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

Abstract

Compounds represented by the provided general formula are excellent materials for organic light-emitting elements. Y1 and Y2 are each an aryl group, a heteroaryl group, or the like, and among R1 to R5, two or more of the radicals are each a donor group bonded by a nitrogen atom, and the others are each a hydrogen atom, a deuterium atom, a non-acceptor heteroaryl group bonded by a carbon atom, an aryl group, or the like.

Description

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

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

[0002] Research into organic light-emitting devices has been actively conducted. For example, research into improving the luminous efficiency of light-emitting devices such as organic electroluminescence devices (organic EL devices) has been actively conducted. In particular, various efforts have been made to improve the luminous efficiency by newly developing and combining electron transport materials, hole transport materials, luminescent materials, etc. that constitute organic electroluminescence devices. Among these efforts, research into organic electroluminescence devices that utilize delayed fluorescent materials has also been observed.

[0003] Delayed fluorescent materials are materials that, in an excited state, undergo reverse intersystem crossing from an excited triplet state to an excited singlet state, and then emit fluorescence when returning from the excited singlet state to the ground state. Fluorescence via this route is observed later than fluorescence from the excited singlet state (normal fluorescence) directly generated from the ground state, and is therefore called delayed fluorescence. Here, for example, when a light-emitting compound is excited by carrier injection, the probability of occurrence of the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to the improvement of luminous efficiency when only fluorescence from the directly generated excited singlet state is used. On the other hand, delayed fluorescent materials can utilize not only the excited singlet state but also the excited triplet state for fluorescence emission via the above-mentioned reverse intersystem crossing route, thereby achieving higher luminous efficiency than ordinary fluorescent materials.

[0004] Since this principle was clarified, various researches have led to the discovery of various delayed fluorescent materials, and their application to organic light-emitting devices such as organic electroluminescence devices has been proposed. These materials include many compounds in which a donor group and an acceptor group are substituted on a benzene ring. For example, a compound has been proposed having a skeleton in which a carbazol-9-yl group, which is a donor group, and a substituted triazinyl group, which is an acceptor group, are substituted on a benzene ring (see Patent Document 1).

[0005] WO2019 / 191665A1

[0006] To date, no compound has been provided that exhibits excellent performance when applied to organic light-emitting devices and has no practical problems. Therefore, it would be even more useful if a compound could be developed that could provide organic light-emitting devices with even better performance. However, improvements to these compounds are still in the trial-and-error stage, and it is not easy to generalize the chemical structures of useful compounds.

[0007] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as compounds for organic light-emitting devices, and have conducted extensive research with the aim of deriving and generalizing a general formula for compounds that are more useful for organic light-emitting devices.

[0008] As a result of intensive research to achieve the above object, the present inventors have found that a compound having a structure that satisfies certain conditions has excellent light-emitting properties, and that use of such a compound can provide an organic light-emitting device with excellent performance. The present invention has been proposed based on this finding, and specifically has the following configuration. [1] A compound represented by the following general formula (1): General formula (1) [In general formula (1), R １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a donor group bonded via a nitrogen atom, a non-acceptor heteroaryl group bonded via a carbon atom, or a substituted or unsubstituted aryl group. １ ~R ５ At least two of Y are donor groups bonded via a nitrogen atom. １ and Y ２ represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Y ２ and R cannot both be hydrogen atoms or deuterium atoms.] [2] R １ ~R ５ [3] The compound according to [1], wherein three or more of R １ ~R ５[4] The compound according to [1] or [2], wherein two of R are donor groups bonded via a nitrogen atom and have different structures. １ ~R ５ [5] The compound according to any one of [1] to [3], wherein one or more of R １ ~R ５ [6] The compound according to any one of [1] to [4], wherein one or more of R １ ~R ５ [7] The compound according to [5], wherein two or more of R １ ~R ５ at least one of R is a substituted or unsubstituted ring-fused carbazol-9-yl group; １ ~R ５ [8] The compound according to any one of [1] to [6], wherein at least one of R is a substituted or unsubstituted carbazol-9-yl group that is not fused with a ring. １ ~R ５ [9] The compound according to any one of [1] to [7], wherein one or two of Y are hydrogen atoms or deuterium atoms. １ and Y ２

[10] The compound according to any one of [1] to [8], wherein Y is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Y ２wherein at least one of the groups is a substituted or unsubstituted aryl group.

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

[10] , which contains at least one deuterium atom in the molecule.

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

[11] .

[13] A film comprising the compound according to any one of [1] to

[11] .

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

[11] .

[15] The organic light-emitting device according to

[14] , which is an organic electroluminescence device.

[16] The organic light-emitting device according to

[15] , which has a layer comprising the compound, and which layer also contains a host material.

[17] The organic light-emitting device according to

[15] or

[16] , which has a layer comprising the compound, and which layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

[18] The organic light-emitting element according to

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

[0009] The compound represented by formula (1) exhibits excellent light-emitting properties and can be used in organic light-emitting devices.

[0010] 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.

[0011] [Compound represented by general formula (1)] The compound represented by the following general formula (1) will be described.

[0012] R in general formula (1) １ ~R ５ At least two of the groups are donor groups bonded via a nitrogen atom. 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] R １ ~R ５The donor group bonded via a nitrogen atom, which can take the form of: preferably has a σp of −0.3 or less, more preferably −0.5 or less, and even more preferably −0.7 or less. For example, it may be selected from the range of −0.9 or less, or −1.1 or less.

[0014] In the present invention, the donor group bonded via a nitrogen atom is preferably 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, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0015] R １ ~R ５ The donor group bonded via a nitrogen atom, which can be represented by the formula (a), is preferably a group represented by the following formula (a):

[0016] 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 R １６ , R １６ and R １７may be bonded to each other to form a cyclic structure.

[0017] Z １ ~Z ４ In one embodiment of the present invention, the number of N's is preferably 0 to 3, and 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 deuterium atom or substituent here may be selected from, for example, Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a plurality of groups A to E. １４ ~R １７ When two or more of R represent deuterium atoms or substituents, the two or more deuterium atoms or substituents may be the same or different. １４ ~R １７ The number of substituents is preferably 0 to 2, for example, R １４ ~R １７ The number of substituents among R may be one, １４ ~R １７ The number of substituents is 0 (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 herein may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to herein may be selected from Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a combination of groups A to E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of the indole, and examples of the deuterium atom or substituent that may be substituted on the aryl group include a deuterium atom or a substituent selected from any of 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 １７are not bonded to each other to form a ring structure.

[0018] 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 a substituted or unsubstituted indole, or an imidazole ring of a substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to here may be selected from Group A described below, Group B described below, Group C described below, Group D described below, or Group E described below, or may be selected from a plurality of groups A to E.

[0019] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0020] 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, Z１ ~Z ４ , Z ６ ~Z ９ In 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.

[0021] R １ ~R ５ The donor group bonded via a nitrogen atom, which may be any of the groups shown in the formula (I), is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent referred to here may be selected from Group A described below, Group B described below, Group C described below, Group D described below, Group E described below, or a combination of groups A to E. For example, it may be substituted with at least a deuterium atom. For example, it may be substituted with at least a cyano group. For example, it may be substituted with at least a deuterium atom, an alkyl group, or an aryl group which may be substituted with an aryl group. For example, it may be substituted with at least an alkyl group which may be substituted with a deuterium atom. Furthermore, one or more rings may be fused to the two benzene rings constituting the carbazol-9-yl group. In a preferred embodiment of the present invention, R １ ~R ５The donor group bonded via a nitrogen atom, which may be any of the groups shown in the formula (I), is a carbazol-9-yl group, which may be substituted with a deuterium atom or a substituent selected from Group E, and which may be fused with one or more rings. When a compound with a short emission wavelength is desired, it is preferable to employ a carbazol-9-yl group substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group or an aryl group. 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 position from the 2- to 7-positions, more preferably at least one position from the 3- or 6-positions, and even more preferably two positions from the 3- and 6-positions.

[0022] In one aspect of the present invention, R １ ~R ５ The donor group bonded via a nitrogen atom that can be taken as R is a carbazol-9-yl group in which one or more rings are fused, and hereinafter this is referred to as a "ring-fused carbazol-9-yl group." １ ~R ５ The ring-fused carbazol-9-yl group represented by the formula (I) may be unsubstituted or substituted with a deuterium atom or a substituent. The deuterium atom or substituent here may be selected from Group A described below, Group B described below, Group C described below, Group D described below, or Group E described below, or may be selected from a plurality of groups A to E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a deuterium atom or a substituent selected from 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 optionally 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.

