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

Abstract

In the present invention, compound having excellent light emission characteristics was developed. The compound is represented by a general formula. In the formula, at least one of R1 to R4 and R1' to R4' represents a donor group. Ar1 represents a benzene ring in which two five-membered rings containing a hetero atom as a ring skeleton constituent atom are condensed, or represents a five-membered ring in which a six-membered ring is condensed.

Description

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

[0001] The present invention relates to a compound having good light-emitting properties, and also to a light-emitting material and an organic light-emitting device using the compound.

[0002] Organic light-emitting devices are light-emitting devices that use organic materials, can be manufactured by coating, and do not use rare elements, which has attracted attention in recent years. Organic electroluminescent devices (organic EL devices) in particular have the advantage of being lightweight and flexible because they emit light spontaneously and do not require a backlight. They also have the characteristics of fast response and high visibility, making them promising next-generation light sources. For this reason, active research is being conducted into the development of materials useful for organic light-emitting devices, including organic electroluminescent devices. Research on light-emitting materials is particularly active (e.g., Non-Patent Document 1). Among these, light-emitting materials having an indolophenazine skeleton have been proposed (see Patent Document 1).

[0003] Chem. Soc. Rev.,2017,46,915

[0004] WO2022 / 168956A1

[0005] On the other hand, there is still room for improvement in the light-emitting properties of organic light-emitting devices, and further improvements in the light-emitting properties are required. Therefore, the present inventors have conducted extensive research with the aim of developing a novel compound that contributes to improving the light-emitting properties of organic light-emitting devices.

[0006] As a result of intensive research, the present inventors have found that a compound in which a group having a characteristic structure is bonded to a specific skeleton is a compound useful for a light-emitting device. The present invention has been proposed based on this finding and has the following configuration.

[0007] [1] A compound represented by the following general formula (1): [In general formula (1), R １ ~R ４ and R １’ ~R ４’R each independently represents a hydrogen atom, a deuterium atom, or a substituent, but at least one represents a donor group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ may be bonded to each other to form a cyclic structure. 1 represents a 5-membered ring to which a 6-membered ring is fused, or represents a benzene ring to which two 5-membered rings containing a heteroatom as a ring skeleton-constituting atom are fused.] [2] The compound according to [1], wherein the donor group is a heteroaryl group bonded via a nitrogen atom. [3] R １ ~R ４ and R １’ ~R ４’ The compound according to [1], wherein at least one of the groups represents a group represented by the following general formula (2): [In the general formula (2), R ５ ~R １５ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 １５may be bonded to each other to form a cyclic structure. X represents a single bond, an oxygen atom, or a sulfur atom. * represents a bonding position.] [4] The compound according to any one of [1] to [3], wherein the heteroatom is an oxygen atom or a sulfur atom. [5] The compound according to any one of [1] to [3], wherein the heteroatom is a nitrogen atom. [6] The compound according to any one of [1] to [5], represented by the following general formula (3): General formula (3) [In the general formula (3), R １ ~R ４ and R １’ ~R ４’ Each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that at least one represents a donor group. 1 is O, S or N-Ar ２ Represents Ar. ２ represents a substituted or unsubstituted aryl group. １ is N or C-R ２１ represents Y ２ is N or C-R ２２ represents Y ３ is N or C-R ２３ represents Y ４ is N or C-R ２４ where Y １ ~Y ４ The number of N's in the R ２１ ~R ２４ Each of X independently represents a hydrogen atom, a deuterium atom, or a substituent. １ is N-Ar ２ and Y ４ is C-R ２４ When Ar ２ The carbon atom at the ortho position in the aryl group represented by is Y ４ may be bonded to the carbon atom of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ may be bonded to each other to form a cyclic structure.] [7] The compound according to any one of [1] to [3], represented by the following general formula (4a) or (4b): General formula (4a): General formula (4b) [In general formulas (4a) and (4b), R １ ~R ４ and R １’ ~R ４’ Each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that at least one represents a donor group. ２ ~X ５ are each independently O, S or N-Ar ２ Represents Ar. ２ represents a substituted or unsubstituted aryl group. ３１ ~R ３８ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ３１ and R ３２ , R ３３ and R ３４ , R ３５ and R ３６ , R ３７ and R ３８ may be bonded to each other to form a cyclic structure.] [8] R ３１ and R ３２ , R ３３ and R ３４ , R ３５ and R ３６ , R ３７ and R ３８are bonded to each other to form an optionally substituted benzene ring. [9] A light-emitting material comprising the compound according to any one of [1] to [8].

[10] A film comprising the compound according to any one of [1] to [8].

[11] An organic semiconductor device comprising the compound according to any one of [1] to [8].

[12] An organic light-emitting device comprising the compound according to any one of [1] to [8].

[13] The organic light-emitting device according to

[12] , wherein the device has a layer comprising the compound, and the layer also contains a host material.

[14] The organic light-emitting device according to

[13] , wherein the layer comprising the compound also contains a delayed fluorescent material in addition to the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

[15] The organic light-emitting device according to

[12] , wherein the device has a layer comprising the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.

[16] The organic light-emitting device according to any one of

[12] to

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

[17] The organic light-emitting element according to

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

[18] The organic light-emitting element according to any one of

[12] to

[17] , which emits delayed fluorescence.

[0008] The compound of the present invention has a short delayed fluorescence lifetime and high orientation, making it useful for light-emitting devices. The compound of the present invention can be used as a light-emitting material, and an organic light-emitting device can be manufactured using the compound of the present invention. The organic light-emitting device using the compound of the present invention has excellent light-emitting properties.

[0009] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the representation of an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted location. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

[0010] [Compound Represented by General Formula (1)] The compound of the present invention is a compound represented by the following general formula (1).

[0011] General formula (1)

[0012] In general formula (1), R １ ~R ４ and R １’ ~R ４’ At least one of R represents a donor group. １ ~R ４ and R １’ ~R ４’The donor groups that can be used do not include substituted or unsubstituted aryl groups. The "donor group" can be selected from groups with a negative Hammett σp value. The "acceptor group" can be selected from groups with a positive Hammett σp value. The Hammett σp value was proposed by L. P. Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, it is the constant (σp) specific to the substituent in the para-substituted benzene derivative, which holds between the substituent and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp. In the above equation, k0 is the rate constant of the benzene derivative without a substituent, k is the rate constant of the benzene derivative substituted with a substituent, K0 is the equilibrium constant of the benzene derivative without a substituent, K is the equilibrium constant of the benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, reference can be made to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0013] The donor group in the present invention preferably has a σp of −0.3 or less, and may be −0.5 or less, or may be −0.7 or less, for example, selected from the range of −0.9 or less, or selected from the range of −1.1 or less.

