformamide (200 mL), and the mixture was stirred at 150 °C for 2 hours. After the reaction solution was returned to room temperature, it was quenched with water, and the precipitated solid was filtered off. The residue was washed with methanol and further purified by silica gel column chromatography to obtain compound 17254 (0.8 g, 1.03 mmol, 42% yield).

[0373] MS(ASAP): 771. Calculated for C 55 H 41 N5:771.

[0374] (Example 2) Preparation and Evaluation of Thin Films

[0375] Vacuum evaporation deposition was performed at a vacuum level of less than 1×10⁻⁶. -3 Compound 53 was deposited on a quartz substrate under Pa conditions to form a thin film of 100 nm thickness, consisting solely of compound 53, and was designated as the pure thin film of Example 1. In contrast, vacuum deposition was performed at a vacuum level of less than 1 × 10⁻⁶ Pa. -3Compound 53 and mCBP were deposited onto a quartz substrate from different evaporation sources under Pa conditions to form a 100 nm thick film with a compound 53 concentration of 20% by weight, which was designated as the doped film of Example 1. In the doped film of Example 1, immediate fluorescence and delayed fluorescence, which emitted fluorescence at a peak emission wavelength of 594 nm, were observed. The lifetime τ2 of the delayed fluorescence was 5.1 μs, confirming excellent properties.

[0376] By replacing compound 53 with compounds 3054, 17254, and other compounds represented by general formula (1), the properties of each pure film and each doped film can be confirmed. The compounds represented by general formula (1) achieve high PLQY in highly doped films. Therefore, by using them in organic light-emitting elements, it is possible to provide elements with high luminous efficiency and good durability.

[0377] (Example 2) Fabrication and Evaluation of Organic Electroluminescent Element

[0378] Vacuum deposition was performed using a vacuum evaporation method with a vacuum degree of 1×10⁻⁶. -6 Pa stacked thin films on a glass substrate having an anode formed of indium / tin oxide (ITO) with a film thickness of 100 nm. First, a 10 nm thick HATCN layer was formed on the ITO, followed by a 30 nm thick NPD layer. Next, a 10 nm thick TrisPCz layer was formed on top, followed by a 5 nm thick Host1 layer. Then, compound 53 and Host1 were co-deposited from different evaporation sources to form a 30 nm thick light-emitting layer. At this time, the concentration of compound 53 was set to 35% by weight. A 10 nm thick SF3TRZ layer was formed on top, and SF3TRZ and Liq were co-deposited from different evaporation sources to further form a 30 nm thick layer. At this time, the SF3TRZ:Liq (weight ratio) was set to 7:3. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm, thereby forming a cathode. Through the above steps, the organic electroluminescent device of Example 1 was fabricated.

[0379] Furthermore, by using compound 3054, compound 17254, and other compounds represented by general formula (1) instead of compound 53, and by fabricating each organic electroluminescent element through the same steps, the effect can be confirmed.

[0380] [Chemical Formula 35]

[0381]

[0382] Symbol Explanation

[0383] 1-Substrate, 2-Anode, 3-Hole injection layer, 4-Hole transport layer, 5-Light emission layer, 6-Electron transport layer, 7-Cathode.

Claims

1. A compound represented by any one of the following general formulas (4a) to (4c), General formula (4a) General formula (4b) General formula (4c) In general formulas (4a) to (4c), R 21 ~R 28 R 41 ~R 44 R 51 R 52 R 61 ~R 68 Each of the following can be independently represented as a hydrogen atom, a deuterium atom, or a D atom, where, R 21 ~R 28 One or two of them are D, R 41 ~R 44 R 51 and R 52 One or two of them are D, R 61 ~R 68 One or two of them are D, where D represents the group shown in the following general formula (2), and R 29 ~R 36 R represents, independently, a hydrogen atom, a deuterium atom, or an alkyl group selected from 1 to 4 carbon atoms. 45 ~R 50 R 69 ~R 72 Each of these groups can independently represent a hydrogen atom, a deuterium atom, or one or more groups selected from the group consisting of alkyl groups having 1 to 4 carbon atoms and aryl groups having 6 to 10 cyclic skeletons. General formula (2) [Chemical Formula 2] In general formula (2), R 5 ~R 15 Each of these elements independently represents a hydrogen atom, a deuterium atom, or a substituent, wherein the substituent is a cyano group or a group composed of one or more groups selected from the group consisting of a cyano group and an alkyl group having 1 to 20 carbon atoms, and the ring skeleton constitutes an aryl group having 6 to 10 atoms, and X represents a single bond. Indicates the bonding location.

2. The application of the compound of claim 1 as a luminescent material.

3. A membrane comprising the compound of claim 1.

4. An organic semiconductor device comprising the compound of claim 1.

5. An organic light-emitting element comprising the compound of claim 1.

6. The organic light-emitting element according to claim 5, wherein, The element has a layer containing the compound, and the layer further contains a host material.

7. The organic light-emitting element according to claim 6, wherein, In addition to the host material, the layer containing the compound also contains a delayed fluorescence material, the lowest excitation singlet energy of which is lower than that of the host material but higher than that of the compound.

8. The organic light-emitting element according to claim 5 or 6, wherein, The element has a layer containing the compound, and the layer further contains a luminescent material having a structure different from that of the compound.

9. The organic light-emitting element according to any one of claims 5 to 7, wherein, The amount of light emitted from the compound is the largest among the materials contained in the element.

10. The organic light-emitting element according to claim 8, wherein, The amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound.

11. The organic light-emitting element according to any one of claims 5 to 7, wherein it emits delayed fluorescence.

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