[0023] 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).

[0024] 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 deuterium atom or a substituent (excluding cases where only a deuterium atom is present) selected from Group E described below, 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.

[0025] 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.

[0026] 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 with a substituent at either the 3-position or the 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.

[0027] In the following, R in general formula (1) １ ~R ５ Specific examples of donor groups bonded via a nitrogen atom that can be taken as follows. The specific examples given here are substituted or unsubstituted carbazole-9-yl groups (the carbazole ring may have a further ring condensed thereto), but the donor groups bonded via a nitrogen atom that can be employed in the present invention should not be construed as being limited by 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, D2 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 (perdeuterated phenyl group). D represents a deuterium atom.

[0028] The compounds D1 to D459 above, in which all hydrogen atoms have been replaced with deuterium atoms, are disclosed as D722 to D1180.

[0029] R １ ~R ５ Among the donor groups bonded at a nitrogen atom that can be taken as above, specific examples that are not substituted or unsubstituted carbazol-9-yl groups are listed below. However, the donor groups bonded at a nitrogen atom that can be used in the present invention should not be construed as being limited by the following specific examples.

[0030] All hydrogen atoms in D1181 to D1208 are replaced with deuterium atoms, and these are disclosed as D1233 to D1260. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1260. １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1180. １ ~R ５The donor group that R can take is selected from the group consisting of D17 to D76, D83 to D118, D185 to D298, D359 to D453, D472 to D519, D526 to D653, and D704 to D710. １ ~R ５ The donor group that R can take is selected from the group consisting of D77 to D82, D119 to D184, D299 to D358, D455 to D459, D520 to D525, D654 to D703, and D712 to D721. １ ~R ５ The donor group that R can take is selected from the group consisting of D460 to D1180 and D1214 to D1260. １ ~R ５ In a preferred embodiment of the present invention, the donor group R １ ~R ５ The donor groups that can be taken are D1 to D13, D17 to D22, D37, D47 to D52, D77 to D82, D119 to D131, D134, D137, D140, D146, D149, D152, D155, D158, D161, D164, D167, D170, D173, D176, D179, D182, D198, D454, D466 to D471, D521 to D525, D54 In a more preferred embodiment of the present invention, R is selected from the group consisting of D3, D712 to D716, D722 to D734, D739 to D743, D758, D768 to D773, D798 to D803, D840 to D852, D855, D858, D861, D867, D870, D873, D876, D879, D882, D885, D888, D891, D894, D897, D900, D903, D919, and D1175. １ ~R ５ The donor group that can be taken by is selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D79, D198, D466, D467, D486, D522, D543, D722, D729, D730, D740, D758, D771, D798, D800, and D919.

[0031] In one aspect of the present invention, R １ ~R ５In a preferred embodiment of the present invention, two of R １ ~R ５ In one embodiment of the present invention, three of R １ ~R ５ In one embodiment of the present invention, four of the R １ ~R ５ In one embodiment of the present invention, five of the R １ ~R ５ In one embodiment of the present invention, the donor groups bonded to at least two nitrogen atoms of R １ ~R ５ In one embodiment of the present invention, the donor groups bonded at the nitrogen atoms of R are all the same. １ ~R ５ In one embodiment of the present invention, only two of the donor groups bonded at the nitrogen atom are the same. １ ~R ５ In one aspect of the invention, at least three of R １ is a donor group bonded via a nitrogen atom. ２ is a donor group bonded via a nitrogen atom. ３ is a donor group bonded via a nitrogen atom. ４ is a donor group bonded via a nitrogen atom. ５ is a donor group bonded via a nitrogen atom. ２ and R ３ In one embodiment of the present invention, R ２ and R ４ In one embodiment of the present invention, R １ and R ２ In one embodiment of the present invention, R １ and R ３ In one embodiment of the present invention, R１ and R ５ In one embodiment of the present invention, R １ and R ５ In a preferred embodiment of the present invention, R ２ and R ３ and R ４ In one embodiment of the present invention, R １ and R ３ and R ４ In one embodiment of the present invention, R １ and R ２ and R ４ In one embodiment of the present invention, R １ and R ２ and R ３ In one embodiment of the present invention, R １ and R ３ and R ５ In one embodiment of the present invention, R １ and R ２ and R ５ In one embodiment of the present invention, R １ and R ２ and R ３ and R ４ In one embodiment of the present invention, R １ and R ２ and R ３ and R ５ In one embodiment of the present invention, R １ and R ２ and R ４ and R ５ In one embodiment of the present invention, R １ ~R ５ All of the R in the general formula (1) are donor groups bonded via a nitrogen atom. １ ~R ５At least one (for example, only two, for example, only three, for example, only four, for example, five) donor group bonded at the nitrogen atom represented by is preferably a substituted or unsubstituted diarylamino group (two aryl groups may be bonded to each other), for example, a substituted or unsubstituted carbazol-9-yl group which may be fused. １ ~R ５ It is also preferred that all of the donor groups bonded via the nitrogen atom represented by R are substituted or unsubstituted diarylamino groups (the two aryl groups may be bonded to each other), for example, substituted or unsubstituted diarylamino groups (the two aryl groups may be bonded to each other), for example, substituted or unsubstituted carbazol-9-yl groups which may be ring-fused, for example, substituted or unsubstituted carbazol-9-yl groups which are ring-fused (substituted or unsubstituted ring-fused carbazol-9-yl groups). In the case of ring-fused rings, the number of rings formed by the ring fusion is preferably 4 to 10, more preferably 5 to 9, for example, 5, for example, 7, for example, 9. In one preferred embodiment of the present invention, R １ ~R ５ In another preferred embodiment of the present invention, two or more of R １ ~R ５ at least one of R is a substituted or unsubstituted ring-fused carbazol-9-yl group; １ ~R ５ At least one other of the above is a substituted or unsubstituted carbazol-9-yl group which is not fused to a ring.

[0032] R in general formula (1) １ ~R ５ Preferably, 0 to 2 of R are hydrogen atoms or deuterium atoms, for example, only one is a hydrogen atom or a deuterium atom, for example, two are hydrogen atoms or deuterium atoms. １ ~R ５ In a preferred embodiment of the present invention, none of R １ and R ５In one embodiment of the present invention, at least one of R １ is a hydrogen atom or a deuterium atom. ２ is a hydrogen atom or a deuterium atom. ３ is a hydrogen atom or a deuterium atom. ４ is a hydrogen atom or a deuterium atom. ５ is a hydrogen atom or a deuterium atom. １ In one aspect of the present invention, only R ２ In one aspect of the present invention, only R ３ In one aspect of the present invention, only R ４ In one aspect of the present invention, only R ５ In one aspect of the present invention, only R １ and R ２ is a hydrogen atom or a deuterium atom. １ and R ３ is a hydrogen atom or a deuterium atom. １ and R ４ is a hydrogen atom or a deuterium atom. １ and R ５ is a hydrogen atom or a deuterium atom. ２ and R ３ is a hydrogen atom or a deuterium atom. ２ and R ４ is a hydrogen atom or a deuterium atom. ２ and R ５ is a hydrogen atom or a deuterium atom. ３ and R ４ is a hydrogen atom or a deuterium atom. ３ and R ５ is a hydrogen atom or a deuterium atom. ４and R ５ is a hydrogen atom or a deuterium atom.