[0014] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. Here, the two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0015] As the donor group in the present invention, it is preferable to use a group represented by the following general formula (2):

[0016] In general formula (2), X represents a single bond, an oxygen atom, or a sulfur atom. In a preferred embodiment of the present invention, X is a single bond. In a preferred embodiment of the present invention, X is an oxygen atom. X may be an oxygen atom or a sulfur atom. In general formula (2), * represents a bonding position. In general formula (2), R ５ ~R １５each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent refers to one group selected from the group consisting of an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a cyano group, or a group combining two or more of these. For example, the substituent may be a cyano group, or an aryl group optionally substituted with one group selected from the group consisting of a cyano group and an alkyl group, or a group combining two or more of these. R ５ ~R １５ When two or more of R represent substituents, the two or more substituents may be the same or different. ５ ~R １５ Of these, 6 to 11 are preferably hydrogen atoms or deuterium atoms, and for example, 8 to 11 may be hydrogen atoms or deuterium atoms. ５ ~R １５ may all be hydrogen atoms or deuterium atoms. Alternatively, 8 to 10 may be hydrogen atoms or deuterium atoms. For example, 8 may be hydrogen atoms or deuterium atoms, 9 may be hydrogen atoms or deuterium atoms, or 10 may be hydrogen atoms or deuterium atoms. 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 １５may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic ring or a heteroaromatic ring is preferred. An example of an aromatic ring is a benzene ring. The heteroaromatic ring refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be adopted as the heteroaromatic ring. In a preferred embodiment of the present 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 referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, or may be substituted with a substituent selected from Substituent Group B, or may be substituted with a substituent selected from Substituent Group C, or may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E. 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 １５Among these, it is preferable that 0 to 2 pairs are bonded to each other to form a cyclic structure, and it is more preferable that 0 or 1 pair are bonded to each other to form a cyclic structure. One or more pairs may be bonded to each other to form a cyclic structure, for example, 1 or 2 pairs may be bonded to each other to form a cyclic structure. Alternatively, only one pair may be bonded to each other to form a cyclic structure. Alternatively, 0 pairs may be bonded to each other to form a cyclic structure.

[0017] Specific examples of the group represented by general formula (2) are shown below. The donor group that can be employed in general formula (1) may be a group containing the structure shown below. For example, it may be a phenyl group substituted with a group having the structure shown below, or a group in which a ring (e.g., a benzene ring) is fused to the benzene ring in the structure shown below. The donor group that can be employed in the present invention should not be construed as being limited by the specific examples shown below. In the specific examples shown below, the wavy line indicates the bonding position.

[0018] The compounds D1 to D136 above in which all hydrogen atoms have been replaced with deuterium atoms are disclosed as D137 to D272.

[0019] As the donor group in the present invention, a group represented by the following general formula (a) can also be used.

[0020] In the general formula (a), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N. Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. １４ and R １５ , R １５ and R１６ , R １６ and R １７ may be bonded to each other to form a cyclic structure.

[0021] Z １ ~Z ４ In one embodiment of the present invention, the number of N's is preferably 0 to 3, more preferably 0 to 2. １ ~Z ４ In one aspect of the present invention, the number of N is 1. １ ~Z ４ The number of N is 0. １４ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. １４ ~R １７ When two or more of R represent substituents, the two or more substituents may be the same or different. １４ ~R １７ It is preferred that 0 to 2 of these be substituents. For example, one may be a substituent, or none may be a substituent (R １４ ~R １７ may be a hydrogen atom or a deuterium atom). １４ and R １５ , R １５ and R １６ , R １６ and R １７may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic ring or a heteroaromatic ring is preferred. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７ In one embodiment of the present invention, a pair of R １４ and R １５ , R １５ and R １６ , R １６ and R １７ are not bonded to each other to form a ring structure.

[0022] In the general formula (a), Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is C, and Ar ５ is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. ５ An example of the aromatic ring that can be used by Ar is a benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. ５ The heteroaromatic ring that can be adopted by Z is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the heteroaromatic ring. In one embodiment of the present invention, Z ５ is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. ５ is N, and the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, may be substituted with a substituent selected from Substituent Group B, may be substituted with a substituent selected from Substituent Group C, may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E.

[0023] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0024] In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ may be bonded to each other to form a cyclic structure. １ ~Z ４ , R １４ ~R １７ For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. ６ ~Z ９ , R １８ ~R ２１ is Z in general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order to Z in general formula (a). １ ~Z ４ , R １４ ~R １７ In one aspect of the present invention, Z １ ~Z ４ , Z ６ ~Z ９In one embodiment of the present invention, the number of N's is preferably 0 to 2, and more preferably 0 or 1. １ ~Z ４ , Z ６ ~Z ９ In a preferred embodiment of the present invention, the number of N groups is 1. １ ~Z ４ , Z ６ ~Z ９ The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0025] In one embodiment of the present invention, the donor group is a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. One or more rings may be further fused to the two benzene rings constituting the carbazol-9-yl group. In one embodiment of the present invention, the donor group may be substituted with a group selected from Substituent Group E, or may be a carbazol-9-yl group to which one or more rings may be fused. When a carbazol-9-yl group not fused with a ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.

[0026] In one embodiment of the present invention, the donor group is a carbazol-9-yl group to which one or more rings are fused, and this will be referred to hereinafter as a "ring-fused carbazol-9-yl group." The ring-fused carbazol-9-yl group may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from Substituent Group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted with an aryl group which may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.

[0027] The total number of fused rings in the ring-fused carbazole-9-yl group is 4 or more, preferably 5 or more, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring is 5. Note that the number of rings here includes the number of fused carbazole rings (i.e., 3).

[0028] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring formed by further condensing these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In one embodiment of the present invention, the fused ring 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 nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from Substituent Group E (excluding cases where the substituent is only a deuterium atom), and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In one embodiment of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group to which a benzothieno structure is fused, for example, two or more carbazol-9-yl groups.

[0029] As the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzofuro[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzofuro[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzofuro[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzofuro[3,2-c]carbazol-5-yl group can be used. Furthermore, as the ring-fused carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[3,2-a]carbazol-12-yl group, a substituted or unsubstituted benzothieno[2,3-b]carbazol-7-yl group, a substituted or unsubstituted benzothieno[3,2-b]carbazol-11-yl group, a substituted or unsubstituted benzothieno[2,3-c]carbazol-8-yl group, or a substituted or unsubstituted benzothieno[3,2-c]carbazol-5-yl group can also be used. Furthermore, examples of the ring-fused carbazol-9-yl group include a substituted or unsubstituted 11-phenylindolo[2,3-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-a]carbazol-12-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-b]carbazol-7-yl group, a substituted or unsubstituted 5-phenylindolo[3,2-b]carbazol-11-yl group, a substituted or unsubstituted 5-phenylindolo[2,3-c]carbazol-8-yl group, and a substituted or unsubstituted 12-phenylindolo[3,2-a]carbazol-5-yl group.