[0033] R in general formula (1) １ ~R ５ Among these, those that are not donor groups bonded via a hydrogen atom, a deuterium atom, or a nitrogen atom are non-acceptor heteroaryl groups bonded via a carbon atom, or substituted or unsubstituted aryl groups. The term "non-acceptor" as used herein means that the Hammett σp value of the entire group is 0.3 or less, preferably less than 0, and may be, for example, -0.2 or less, -0.4 or less, or -0.6 or less. １ ~R ５ The heteroaryl group that can be adopted has a structure in which a heteroaromatic ring is fused to a benzene ring, and is preferably a group bonded to a carbon atom constituting the ring skeleton of the benzene ring. The number of heteroaromatic rings fused to the benzene ring may be one or two. Furthermore, a benzene ring or a heteroaromatic ring may be fused to the heteroaromatic ring fused to the benzene ring. A case in which a benzene ring is fused to a heteroaromatic ring fused to the benzene ring is preferred. The heteroatom constituting the ring skeleton of the heteroaromatic ring is preferably a nitrogen atom, an oxygen atom, or a sulfur atom, such as a nitrogen atom, an oxygen atom, or a sulfur atom. The heteroaromatic ring referred to here means a ring exhibiting aromaticity containing 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 employed. A 5-membered ring is most preferred. In a preferred embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. The hydrogen atoms of the benzene ring or heteroaromatic ring may be substituted with deuterium atoms or substituents. The deuterium atoms or substituents may be selected from, for example, Group A, Group B, Group C, Group D, or Group E, which will be described later. In one aspect of the present invention, R １ ~R ５Examples of heteroaryl groups that R can take include dibenzofuran-1-yl, dibenzofuran-2-yl, dibenzofuran-3-yl, dibenzofuran-4-yl, dibenzothiophen-1-yl, dibenzothiophen-2-yl, dibenzothiophen-3-yl, and dibenzothiophen-4-yl groups, and the hydrogen atoms in these groups may be substituted with deuterium atoms or substituents. １ ~R ５ Examples of heteroaryl groups that R can take include a carbazol-1-yl group, a carbazol-2-yl group, a carbazol-3-yl group, and a carbazol-4-yl group, and the hydrogen atoms in these groups may be substituted with deuterium atoms or substituents. １ ~R ５ Specific examples of optionally substituted heteroaryl groups that can be used are listed below. However, the heteroaryl 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 a bonding position. Also, methyl groups are omitted. Therefore, X20 and X40 represent structures substituted with methyl groups.

[0034] X113 to X173 are disclosed as groups in which all hydrogen atoms present within the above X1 to X60 have been replaced with deuterium atoms. In one aspect of the present invention, a heteroaryl group is selected from X1 to X40, X61 to X92, and X113 to X152. In one aspect of the present invention, a heteroaryl group is selected from X41 to X60, X93 to X112, and X153 to X173. In one aspect of the present invention, a heteroaryl group is selected from X61 to X112. In one aspect of the present invention, a heteroaryl group is selected from X113 to X173. In a preferred aspect of the present invention, a heteroaryl group selected from the group consisting of X3, X23, X43, X95, X115, X135, and X155 is employed.

[0035] R １ ~R ５The substituted or unsubstituted aryl groups that can be taken by Y are described below. １ and Y ２ Explanation and specific examples of substituted or unsubstituted aryl groups that can be used by Y １ and Y ２ In one embodiment of the present invention, R １ ~R ５ The aryl group that R can take is selected from the group consisting of Ar1 to Ar69. １ ~R ５ The aryl group which can be taken by is selected from the group consisting of Ar1, Ar12 and Ar14.

[0036] In one aspect of the present invention, R １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a donor group bonded via a nitrogen atom, or a non-acceptor heteroaryl group bonded via a carbon atom; R １ ~R ５ In a preferred embodiment of the present invention, two or more of R １ ~R ５ are donor groups bonded via nitrogen atoms, and the remaining are hydrogen atoms or deuterium atoms, and more preferably, R １ ~R ５ are donor groups bonded via a nitrogen atom, and the remaining two are hydrogen atoms or deuterium atoms, and in this case, for example, at least R ２ is a donor group bonded via a nitrogen atom, and for example, at least R ３ is a donor group bonded via a nitrogen atom. ２ ~R ４ is a donor group bonded via a nitrogen atom, and R １ and R ５ is a hydrogen atom or a deuterium atom. In another preferred embodiment of the present invention, R １ ~R ５are donor groups in which three or more of the above are bonded via nitrogen atoms, and at least one of the donor groups is a fused substituted or unsubstituted carbazol-9-yl group. In this case, it is preferable that the donor groups bonded via three or more nitrogen atoms are not all the same group. More preferably, R １ ~R ５ are donor groups bonded via a nitrogen atom, at least one of which is a fused substituted or unsubstituted carbazol-9-yl group, and R １ ~R ５ The remaining two are hydrogen atoms or deuterium atoms. ２ ~R ４ are donor groups bonded via a nitrogen atom, at least one of which is a fused substituted or unsubstituted carbazol-9-yl group, and R １ and R ５ is a hydrogen atom or a deuterium atom.

[0037] In general formula (1), Y １ and Y ２ represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Y ２ are not both hydrogen atoms or deuterium atoms. １ and Y ２ At least one of Y is a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and preferably both are these groups. １ and Y ２ are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ and Y ２ In one embodiment of the present invention, at least one of Y is a substituted or unsubstituted aryl group. １ and Y ２ are each independently a substituted or unsubstituted aryl group, for example, Y １ and Y ２ are the same, for example, Y １and Y ２ In one aspect of the present invention, Y １ and Y ２ In one embodiment of the present invention, one of Y is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group. １ and Y ２ are each independently a substituted or unsubstituted heteroaryl group, for example, Y １ and Y ２ are the same, for example, Y １ and Y ２ is different. １ and Y ２ The substituted or unsubstituted aryl group represented by 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 naphthalene ring, an anthracene ring, a phenanthrene ring, and a pyrene ring. Specific examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, and a 9-anthracenyl group. The number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, and may be selected within the range of 6 to 14, or may be selected within the range of 6 to 10. In the following, Y １ and Y ２ Specific examples of optionally substituted aryl groups that can be used are listed 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 a bonding position. Also, methyl groups are omitted. Therefore, Ar2 to Ar7 represent structures substituted with methyl groups.

[0038] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar25 are substituted with deuterium atoms are exemplified here as Ar45 to Ar69 in this order. １ and Y ２The aryl group represented by Y is selected from the group consisting of Ar1 to Ar69. １ and Y ２ The aryl group represented by Y is selected from the group consisting of Ar1, Ar2, Ar5, Ar7, Ar10, Ar12, Ar13, Ar14, Ar19, Ar20, Ar36, Ar37, Ar38, Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar57, Ar58, Ar63, and Ar64. １ and Y ２ The aryl group represented by Y is selected from the group consisting of Ar1, Ar12, Ar13, Ar14, Ar36, Ar37, Ar38, Ar45, Ar56, Ar57, and Ar58. １ and Y ２ The aryl group represented by Y is selected from the group consisting of Ar26 to Ar69. １ and Y ２ The aryl group which can be taken by Ar is selected from the group consisting of Ar45, Ar46, Ar49, Ar51, Ar54, Ar56, Ar58, Ar63 and Ar64.

[0039] Y １ and Y ２ The substituted or unsubstituted heteroaryl group which can be taken by is preferably a group which is bonded via a nitrogen atom constituting an aromatic heterocycle. Examples of the aromatic heterocycle containing a bonded nitrogen atom include a pyrrole ring, a pyridine ring, a pyrimidine ring, and a triazine ring. These aromatic heterocycles containing a bonded nitrogen atom may be substituted, or may be fused with other rings. Examples of other rings include aromatic hydrocarbon rings and aromatic heterocycles, and rings to which these rings are further fused may be fused with the aromatic heterocycle containing a nitrogen atom. In one aspect of the present invention, Y １ and Y ２ Examples of the substituted or unsubstituted heteroaryl group that can be taken by R include the donor group represented by the general formula (a) above, and further include the donor group represented by the general formula (b) above. １ ~R ５In one embodiment of the present invention, the donor group Y １ and Y ２ The heteroaryl group that Y can take is selected from among the above-mentioned D1 to D1260. １ and Y ２ The heteroaryl group that Y can take is selected from among the above-mentioned D1 to D1180. １ and Y ２ The donor group that can be taken by is selected from the group consisting of D1, D8, D9, D19, D37, D50, D77, D79, D198, D466, D467, D486, D522, D543, D722, D729, D730, D740, D758, D771, D798, D800, and D919. More preferably, it is selected from the group consisting of D1, D8, D9, D19, D37, D50, D466, D467, D486, D722, D729, D730, D740, D758, and D771.

[0040] In general formula (1), R １ ~R ５ Two of R １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ do not bond to each other to form a cyclic structure. The compound represented by general formula (1) has a structure in which the benzene ring can freely rotate around the single bond between the upper pyrimidine ring and the lower benzene ring. For this reason, R １ , R ２ The descriptions are R ５ , R ４ Therefore, for example, R ４ Even in a compound where R is a specific group, by rotating the benzene ring, R ２ can be regarded as a compound in which is a specific group, and if the compound also satisfies all other conditions of general formula (1), it can be said to be a compound encompassed by general formula (1).

[0041] Compound group 1 used in the present invention includes compounds represented by the general formula (1) R ２ and R ３ and R ４ are each independently a donor group bonded via a nitrogen atom. ２ and R ３ and R ４ Compound group 1a, in which R ２ and R ４ are the same and R ３ Compound group 1b, in which R ２ and R ３ are the same and R ４ Compound group 1c, where R ２ and R ３ and R ４ and R are all different. Compound groups 1a to 1d each further include a case where at least one of the following additional conditions is satisfied. In one embodiment of the present invention, the donor groups bonded at the nitrogen atom are not all the same group. In one embodiment of the present invention, at least one (preferably two or more) of the donor groups bonded at the nitrogen atom is a substituted or unsubstituted ring-fused carbazol-9-yl group. In one embodiment of the present invention, at least one (preferably two or more) of the donor groups bonded at the nitrogen atom is a substituted or unsubstituted ring-fused carbazol-9-yl group, and at least one of the donor groups is a substituted or unsubstituted carbazol-9-yl group not fused to a ring. In one embodiment of the present invention, １ ~R ５ is a hydrogen atom or a deuterium atom. １ and Y ２ are each independently a substituted or unsubstituted aryl group. １ and Y ２ are each independently a substituted or unsubstituted heteroaryl group. １ and Y ２ In one embodiment of the present invention, Y is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group. １ and Y ２ are identical.

[0042] Compound group 2 used in the present invention includes compounds represented by the general formula (1) R １ and R ３ and R ５ are each independently a donor group bonded via a nitrogen atom. １ and R ３ and R ５ Compound group 2a, in which R ３ and R ５ are the same and R １ Compound group 2b, where R １ and R ５ are the same and R ３ Compound group 2c, where R １ and R ３ and R ５ Compound Groups 2a to 2d each further include compounds that satisfy at least one of the additional conditions described for Compound Group 1.

[0043] Compound group 3 used in the present invention includes compounds represented by the general formula (1) R １ and R ２ and R ５ are each independently a donor group bonded via a nitrogen atom. １ and R ２ and R ５ Compound group 3a, in which R ２ and R ５ are the same and R １ Compound group 3b, where R １ and R ５ are the same and R ２ Compound group 3c, where R １ and R ２ are the same and R ５ Compound group 3d, where R １ and R ２ and R ５ Compound Groups 3a to 3e each further include compounds that satisfy at least one of the additional conditions described for Compound Group 1.

[0044] Compound group 4 used in the present invention includes compounds represented by general formula (1) R １ and R ２ and R４ are each independently a donor group bonded via a nitrogen atom. １ and R ２ and R ４ Compound group 4a, in which R ２ and R ４ are the same and R １ Compound group 4b, where R １ and R ４ are the same and R ２ Compound group 4c, where R １ and R ２ are the same and R ４ Compound group 4d, where R １ and R ２ and R ４ Compound Groups 4a to 4e each further include compounds that satisfy at least one of the additional conditions described for Compound Group 1.

[0045] Compound group 5 used in the present invention includes compounds represented by the general formula (1) R １ and R ３ and R ４ are each independently a donor group bonded via a nitrogen atom. １ and R ３ and R ４ Compound group 5a, in which R ３ and R ４ are the same and R １ Compound group 5b, in which R １ and R ４ are the same and R ３ Compound group 5c, where R １ and R ３ are the same and R ４ Compound group 5d, where R １ and R ３ and R ４ Compound Groups 5a to 5e each further include compounds that satisfy at least one of the additional conditions described in Compound Group 1.

[0046] Compound group 6 used in the present invention includes compounds represented by general formula (1) R １ and R ２ and R ３are each independently a donor group bonded via a nitrogen atom. １ and R ２ and R ３ Compound group 6a, in which R ２ and R ３ are the same and R １ Compound group 6b, where R １ and R ３ are the same and R ２ Compound group 6c, where R １ and R ２ are the same and R ３ Compound group 6d, where R １ and R ２ and R ３ Compound Groups 6a to 6e each further include compounds that satisfy at least one of the additional conditions described for Compound Group 1.

[0047] When a compound emitting light with a short wavelength is provided, it is preferable to employ a compound having, in the molecule, a deuterium atom or a carbazol-9-yl group substituted with an aryl group which may be substituted with an alkyl group or an aryl group.

[0048] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing no hydrogen atoms but containing deuterium atoms.

[0049] In the present specification, "Group A" refers to a deuterium atom, 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 atoms constituting the ring skeleton), a heteroaryloxy group (for example, The group consisting of alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), heteroarylthio groups (e.g., having 5 to 30 ring atoms), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. The alkyl groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, heteroaryl groups, heteroaryloxy groups, heteroarylthio groups, acyl groups, alkenyl groups, alkynyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, heteroaryloxycarbonyl groups, silyl groups, and nitro groups may be substituted with a deuterium atom constituting group A and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. As used herein, "Group B" refers to a group consisting of deuterium atoms, 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 skeleton atoms), heteroaryloxy groups (e.g., having 5 to 30 ring skeleton atoms), and diarylaminoamino groups (e.g., having 0 to 20 carbon atoms). The alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heteroaryl groups, heteroaryloxy groups, and diarylaminoamino groups referred to here may be substituted with the deuterium atoms constituting Group B and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded.As used herein, "Group C" refers to a group consisting of deuterium atoms, 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 skeleton atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). The alkyl groups, aryl groups, heteroaryl groups, and diarylamino groups referred to here may be substituted with a deuterium atom constituting Group C and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group D" refers to a group consisting of deuterium atoms, 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). The alkyl groups, aryl groups, and heteroaryl groups referred to here may be substituted with a deuterium atom constituting Group D and a substituent having a structure in which one or more of the above-mentioned substituents are bonded. As used herein, "Group E" refers to a group consisting of a deuterium atom, alkyl groups (e.g., having 1 to 20 carbon atoms), and aryl groups (e.g., having 6 to 22 carbon atoms). The alkyl group and aryl group referred to here may be substituted with a deuterium atom constituting Group E and a substituent having a structure in which any one or two or more of the above-mentioned substituents are bonded. In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted," the substituted deuterium atom or substituent may be selected, for example, from Group A, Group B, Group C, Group D, or Group E.

[0050] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 3 below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, among the compounds represented by general formula (1), Y １ and Y ２ is a phenyl group (Ar1), and R １ and R ５ is a hydrogen atom, and R ２ , R ３ , R ４The following are specific examples of compounds in which R is the same and is any one of D1 to D1260. That is, R of a compound having the following structure ２ , R ３ , R ４ The structures of compounds 1 to 1260 are individually identified by listing them in order in Table 1.

[0051] In Table 2, the structures of compounds 1 to 392784 are shown as variations of the structure represented by general formula (1). １ and Y ２ is a phenyl group (Ar1), and R １ ~R ５ is a group specified in Table 2. That is, R of a compound having the following structure １ ~R ５ The structures of compounds 1 to 392784 are individually identified by showing them in order in Table 2. The columns of compounds 1 to 1260 in Table 2 are １ and Y ２ is fixed to the phenyl group (Ar1), and R １ and R ５ is fixed to a hydrogen atom (H), and R ２ , R ３ , R ４ In other words, the column of Compounds 1 to 1260 in Table 2 shows the structures of Compounds 1 to 1260 in Table 1 all together in one column. The column of Compounds 1261 to 2519 in Table 2 shows the structures of Compounds 1 to 1260 in Table 1 all together in one column. １ and Y ２ is fixed to the phenyl group (Ar1), and R １ and R ５ is fixed to a hydrogen atom (H), and R ３ is fixed to D1, and R ２ and R ４ The compounds D2 to D1260 having the same structure are identified as compounds 1261 to 2519 in order. １ and Y ２ is fixed to the phenyl group (Ar1), and R１ and R ５ is fixed to a hydrogen atom (H), and R ３ is fixed to D8, and R ２ and R ４ The compounds D1 to D7 and D9 to D1260, which have the same structure, are identified as compounds 2520 to 3778, respectively. The structures of the compounds in the following rows are identified in the same manner. As shown in the rightmost column of Table 2, for example, compounds 1 to 1260 in the top row have the same structure as R ２ and R ３ and R ４ indicates that they are the same.