[0030] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0031] Specific examples of the group represented by general formula (a) are shown below. The donor group that can be employed in general formula (1) may be a group containing the following structure. For example, it may be a phenyl group substituted with a group having the following structure, or a group in which a ring (e.g., a benzene ring) is fused to the benzene ring in the following structure. The donor group that can be employed in the present invention is not limited to the following specific examples. In the following specific examples, Ph represents a phenyl group (C ６ H ５ ) and * indicates the bond position. Methyl groups are omitted, so for example, D274 has one methyl group. However, deuterated methyl groups are ３ Also, C ６ D ５ represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0032] All hydrogen atoms present in the above D273 to D760 are substituted with deuterium atoms and are disclosed as D1047 to D1534.

[0033] In one embodiment of the present invention, the donor groups are selected from the group consisting of D1 to D1534. In a preferred embodiment of the present invention, at least one of the donor groups is selected from the group consisting of D1 to D272. In a preferred embodiment of the present invention, all of the donor groups are selected from the group consisting of D1 to D272. In one embodiment of the present invention, at least one of the donor groups is selected from the group consisting of D1 to D272 and at least one of the donor groups is selected from the group consisting of D273 to D1462. In one embodiment of the present invention, at least one or all of the donor groups are selected from the group consisting of D1 to D136. In one embodiment of the present invention, at least one or all of the donor groups are selected from the group consisting of D137 to D272. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D1, D9 to D23, D45, D50, D89, D111, D134 to D137, D145 to D159, D181, D186, D225, D247, and D270 to D272. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D2 to D8, D24 to D44, D46 to D49, D51 to D88, D90 to D110, D112 to D133, D138 to D144, D160 to D180, D182 to D185, D187 to D224, D226 to D246, and D248 to D269. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D273 to D1534. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D273 to D288, D761 to D772. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D289 to D348, D384 to D419, D486 to D599, D660 to D754, D773 to D820, D851 to D978, and D1029 to D1035. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D349 to D354, D420 to D485, D600 to D659, D756 to D760, D821 to D826, D979 to D1028, and D1037 to D1046. In one embodiment of the invention, at least one or all of the donor groups are selected from the group consisting of D355 to D383 and D827 to D850.

[0034] In general formula (1), R １ ~R ４ and R １’ ~R ４’ At least one of these represents a donor group, but there are no particular limitations on anything other than the donor group. Preferably, it is selected from the group consisting of a hydrogen atom, a deuterium atom, a group having a cyano group, a group bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom, and a substituted or unsubstituted aryl group. The "group having a cyano group" referred to here may be a cyano group or a group to which a cyano group is bonded via a linking group. The linking group is preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. It may also be a group in which a substituted or unsubstituted aryl group is linked to a substituted or unsubstituted heteroaryl group. Examples of the linking group include a phenyl group having at least one (preferably 1 to 3, e.g., 1, e.g., 2) cyano group bonded to the phenyl group, and a heteroaromatic ring group having at least one phenyl group bonded to the phenyl group (preferably a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom, such as a pyridine ring, a pyrimidine ring, or a triazine ring). The above-mentioned "group bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom" is preferably a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted triazinyl group. The above-mentioned "group having a cyano group" and "group bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom" are acceptor groups having a negative Hammett σp value. The substituents that may be contained in these groups may be selected from Substituent Group A, Substituent Group B, Substituent Group C, or Substituent Group D, but are preferably selected from Substituent Group E. In the following, R １ ~R ４ and R １’ ~R ４’Specific examples of "a group having a cyano group" and "a group bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom" that can be adopted are shown below. However, the groups that can be adopted in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position. Also, methyl groups are omitted. For example, A16 is a group having two 4-methylphenyl groups.

[0035] All hydrogen atoms in A2 to A9 and A11 to A34 are replaced with deuterium atoms and are disclosed as A35 to A66.

[0036] R in general formula (1) １ ~R ４ and R １’ ~R ４’ may be a substituted or unsubstituted aryl group. Preferably, it is a substituted or unsubstituted phenyl group, a substituted or unsubstituted 1-naphthyl group, or a substituted or unsubstituted 2-naphthyl group. The hydrogen atom of the aryl group may be substituted with a deuterium atom, or may be substituted with a substituent. Examples of the substituent include an aryl group, an alkyl group, and a group combining these. In the following, R １ ~R ４ and R １’ ~R ４’ Specific examples of substituted or unsubstituted aryl groups that can be used are shown below. However, the aryl groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position. Also, methyl groups are omitted. For example, N4 is a 4-methylphenyl group.

[0037] The above N1 to N11 are disclosed as N12 to N22, in which all hydrogen atoms present in the N1 to N11 are replaced with deuterium atoms.

[0038] R in general formula (1) １ ~R ４ and R １’ ~R ４’The number of substituents is preferably 1 to 4, for example 1 to 3, for example 1, for example 2. In one embodiment of the present invention, at least R ２ is a substituent. In one embodiment of the present invention, at least R ３ is a substituent. In one aspect of the present invention, R ２ , R ３ , R ４ , R ２’ , R ３’ , R ４’ In one aspect of the invention, only 1 to 4 of R ２ , R ３ , R ２’ , R ３’ In one aspect of the invention, only 1 to 4 of R ２ and R ２’ In one aspect of the invention, only one or two of R ３ and R ３’ Only one or two of the groups are substituents. For example, R ３ is the only substituent. For example, R ３ and R ３’ is the only substituent. In one aspect of the invention, at least R ２ , R ３ , R ４ is a substituent. When there are two or more substituents, the substituents may be the same or different. At least one is preferably a group represented by general formula (2) or general formula (a), and more preferably a group represented by general formula (2). When there are two or more substituents, all of the substituents may be groups represented by general formula (2), or some may be groups represented by general formula (2) and the rest may be groups represented by general formula (a), or some may be groups represented by general formula (2) and the rest may be substituted or unsubstituted aryl groups, or some may be groups represented by general formula (2) and the rest may be groups having a cyano group, or some may be groups represented by general formula (2) and the rest may be groups bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom. In a preferred embodiment of the present invention, R １ ~R ４ and R １’ ~R ４’Among R ３ is a donor group, for example, a group represented by general formula (2), for example, a group represented by general formula (a). In a preferred embodiment of the present invention, R １ ~R ４ and R １’ ~R ４’ Among R ２ is a donor group, for example, a group represented by general formula (2), for example, a group represented by general formula (a). ２ and R ３ One of R is a donor group, and the other is, for example, a hydrogen atom or a deuterium atom, for example, a group having a cyano group, for example, a group bonded via a heteroaromatic ring having a nitrogen atom as a ring skeleton-constituting atom. ２ is a donor group, and R ３’ is a group having a cyano group. ３ and R ３’ are donor groups, for example, both are groups represented by general formula (2), for example, both are groups represented by general formula (a). ３ and R ３’ is a donor group, and R ３’ is a group having a cyano group. ２ and R ３ is a donor group, and R ３’ is a group having a cyano group. ２ and R ３ and R ４ is a donor group. In one embodiment of the present invention, R ２ and R ３ and R ２’ and R ３’ is a donor group. For example, R ２ and R ３ and R ２’ and R ３’ are the same donor groups, e.g., R ２ and R ２’ is a common first donor group, and R ３ and R ３’ is a common second donor group. In one aspect of the present invention, R ３ and R ３’is a donor group, and R ２ and R ２’ is a substituted or unsubstituted aryl group.