[0052] In Table 2, Y in general formula (1) １ and Y ２ The structures of Compounds 1 to 392784 in which Y is fixed to the phenyl group (Ar1) were identified. Table 3 shows the structure of each of Compounds 1 to 392784. １ and Y ２ The compounds in which the phenyl group (Ar1) is changed as shown in Table 3 are listed in order in the form of a table. In Table 3, in order to make the correspondence easier to understand, １ and Y ２ In the second row of Table 3, for example, Compound 1(1) is a compound 1 in which Y is a phenyl group (Ar1). １ and Y ２ In addition, Compound 2(1) represents a compound having a structure in which Y in Compound 2 is substituted with Ar2. １ and Y ２ In the same manner, compound 392784 (1) can be obtained by substituting Y of compound 392784. １ and Y ２The structures of compounds 1(2) to 392784(2) onwards in the third row are specified in the same way as in the second row.

[0053] All compounds identified by the above numbers are considered to be individually disclosed. It should be noted that, among the specific examples of compounds listed above, when rotamers exist, the mixture of rotamers and each separated rotamer are also considered to be disclosed herein. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1 to 392784 and Compounds 1(n) to 392784(n) [where n is 1 to 437]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1 to 392784 and Compounds 1(n) to 392784(n) [where n is 1 to 68]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 392784(n) [where n is 69 to 233]. In one aspect of the present invention, a compound is selected from the group of compounds consisting of Compounds 1(n) to 392784(n) [where n is 234 to 310]. In one aspect of the present invention, the compound is selected from the group consisting of compounds 1(n) to 392784(n), where n is 311 to 325. In one aspect of the present invention, the compound is selected from the group consisting of compounds 1(n) to 392784(n), where n is 326 to 437.

[0054] Examples of preferred compounds represented by formula (1) are listed below.

[0055] Examples of the compounds represented by general formula (1) are listed below.

[0056] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, and can be, for example, 1000 or less, when an organic layer containing the compound represented by general formula (1) is intended to be formed into a film by vapor deposition and used. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) is useful as a light-emitting material and can be used as a delayed fluorescent material. For example, the compounds represented by general formula (1) include compounds with short delayed fluorescent lifetimes. For example, the compounds represented by general formula (1) include compounds with a high delayed fluorescent component in the emitted light. Organic light-emitting devices using the compounds represented by general formula (1) have good light-emitting properties. For example, the compounds represented by general formula (1) include compounds that can extend the device lifetime when used in organic light-emitting devices. For example, the compounds represented by general formula (1) include compounds that can reduce the driving voltage when used in organic light-emitting devices. For example, the compounds represented by general formula (1) include compounds that exhibit high alignment when formed into a film. The compounds represented by general formula (1) may be formed into a film by a coating method regardless of their molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in an organic solvent. Therefore, the compound represented by general formula (1) is easy to apply the coating method to and is easy to purify to increase its purity.

[0057] By applying the present invention, it is also conceivable 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 pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and 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 having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0058] 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.

[0059] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ 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. １０１ , R １０２ , R １０３ and R １０４each 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 following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0060] Specific structural examples of the repeating unit include structures represented by the following formulas.

[0061] A polymer having a repeating unit containing these formulas can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group.

[0062] 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.

[0063] The compound represented by general formula (1) is a compound that can be used in various semiconductor devices. For example, it can be used in organic light-emitting devices that emit light, organic light-receiving devices that receive light, and devices that cause light-mediated energy transfer within the device. For example, an organic electroluminescence device can be fabricated using a compound represented by general formula (1). For example, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1). For example, a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). Compounds represented by general formula (1) include compounds that can emit delayed fluorescence. Compounds represented by general formula (1) include compounds with a high proportion of delayed fluorescence components. For example, compounds in which 70% or more of the total emission is a delayed fluorescence component, compounds in which 80% or more of the total emission is a delayed fluorescence component, and compounds in which 90% or more of the total emission is a delayed fluorescence component are included. In certain embodiments of the present disclosure, compounds 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 certain embodiments of the present disclosure, compounds 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 certain embodiments of the present disclosure, compounds 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 certain embodiments of the present disclosure, compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means.In some embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm). In some embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the ultraviolet region of the spectrum (e.g., 280-400 nm). In some embodiments of the present disclosure, compounds represented by general formula (1) when excited by thermal or electronic means can emit light in the infrared region of the spectrum (e.g., 780 nm to 2 μm).

[0064] 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 ＳＴ The 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.

[0065] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. The compound represented by general formula (1) can be synthesized by combining R １ ~R ５ Two to five of these groups are donor groups, and for example, by reacting a precursor in which the donor group site is a fluorine atom with a substituted or unsubstituted carbazole, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is the donor group can be synthesized. For details of the reaction conditions, please refer to the synthesis examples described below.

[0066] 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).

[0067] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing a compound represented by general formula (1) 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 printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing a compound represented by general formula (1) 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 a compound represented by general formula (1) 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 thereto. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or a mixture of the compounds may be co-deposited from a single deposition source. When a single vapor deposition source is used, a mixed powder of compound powders may be used, a compression molded body 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 is performed under conditions where the deposition rates (weight loss rates) of the multiple compounds contained in a single vapor deposition source are identical or nearly identical, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the vapor deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed as a vapor deposition source, a film having a desired composition ratio can be easily formed. In some embodiments, the temperature at which each compound to be co-deposited has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0068] [Organic Light-Emitting Device] An organic light-emitting device containing a compound represented by general formula (1) will be described. An organic light-emitting device using a compound represented by general formula (1) has excellent performance. For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the alignment of the light-emitting layer is improved by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the device life can be extended by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the luminous efficiency is improved by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the driving voltage is reduced by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the proportion of delayed fluorescence components in light emission is increased by using a compound represented by general formula (1). For example, organic light-emitting devices containing a compound represented by general formula (1) include those in which the delayed fluorescence life can be shortened by using a compound represented by general formula (1). In one embodiment of the present invention, a compound represented by general formula (1) is used as a light-emitting material for an organic light-emitting device. For example, a compound represented by general formula (1) is used as the light-emitting material in the light-emitting layer. Compounds represented by general formula (1) include compounds with a high delayed fluorescent component content. Therefore, in one embodiment of the present invention, a compound represented by general formula (1) is used as a delayed fluorescent material, for example, to generate delayed fluorescence from the compound represented by general formula (1), thereby achieving high light emission efficiency. In one embodiment of the present invention, a compound represented by general formula (1) is used as a host material. In one embodiment of the present invention, a compound represented by general formula (1) is used together with one or more light-emitting materials. The light-emitting material referred to here may be a fluorescent material, a phosphorescent material, or a delayed fluorescent material. For example, a fluorescent material having a lower minimum excited singlet energy than the compound represented by general formula (1) is used together with the compound represented by general formula (1). In one embodiment of the present invention, a compound represented by general formula (1) is used as a hole-transporting material. In one embodiment of the present invention, a compound represented by general formula (1) is used as an electron-transporting material.In some embodiments, the light-emitting layer of an organic light-emitting device 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 light-emitting layer. The organic light-emitting device of the present invention is particularly preferably used as an organic light-emitting diode, etc. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device). In some embodiments, the organic light-emitting device is an organic electroluminescence device (organic EL device). In some embodiments, 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 lowest excited singlet energy level of the compound represented by general formula (1) contained in the light-emitting layer 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 photoluminescent device includes at least one light-emitting layer. In one embodiment, the organic electroluminescent 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 transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer 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.

[0069] 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 one or more compounds 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. In other words, any host material that can achieve high light emission efficiency can be used in the present invention without any 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, TADF molecules 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. In some embodiments, an organic electroluminescent device has a layer containing a compound represented by general formula (1). In some embodiments, the layer also contains a host material.In one embodiment, the layer containing the compound represented by general formula (1) and a host material also contains a delayed fluorescent material having a structure outside the scope of general formula (1), 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 represented by general formula (1). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the compound represented by general formula (1) is maximized. In another embodiment, the organic electroluminescent device has a layer containing the compound represented by general formula (1) and a light-emitting material having a structure outside the scope of general formula (1) (this layer may further contain a host material). In this case, in one embodiment, when the organic electroluminescent device is energized, the amount of light emitted from the light-emitting material having a structure outside the scope of general formula (1) is maximized.

[0070] When the 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.