[0039] R in general formula (1) １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ may be bonded to each other to form a cyclic structure. The cyclic structure formed and its preferred range are described in detail in R ５ and R ６ In one embodiment of the present invention, the cyclic structure formed by bonding R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ In one embodiment of the present invention, at least one pair of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ２１ and R２２ , R ２２ and R ２３ , R ２３ and R ２４ None of them form a cyclic structure.

[0040] In the general formula (1), Ar 1 represents a 5-membered ring fused with a 6-membered ring, or a benzene ring fused with two 5-membered rings containing a heteroatom as a ring skeleton-constituting atom. 1 When Ar represents a 5-membered ring fused with a 6-membered ring, the 5-membered ring preferably contains a heteroatom as a ring skeleton-constituting atom, and is more preferably a heteroaromatic ring. Examples include a furan ring, a thiophene ring, and a pyrrole ring. Furthermore, the 6-membered ring is preferably a benzene ring or a ring containing a nitrogen atom as a ring skeleton-constituting atom. Examples include a benzene ring and a pyridine ring. 1 When is a 5-membered ring fused with a 6-membered ring, the compound represented by general formula (1) is preferably a compound represented by the following general formula (3):

[0041] In general formula (3), R １ ~R ４ and R １’ ~R ４’ R each independently represents a hydrogen atom, a deuterium atom, or a substituent, but at least one represents a donor group. １ ~R ４ and R １’ ~R ４’ For details and preferred ranges of X in general formula (3), the corresponding description of general formula (1) can be referred to. 1 is O, S or N-Ar ２ In one aspect of the present invention, X 1 is O or S. In one aspect of the invention, X 1 is N-Ar ２ Ar ２ represents a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected from Substituent Group D, or may be selected from Substituent Group E, for example. In one embodiment of the present invention, Ar ２is a phenyl group which may be substituted with an alkyl group or a deuterium atom, for example, a phenyl group which may be substituted with a deuterium atom. １ is N or C-R ２１ represents Y ２ is N or C-R ２２ represents Y ３ is N or C-R ２３ represents Y ４ is N or C-R ２４ where Y １ ~Y ４ The number of N's among Y is 0 or 1. In one aspect of the present invention, the number of N's is 0. In one aspect of the present invention, the number of N's is 1. For example, Y １ is N. For example, Y ２ is N. For example, Y ３ is N. For example, Y ４ is N. R ２１ ~R ２４ each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent is one group selected from the group consisting of an alkyl group, an aryl group, a cyano group, and a pyridyl group, or a combination of two or more groups. For example, the substituent is an aryl group which may be substituted with a deuterium atom, an alkyl group, or a cyano group. For example, the substituent is a cyano group. For example, the substituent is an alkyl group which may be substituted with a deuterium atom, an aryl group, or a cyano group. In one embodiment of the present invention, R ２１ ~R ２４ are each independently a hydrogen atom or a deuterium atom. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’, R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ may be bonded to each other to form a cyclic structure. For the cyclic structure formed, the description of the corresponding cyclic structure in general formula (1) can be referred to. Y in general formula (3) ４ is C-R ２４ When Ar ２ The carbon atom at the ortho position in the aryl group represented by is Y ４ The compound having such a bond is resistant to deterioration and has excellent durability. In this case, the compound preferably has a structure represented by the following general formula (3a):

[0042] R in general formula (3a) １ ~R ４ , R １’ ~R ４’ , R ２１ ~R ２３ For the definition and explanation of R in general formula (3a), reference can be made to the corresponding description of general formula (3). ２５ ~R ２８ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２５ ~R ２８ The description and preferred range of R in general formula (3) ２１ ~R ２４ Reference can be made to the corresponding description in

[0043] Ar in general formula (1) 1 When Ar represents a benzene ring formed by condensing two five-membered rings containing heteroatoms as ring skeleton-constituting atoms, examples of the heteroatoms include oxygen atoms, sulfur atoms, and nitrogen atoms. The five-membered ring containing heteroatoms as ring skeleton-constituting atoms is preferably a heteroaromatic ring. Examples of the five-membered ring containing heteroatoms as ring skeleton-constituting atoms include a furan ring, a thiophene ring, and a pyrrole ring. 1 represents a benzene ring in which two 5-membered rings containing heteroatoms are fused as ring skeleton-constituting atoms, the compound represented by general formula (1) is preferably a compound represented by the following general formula (4a) or (4b): General formula (4b)

[0044] In general formulas (4a) and (4b), R １ ~R ４ and R １’ ~R ４’ R each independently represents a hydrogen atom, a deuterium atom, or a substituent, but at least one represents a donor group. １ ~R ４ and R １’ ~R ４’ For details and preferred ranges of X in general formula (4a) and (4b), the corresponding description of general formula (1) can be referred to. ２ ~X ５ are each independently O, S or N-Ar ２ Represents Ar. ２ represents a substituted or unsubstituted aryl group. ２ For details and preferred ranges of X, please refer to the corresponding description of general formula (2). ２ and X ３ In one aspect of the present invention, X ２ and X ３ is O. In one aspect of the present invention, X ２ and X ３ is S. In one aspect of the invention, X ２ and X ３ is N-Ar ２ X ４ and X ５ In one aspect of the present invention, X ４ and X ５ is O. In one aspect of the present invention, X ４ and X ５ is S. In one aspect of the invention, X ４ and X ５ is N-Ar ２ R in general formulas (4a) and (4b) ３１ ~R ３８each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the substituent is one group selected from the group consisting of an alkyl group, an aryl group, a cyano group, and a pyridyl group, or a combination of two or more groups. For example, the substituent is an aryl group which may be substituted with a deuterium atom, an alkyl group, or a cyano group. For example, the substituent is a cyano group. For example, the substituent is an alkyl group which may be substituted with a deuterium atom, an aryl group, or a cyano group. In one embodiment of the present invention, R ３１ ~R ３８ are each independently a hydrogen atom or a deuterium atom. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ３１ and R ３２ , R ３３ and R ３４ , R ３５ and R ３６ , R ３７ and R ３８ may be bonded to each other to form a cyclic structure. For the cyclic structure to be formed, reference can be made to the description of the corresponding cyclic structure in general formula (1).

[0045] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 7 below. However, the compounds represented by general formula (1) that can be used in the present invention are not limited to these specific examples. In Table 1, among the compounds represented by general formula (1), Ar １ is a furan ring fused with a benzene ring, and R １ , R ２ , R ４ , R １’ ~R ４’is a hydrogen atom. That is, R of the compound having the following structure is ３ The structures of compounds 1 to 1534 are identified by listing them in order in Table 1.

[0046] In Table 2, the structures of compounds 1 to 1474652 are shown as variations of the structures shown in Table 1. In Table 2, Y in general formula (3) １ ~Y ４ , X １ , R １ ~R ４ , R １’ ~R ４’ The columns of compounds 1 to 1534 in Table 2 identify the structures by showing Y １ ~Y ４ is fixed to CH, and X １ is fixed to O, and R １ , R ２ , R ４ , R １’ ~R ４’ is fixed at H, and R ３ In other words, the column of Compounds 1 to 1534 in Table 2 shows the structures of Compounds 1 to 1534 in Table 1 all together in one column. The column of Compounds 1535 to 102778 in Table 2 shows the structures of Compounds 1 to 1534 in Table 1 all together in one column. １ ~Y ４ is fixed to CH, and X １ is fixed to O, and R １ , R ４ , R １’ ~R ４’ is fixed at H, and R ２ is any one of A1 to A66, and R ３ In this stage, R ２ varies from A1 to A66, and R ３varies from D1 to D1534, but when there are two types of variables, the first one (the one written to the left of Table 2) is fixed first, and the second one (the one written to the right of Table 2) is varied, and the compound numbers are assigned in order. ２ First, fix it to A1, and then use R ３ These compounds are designated D1 to D1534 in order and are identified as compounds 1535 to 3068 in order. ２ Fix it to A2 and R ３ These compounds are designated D1 to D1534 in order and are identified as compounds 3069 to 4602 in order. ２ Fix it to A3 and R ３ These are identified in order as D1 to D1534 and are identified in order as compounds 4603 to 6136. ２ Fix it to A66 and R ３ These are designated D1 to D1534 in order and are identified as compounds 101245 to 102778 in order. The structures of the compounds are identified in the same manner for compounds 102779 to 204022 in Table 2 and compounds 1131389 to 1474652 in the bottom row. As shown in the rightmost column of Table 2, for example, for compounds 1131389 to 1474652 in the bottom row, R ２ and R ２’ are the same, and R ３ and R ３’ is the same.

[0047]

[0048] Table 3 below further illustrates compounds represented by general formula (3) in the form of a table. In Table 3, a compound number is further assigned to a structure obtained by further substituting a part of the structure specified by the compound number. For example, in the top row of Table 3, compounds 1474653 to 2949304 (shown as No. 1474653 to 2949304 in the table) have the same structure as compounds 1 to 1474652 except for the Y １ ~Y ４In the second row of Table 3, compounds 2949305 to 4423956 represent compounds in which Y is substituted with C-D (a carbon atom bonded to a deuterium atom). １ represents a compound in which a carbon atom bonded to a cyano group is substituted with C—CN (a carbon atom bonded to a cyano group). The structure of each compound listed in Table 3 is specified in this manner. In the table, "C-(2-Py)" represents a carbon atom bonded to a 2-pyridyl group, "C-(3-Py)" represents a carbon atom bonded to a 3-pyridyl group, and "C-(4-Py)" represents a carbon atom bonded to a 4-pyridyl group. In addition, "N-C" at the bottom of Table 3 represents a ６ H ４ -" is a phenyl group (Ar) bonded to a nitrogen atom as shown below. ２ The carbon atom at the ortho position in ４ The structure shows a single bond to the carbon atom of (compounds 176958241 to 221197800).

[0049]

[0050] Table 4 below lists compounds represented by general formula (4a) in the form of a table. Table 4 is written in the same manner as Table 2. In Table 4, R ３１ and R ３２ In the column, enter "(CH ２ ) ４ " is written in R ３１ and R ３２ are bonded to each other - (CH ２ ) ４ This indicates that a benzene ring is formed. ３１ and R ３２ In the column, enter "(CD ２ ) ４ " is written in R ３１ and R ３２ are bonded to each other (CD ２ ) ４ This indicates that a deuterated benzene ring is formed. ３３ and R ３４ In the column "(CH ２ ) ４ " and "(CD ２ ) ４ " is also the same.

[0051]

[0052] Table 5 below further illustrates compounds represented by general formula (4a) in tabular form. In Table 5, compound numbers are further assigned to structures obtained by further substituting a portion of the structure identified by the compound number. Table 5 is written in the same manner as Table 3.

[0053]

[0054] The compounds represented by general formula (4b) are listed in the form of a table in Table 6 below. Table 6 is written in the same manner as Tables 2 and 4.

[0055]

[0056] Table 7 below further illustrates compounds represented by general formula (4b) in the form of a table. In Table 7, compound numbers are further assigned to structures obtained by further substituting a part of the structure identified by the compound number. Table 7 is written in the same manner as Tables 3 and 5.

[0057]

[0058] Compounds 1d to 256589448d are also disclosed as compounds obtained by substituting all hydrogen atoms present in the molecules of compounds 1 to 256589448 with deuterium atoms. When rotamers exist among the compounds exemplified above, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification.

[0059] In one embodiment of the present invention, a compound having an axisymmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, a compound having an asymmetric structure is selected as the compound represented by general formula (1). In one embodiment of the present invention, compounds 1 to 256589448 and 1d to 256589448d are selected as the compound represented by general formula (1). In one embodiment of the present invention, compounds 1 to 221197800 and 1d to 221197800d are selected as the compound represented by general formula (1). In one embodiment of the present invention, compounds 221197801 to 238893624 and 221197801d to 238893624d are selected as the compound represented by general formula (1). In one embodiment of the present invention, compounds 238893625 to 256589448 and 238893625d to 256589448d are selected as the compound represented by general formula (1).

[0060] In one embodiment of the present invention, a compound selected from the following group is used as the compound represented by general formula (1).