[0071]

[0072] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with an assist dopant having a structure represented by general formula (1).

[0073] Further preferred light-emitting materials include compounds represented by the following general formula (2).

[0074] In general formula (2), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , 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 , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４At least one of the C-R groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0075] In one aspect of the present invention, X ２ When is O or NR, R ７ is an acceptor group, or R ６ and R ７ are bonded to each other to form an acceptor group, or R ７ and R ８ In one embodiment of the present invention, X ３ When is O or NR, R １０ is an acceptor group, or R ９ and R １０ are bonded to each other to form an acceptor group, or R １０ and R １１ In one embodiment of the present invention, X ４ When is O or NR, R １５ is an acceptor group, or R １４ and R １５ are bonded to each other to form an acceptor group, or R １５ and R １６ In one embodiment of the present invention, X ２ is NR, R is a substituted or unsubstituted phenyl group, and R ８In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ３ is NR, R is a substituted or unsubstituted phenyl group, and R ９ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. ４ is NR, R is a substituted or unsubstituted phenyl group, and R １６ In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. １ is NR, R is a substituted or unsubstituted phenyl group, and R １ In one embodiment of the present invention, the compound is represented by the following general formula (2a):

[0076] In general formula (2a), R １ , R ３ , R ６ ~R １１ , R １４ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R １１ , R１４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of Ar is O or NR, and the remaining may be O or NR or may not be linked. When not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ Each of C-R in general formula (2a) independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. １ , C-R ３ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0077] Further preferred light-emitting materials include compounds represented by the following general formula (3).

[0078] In general formula (3), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R８ , R ８ and R ９ , R ９ and R ２ , R ２ 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 , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0079] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted phenyl group which may be fused with another ring. ３ and R １０ are each independently a substituted amino group. １ and R ３ , and R ２ and R １０ In one embodiment of the present invention, the cyclic structure includes a benzoazaborine ring.

[0080] Further preferred light-emitting materials include compounds represented by the following general formula (4).

[0081] In general formula (4), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ 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 ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together 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, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0082] In one aspect of the present invention, Z １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. １ ~R ９ are each independently a substituted or unsubstituted aryl group or an acceptor group, or R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. ８ is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, a benzothiophene ring, and an indole ring.

[0083] Further preferred light-emitting materials include compounds having a fused ring structure A (in which a hydrogen atom may be substituted with a deuterium atom or a substituent) in which a carbon-carbon bond a in the following structure α is fused with a furan ring constituting a substituted or unsubstituted benzofuran ring, a thiophene ring constituting a substituted or unsubstituted benzothiophene ring, or a pyrrole ring constituting a substituted or unsubstituted indole ring, or a carbon-carbon bond b is fused with a benzene ring constituting a substituted or unsubstituted dibenzofuran ring, a benzene ring constituting a substituted or unsubstituted dibenzothiophene ring, a benzene ring constituting a substituted or unsubstituted carbazole ring, or a benzene ring constituting a substituted or unsubstituted dibenzodioxane ring.

[0084] In the structure α, X １ and X ２ each independently represents a substituted or unsubstituted aryl group, a nitrogen atom to which a substituted or unsubstituted aryl group is bonded, or an oxygen atom; Z represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent; Z and X ２ In the fused ring structure A, the structure fused to b and X may be bonded to each other to form a cyclic structure. １ , b and Z, Z and X ２ may be bonded to each other to form a cyclic structure.

[0085] Further preferred light-emitting materials include compounds represented by the following general formula (5).

[0086] In the general formula (5), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0087] Further preferred light-emitting materials include compounds represented by the following general formula (6).

[0088] In the general formula (6), X ３ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ ~R ７ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R３ At least one pair of these is bonded to each other to form a ring structure.

[0089] Further preferred light-emitting materials include compounds represented by the following general formula (7).

[0090] In the general formula (7), X ４ represents an oxygen atom or a sulfur atom, Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ４ａ ~R ７ａ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ , R ４ａ and R ５ａ , R ５ａ and R ６ａ , R ６ａ and R ７ａ , R ７ａ and R １ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0091] Further preferred light-emitting materials include compounds represented by the following general formula (8).

[0092] In the general formula (8), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ８ ~R １４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , 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 Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0093] Further preferred light-emitting materials include compounds represented by the following general formula (9).

[0094] In the general formula (9), Z １ and Z ４ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R １５ ~R １７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ３ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , Z ４ and R １５ , R １５ and R １６ , R １６and R １７ , R １７ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure.

[0095] Further preferred light-emitting materials include compounds represented by the following general formula (10).

[0096] In the general formula (10), Z １ and Z ５ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ３ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ５ , Z ５ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0097] Further preferred light-emitting materials include compounds represented by the following general formula (11).

[0098] In the general formula (11), Z １represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２１ ~R ２７ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ , R ２６ and R ２７ may be bonded to each other to form a cyclic structure.

[0099] Further preferred light-emitting materials include compounds represented by the following general formula (12).

[0100] In the general formula (12), Z １ and Z ６ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ and R ２８ ~R ３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.１ and Z １ , R ２ and Z ２ , Z ２ and R ２８ , R ２８ and R ２９ , R ２９ and R ３０ , R ３０ and Z ６ may be bonded to each other to form a cyclic structure.

[0101] Further preferred light-emitting materials include compounds represented by the following general formula (13).

[0102] In the general formula (13), Z １ and Z ７ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ７ , Z ７ and R ３ At least one pair of these is bonded to each other to form a ring structure.)

[0103] Further preferred light-emitting materials include compounds represented by the following general formula (14).

[0104] In the general formula (14), Z １ represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ３１ ~R ４４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R ３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ , R ３７ and R ３８ , R ３８ and R ３９ , R ３９ and R ４０ , R ４０ and R ４１ , R ４１ and R ４２ , R ４２ and R ４３ , R ４３ and R ４４ may be bonded to each other to form a cyclic structure.

[0105] Further preferred light-emitting materials include compounds represented by the following general formula (15).

[0106] In the general formula (15), Z １ and Z ８ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ５１ ~R ６０ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z１ , R ５１ and R ５２ , R ５２ and R ５３ , R ５３ and R ５４ , R ５４ and R ５５ , R ５５ and R ５６ , R ５６ and R ５７ , R ５７ and R ５８ , R ５８ and R ５９ , R ５９ and R ６０ , R ６０ and Z ８ may be bonded to each other to form a cyclic structure.

[0107] Further preferred light-emitting materials include compounds represented by the following general formula (16).

[0108] In the general formula (16), Z １ , Z ８ and Z ９ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６１ ~R ６６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and Z １ , Z ９ and R ６１ , R ６１ and R ６２ , R ６２ and R ６３ , R ６３ and R ６４ , R ６４ and R ６５ , R ６５ and R ６６ , R ６６ and Z ８ may be bonded to each other to form a cyclic structure.

[0109] Further preferred light-emitting materials include compounds represented by the following general formula (17).

[0110] In the general formula (17), Z １ , Z ９ and Z １０ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ６７ ~R ６９ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７０ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , Z ９ and R ６７ , R ６７ and R ６８ , R ６８ and R ６９ , R ６９ and Z １０ , Z １０ and R ７０ may be bonded to each other to form a cyclic structure.

[0111] Further preferred light-emitting materials include compounds represented by the following general formula (18).

[0112] In the general formula (18), Z １ , Z １１ and Z １２ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７２ ~R ７４ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R ７１ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R７１ and Z １１ , Z １１ and R ７２ , R ７２ and R ７３ , R ７３ and Z ７４ , R ７４ and Z １２ may be bonded to each other to form a cyclic structure.

[0113] Further preferred light-emitting materials include compounds represented by the following general formula (19).

[0114] In the general formula (19), Z １ and Z １１ each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R １ and R ７６ ~R ８２ each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R ７５ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Z １ , R ７５ and Z １１ , Z １１ and R ７６ , R ７６ and R ７７ , R ７７ and R ７８ , R ７８ and R ７９ , R ７９ and R ８０ , R ８０ and R ８１ , R ８１ and R ８２ may be bonded to each other to form a cyclic structure.

[0115] Further preferred light-emitting materials include compounds represented by the following general formula (20).