[0061] In one embodiment of the present invention, a compound selected from the following group is used as the compound represented by general formula (1).

[0062] In one embodiment of the present invention, a compound selected from the following group is used as the compound represented by general formula (1).

[0063] The molecular weight of the compound represented by general formula (1) is preferably 1,500 or less, more preferably 1,200 or less, even more preferably 1,000 or less, and even more preferably 900 or less, when, for example, an organic layer containing the compound represented by general formula (1) is intended to be formed into a film by a vapor deposition method and used. The lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. Using a coating method, even compounds with relatively large molecular weights can be formed into a film. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and can be easily purified to increase its purity. The number of carbon atoms constituting the ring skeleton constituting the fused ring structure containing a pyrazine ring (the entire structure of rings directly or indirectly fused to the pyrazine ring) of the compound represented by general formula (1) is 21 or more, and may be, for example, 26 or more, or 31 or more.

[0064] It is also conceivable to apply the present invention to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by polymerizing a polymerizable group that is previously present in the structure represented by general formula (1) and using the polymerized group as a light-emitting material. Specifically, it is conceivable to prepare a monomer containing a polymerizable functional group in one of the structures represented by general formula (1), and to polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds represented by general formula (1) together to obtain dimers or trimers, and use these as light-emitting materials.

[0065] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0066] In the above general formula, Q represents a group containing a structure represented by general formula (1), L１ and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. ２０１ , R ２０２ , R ２０３ and R ２０４ each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the formula (1) may be located at any position of the structure constituting Q (for example, Ar １ ,D.A.R. １ ~R ４ Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.

[0067] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0068] The polymer having a repeating unit containing these formulas may be any of the structures represented by general formula (1) (e.g., Ar １ ,D.A.R. １ ~R ４The compound can be synthesized by introducing a hydroxy group into the polymerizable compound (either of the above), reacting the compound with the compound shown below as a linker to introduce a polymerizable group, and polymerizing the polymerizable group.

[0069] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0070] It is preferable that the compound represented by general formula (1) does not contain a metal atom. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. For example, the compound represented by general formula (1) can be selected from the group consisting of carbon atoms, hydrogen atoms, and nitrogen atoms.

[0071] In this specification, the term "alkyl group" may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched moieties may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group serving as a substituent may be further substituted with an aryl group. The "aryl group" and "heteroaryl group" may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthyridine ring, and these may be fused rings. Specific examples of the aryl group or heteroaryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected from the range of 6 to 14, or may be selected 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 may be selected from the range of 5 to 14, or may be selected from the range of 5 to 10. The terms "arylene group" and "heteroarylene group" can be understood by changing the valence of the aryl group and heteroaryl group from 1 to 2.

[0072] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl ... It means one group or a combination of two or more groups selected from the group consisting of a heteroarylthio group (for example, having 5 to 30 atoms constituting the ring skeleton), an acyl group (for example, having 1 to 40 carbon atoms), an alkenyl group (for example, having 1 to 40 carbon atoms), an alkynyl group (for example, having 1 to 40 carbon atoms), an alkoxycarbonyl group (for example, having 1 to 40 carbon atoms), an aryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a heteroaryloxycarbonyl group (for example, having 1 to 40 carbon atoms), a silyl group (for example, a trialkylsilyl group having 1 to 40 carbon atoms), and a nitro group. In the present specification, "substituent group B" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring atoms), heteroaryloxy groups (e.g., having 5 to 30 ring atoms), and diarylamino groups (e.g., having 0 to 20 carbon atoms). In the present specification, "substituent group C" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). As used herein, "substituent group D" means one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms) and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms) and aryl groups (e.g., having 6 to 22 carbon atoms). In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0073] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can 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). In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the ultraviolet region of the spectrum (e.g., 280 to 400 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the infrared region of the spectrum (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can be used to fabricate organic semiconductor devices. For example, the compound represented by general formula (1) can be used to fabricate CMOS (complementary metal-oxide semiconductor) devices.In an embodiment of the present disclosure, the compound represented by general formula (1) can be used to fabricate organic optical devices such as organic electroluminescence devices and solid-state imaging devices (for example, CMOS image sensors).

[0074] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴThe quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., 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.

[0075] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) is a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. For specific synthesis conditions, please refer to the synthesis examples described below.

[0076] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0077] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) of the present invention can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

[0078] [Examples of Use of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferably used in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of compounds represented by general formula (1) of the present invention as light-emitting materials for organic light-emitting devices. In some embodiments, compounds represented by general formula (1) of the present invention can be effectively used as light-emitting materials in the light-emitting layer of organic light-emitting devices. In some embodiments, compounds represented by general formula (1) include delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of compounds represented by general formula (1) as delayed fluorescent materials. In some embodiments, the present invention can be used as a host material and can be used together with one or more light-emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF. In some embodiments, the compounds represented by general formula (1) can also be used as hole-transporting materials. In some embodiments, the compounds represented by general formula (1) can be used as electron-transporting materials. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves the light extraction efficiency from the emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound represented by general formula (1) as an emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device).In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic light-emitting device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole-transporting layer, a hole-injecting layer, an electron-blocking layer, a hole-blocking layer, an electron-injecting layer, an electron-transporting layer, and an exciton-blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0079] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is a compound represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0080] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[0081]

[0082] In addition, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 and the compounds having a pyrromethene boron skeleton described in WO2021 / 015177 can also be particularly preferably used as light-emitting materials used together with the assist dopant having a structure represented by general formula (1).

[0083] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0084] In some embodiments, the host material is selected from the group consisting of:

[0085] In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of the present invention may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0086] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0087] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0088] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0089] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0090] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0091]

[0092] Next, examples of preferred compounds that can be used as the electron injection material will be given.

[0093] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside 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 have both the functions of an electron blocking layer and an exciton blocking layer.

[0094] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0095]

[0096] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0097]

[0098] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive 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 present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0099] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0100]

[0101] Electron Transport Layer: The electron transport layer comprises an electron transport material. In some embodiments, the electron transport layer is a single layer. In some embodiments, the electron transport layer has multiple layers. In some embodiments, the electron transport material only needs to transport electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole-blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives, or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymer material. Specific examples of preferred compounds that can be used as electron transport materials are listed below.

[0102]

[0103] Furthermore, examples of compounds that can be added to each organic layer are given below, which may be added as a stabilizing material, for example.

[0104]

[0105] Although specific examples of preferred materials that can be used in organic electroluminescence devices have been given, the materials that can be used in the present invention should not be construed as being limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials having specific functions can be diverted to be used as materials having other functions.

[0106] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0107] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (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 two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0108] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0109] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0110] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0111] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film 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, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0112] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0113] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0114] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0115] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0116] The features of the present invention will be explained in more detail below with reference to synthesis examples and working examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334 model).

[0117] (Synthesis Example 1) Synthesis of Compound A

[0118] Intermediate a: Under a nitrogen atmosphere, acetic acid (500 ml), ethanol (175 ml), and triethylamine (2.5 ml) were added to a mixture of 1-phenylisatin (5.58 g, 25.0 mmol) and 3,6-dibromo-9,10-phenanthrenediamine (10.1 g, 27.5 mmol), and the mixture was allowed to react at 120°C for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, methanol was added, and the precipitated solid was filtered and washed with methanol. The resulting solid was reprecipitated with toluene and methanol to give Intermediate a (1.10 g, 1.99 mmol, 8.0% yield). ASAP mass spectrometry analysis: theoretical 552.96, observed 554.19.

[0119] Intermediate b: Under a nitrogen atmosphere, degassed toluene (100 mL) was added to a mixture of intermediate a (1.10 g, 1.99 mmol), 2-(1-fluoro-9H-carbazol-9-yl)benzenamine (1.21 g, 4.37 mmol), palladium(II) acetate (44.6 mg, 0.199 mmol), bis[2-(diphenylphosphino)phenyl]ether (214 mg, 0.398 mmol), and sodium tert-butoxide (382 mg, 3.98 mmol). The mixture was heated to 125°C and reacted for 24 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted. The resulting mixture was purified by silica gel column chromatography to yield intermediate b (200 mg, 0.212 mmol, 11% yield). 1 H-NMR (400 MHz, DMSO-D6) δ 9.06 (dd, J = 8.9, 1.6 Hz, 1H), 8.72-8.70 (m, 1H), 8.48 (d, J = 7.6 Hz, 1H), 8.24 (d, J = 1.6 Hz, 1H), 8.18-8.15 (m, 3H), 8.01-7.98 (m, 2H), 7.89-7.85 (m, 4H), 7.77-7.57 (m, 7H), 7.52-7.29 (m, 9H), 7.22-7.09 (m, 10H) ASAP mass spectrum analysis: Theoretical value 943.32, observed value 944.80.

[0120] Compound A: Under a nitrogen atmosphere, degassed dimethylformamide (15 mL) was added to a mixture of intermediate b (200 mg, 0.212 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (21.2 mg, 0.530 mmol). The mixture was heated to 150°C and reacted for 24 hours. After the reaction was complete, the mixture was cooled to room temperature, purified water was added, and the precipitated solid was filtered and washed with purified water and methanol. The resulting mixture was purified by silica gel column chromatography to obtain Compound A (175 mg, 0.194 mmol, 91% yield). 1 H-NMR (400 MHz, DMSO-D6) δ 9.77 (d, J = 8.7 Hz, 1H), 9.39 (d, J = 8.5 Hz, 1H), 9.24 (s, 2H), 8.67 (d, J = 7.6 Hz, 1H), 8.17 (dd, J = 8.6, 5.4 Hz, 2H), 8.09 (dd, J = 7.0, 4.5 Hz, 2H), 8.02-7.98 (m, 3H), 7.92 (dd, J = 8.7, 1.8 Hz, 1H), 7.85-7.77 (m, 5H), 7.73 (d, J = 8.2 Hz, 1H), 7.67-7.60 (m, 2H), 7.53-7.48 (m, 2H), 7.29 (td, J = 7.6, 3.4 Hz, 2H), 7.23 (dd, J = 7.3, 5.5 Hz, 2H), 6.83-6.77 (m, 2H), 6.72-6.66 (m, 4H), 6.10 (dd, ASAP mass spectrum analysis: theoretical value 903.31, observed value 904.92.

[0121] (Synthesis Example 2) Synthesis of Compound B

[0122] Intermediate c: To a mixture of thioisatin (2.00 g, 12.1 mmol) and 3-bromo-9,10-phenanthrenediamine dihydrochloride (4.35 g, 12.1 mmol), acetic acid (242 ml) and triethylamine (10.0 ml) were added and the mixture was reacted at 140°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature, and the precipitated solid was filtered and washed with dichloromethane and methanol to obtain Intermediate c (4.02 g, 9.69 mmol, 80.0% yield). ASAP mass spectrometry analysis: theoretical 415.30, observed 417.10.

[0123] Intermediate d Under a nitrogen atmosphere, degassed toluene (100 mL) was added to a mixture of intermediate c (1.00 g, 2.40 mmol), 4-amino-3-(1-fluoro-9H-carbazol-9-yl)benzonitrile (0.795 g, 2.64 mmol), palladium(II) acetate (53.8 mg, 0.240 mmol), bis[2-(diphenylphosphino)phenyl]ether (129 mg, 0.240 mmol), and cesium carbonate (1.56 g, 4.80 mmol), and the mixture was heated to 130°C and reacted for 4 hours. After completion of the reaction, the resulting mixture was purified by silica gel column chromatography to obtain intermediate d (827 mg, 1.30 mmol, yield 54.4%). 1H-NMR (400 MHz, CDCl3) δ 8.69-8.61 (m, 1H), 8.44-8.37 (m, 1H), 8.28-8.23 (m, 1H), 8.20-8.15 (m, 1H), 7.99-7.89 (m, 2H), 7.82-7.58 (m, 7H), 7.56-7.43 (m, 2H), 7.42-7.36 (m, 1H), 7.30-7.09 (m, 5H), 6.30-6.25 (m, 1H) ASAP mass spectrum analysis: theoretical value 635.72, observed value 636.30.

[0124] Compound B: Under a nitrogen atmosphere, degassed dimethylformamide (130 mL) was added to a mixture of intermediate d (828 mg, 1.30 mmol) and sodium hydride (60%, dispersed in liquid paraffin) (57.1 mg, 1.43 mmol). The mixture was heated to 150°C and reacted for 12 hours. After completion of the reaction, the precipitated solid was filtered and washed with methanol. The resulting mixture was purified by silica gel column chromatography to obtain Compound B (600 mg, 0.974 mmol, 74.9% yield). ASAP mass spectrometry analysis: theoretical value 615.71, observed value 616.29.