[0116] In the general formula (20), X ５represents an oxygen atom, a sulfur atom, or a nitrogen atom to which a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is bonded; R １０１ ~R １３０ each independently represents a hydrogen atom, a deuterium atom, or a substituent; R １０１ and R １０２ , R １０２ and R １０３ , R １０３ and R １０４ , R １０４ and R １０５ , R １０５ and R １０６ , R １０６ and R １０７ , R １０７ and R １０８ , R １０８ and R １０９ , R １０９ and R １１０ , R １１０ and R １１１ , R １１１ and R １１２ , R １１２ and R １１３ , R １１３ and R １１４ , R １１４ and R １１５ , R １１５ and R １１６ , R １１６ and R １１７ , R １１７ and R １１８ , R １１８ and R １１９ , R １１９ and R １２０ , R １２０ and R １２１ , R １２１ and R １２２ , R １２２ and R １２３ , R １２３ and R １２４ , R １２４ and R １２５ , R １２５ and R １２６ , R １２６ and R １２７ , R １２７ and R １２８ , R １２８ and R １２９ , R １２９ and R １３０ , R１３０ and R １０１ may be bonded to each other to form a cyclic structure.

[0117] Further preferred light-emitting materials include compounds represented by the following general formula (21).

[0118] In general formula (21), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２ At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R ２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １ may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0119] In one aspect of the present invention, R １ and R ２ are each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted phenyl group, or a group containing one or more ring structures selected from the group consisting of a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, and a substituted or unsubstituted indole ring. １ and Z ２ are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, a pyrrole ring fused with a substituted or unsubstituted benzene ring, a benzene ring fused with a substituted or unsubstituted benzofuran ring, a benzene ring fused with a substituted or unsubstituted benzothiophene ring, or a benzene ring fused with a substituted or unsubstituted indole ring. １ and Z １ are bonded to each other to form a ring structure. １ and Z １ are bonded to each other to form a pyrrole ring.

[0120] Further preferred light-emitting materials include compounds represented by the following general formula (22).

[0121] In the general formula (22), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R１ ~R ６ At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring. For a detailed description of the compound represented by general formula (22), a preferred range, and specific examples thereof, reference can be made to

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of the present specification.

[0122] In some embodiments, when a host material is used, the amount of the compound used in the present invention as the emissive material in the emissive layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of general formula (1) as the emissive material in the emissive layer is 10% by weight or less. In some embodiments, the host material in the emissive layer is an organic compound having hole transport and electron transport functions. In some embodiments, the host material in the emissive layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the emissive layer is an organic compound having a high glass transition temperature.

[0123] In some embodiments, the host material is selected from the group consisting of: 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 general formula (1) 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 only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting only of 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 general formula (1), 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.

[0124] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0125] 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.

[0126] 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.

[0127] 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.

[0128] 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:

[0129]

[0130] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0131] 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.

[0132] 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.

[0133]

[0134] 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.

[0135]

[0136] 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.

[0137] 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.

[0138]

[0139] 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.

[0140]

[0141] 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.

[0142]

[0143] 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.

[0144] 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).

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] The features of the present invention will be explained in more detail below with reference to 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 (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.).

[0155] (Synthesis Example 1) Synthesis of Compound A

[0156] Under a nitrogen atmosphere, a previously degassed mixture of tetrahydrofuran (30 mL) and water (15 mL) was added to a mixture of 1,2,3-trifluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzene (0.85 g, 3.29 mmol), 2-chloro-4,6-diphenyl-5-pyrimidinecarbonitrile (1.01 g, 3.46 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.23 g, 0.33 mmol), and sodium carbonate (0.70 g, 6.59 mmol). The mixture was heated to 75°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature and the water was separated. The resulting organic layer was concentrated and washed with hot toluene and ethyl acetate to obtain intermediate a (0.48 g, 1.24 mmol, yield 37.7%). ASAP mass spectrometry: theoretical 387.37, observed 388.32.

[0157] Under a nitrogen atmosphere, dimethylformamide (20 mL) was added to a mixture of intermediate a (0.70 g, 1.81 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.33 g, 1.90 mmol), and potassium carbonate (0.50 g, 3.61 mmol). The mixture was heated to 50°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was recrystallized to give intermediate b (0.86 g, 1.58 mmol, 87.3% yield). ASAP mass spectrometry analysis: theoretical 542.62, observed 543.33.

[0158] Under a nitrogen atmosphere, dimethylformamide (15 mL) was added to a mixture of intermediate b (0.72 g, 1.33 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.70 g, 3.98 mmol), and potassium carbonate (0.73 g, 5.31 mmol), and the mixture was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain Compound A (0.12 g, 0.14 mmol, yield 10.6%). 1 H NMR (400 MHz, CDCl3): δ 9.20 (s, 2H), 8.17-8.14 (m, 4H), 7.60-7.53 (m, 6H). ASAP mass spectrometry: calcd 853.13, observed 852.94

[0159] (Synthesis Example 2) Synthesis of Compound B

[0160] Under a nitrogen atmosphere, pre-degassed tetrahydrofuran (650 mL) was added to a mixture of 3,4,5-trifluorobenzonitrile (10.00 g, 63.65 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (11.16 g, 63.65 mmol), and the mixture was stirred at -40°C for 1 hour. Sodium hydride (1.48 g, 61.74 mmol) was added to the mixture, and the temperature was raised to 0°C and the mixture was stirred overnight. After completion of the reaction, the mixture was returned to room temperature, water was added, and the layers were separated. The organic layer was concentrated. The resulting solid was purified by silica gel column chromatography to obtain intermediate c (16.15 g, 51.70 mmol, yield 81.2%). 1 H NMR (400 MHz, CDCl3): δ 7.54-7.52 (d, J = 6.8 Hz, 2H). ASAP mass spectrometry: calcd 312.35, observed 312.29.

[0161] Under a nitrogen atmosphere, dimethylformamide (200 mL) was added to a mixture of intermediate c (6.00 g, 19.21 mmol), 5H-benzofuro[3,2-c]carbazole (17.30 g, 67.23 mmol), and potassium carbonate (10.62 g, 76.84 mmol). The mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was washed with toluene to obtain intermediate d. ASAP mass spectrometry analysis: theoretical value 786.92, observed value 787.54.

[0162] Under a nitrogen atmosphere, pre-degassed tetrahydrofuran (60 mL) was added to intermediate d (15.00 g, 19.06 mmol), and the mixture was stirred at 0°C for 1 hour. Lithium bis(trimethylsilyl)amide (29.00 mL, 38.12 mmol) was added to the mixture, and the mixture was allowed to warm to room temperature and stirred overnight. After completion of the reaction, the mixture was cooled to 0°C, and 6 M hydrochloric acid (75 mL, 450 mmol) was added. The mixture was allowed to warm to room temperature, and the resulting precipitate was filtered and washed with methanol to obtain intermediate e.

[0163] Under a nitrogen atmosphere, dimethylformamide (200 mL) was added to a mixture of intermediate e (15.52 g, 19.30 mmol), benzoylacetonitrile (5.60 g, 38.61 mmol), benzaldehyde (4.10 g, 38.61 mmol), and sodium carbonate (6.14 g, 57.91 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and recrystallized to obtain compound B (1.26 g, 1.23 mmol, yield 6.4%). 1H NMR (400 MHz, CDCl3): δ 9.30 (s, 2H), 8.26-8.25 (d, J= 7.6 Hz, 2H), 8.16-8.14 (d, J = 6.8 Hz,4H), 7.87-7.85 (d, J = 7.2 Hz,2H), 7.65-7.53 (m, 10H), 7.40-7.30 (m, 8H), 7.28-7.11 (m, 4H). ASAP mass spectrum analysis: theoretical value 1017.19, observed value 1017.92.

[0164] (Synthesis Example 3) Synthesis of Compound C

[0165] Under a nitrogen atmosphere, dimethylformamide (60 mL) was added to a mixture of intermediate c (2.00 g, 6.40 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (7.47 g, 22.41 mmol), and potassium carbonate (3.54 g, 25.61 mmol). The mixture was heated to 150°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was washed with toluene to give intermediate f (2.37 g, 2.52 mmol, 39.4% yield). ASAP mass spectrometry analysis: theoretical 939.12, observed 939.98.

[0166] Under a nitrogen atmosphere, pre-degassed tetrahydrofuran (60 mL) was added to intermediate f (2.37 g, 2.52 mmol), and the mixture was stirred at 0°C for 1 hour. Lithium bis(trimethylsilyl)amide (3.85 mL, 5.00 mmol) was added to the mixture, and the mixture was allowed to warm to room temperature and stirred overnight. After completion of the reaction, the mixture was cooled to 0°C, and 6 M hydrochloric acid (10 mL, 60.0 mmol) was added. The mixture was allowed to warm to room temperature, and the resulting precipitate was filtered and washed with methanol to obtain intermediate g.