[0125] (Example 1) Preparation and evaluation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Compound A and Host 1 were evaporated from different evaporation sources under conditions of less than 10 Pa, and a thin film with a compound A concentration of 20 wt % was formed to a thickness of 100 nm, which was designated as a thin film of Compound A. Furthermore, thin films of Compound B, Comparative Compound A, and Comparative Compound B were also prepared according to the same procedure using Compound B, Comparative Compound A, and Comparative Compound B instead of Compound A. When each prepared thin film was irradiated with excitation light (wavelength 299 nm), immediate fluorescence and delayed fluorescence emitted later were observed. The results of measuring the lifetime (τ2) of delayed fluorescence for each thin film are shown in Table 8. It was confirmed that the lifetime of delayed fluorescence of Compound A and Compound B was shorter than that of Comparative Compound A and Comparative Compound B. Separately, Compound A and Host 1 were evaporated from different evaporation sources to form a thin film with a compound A concentration of 40 wt % to a thickness of 100 nm, which was designated as a thin film of Compound A. Furthermore, a thin film of Comparative Compound B was also prepared according to the same procedure using Comparative Compound B instead of Compound A. Furthermore, Comparative Compound A and Host 2 were evaporated from different evaporation sources to form a thin film with a thickness of 100 nm, in which the concentration of Comparative Compound A was 20 wt %. This was used as a thin film of Comparative Compound A. The S value, which is an index of the degree of orientation, was measured according to the method described in J. Appl. Phys. Lett., 2005, pp. 7, 8405. The S value of Compound A was clearly lower than the S values ​​of Comparative Compound A and Comparative Compound B, confirming that Compound A had a high degree of orientation.

[0126] It has been confirmed that the compound represented by general formula (1) has a short delayed fluorescence lifetime and high orientation. Therefore, by using the compound represented by general formula (1) in an organic light-emitting element, it is possible to provide an element with good light-emitting properties (including durability).

[0127] (Example 2) Fabrication of an organic electroluminescence element Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a film thickness of 100 nm was formed by vacuum deposition at a vacuum degree of 1×10 －６ The layers were laminated at 100 Pa. First, HATCN was formed on ITO to a thickness of 10 nm, and NPD was formed on top of that to a thickness of 30 nm. Next, TrisPCz was formed on top of that to a thickness of 10 nm, and Host1 was further formed on top of that to a thickness of 5 nm. Next, Compound A 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 A was 35 wt%. SF3TRZ was formed on top of that to a thickness of 10 nm, and SF3TRZ and Liq were co-deposited on top of that to a thickness of 30 nm from different evaporation sources. At this time, the SF3TRZ:Liq (weight ratio) was 7:3. Next, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form a cathode. Using the above procedure, an organic electroluminescent device was fabricated. Instead of compound A, compound B and comparative compound B were used, and a device using compound B and a device using comparative compound B were also fabricated according to the same procedure. A current was applied to each of the fabricated devices to measure the maximum external quantum efficiency (EQE) and the maximum value of 15.4 mA / cm. ２ The values ​​at 1000 kJ / cm2 were measured. The results are shown in Table 9 below. The devices using Compound A and Compound B exhibited higher luminous efficiency than the device using Comparative Compound B.

[0128]

[0129] Also, 50 mA / cm ２The time (LT95) until the luminous intensity reached 95% of that immediately after the start of current application was measured, and the device using compound B had a lifespan that was about 6.7 times longer than that of the device using comparative compound B. From the above, it was confirmed that the device using the compound represented by general formula (1) has high luminous efficiency and a long device lifespan.

[0130] By using the compound represented by general formula (1), an organic light-emitting device having good light-emitting properties can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): General formula (1) [In the general formula (1), R １ ~R ４ and R １’ ~R ４’ Each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that at least one represents a donor group. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ may be bonded to each other to form a ring structure. 1 represents a 5-membered ring fused with a 6-membered ring, or represents a benzene ring fused with two 5-membered rings containing a heteroatom as a ring skeleton-constituting atom.

2. The compound of claim 1, wherein the donor group is a heteroaryl group attached at a nitrogen atom.

3. R １ ~R ４ and R １’ ~R ４’ The compound according to claim 1, wherein at least one of the groups represents a group represented by the following general formula (2): [In the general formula (2), R ５ ~R １５ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 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 may be bonded to each other to form a ring structure. X represents a single bond, an oxygen atom or a sulfur atom. * represents the bonding position.

4. The compound according to claim 1, wherein the heteroatom is an oxygen atom or a sulfur atom.

5. The compound of claim 1, wherein the heteroatom is a nitrogen atom.

6. The compound according to claim 1, which is represented by the following general formula (3): General formula (3) [In the general formula (3), R １ ~R ４ and R １’ ~R ４’ Each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that at least one represents a donor group. 1 is O, S or N-Ar ２ Represents Ar. ２ represents a substituted or unsubstituted aryl group. １ is N or C-R ２１ represents Y ２ is N or C-R ２２ represents Y ３ is N or C-R ２３ represents Y ４ is N or C-R ２４ where Y １ ~Y ４ The number of N's in the set is 0 or 1. ２１ ~R ２４ Each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ is N-Ar ２ And Y ４ is C-R ２４ When Ar ２ The carbon atom at the ortho position in the aryl group represented by ４ may be bonded to a carbon atom of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ may be bonded to each other to form a cyclic structure.

7. The compound according to claim 1, which is represented by the following general formula (4a) or (4b): General formula (4a) General formula (4b) [In the general formulas (4a) and (4b), R １ ~R ４ and R １’ ~R ４’ Each independently represents a hydrogen atom, a deuterium atom, or a substituent, provided that at least one represents a donor group. ２ ~X ５ Each independently represents O, S, or N-Ar ２ Represents Ar. ２ represents a substituted or unsubstituted aryl group. ３１ ~R ３８ Each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R １’ and R ２’ , R ２’ and R ３’ , R ３’ and R ４’ , R ３１ and R ３２ , R ３３ and R ３４ , R ３５ and R ３６ , R ３７ and R ３８ may be bonded to each other to form a cyclic structure.

8. R ３１ and R ３２ , R ３３ and R ３４ , R ３５ and R ３６ , R ３７ and R ３８ The compound according to claim 7, wherein are bonded to each other to form an optionally substituted benzene ring.

9. A light-emitting material comprising the compound according to any one of claims 1 to 8.

10. A membrane comprising a compound according to any one of claims 1 to 8.

11. An organic light-emitting device comprising the compound according to any one of claims 1 to 8.

12. The organic light-emitting device of claim 11, wherein the device has a layer comprising the compound, the layer also comprising a host material.

13. The organic light-emitting element according to claim 12, wherein the layer containing the compound also contains a delayed fluorescent material in addition to the host material, and the minimum excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

14. The organic light-emitting device of claim 11, wherein the device has a layer that includes the compound, the layer also including a light-emitting material that has a structure different from that of the compound.

15. The organic light-emitting device according to claim 11, wherein the compound emits the greatest amount of light of any of the materials contained in the device.

16. The organic light-emitting device according to claim 14, wherein the amount of light emitted from said light-emitting material is greater than the amount of light emitted from said compound.

17. The organic light-emitting element according to claim 11, which emits delayed fluorescence.

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