[0167] Under a nitrogen atmosphere, dimethylformamide (30 mL) was added to a mixture of intermediate g (2.41 g, 2.52 mmol), benzoylacetonitrile (0.55 g, 3.78 mmol), benzaldehyde (0.40 g, 3.78 mmol), and sodium carbonate (0.80 g, 7.56 mmol), and the mixture was heated to 80°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and recrystallized to obtain compound C (0.88 g, 0.75 mmol, yield 29.9%). 1 H NMR (400 MHz, CDCl): δ 9.32 (s, 2H), 8.45 (s, 2H), 8.17-8.14 (m, 4H), 7.89-7.86 (m, 2H), 7.67-7.26 (m, 30H). ASAP mass spectrometry: calculated 1169.39, observed 1170.07.

[0168] (Synthesis Example 4) Synthesis of Compound D

[0169] Dimethylformamide (25 mL) was added to a mixture of intermediate a (0.86 g, 2.22 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (0.78 g, 2.33 mmol), and potassium carbonate (0.61 g, 4.44 mmol) under a nitrogen atmosphere. The mixture was heated to 50°C and stirred overnight. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the resulting precipitate was filtered and washed with methanol. The resulting precipitate was recrystallized to obtain intermediate h. ASAP mass spectrometry analysis: theoretical value 700.75, observed value 701.43.

[0170] Dimethylformamide (25 mL) was added to a mixture of intermediate h (1.60 g, 2.28 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.00 g, 5.71 mmol), and potassium carbonate (0.95 g, 6.85 mmol) under a nitrogen atmosphere, and the mixture was heated to 150°C and stirred overnight. After completion of the reaction, the mixture was cooled to room temperature, water was added, and the precipitate was filtered and washed with methanol. The resulting precipitate was purified by silica gel column chromatography and then recrystallized to obtain compound D (0.31 g, 0.31 mmol, yield 13.4%). 1 H NMR (400 MHz, CDCl3): δ 9.24 (s, 2H), 8.17-8.14 (m, 4H), 8.01 (s, 1H), 7.76-7.74 (d, J = 7.6 Hz 1H), 7.58-7.51 (m, 10H), 7.40-7.28 (m, 4H), 7.22-7.20 (d, J = 8.4 Hz 1H), 7.06-6.92 (m, 3H). ASAP mass spectrum analysis: theoretical value 1011.26, observed value 1012.05.

[0171] (Example 1) Preparation and evaluation of thin film Compound A was deposited on a quartz substrate at a vacuum of 1×10 －３ Compound A and Compound H1 (described later) were evaporated from different evaporation sources on a quartz substrate at a vacuum of 1×10 －３The doped thin film was evaporated at less than 100 Pa to form a 100 nm thick film containing 35 wt % Compound A. Neat and doped thin films were formed in the same manner using Compounds B, C, and Comparative Compound 1 instead of Compound A. However, the concentration of Comparative Compound 1 was 20 wt %, and Compound H2 (described below) was used instead of Compound H1. The HOMO and LUMO energies were measured using each neat thin film. Furthermore, photoluminescence was analyzed when each doped thin film was irradiated with 300 nm excitation light, and the emission peak wavelength (λmax), photoluminescence quantum yield (PLQY), lifetime of the delayed fluorescent component (τ2), and proportion of the delayed fluorescent component in the emitted light were measured. The degree of orientation (S value) of Compounds A to C and Comparative Compound 1 in each doped thin film was also measured. The degree of orientation was measured using the method described in Scientific Reports 2017, The PLQY was determined by the method described in JP-A-2002-20405, No. 7, 8405. The results are shown in the table below. All thin films showed a high PLQY exceeding 70%. On the other hand, thin films of Compound A, Compound B, and Compound C represented by general formula (1) were confirmed to have particularly short delayed fluorescence lifetimes and high orientation. Among them, Compound B and Compound C were confirmed to have a high proportion of delayed fluorescence components in their emitted light and extremely high orientation.

[0172] (Example 2) Fabrication and Evaluation of Organic Electroluminescence Device Each thin film was deposited by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed, at a vacuum degree of 5.0×10 －５The layers are laminated at a pressure of 10 Pa. First, a compound HAT-CN (described later) is formed on ITO to a thickness of 10 nm, a compound NPD (described later) is formed thereon to a thickness of 30 nm, a compound TrisPCz (described later) is formed thereon to a thickness of 10 nm, and a compound EBL1 (described later) is formed thereon to a thickness of 5 nm. Next, a compound H3 (described later) and a compound A (described later) are co-deposited from different evaporation sources to form a layer with a thickness of 40 nm, which serves as an emitting layer. The concentration of compound A in the emitting layer is 35% by mass. Next, a compound SF3-TRZ (described later) is formed to a thickness of 10 nm, and then compounds Liq and SF3-TRZ (described later) are co-deposited from different evaporation sources to form a layer with a thickness of 30 nm. The concentrations of Liq and SF3-TRZ in this layer are 30% by mass and 70% by mass, respectively. Further, Liq is formed to a thickness of 2 nm, and then aluminum (Al) is vapor-deposited to a thickness of 100 nm to form a cathode, thereby completing an organic electroluminescence device. Each organic electroluminescence device is fabricated by the same procedure using Compound B or Compound C instead of Compound A.

[0173] Example 3 Preparation and Evaluation of Organic Electroluminescence Device Using Assist Dopant Organic electroluminescence devices were prepared by the same method as in Example 2, except that the light-emitting layer was formed by co-depositing the below-described Compound H3, Compound A, and below-described Compound ET1 from different evaporation sources to a thickness of 40 nm and containing 64.2 wt % of Compound H3, 35.0 wt % of Compound A, and 0.8 wt % of Compound ET1. Organic electroluminescence devices were prepared by the same procedure using Compound B and Compound C, respectively, instead of Compound A.

[0174]

[0175]

[0176] The compound represented by general formula (1) has high alignment and good light-emitting properties, and by using the compound represented by general formula (1), an organic light-emitting device with good 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 ５ each independently represents a hydrogen atom, a deuterium atom, a donor group bonded via a nitrogen atom, a non-acceptor heteroaryl group bonded via a carbon atom, or a substituted or unsubstituted aryl group. １ ~R ５ At least two of Y are donor groups bonded via a nitrogen atom. １ and Y ２ represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and Y ２ cannot both be hydrogen or deuterium atoms.

2. R １ ~R ５ The compound according to claim 1 , wherein three or more of the groups are donor groups bonded at a nitrogen atom.

3. R １ ~R ５ The compound according to claim 1 , wherein two of the groups are donor groups bonded via a nitrogen atom and have structures different from each other.

4. R １ ~R ５ The compound according to claim 1, wherein one or more of the following is a substituted or unsubstituted carbazol-9-yl group.

5. R １ ~R ５ The compound according to claim 1, wherein one or more of the following is a substituted or unsubstituted ring-fused carbazol-9-yl group.

6. R １ ~R ５ The compound according to claim 1, wherein two or more of the following are substituted or unsubstituted ring-fused carbazol-9-yl groups:

7. R １ ~R ５ At least one of R is a substituted or unsubstituted ring-fused carbazol-9-yl group; １ ~R ５ The compound according to claim 1, wherein at least one other of the above is a substituted or unsubstituted carbazol-9-yl group not condensed with a ring.

8. R １ ~R ５ The compound according to claim 1, wherein one or two of are hydrogen atoms or deuterium atoms.

9. Y １ and Y ２ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

10. Y １ and Y ２ The compound according to claim 2, wherein at least one of is a substituted or unsubstituted aryl group.

11. The compound of claim 1, containing at least one deuterium atom in the molecule.

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

13. A membrane comprising a compound according to any one of claims 1 to 11.

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

15. The organic light-emitting device according to claim 14, which is an organic electroluminescence device.

16. The organic light-emitting device of claim 15, wherein the organic electroluminescent device has a layer comprising the compound, the layer also comprising a host material.

17. The organic light-emitting device according to claim 15, wherein the organic electroluminescent device has a layer containing the compound, and the layer also contains a light-emitting material having a structure outside the scope of the general formula (1).

18. The organic light-emitting device according to claim 17, wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

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